Why did we write this guide?

When deciding to leave the law in 2015-2016, there wasn’t a great deal of good – let alone inspiring – information about alternative career paths.  The suggestions were usually very dull, or heavily circumscribed. 

The typical suggestions were: 

  1. Change law firm
  1. Do a secondment / go in-house
  1. Become a law professor
  1. Quit (without good alternatives)

All fine options (maybe not the last one given most lawyers’ risk appetite), but not particularly broad or inspired in the sense of offering something different.

Since then, several of us at lawtomated have stumbled into legaltech, legal ops and innovation roles.  

Emphasis on the world stumbled

Why is this important? 

It’s important because careers are non-linear. Careers look less like this:

Linear Career

And usually look more like this:

Non-Linear Career

As Steve Jobs said in his famous Stanford graduation address:

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”

In other words, at any point in your career – and especially at the start – it’s hard to see the path from A to B to C.  Often there isn’t a single path, but multiple circuitous options.  

Even careers that seem like a lockstep progression are, when zoomed in, more like a messy spaghetti of tangled decisions, a lot of luck and often knowing the right people and being in the right place at the right time (or not). A lot like a stock price’s chart:

Linear Career Zoomed In

Why is this important?

It’s easy for anyone to look at other people’s successes (or their own) and fall into a post-hoc rationalization that everything was planned, executed and immediately and increasingly successful.  And done in a sprint.  

The reality more closely resembles a topsy turvy marathon rather than a sprint.  Often what you see is the tip of an iceberg.  The below the water line elements are the hard graft and years of smaller steps that together add up to a larger success (hopefully).

Career Iceberg

This guide, part 6 of our 8 part legaltech careers guide, distils principles to consider before, during and after you decide to move from traditional law into the growing number of roles focused on legaltech, legal ops, innovation and product.  

Why do you want to leave the law?

Start with why?

As Simon Sinek popularised, in the context of organisational, and later individual, decision making, successful decision-making processes start by asking “why?”.

5 Whys Simon Sinek
Source: here

All businesses, organizations, and careers operate on three levels:

  1. WHAT we do.
  2. HOW we do it.
  3. WHY we do it.

We all know what we do, i.e. the products / services we sell, the jobs we do for ourselves and others at work etc.  

Few of us know how we do it – the things that differentiate us from others.  

And even fewer know why we do what we do.  To make a big decision, you need to understand your why!

For a deeper understanding of this concept, we recommend you check out Simon Sinek’s book or his original TED talk, each of which describes the concept in greater detail:

Know your why?

Why is the purpose, cause or belief that drives an individual or organisation. 

Applying this to your career:

  • Why are you a lawyer? 
  • Why did you become one? 
  • Why is being a lawyer no longer what you want to do? Why is that? 
  • What’s your purpose, and why?
  • Why will changing careers make things better? 
  • Why is leaving the law for legaltech (or innovation, ops, product or other related roles) something you’re interested in?
  • Why will making the move improve things? (Will it?)
  • Why not stay put?

You get the picture. The crux is to understand why you’re considering a move and this specific move, and also why you are where you are at in your career.  

It’s about understanding which factors and why are pushing you from your current career and equally which factors and why are pulling you toward something else? 

Why you need to get specific

Let’s take a specific example.

Why is being a lawyer no longer what you want to do? Why is that? 

Typical responses might include:

  • “I find law boring”
  • “I have no life” 
  • “It’s not creative” 
  • “It’s not commercial enough”
  • “I have no control”

This is a start, not the end of your enquiry.  


These are symptoms of your unhappiness, not their causes.  You need to identify, and tackle, the root causes if you are to solve your unhappiness and make good decisions.  It’s about getting the best available data together in order to inform your decision making process.

So how to get deeper?

Getting specific and how to do it

Apply something called the 5 Whys.  It is an iterative interrogative technique used to explore the cause-and-effect relationships underlying a particular problem. The primary goal of the technique is to determine the root cause of a defect or problem by repeating the question “Why?”. Each answer forms the basis of the next question.

It’s typically applied to business processes or to investigate problems in order to decide countermeasures.

Let’s take a legal example – NDAs:

5 Whys NDAs

As in the above, most complex problems require more than 5 Whys, plus branching, to map the full list of causes and effects. It’s a framework to force your thinking down deeper and deeper until you reach the root cause(s). Only then can you identify countermeasures to resolve your initial problem.

Applying this to a decision to leave the law might look something like this:

5 Whys Careers

Chances are you might not have asked nor answered this question in any detail, or at least not this level of depth. You probably stopped at x 1 Why, or simply “I hate my job”.  But that’s too superficial to kickstart real change.

Why bother?

Pausing for thought here will help you assess whether leaving the law / embarking on a legaltech or other career is the right thing for you. 

What you’ll understand

You will:

  1. Understand why your current career makes you uneasy (specifically the root causes).
  1. Be more discerning about what you want from your next role, and hopefully avoid roles or organisations that replicate the root causes for your current unhappiness.
  1. Appreciate if there are root causes within your current role you can improve, either at your current employer (e.g. adopting a different mindset, moving teams, working with others, taking on different internal projects) or by moving elsewhere.  A positive change doesn’t have to be drastic to be determinative.
  1. Know in much greater detail how (if at all) leaving the law / embarking on a leagltech or similar career will benefit you, and importantly how it fits (or not) with your wider purpose and career / life goals.
  1. Be authentic with yourself: are you actually interested in legaltech and similar, or simply because everyone else is doing / suggesting it? (i.e. FOMO, which is definitely not a good reason to jump ship, especially from a career such as law where there is a ton of investment costs in terms of training, education and so on)

If you don’t understand why you are unhappy with the status quo there is a good chance you’ll make:

  • the wrong decision entirely;
  • the right decision made for the wrong reasons; or 
  • end up in a role or organization that fails to cure the root causes for your current unhappiness, thereby repeating the cycle of career disillusionment.  

Why consider leaving the law?

The reasons we most often hear divide into:

  • push factors – things you dislike about being a lawyer; and 
  • pull factors – things you find more attractive than being a lawyer. 

Representative but non-exhaustive examples include:

Push Factors


Lawyer unhappiness is a big problem.  A Law Society (the representative body for solicitors in England & Wales) report from 2017 identified that:

  1. “more than 90% of junior lawyers” are impacted by anxiety, stress and depression;
  1. “more than a quarter describing stress levels as ‘severe’ or ‘extreme’”; and
  1. “more than half” said “they regularly or occasionally feel unable to cope at work because of pressure”.

Pretty dire.

A 2019 report by the Law Society’s Junior Lawyer Division recorded similar results, including:

  • “77% of respondents said that their firm could do more to support stress at work”;
  • “one in 15 junior lawyers (6.4%) experienced suicidal thoughts”;
  • 47% had experienced mental ill-health from work-related stress; and
  • only 20% of those individuals experiencing mental health issues had made their employer aware.

See here for a more detailed explanation of why lawyers are unhappy. 

Work/Life Balance

This is a massive factor, and not just for Big Law lawyers. A lot of lawyers struggle with balance. 

Client expectations have raced to the bottom in terms of responsiveness. Lawyers are expected to be on call 24/7 and to drop everything whenever a client or partner demands it. 

This makes it incredibly hard to enjoy life, let alone plan anything, whether it’s a birthday party, a casual drink after work, a holiday, wedding or funeral… even surgery (according to one person who spoke to us!). 

Deflated Expectations

If you browse the marketing materials for most legal organisations you are greeted with fresh faces, smiles, the promise of the most intellectually exciting work, a demand to hire only the most ‘entrepreneurial’ and well-rounded individuals.  

Depending on where you work, what type of law you do and your team, the reality is often spending a significant portion of your career doing what is mostly non-legal specific and usually unstimulating work that makes little use of legal acumen nor develops particularly transferable skills.

We’re talking about the parts of legal roles that involve a lot of this:

  • renaming files;
  • checking cross-references in a contract;
  • checking capitalised terms are defined in a contract;
  • checking defined terms are used in a contract;
  • running 10s or 100s of redlines of new vs. old versions of documents;
  • typing up handwritten mark-ups of legal documents provided by clients or senior lawyers;
  • data entry of data into forms for filings or claims systems;
  • weeks or months sat plugged into Tinder like swipe left or right interfaces to sift millions of eDiscovery evidence or due diligence; 
  • duplicating out templates for 10s or 100s of entities, only to change half a dozen basic details;
  • updating 10s or 100s of documents for basic details (multiple times a day or week) due to client decisions, negotiations, errors or the non-stop fussing of senior lawyers; and
  • endless printing, dating and scanning of documents.

You get the picture.  

These tasks often remain a feature of modern legal work until you become quite senior, in some cases remaining a feature of your career for the first 5+ years of practice.

In our opinion, there is a lot of misaligned labour within legal – it doesn’t make sense to have highly educated, expensive to train, hire and retain individuals driving copy / paste driven processes that, viewed in the cold light of day, don’t require any legal skills. 

This is poor value for clients and for lawyers. But that’s a bigger conversation for another time!

Low decision latitude

Low decision latitude is both a cause and effect of the highly repetitive low value cognitive labour that defines a lot of modern legal work.  

If everything is 100% manual and repetitive, you and your team simply won’t have the time or means to choose how to work.

It’s also very unlikely that you will have the time and mental bandwidth to sit down as a team and critically redesign your current processes so that it is more standardized and therefore capable of automation or augmentation with technology, which in turn may free up capacity to tackle more interesting and varied legal work.

This creates a vicious cycle within legal organisations, that looks something like this:  

Cavemen and the wheel

Management structures further impede decision latitude.  Legal organisations have very command and control led processes, leaning toward excessive micromanagement.  

A draft document will be prepared by a trainee, reviewed by an associate, and possibly one or both of a senior associate and partner depending on the document’s complexity or value.  

At the junior end, you can quite easily be the person that spends all day every day mindlessly typing another person’s changes into a document, or providing detailed instructions to someone else to effect the same – literally no creative or intellectual input required.  And no legal skill requirement. 

Senior lawyers will tell you that this is how junior lawyers learn how to mark up and review documents… let’s be brutally honest – they don’t. 

The sheer volume of work and limited time to deliver it mean that junior lawyers are more often than not mindlessly thrashing out amendments based on senior lawyer mark-ups, and consequently have zero time to read, let alone understand what these comments mean or, most importantly, have the opportunity to ask the senior lawyer why they made X change and not Y.

Given law generally selects for exceptional academics, this “humans as tools” vs “humans using tools” approach doesn’t make sense!  

Most intellectual people like a challenge and are creative and thinkers.  Putting them into roles where none of that is possible (or rarely so) is a poor use of brainpower, both for the individual and for the organization.  

Pull Factors

To recap, these are factors that are drawing you away from law. Typical ones we hear are the following:

I want to do something “more commercial”

This is usually (and unsurprisingly) but not always a desire of lawyers working in commercial practice areas. That said, we’ve met lawyers doing personal injury or A2J work that also cite this desire.

But first, imagine someone buying a customised Ferrari.

The exciting decisions about the Ferrari being built to order are the colours, the interior, the custom wrap, the upgraded features.  

The excitement is what the Ferrari promises the buyer, perhaps:

  • status; 
  • validation;
  • the ability to go fast; and
  • maybe the chance to make up for other defects in their otherwise successful visage.  

So where do the lawyers fit in?

The seatbelts. 

Lawyers are like Ferrari seatbelts

Lawyers often function like the secret services, whose successes are private and their failures public.

No one pays attention to the seatbelts unless and until they go wrong. But they need to be there, need to work well and be ready on time with the rest of the Ferrari.

If the buyer changes their mind several times regarding their preferred bucket seat, rendering previous seatbelt implementations obsolete, well tough.  Start again. Work late until the new seatbelts are finished.

As in the above, the exciting parts of the transaction are a few hops removed from the lawyers.  A lawyer’s ability to drive the big decisions the client really cares about are limited.  

Rather than being in the driving seat, lawyers are driven by their clients’ wider decisions.

This further reduces decision latitude.

This analogy best fits transactional work, but it does have some application to non-transactional work, e.g. litigation or advisory or personal injury.  Ultimately the client still drives the decisions that matter. They can choose to heed or ignore legal input. That said, litigation is an example of a practice area that permits a lot more decision latitude and places more of the driving force in the hands of the lawyer.

And that’s fine. That’s how it is. Law is (traditionally) a client service industry.  

But that’s not to say lawyers cannot get involved in exciting, strategic and commercial decisions. The best lawyers are often doing exactly that: the trusted advisor who combines commercial and legal acumen, and who can cut through the noise.

However, as a rule (and of course there are plenty of exceptions that prove the rule) those roles are rightly the result of a very senior career, and even then highly dependent on the practice area.  

It’s worth noting that unsurprisingly, creative areas of business with non-standard transactions can also be hugely rewarding and commercially driven for lawyers, e.g. emerging companies work, film, media and technology transactions work etc.  In these areas, there are some truly fantastic opportunities for lawyering and being commercial, even quite early on in your career – do not discount them.

I want to work in tech?

As Marc Andreessen famously concluded, ‘software is eating the world’.  Tech is everywhere and repeatedly beatified by the media, supercharged by a minority of high profile blockbuster unicorn success stories and founder hagiographies (e.g. The Social Network).

Tech is attractive because it promises creativity, change, an ability to tap into the circulatory system of modern life (software and hardware), and let’s face it, for most people the chance of incredible wealth and success.  

Launching the next unicorn is easy. Just do this:

Tech Billionaire Master Plan

Obviously this is nonsense! 

Most unicorns are overnight successes many years, and sometimes decades in the making.  

As obvious as ideas like AirBnB look today, they weren’t.  Multiple investors laughed the AirBnB founders out of the room when they pitched the idea of people letting strangers stay in their homes or stay in other people’s.  

Would you have paid to do that in the early 2000s? 

Probably not.  

The AirBnB founders – as brilliantly told in Brad Stone’s The Upstarts – also spent most of their early years flirting with bankruptcy, maintaining a plastic wallet of maxed out credit cards… and even selling novelty cereal to keep things going! 

The point isn’t don’t try tech, or that you can’t be successful.  The point is: be realistic. 

Tech isn’t a silver bullet providing an easier, wealthier and better work / life balance vs. law.  It might, but you’ll likely need to compromise or optimise one or more factors over the other depending on you why. Also, even if you’re really smart, learning to code isn’t a walk in the park and will require some serious effort, and in any case, building great businesses – even software businesses – is about more than coding. 

To learn more about whether lawyers should learn to code, or whether they should consider learning other technology related skills, see here.

I want a “more interesting” career

Again, like vaguely wanting to do something “more commercial” or “work in tech”, “more interesting” is too loose to be actionable.  

Using the 5 Whys exercise might help you get to the root cause of why your current role isn’t interesting enough, or in the right sense.  

Armed with that knowledge you can better identify what actually interests you about something else and thereby find specific roles and organisations that tick those boxes.

What specifically does “more interesting” mean to you?

Why consider a career in Legaltech?

Reasons to consider

Sideways vs starting from the bottom

A common anxiety for any career pivot is the risk / reward of starting again. If you’re weighing up a drastic career change, this can mean re-training and starting at the bottom.  

Depending on your station in life (e.g. student or equity partner) the costs of restarting may be more or less terrifying relative to your obligations.

The more senior you are, the more likely you have accumulated a portfolio of responsibilities: a mortgage, maybe some kids and everything that goes with that. You may even feel you can’t learn new things. 

Junior career changers may worry (and be told by senior people, friends and family) that they need to “stick at it” for a bit longer, or that “it gets better”.  Sometimes that’s the right advice, sometimes it’s not.  Oftentimes it can simply be more senior folk justifying their own decisions to stay put, rather than try something new. 

There is also an element of the sunk costs fallacy to some of these deliberations, i.e. I’ve come this far, so I should keep going.

Whether you are a senior or junior career changer, if you have some grounding in law (a little or a lot), legaltech can be a great sideways move that on the one hand leverages your existing legal skills, experience, network and often a reasonable amount of your current earning potential, whilst also providing some downside risk. As we shall demonstrate, there are paths back to law if you so desire it.

Career restart vs. sideways graph

Going sideways is easier to swallow than a full restart.  But easy isn’t always better.  Don’t disregard a larger restart if ultimately it will mean greater fulfilment.

Better work / life balance

First things first: working at a start-up, or worse still, founding one isn’t a walk in the park.  If you want to join or found an early stage start-up, be prepared to work hard and unpredictable hours, often for little or even no pay, or certainly less substantial pay than a lawyer typically commands.

For first hand accounts of the start-up founder life, check out our interviews with legaltech founders such as David Howorth and Eliot Benzecrit from Avvoka, Mary Bonsor from Flex Legal, Devshi Mehrotra from JusticeText, Tunji Williams from ShareThing and Sam Smolkin from Office & Dragons.  

We’re not saying don’t bother being a founder or join an early stage start-up, but be realistic and honest with yourself about what you really want and why.

Early stage legaltech start-ups aside, even more mature businesses will be unpredictable, and at times, all consuming, albeit in different ways to law firms or in-house roles which tend to be more mature and time-tested with longstanding reporting lines and a sense of who does X or Y and when.  

In either case, that doesn’t have to be a bad thing.  

It is usually a good thing. 

Especially if you are genuinely interested in the mission, the product and the people you work with and are trying to help.

A lot of people we meet and speak to who made the move to start-ups are still very busy, but enjoy the busyness.  

They don’t dread every conversation or request to pitch in; instead they volunteer and are eager to grow their skills and experience. As a whole, especially if they came from Big Law, they aren’t doing anywhere near the consistently brutal hours all day every day 365 days a year.

The quid pro quo of earning less overall is that the hours are much better and weekend / evening / holiday interruptions / cancellations extremely rare, if entirely absent.  

How much is your time and happiness worth? 

When we speak to people, we always suggest they work out how much they are really paid per hour. Not billable hours, but hours spent working or thinking about work.

When they compare that to non-legal jobs and those jobs’ work / life balance + salaries, the difference in hourly pay is often a lot less significant than they would have intuited. 

Try it for yourself!

Salary comparison graph

Yes, the above is simplistic and assumes a 40 hour work week (680 hours per year) for the legaltech role and 2,500 worked (not necessarily billable) hours for the Big Law attorney role, but it is representative of those types of roles and the general idea.

The idea is that you can take a lower salary (albeit £100,000 is still a very high salary in the UK on average) but work significantly fewer hours, and still end up earning more per hour, or at the very least the same.  

When you factor in the value of having more time to enjoy life, your hobbies, your health, your friends, your family and a general ability to enjoy holidays and weekends uninterrupted then the value is even higher (in our opinion). 

If you have no life, you may decide otherwise – but it’s up to you! That’s why it is important to know your why.

If you’re interested to understand remuneration vs. work / life balance for legaltech, legal ops and innovation roles, see here.

And this improved work / life balance outside of law is because of…

Greater variety; more control

Overall, especially if you are coming to legaltech from a Big Law role, working in legaltech will afford you something legal roles seldom do: the ability to choose when to work, where to work, how to work, with whom and why. 

In other words, you will likely enjoy greater decision latitude vs. your legal role. 

Of course there will be deadlines and people that are a pain to work with or for, but you will generally have more flexibility and greater decision latitude vs. becoming a deep expert in a niche type of contract, transaction or litigation specialism.

This can make the work / life balance more enjoyable because you have greater control, and hopefully greater interest in a more varied subject matter and set of challenges. 


Legal innovation is rife with spinnovation, or innovation by press release

To an outsider, it may seem all the innovation has happened, or that it’s too late to make a real difference. 

The reality is very different. 

Sure, most legal organisations have backbone IT systems and may even use a few newer pieces of legaltech, even ones with fancy buzzy technologies inside of them such as AI…

…but having the tools is one thing, knowing how to use them, use them well and use them widely are other things entirely.

Law firms and in-house legal teams still have a long way to go in terms of improving their underlying business models, which comprise their processes, culture and incentives. There is much to be improved, and at some point, innovated with regard to these elements of legal practice. 

In fact, the absence of significant change to these aspects – i.e. business model innovation – of most legal organisations is what holds back the wider usage, understanding, adoption and ROI of technology generally.

For an industry measured by how long tasks take, is it any wonder there is often lukewarm engagement for improved organisation of people, process and technology that reduces time per task or creates genuinely innovative new value? 

But this can’t last forever. 

Right now, it means there’s no shortage of opportunities to significantly improve legal processes with or without technology that can create easy ROI via quick wins and marginal gains, let alone moonshot ideas. 


Legaltech, legal ops and legal innovation roles are incredibly creative. 

Creativity comes in all forms, e.g.

  • finding ways to pitch a product; 
  • designing ways to test a product; and
  • formulating the right strategic approaches to drive engagement and influence decision makers or adoption of new processes and technology.

Every day is different, and whilst there are processes to be followed, in a lot of cases you will have space to flex your creative fibres and try new ideas most days. 

These roles will not require you to “do things the way we’ve always done them” as is all too common for most legal roles. In many cases, it will be up to you to figure out how best to do X or Y.


Unsurprisingly, given the creativity there is a lot of variety in legaltech, legal ops and legal innovation roles. 

Vendor side you may meet one prospect in a new industry and have an exciting conversation about their challenges and how your product might solve their needs; the day after you might be workshopping new features with the product team based on a major round of customer feedback. 

In a law firm innovation role you might be leading a large innovation project one day, and the next pitching a client on the firm’s blended alternative service offering and its innovative organisation of people, process and tech. Another day you might be facilitating a process mapping and measurement exercise, unearthing surprising insights and helping a team redesign and optimise the way they work, or perhaps creating a new product or service through such means. 

Variety is the spice of life, and there’s significantly more variety to these roles than traditional legal roles.

Reasons not to consider


Don’t leap into legaltech driven by a fear of missing out (FOMO).  Deciding anything based on FOMO is rarely the right thing to do and often leaves you sorely disappointed. 

FOMO frequently provokes feelings of anxiety and restlessness, generated by competitive thoughts that others are experiencing more pleasure, success, or fulfillment in their lives than you are. If you are a legal professional, you are probably vulnerable to FOMO given many lawyers suffer from anxiety and are usually type A competitive overachievers.  

Check yourself.  

Pause and think whether you are interested in legaltech because it is a genuinely interesting space with exciting challenges, or drawn to it because a university friend or acquaintance made the move and seems a lot happier than they were as a lawyer or gets to wear trainers, a t-shirt and jeans to work.  

If FOMO is a part of your decision, that’s fine.  But absolutely do not take a major career decision based exclusively on FOMO.

Get rich quick 

Legaltech is not a get rich quick scheme, let alone a get rich more easily scheme.  If you are a lawyer at a big firm, you are already paid well above most national averages.  Tied to that, lockstep progression and relative job security aren’t to be scoffed at.  Outside of legal, progression is neither guaranteed nor predictable, and recessions bite.

To have a chance of getting rich in legaltech, or any business, you generally need to be a founder or early employee (e.g. employee 1 – 5) in a start-up that becomes exceptionally successful.  

But this is very rarely a quick route to riches.  

Like all industries, there are few unicorns, and this is true of Legaltech. And unicorns take time to build whatever industry they are in.  

Legal is a slow business with an extremely slow buying cycle for legaltech, so it takes time to build sales pipelines that convert to licences, subscriptions and attractive valuations.  This can make the road to big numbers even longer.  

Ironclad (an innovative contract lifecycle management platform) recently raised a $100m Series D round, valuing it at unicorn status.

An overnight success? No, it’s a success 6 years in the making, with some way still to go in an ever crowded CLM market.

The point isn’t to put you off, but to help you be realistic about what is involved.  Time, grit and in the early days a very likely extended run of no income whilst you sink capital (probably credit cards or savings) into getting your start-up up and running.

All that said, if you are very lucky you might be able to find a senior role within legaltech that pays well and / or provides some equity or equity options.  These tend to be the purview of very senior executives who join at director or C-level, and who usually come from outside legal and have a track record of starting or scaling businesses generally, so unfortunately these types of roles don’t typically draw on former lawyers.  

Job security 

Vendor roles

Legal roles tend to be very secure.  Perhaps not as secure as they once were.  The 2007/2008 crash proved that. But they remain more secure vs. non-legal jobs on the whole. 

Moving into legaltech is much less secure, especially the vendor side.  Like tech start-ups generally, legaltech start-ups rise and fall all the time. What’s hot today, might have flamed out tomorrow.

In the past few years these legaltech companies have died:

And these further companies have been subsumed by bigger players through acquisition:

If you join a legaltech start-up, be mindful that the business might cease to exist if it is outmanoeuvred by a competitor or simply mismanaged. 

Likewise, although being acquired sounds exciting it really isn’t if you are an employee.  If you are a founder, or perhaps an early employee, you might receive a windfall. 

Outside of that limited clique, employees tend to get a raw deal post-acquisition.  Your role, responsibilities, remuneration and progression will all take a hit as the combined business tries to figure out what the heck to do with the combined business. Integrating teams and cultures can quickly expose, or create, never-ending and soul-sucking politics that further drag down morale and any ability to generally get sh*t done.

If you are lucky, your career might get accelerated.  But this is more typical if you are the acquirer rather than the acquired.  As a general rule, various studies continue to prove that “M&A is a mug’s game, in which some 70% to 90% of acquisitions are abysmal failures.”  

This is usually because the businesses bought don’t gel with the acquiring business, whether that be at the levels of customer base, management teams, office systems, product alignment or cultural values.  A further and typical failure is to not invest in post-merger integration expertise, whether before, during or after the acquisition. Post-acquisition integration doesn’t just happen – it needs a steady and empathetic hand, and is sadly often missing entirely.

The result? Assured failure of the M&A.

Law firm legaltech / innovation / ops roles

Legaltech roles at law firms and in-house are perhaps more secure than vendor roles, but are non-critical to such businesses when times are hard.  

Another thing to consider is that within a law firm, in an innovation role, you will be a second class citizen under the binary model law firms operate that distinguishes between: (a) fee earners (lawyers); and (b) non-fee earners (everyone else, or pejoratively referred to as “fee burners” by lawyers).  


Of course, this is gross and antiquated but “this is the way” as the Mandalorian would say.  

Granted many firms have done, and still do, a lot to reset this balance at least in terms of optics, but in terms of substance, the highest paid, most influential and most retained people in law firms are… lawyers. That isn’t going to change anytime soon so long as the partnership model continues (i.e. a legal business run by lawyers for lawyers).

This isn’t to say legaltech roles in law firms aren’t exciting or worthwhile, but simply that they aren’t the main event and never will be. 

The good thing is that this may change over time as law firms recognise the importance of standardisation as a means to systematize and potentially commoditize and scale what they do, and to do so beyond the linear scaling of throwing more lawyers at the same old work. If that happens, legaltech and innovation roles within law firms may become more influential day-to-day.

Pay, progression and choose your own adventure

The greater variety of roles outside of law is a double edged sword for most lawyers.  

Lawyers are either drawn to the predictability of legal roles, or become comfortable with it. 

The increased decision latitude day to day, and the multitude of different directions in which non-legal careers can diverge, can be intimidating if you are used to low decision latitude day-to-day, lockstep progression with known payrises and bonuses etc.  

This last point – lockstep pay and progression – is very significant when we talk to lawyers.

You are a first year, then a second year and so on and eventually become a partner (if you are lucky).  

At each year group your pay is usually increased by some arbitrary and often flat amount largely regardless of merit (aside from major screw ups), and any bonus will also jump up into a preset range that adjusts up or down a little based on how many hours above or below your target billable hours you billed.  

Whatever the parameters, the fact these are disclosed and predictable parameters at each stage of your career means you can plot in a simple excel how much you will earn 5 years or 10 years from now, all things being well and provided you don’t get sick or screw up. 

There’s comfort in that and seeing your networth rise and rise more or less independent of any merit (beyond your ability at not messing things up), provided that you are consistently billing the required hours.  

Of course, the more senior you go, the more merit, relationships and business development come into play, which can make or break whether or not you make it to partner and then to equity partner.  But for the early years (0 to 5 – 8 years PQE), it’s mostly set and forget.  

Clock in, do the hours, clock out, earn X base and bonus Y.  Rinse and repeat.

Generous salaries – especially in Big Law – and lockstep progression tracks can be hugely anxiety reducing, especially if you have or plan to have a family, a mortgage and so on.  

It is also extremely hard to reconsider the salary and security if you aren’t from money, and have snuck into Big Law from a less typical background, e.g. you are a minority, first generation university graduate and / or went to a state school etc.

Law firms, particularly large ones, are expert at paying just enough to keep you there, but not life changing amounts.  In boom times, they also throw bonus after bonus at overworked associates to stop them leaving, as is the case during COVID-19 at the Big Law firms.

The higher you go the higher your earnings, and for most people their outgoings will creep up with earnings.  Very soon you can end up with an expensive mortgage, too many kids in expensive private schools, a ridiculous car or two and too many dinners out at whatever the latest and greatest restaurant is said to be.  

In the blink of an eye it can become impossible to countenance a 5%, let alone 50% or more drop in salary, even if temporarily. That is the pay cut you may end up taking to leave the law and to try something different, including something sideways like legaltech.  The more senior you get, the more significant this drop becomes as your earnings creep up as your experience narrows further and further and becomes less transferable. 

So you have a choice.

On the one hand, moving away from a career with lockstep progression presents an opportunity for you to advance based on merit (subject to the usual inescapable truths about careers such as luck, politics and network), and perhaps carve your own path.  

On the other hand, outside of legal, there is rarely a set formula you can blindly follow and be sure to reach X or Y level in another industry.

Don’t underestimate this factor. Ambiguity isn’t for everyone.

Consider whether absence of lockstep progression excites or terrifies you. How does this align with your broader goals regarding finances and retirement, e.g. if you wish to achieve X level of financial security by Y age, does quitting the law offer a path to that goal that satisfies your need for predictability and timing?  It might do, but it might be less of a sure thing and require you to be more tenacious than if you stick with law.


Being a lawyer remains a high status profession for the most part despite the general public’s conflicting dislike of lawyers per se and what they represent (eg. stereotypes of unscrupulous and immoral lawyers defending criminals or frauds etc).  

A large part of becoming a lawyer, particularly for individuals who are the first in a family to go to university, and usually from a working class or lower middle class background, is the status or promise of status it affords the individual and their family.  

Leaving that behind can be hard. Wrapped up in the guilt is a sense that you are foregoing something you and your family fought to break into – law remains a very gated profession and leans heavily toward privately educated, Oxbridge and wealthier socio-economic backgrounds, at least in the UK and especially for the top jobs. 

Moving into legaltech or similar doesn’t have that status. That said, as technology becomes more and more a staple of everyday life, this could change.

Culture shock

Working in a legal organisation typically involves a command and control structure.  Tasks are heavily prescribed in terms of the what, who, who, when, where and why of their execution. As we note, this means low decision latitude, and deadlines are rife and often false but met with unflinching commitment at the expense of personal sanity and sleep.  The expectation is usually that the client is always right and no matter how insane the demand, will have their demands met come hell or high water.  

Attention to detail in all things borders on the insane.  Spending an hour re-reading and fiddling with a 5 line email and checking and re-checking the 12 recipients and 3 attachments is not a sign of madness, but a job well done.

Outside of law, you’re in for a shock.

A big one.

In the real world, standards are very different, especially attention to detail.  Within your first few weeks of moving beyond law you will be aghast (from a lawyer’s perspective) at how little attention to detail exists. 

Emails are sent to the wrong people, the incorrect attachments included, spelling mistakes are everywhere… deadlines are missed or forgot altogether.

But don’t worry.  The reality is that in the real world most people don’t care and don’t need to.  

This isn’t to say people are generally careless and lazy. Not at all.  It’s just that they are pragmatic and see perfection as the enemy of done, or good enough.  

The world keeps spinning despite a typo.  

Spending an extra hour checking something rarely makes a meaningful difference. 

Of course, extreme attention to detail in law makes sense: you are paid to manage other people’s risk so they don’t have to. 

In the real world, this is rarely the case unless you work in compliance or medicine etc where carelessness has a huge and irreversible cost.

This adjusted threshold for acceptable attention to detail will either be liberating or terrifying, and perhaps anxiety inducing for lawyers making the move.  It can also make it hard to work with new colleagues if they are committing errors that – in a legal setting – would be reasons for reprimand or worse, termination.  

Our advice:

  • Rein in your lawyer perfectionism and understand what matters and what doesn’t.  
  • Don’t sacrifice your attention to detail – it can actually elevate you if your work is consistently excellent relative to peers, both in terms of accuracy but more so in terms of completeness of thought and execution.  
  • However, don’t feel the need to hold yourself and others to the same exacting and often insane standards lawyers in a legal setting require. It’s often unnecessary.

As the saying goes, perfection is the enemy of good enough (or done).

Perfection is the enemy of good enough graph
Source: here

Common blockers for career changing lawyers

The below is a list of blockers assembled from experiences within the lawtomated team and numerous interviews with lawyers seeking a career change into legaltech, legal innovation and legal ops. 

By blockers we mean things that either:

  • hold lawyers back from making the move; or
  • having made the move, hinder their success.

Why care? 

The below blockers often go unsaid. They shouldn’t. Acknowledging them is the first step to thinking critically about whether they apply to you, and if they do, whether they suggest you’d be better off sticking with law, or choosing something different… or if switching away from law, any areas for personal development. 

Failure to think these through could mean you jump ship for the wrong reasons and into the wrong alternative, making you even unhappier.  Or worse, having made the right move for the right reasons you self-sabotage your success.

We don’t want you to do that!


Lawyers tend to have, or cultivate through their training and work experience, a pessimistic explanatory style. Events are viewed as persistent, uncontrollable and pervasive.  

Conversely, optimists see troubles as local, temporary and changeable. The pessimistic explanatory style can quickly create a narrative that says “no” to career change, e.g. 

“It’s too late… I don’t have the skills or connections… I’m in too deep to turn back now…”. 

This pessimistic explanatory style can also create a tendency to pick holes in just about anything and everything.

Business is about cost-benefit analyses and systems, not edge cases as the dominating or driving factor.  

Law is necessarily focused on the latter; lawyers are paid to foresee, manage and mitigate as much risk as possible (often with little regard to proportionality).  

This is especially crucial given a lot of people preconceive lawyers as incapable of seeing the bigger picture and instead getting bogged down in inconsequential and highly remote or easily managed risks.

Risk and reward are two sides of the same coin.  Make sure you can and demonstrate an ability to see both sides of the coin but appraise them with a sense of proportion, always having in mind the big picture.  


Perfectionism and the tendency of law to recruit insecure overachievers is also limiting if unchecked.  

A maximising insecure overachiever mindset can make it incredibly hard to change careers, which often requires at least some temporary drop in salary, seniority and status for the simple fact you might be an experienced finance lawyer, but you aren’t that experienced in areas X, Y, Z important to where you’d like to move.  

Perfectionism can also impair your ability to operate commercially.

Let’s take a typical legal process that everyone hates and would love to improve: NDAs.

Now the best solution would be an ideally single and widely accepted industry standard – as is the aim of the One NDA Project. We hope that project succeeds, but it might not.  

Absent of that project succeeding, consider a modern NDA process:

  1. Receive third party NDA.
  1. Mark-up third party NDA per client’s playbook (i.e. guide or rules).
  1. Return to sender; negotiate through to signing.

There now exist some great tools, e.g. BlackBoiler, whose AI capabilities can be trained with precedent mark-ups (i.e. third party NDAs amended in line with a client playbook) in order to make automated natural language mark-ups in track changes for new third party NDAs in the same way a lawyer would.

But AI isn’t perfect. For the typical legal user, the expectation or goal is usually a perfect system. An AI that is 100% accurate 100% of the time in 100% of scenarios. 

In this example, the lawyer’s expectation is an AI that produces 100% client or counterparty ready mark-ups requiring zero human oversight. 

The shocker? 

The solution, whether BlackBoiler or something else, doesn’t need to be human equivalent in order to be better than the status quo.

Putting data science definitions of accuracy to one side (see here), if the AI mark-up is on average 80% client ready isn’t this a win? 

But wait, the lawyers still need to review and finish the final 20%! Won’t that require them to read the NDA to some degree?


Does it matter? 



The net result is a shortened time to done vs. status quo because the tech assisted lawyer’s review is faster (because the system has made most of the mark-up) than the manual process alone.

All other things being equal (including quality and accuracy of final output), why isn’t this a win? 

  • Clients want signed NDAs to exchange information as quickly as possible and minimise opportunity cost. 
  • Law firms usually want to reduce the inevitable write-offs NDA review entails.

What’s not to like if tasks such as these can be significantly reduced in terms of human input, albeit not entirely absolving any human input?

If you already are, or wish to be, involved in legaltech or innovation projects in your current role, or join a legaltech business, be mindful of this lawyer trait for unrelenting perfectionism.  It’s a fantastic attribute for legal work, but a self-sabotaging trait for commercial roles.  In the above example, it’s easy to see how this trait would dismiss the revised process because it isn’t perfect, but as we’ve shown, better doesn’t require perfect.

Don’t let perfection get in the way of good enough! 


Tied to the above is perspective.  Reframing problems is one way to rewire your own lawyer brain.

As noted above, lawyers tend to shoot for perfect.  Instead, shoot for better.

One way to reframe is this: can we redesign the process or product so that the lawyer starts their task at greater than 0% complete?

The good news is that lawyers already do this.


Templates and precedents. 

These mean legal tasks very rarely start from a blank slate. You rarely start from 0% complete in terms of your client work product; instead you stand on the shoulders of giants – the combined knowledge encapsulated in your templates and precedents. 

You can apply this to systems and products.

Does the product or process improvement mean the lawyer starts their task at greater than 0% done, and more precisely, does the net result mean they complete their task faster and with equivalent value or volumes (all other things being equal)?

Adopt this thinking and find ways to demonstrate it when you explain examples to recruiters or during legaltech recruitment processes.

This leads nicely into..

Critical thinking vs. systems thinking

Expertly stated by Jason Barnwell, an attorney at Microsoft:

[s]ome legal professionals struggle to see the patterns in their work because they developed strong critical thinking skills to the exclusion of system thinking skills. They are so adept at distinguishing and advocating for why things that seem the same are different that they are challenged to observe and describe patterns based upon similarity.

Concretely, how does this manifest? For instance, when analysing:

  1. a process (e.g. the lifecycle of an NDA),
  1. a problem (e.g. “we spend too much time making the same NDA mark-ups”) or 
  1. a product (e.g. a tool that automates repetitive NDA mark-ups),

lawyers tend to place disproportionate and usually distracting emphasis on edge cases, finding reasons for why their process, problem or product need is overwhelmingly unique and differentiated from anyone else’s and therefore why a suggested process, problem solution or product couldn’t possibly provide any value.  

If you have ever tried to sell a lawyer or legal team on a product, whether as a vendor or innovation lead, you will have heard objections such as “all of our work is too bespoke for your product” or “your product is great, but it wouldn’t work in this specific [super rare] scenario so it’s a ‘no’ from us”.

For instance, assume that 5% of the time the NDA AI mark-ups are suboptimal enough that it’s easier to start the mark-up again by hand. 

Game over! 

Or is it?

It’s not. 

If in the remaining 95% of cases the NDA AI mark-ups are optimal enough that the lawyer need only spend 5 – 10 minutes proofreading and making a few final tweaks, and that the net time to done per mark-up is reduced on average by 40% then why wouldn’t you adopt the faster process if the quality of output is equivalent to manual efforts alone?

It’s the difference between:

  • working smart – using streamlined processes, automations, and augmentation to reduce manual effort and reduce time to done; and
  • working hard – using bespoke, manual and variable processes without automation or augmentation to reduce manual effort.
Time to done graph

Most lawyers and legal teams work hard, not smart. And this is a shame. The net result of working smart is reduced lawyer time per task, meaning more time to:

  • handle greater volume of NDAs;
  • focus on high value work, e.g. negotiation leverage on the more important contracts;
  • lower cost per task, meaning better margin and opportunities competitive pricing or even premium pricing for faster turnarounds (e.g. how Amazon’s incredible logistics and pricing optimization enables Amazon Prime),

and, heretically to some lawyers, a better work / life balance whilst remaining profitable!

Path dependency 

Path dependence is when the decisions presented to people are dependent on previous decisions or experiences made in the past.  Law inherently has high path dependency.  

Most legal systems are precedential to one degree or another, advancing by incrementalism rather than giant leaps or pivots.  Likewise, a legal career is highly path dependent.  There is a set series of steps to be completed to become a lawyer, and to advance as one.  

At each step, the investment lock-in increases quite quickly given the lockstep nature of legal pay rises, which are based mostly on tenure above all else (even more so at large law firms).  

It becomes easier (and cheaper in terms of decision making and salary considerations) to stick, rather than switch careers. 

Be aware of this when making your decision. A lot of people aren’t aware it is at play in their decision-making. If you are feeling you “can’t give up now”, you may be experiencing the path dependency blocker!


You study hard from GCSE to A-Level and through University (in the UK), competing at every stage to get the best grades and then again to get the best training contract at the best law firm, and if you succeed, you might be rewarded – at a very young age – with a generous salary and prestigious job, in many ways totally out of kilter with the real world. 

Reinforcing that feeling might be the fact you are a first generation University student and lawyer, the investment into your career made by your family and so on.

Don’t try to ignore this feeling. Recognise it, but remember your happiness is ultimately the most important thing, and if your friends and family care about you, they will only want to see you happy and fulfilled.


Being a lawyer is often inextricably linked with a person’s identity, both individually and among their family and friends.  

The law’s priestlike traditions (how many interviewees for legal jobs have been pressed – semi-religiously – about their “commitment to law”?), unique language, systemic importance socially and politically and the fact it is generally closed to outsiders and accessible only via lawyers reinforces this sense of identity. 

If you are a barrister, you will even dress in a strange costume and wig! 

But don’t let yourself conflate what you do with what you are. Although they may seem closely intertwined, it can be liberating to carve a new path and establish a new identity separate from what you do right now, and perhaps separate from what you do next. 

The law of large numbers and opinions of one

In probability and statistics, the law of large numbers states that as a sample size grows, its mean gets closer to the average of the whole population.  This can be invaluable when building products or systems.

DocuSign is a great example.  

It’s optimized to remove the friction of signing contracts in general

That’s why DocuSign is deliberately missing the various features that:

  • Big Law lawyers expect, e.g. escrow abilities resembling the way electronic signature is handled over email and PDF; and 
  • regulators for specific legal products demand, e.g. the England & Wales Land Registry requirements for witnessing and multi-factor authentication or EU centric AES and QES requirements.

DocuSign is purposefully optimised to serve the mean, not the extremes.  


Servicing a greater number of simpler signing scenarios is a massive market vs. dealing with Big Law or regulator specific edge cases that are costly to implement and excrutiating for users to adopt.

Believe it or not, the number and type of signings law firms (especially Big Law) deal with day to day are a much smaller % vs. the number of contracts signed everyday in the B2B and consumer space.

This type of focus is the result of user research and iterative feedback, not the vision of one person’s signing experience. If it had been, it would probably look very different and be less scalable and probably less successful.

Why is this relevant to lawyers considering a career in legaltech? 

It’s very easy to assume that because you are a lawyer you have all the answers to redesign someone else’s product, or build your own better version. 

Your experiences, however valuable, are, at the end of the day, an opinion of one. 

This doesn’t mean they are wrong, nor that they are worthless.  It simply means you won’t and can’t have all the answers (or all the data about a problem), so don’t work on that basis.  Be open minded and demonstrate you have this self-awareness. 

The risk of doing otherwise is either redesigning someone else’s product or creating your own product to solve a need of one, not most.  The latter is a much larger opportunity!

If you work with product management, you might also rub people up the wrong way if you come across as too pushy and conflate singular experience with all experiences.  Yes, great products usually stem from one person’s idea or painpoint, but they become great products by refining initial assumptions through wider user testing and feedback. 

Master of the universe syndrome

Related to the error of conflating singular experience with all experience, lawyers are stereotypically type A overachievers, and unsurprisingly legal businesses self-select for these same traits.  

Top schools and universities, top grades, top internships and top firm etc.

As stated in the excellent book, “What got you here won’t get you there”, success at X doesn’t guarantee success at Y.  

Likewise, ability at X doesn’t beget ability at Y… and it certainly doesn’t equate to experience in Y.

We say this because lawyers, rightly or wrongly, get a bad wrap for being sometimes overconfident and condescending when appraising the breadth of their abilities and experiences.  

Just because you are a great lawyer, doesn’t mean you are instantly a world-beating product manager or salesperson or marketing guru etc.  Often the opposite is true. You’ll have much to learn, so be humble. 

For instance, if you want to become a product manager for a legaltech, you will be competing with experienced product managers expert in frameworks, their own experiences building products and so on.  You will need to skill up.  

Simply being a customer won’t be enough. It’s a start, but that’s it.

Likewise, if you do join a legaltech business, or work on legaltech projects within your current organisation, you need to be respectful of other people’s skills and expertise.  

If a career product manager politely suggests something, don’t shut them down with something like: “as a lawyer with 15 years experience you can’t tell me I don’t know how this feature is to be built”.

You might have 15 years experience.  But building a product is about finding common threads across multiple experiences, not optimizing for a single and often biassed experience of a problem.  

Also, how sure are you that the way you work (and perhaps have worked for many years) is the best way? How do you know? What evidence can you provide to support that conclusion?

In summary: don’t conflate singular experience, or prior successes in other domains, with inevitable excellence at other things.  You aren’t the master of the universe.  You also don’t want to be perceived as someone who thinks like that.  Stay humble and…

Be curious 

Related to the above, is asking questions.  Lawyers are trained as expert advisors in a narrow domain (law), and typically specialise in even narrower niches, e.g. English law copyright. People typically ask you the questions and you take great pride in answering them and knowing things other people cannot know (because law is a very closed source system).

But how often do you ask questions you genuinely don’t know the answer to?

Maybe not as much as you’d think.  

When working in legaltech, particularly in a sales or product role, the best people ask a LOT of questions. In part, because there is often a lot of information that is unknown at the outset, and unknowable, without asking the right questions. 

Sales people do it to build rapport and qualify leads.  They make money by cultivating only the buyers who are most likely to have a need to buy. 

How do they know who that is?

By asking questions to tease out their needs, whether they have a budget, whether the individual they are working with has the chequebook or decision making power (if not, then they will ask who that is and how to get to them and get them on side) etc.  

Product people ask questions to unpick what people do, how they do it, why they do it, when they do it, where they do it and with whom they do it.  Without this it’s impossible to understand the people, process, problems and priorities worth solving as means to finding product-market fit.

This is uncomfortable if it isn’t part of your everyday routine.  Litigators are perhaps far better at this, but are usually fitting questions to things they already know and simply need someone to surface in response to a barbed question.  

In product and sales conversations, you often know roughly what you want to find out, but not necessarily any inkling of what the answers might be, or where those will lead.

It’s hard to ask open questions where you genuinely have no idea what the answer is or whether the question is dumb.  It’s like being back at school – that confidence to stick your hand up and make yourself vulnerable by saying “I don’t understand, can you please explain to me how…”.  

An easy way to get over this is… doing it.  

Ask more open ended questions of clients and colleagues. The best lawyers are excellent at asking questions and even better listeners, but they are few and far between.  

These are the lawyers that ask questions early and often and thereby avoid last minute client led firedrills, e.g. knowing at the start of a process what things are important and why can help avoid costly negotiations or litigations based on assumptions about what is really driving the client. These lawyers are usually much more fun to work with or for.

Don’t be afraid to not know the answer. 


Strap in. Brace for a contrarian view.

There is a limited amount of ambiguity in the majority of modern legal practice.

Heresy! Law is about finding and weaponizing ambiguity.  The ambiguity between negotiating positions, the application of case law or legislation to novel situations, and so on.  

But is it? 

Most modern legal work is less and less like this. This is especially true of transactional work.

Sure, there are and will continue to be exciting negotiations and academic jousting about whether black is white or vice versa, and whether one shade of grey is different from the next and other conversations about the interactions of minutiae beyond even the comprehension of a CERN quantum physicist expert in subatomic nuance.

To be precise, modern legal is unambiguous at both the task level and the career level.  At the task or process level, many legal processes follow checklists or templates and are largely driven by precedential concerns, i.e. this is the way we always do it.

Reporting lines are simple and clear.  Progression is lockstep: you reach X years PQE and you earn Y.  In X+1 years you earn Y+1 etc. As we’ve said above, this is comforting.  

Outside of law there are definitely tasks or processes disambiguated by checklists and so on.  But day to day, decision making at the organizational and individual level, will be more ambiguous. 

How do we grow our market share of X by Y? Where do we hire and expand into next? Do we build this feature X instead of Y? Etc.

Of course, these types of decisions are possible in law, but only if you are a very senior law firm leader.  In other careers, these decisions are more plentiful and distributed.  

Progression will be less lockstep outside of law as we’ve said, and much more driven by opportunity, merit and of course politics.  Payrises are earnt, not given.  

Weigh up how you will handle this heightened level of everyday ambiguity, both your ability to work in ambiguous set-ups and decision making spaces, but also the ambiguity of where a non-legal career will take you and the major absence of lockstep mechanics for pay and seniority.


Lawyers need to be good influencers, whether to win a litigation, negotiation points, steer clients to good decisions or progress and manage a legal business.  

However, there is a potential blindspot.    

A lot of influencing and persuasion skills in legal are applied lawyer to lawyer.  

When negotiating as a lawyer you are often dealing with another lawyer. When litigating, you are ultimately trying to influence another lawyer (a judge).  Even in a jury trial, influencing the judge is a not insignificant component, e.g. if you want something thrown out.

We’d argue that influencing lawyers is a different, but by no means redundant skillset.  

Again, like a lot of the points we’ve stressed, the best lawyers get this.  They have good general purpose people skills, able to listen, empathise, anticipate, and use suggestion to influence decisions.  

A specific example of getting this wrong is passive aggressive behaviour.  This can serve quite well in law given its typically adversarial set-up, whether litigating or negotiating. In real life, outside of law, being passive aggressive and anal about everything to put your point across falls on deaf ears for the most part.

Being a smart ass gets you nowhere. 

Just because you’re right, doesn’t mean people will follow you. In legaltech roles, particularly commercial ones, you need to develop an ability to influence different personas by understanding them, anticipating their needs and how these fit together.  Making others feel dumb won’t get you anywhere.  

You need to make them feel the decision was theirs, not yours.

For instance, at a legaltech company you may be in charge of a project, or have an idea for a new product feature.  To make it successful you might have to influence:

  • The product manager, who will have done extensive user discovery research and a roadmap of features at different stages of development.  Why should they listen to you? Be mindful your feature – if it’s the right idea – might undo their hard work (rightly or wrongly) or add to their workload. How can you minimise upset?
  • The sales director, who will have perfected a patter and pitch deck based on the existing product. How does this feature help them sell more and make more commission? How much will it alter their tried and tested pitch and value proposition? How can you help them?
  • The CFO, who will want to know how much will this cost vs. return on investment to test and develop. How can you present a solid business case?
  • The CEO, who will want to know how this will align with company strategy and the general ability of the business to get this done and why it should be done over other options? How can you align your idea to broader strategy?

And so on. You get the idea.  

In legal this type of influencing day-to-day is less common.  In-house roles are a useful exception.  In the right in-house role, particularly at a smaller business, you may well get involved in this type of activity.  If so, you’ll be well equipped!

If you want to learn these skills in detail, we cannot recommend enough reading Influence by Robert Cialdini and his follow-up Pre-suasion.  An oldie, but a goodie, is also How to Win Friends and Influence People by Dale Carnegie.  It’s a classic for a reason.  For a slightly more legal centric, but much more widely applicable take, Never Split the Difference by former FBI hostage negotiator Chris Voss is excellent, particularly with regard to how reframing questions can be a fantastic way of helping other people solve your problems for you whilst getting their buy-in.  It’s focused on negotiation, but is very easy and practical to apply to situations where you need to talk people around to your way of thinking.

Pay (and finances)

Lawyers are generally paid above the national average, which is currently £31,461 in the UK ($43,748.09).  

This is all the more so at Big Law firms, especially US law firms where a newly qualified lawyer can expect to earn £143,000 before bonus, benefits and pension upon qualification, after only 2 years of practical experience.  

This figure quickly progresses lockstep in larger and larger quantities, alongside bonuses. At that level, it is hard to find other career options at such a young and inexperienced age that offer the same remuneration opportunities, with the possible exception of certain investment banking and private equity roles (which themselves can be hard to sidestep into from law, at least with regard to non-legal roles).

Legaltech, legal innovation and legal ops roles aren’t like this, especially not junior roles for career changers.  

In fact, few other industries are.  

A C-Level or senior director in a large company is unlikely to earn much more than £150,000 – £250,000 before options and bonuses.  And that will usually be the reward for 10+ years in that industry or organisation, not their starting salary 2 years into the job straight out of university.

The point is this: be realistic about what you can hope to earn outside of being a lawyer.  

Your skills, whilst valuable within law, are less valuable (but certainly not worthless) outside lawyering. This may very likely require you to readjust your personal finances, and plan to take a hit in salary for some months, or possibly years, whilst you reinvent yourself.

There’s no two ways about it: if you work in law, particularly commercial law or at a Big Law firm, you need to accept you might earn less doing something else, at least initially. 

Seriously appraise your finances and whether you can stomach a paycut, and the less certain progression of roles outside of legal ones.

What will other people think?

Law can be very status driven, especially in Big Law. The majority of lawyers went to the best schools, best universities, got the best grades, and generally like to spend their earnings on expensive things like living in a nice area and sending kids to the best school etc.  Your circle of peers will reinforce this with their own behaviour.  

Changing careers is a good opportunity to reassess this behaviour:

  • Do you need all this status and stuff? 
  • Is it a substitute for a personality, hobbies and the things you used to enjoy as a kid or teenager? 
  • How much time do you spend with your partner, family and friends? 
  • How often do you get to enjoy your holidays and weekends, as opposed to spending them glued to your inbox?

And honestly, try to care less about what other people have and might think.  

Their choices aren’t your choices.  

Choose your own happiness, don’t let that be defined by others.

Can I still become a partner?

Possibly. There are a few notable examples of individuals who were lawyers, moved into or built legaltech or similar roles and functions for themselves and their organisation, later to be made up to partner.

But first, if becoming a partner is important to you – make sure you understand why? Is it status? Is it the ability to influence law firm decision making? Is it remuneration? Is it all of these things or something else?  

If being a law firm partner is what you really want to do, then for the time being – apart from a high profile minority who have been lawyers and moved into innovation and then partnership –  it’s probably more likely you will become a partner via the traditional route.

Examples of those who have been made up to partner from innovation or legaltech roles include:

Dr Catriona Wolfenden, Partner & Innovation Manager – Weightmans

Catriona is Weightmans’ Innovation Manager, responsible for the development, delivery and management of the firm’s innovation and technology projects, as well as their broader innovation programme and is a former litigator.

Kerry Westland, Partner – Head of Innovation and Legal Technology at Addleshaw Goddard

Kerry is a lawyer who began her legal career as a paralegal, later building out several teams at Addleshaw Goddard driving the use of technology and developing solutions to deliver a wide range of legal work across the firm, including setting up and managing the Innovation and Legal Technology Team who focus solely on the application of existing and new technologies.

Lucy Shurwood, Partner – Pinsent Masons

Lucy was one of the first women in legaltech to make partner. Shurwood was previously a banking lawyer but now specialises in technology and innovation across the financial services sector at Pinsent Masons. She was promoted to the partnership in 2016.

Shruti Ajitsaria, Partner – Head of Fuse at Allen & Overy 

Shruti is a derivatives lawyer by background.  Shruti pitched the concept for Fuse, Allen & Overy’s flagship tech legaltech, fintech and regtech incubator, to the senior leadership team back in 2017 and created a business plan while on maternity leave with her third child. 

Launched in Q3 2017, Fuse has gone from strength to strength, elevating the firm’s innovation profile and providing a fantastic space for start-ups and for A&O’s lawyers and clients to influence and understand exciting emerging tech companies.  

In 2019, Shruti’s efforts saw her made up to partner.

What if I change my mind? Can I go back to law?

Yes.  Don’t believe us? We know several examples.  Here’s two different career paths that led back to law: 

Routes back into law from legaltech

The first individual was a lawyer, then switched to various technical and commercial roles at technology start-ups and scale-ups before returning to their original area of practice at a law firm.

The second individual was a lawyer, pivoted to commercial roles at a start-up and then a scale-up before taking on an innovation role at a law firm.

In each case, they found different paths back into a large law firm, albeit into different legal roles: one practising and one non-practising.


Those you have – transferable skills

A major challenge when career changing away from law into anything is demonstrating transferable skills relevant to your new career direction. 

So what skills do lawyers have that are transferable to legaltech, legal ops and legal innovation roles? 

Project Management

Whether you are a litigator or transactional lawyer, you will be used to managing complex projects with multiple internal and external stakeholders, deadlines, dependencies and so on. You will often have to design and document the project, e.g. managing things like:

  • CP / closing checklists 
  • Issues trackers
  • Q&A trackers
  • Risk logs
  • Deadlines and reminders

Yes, you may not have industry standard project management qualifications (e.g. PRINCE2 etc), but you will have successfully managed complex projects. You may have even used appropriate technology solutions to streamline these processes and enhance collaboration.

If you go into a legaltech, legal ops or legal innovation role you will very likely be responsible for project managing various activities, e.g. managing the selection, testing, implementation and on-going monitoring of new software procured for a legal organisation. 

You might even end up programme managing, i.e. managing an interlocking suite of projects aligned to a macro aim, e.g. improving technology adoption across a large legal organization by X% in Y time frame.

Managing stakeholders

Tied to the above, as a lawyer a lot of your job is managing demanding stakeholders: clients, opposing counsel, your senior internal stakeholders and similar. You will hopefully have developed good negotiation skills and an ability to pre-empt issues where possible by thinking ahead and where issues arise, being able to resolve these amicably. Be sure to have demonstrable examples at the ready for interviews.

Managing a team

Depending on your seniority, you may manage a team. This could be managing trainees as a junior associate, or a senior associate managing a team of associates and trainees. It might also be managing a team of paralegals or other specialists within your organisation, e.g. an eDiscovery team. 

Unsurprisingly, a lot of legaltech, legal ops and legal innovation roles require team management (much like most jobs!). 

In many cases you will be delivering projects involving teamwork and leadership, e.g. deploying software to a client, rolling out new software around a law firm and so on. 

Think about examples where you have done this, the challenges and how you overcame them.

Problem solving

Lawyers spend a lot of time assimilating large volumes of information, spanning facts about a client’s need and the relevant legal requirements and how they apply to the former. 

Oftentimes lawyers need to do this very quickly and accurately to solve client problems to tight deadlines.  These abilities are hugely valuable in commercial roles, e.g. you might need to understand and solve why users aren’t adopting X or Y tech, or figure out why your pitch isn’t converting to sales and so on. 

Organisation and prioritisation

Lawyers are typically highly organised and good at prioritising competing workloads. This skill is immensely valuable outside of legal. You will have countless examples of managing competing workloads.  For instance, if you land a sales role you will need to be super organised and good at prioritising competing interests regarding sales prospects and customers and ensuring these are tended to at the right time for maximum success, and selectively limiting the time you spend on unlikely or overly demanding prospects.

Excellent written / oral communication

Lawyers work with words. As a lawyer you need to write clearly and concisely. Conveying complexity and its application to fact specific scenarios comes naturally. 

In legaltech, legal ops and legal innovation roles you will often need to communicate ideas, whether it’s a new process, a product, or a business case and so on. Your written and oral communication skills will be a massive help in this regard. 

However, where lawyers fall down is visual communication. 

Try to improve your ability to communicate information visually, especially if preparing pitch decks or marketing materials where visual elements will outweigh reams and reams of text.

For a fantastic interview on this very subject, together with various books and other resources to become a better visual communicator, check out the Advocacy Podcast’s interview with Justin Kahn, a litigator who uses learnings from visual storytelling, neuroscience and stage magic to be a more effective litigator.

Attention to detail 

Lawyers have great attention to detail. It’s drilled into you from day one. Your attention to  detail will set you apart. Be mindful, it may seem excessive to others if you constantly nitpick inconsequential details – so use this superpower wisely.  If a change needs to be made for good reasons, e.g. a typo, then make it. If a change is stylistic and immaterial – don’t make it.  

Attention to detail can be really useful when testing software, pitches and demos – you’ll likely spot things others do not, and this can be very valuable as a means to enhance those activities, but don’t be an insufferable pedant. Learn to communicate criticism constructively.

Analytical thinking

Lawyers are great analytical thinkers. In legaltech, legal ops and innovation roles you can use this to your advantage. Your analytical skills will help you analyse problems and spot dependencies and risks others may not. 

Now the trick is – as noted above regarding critical vs. systems thinking – not to get too bogged down in issue spotting; always be mindful of proportionality. If you spot risks, how significant are they in the grand scheme of things? Are they material? How likely are they to transpire? Make sure you can demonstrate this awareness of proportionality.

Those you lack – skills to fill

Many of the commercial skills relevant to legaltech, legal ops and legal innovation roles aren’t ones lawyers necessarily develop. 

Uh oh. 

Not so fast, we’ve got you covered. We’ve created two guides outlining:

  • the 21 skills common to most legaltech, legal innovation and legal ops roles, available here; and
  • how to find routes into these roles, as well as practical ways to build technical expertise, ranging from coding to deeper understanding of legaltech and general business technology as it applies to legal – see here for that guide.

The salary question

The good news is that legaltech, legal ops and innovation roles can (but don’t always) pay quite a lot, especially relative to work / life balance. 

For a full rundown of different roles, their activities, skills, progression opportunities, remuneration structures (including salary ranges) and work / life balance, please see our in depth guide here

To whet your appetite, here’s an infographic describing a typical law firm innovation role:

Innovation Lead Infographic

⚡Don’t forget the rest of the guide ⚡
This article forms part 6 of our 8 part series on careers in legaltech, legal ops and innovation. Please check out the other articles and career profiles for more inspiration and guidance!

The post Leaving the Law for Legaltech, Legal Ops or Legal Innovation appeared first on lawtomated.