If you have been asked to do something and are unclear about the way forward, ask – don’t assume. In my view the role of any boss is to set out clearly what is expected and when. If you are in doubt then either he or she has not done so in enough detail for you or you have not listened attentively enough. ASK! Admitting early on to not listening properly is better than delivering the wrong thing. Give yourself and them time to get the task done the way they need it. Don’t present a work product that does not meet their requirements at the eleventh hour.
In my experience the greater the lack of common understanding between your boss and you the greater the scope for catastrophe. If this is a new team or boss, do you properly understand what the expectations are? If you do not have a clear picture of that, are there other team members whose opinions you can rely on if you don’t want to go back to your boss? If not how should you go back?
Really early in the assignment I would email back to your boss your understanding of the task and how you will go about it, or better still speak to him or her in as much detail as you think appropriate. They may be so busy that they do not immediately reply (if by email), carry on with the task as you outlined in the meantime. DON NOT WAIT!
When you have a first draft of your work product, send it to your boss for their approval, asking any points of clarification, including possible things from your first email if that has not been responded to. You may be criticised by your boss for over-communicating but better that than not meeting their expectations, and remember you are only doing this because you feel some things were not clear. Hopefully your boss will recognise their part in any confusion.
Set yourself a deadline for the task well in advance of when your boss needs completion. That way he or she will have a chance to read it and you can make any required changes. Keep them appraised of where you are in the task. Communicate, communicate, communicate.
Working remotely will place greater burdens on achieving this progress. Being in the same office may allow you informally to speak to your boss or other colleagues. If working remotely, telephone calls may work better than emails. Everyone’s inbox these days is a nightmare, don’t rely on getting an immediate reply.
As you spend longer in the team and know your boss better you will learn and understand more of what is expected and needed. You will be able to act more and more independently, complete things faster, but remember, if in doubt communicate. Send early drafts, confirm understanding and deliver well before the deadline.