When to Be Strategic and When to Just Execute
A big challenge of leadership is trading off strategic and tactical thinking. When do you keep your head down and execute (getting things done) and when do you pop up and look around (am I getting the right things done)?
First, acknowledge it’s a rhythm. You have to switch back and forth between the two and not try to do both at the same time.
Second, give yourself permission to carve out time in the future and table all strategic conversations until then.
For example, say you’re looking for product-market fit in six to 10 verticals. Pick one - say quick-service restaurants - and give yourself a couple weeks to evaluate it. Assume quick-service restaurants are the right vertical and you just need to find a way to do it. Talk to customers like crazy. Even if you have doubts, even if people tell you your idea won’t work, keep going until you reach your predetermined stopping point. Then at that point reevaluate. It gives you the confidence to go run at it without freaking out that you're wrong and second-guessing yourself just because it's hard.
It will take awhile to find the rhythm that’s right for you (and it's different per project, role, etc). As part of your evaluation, ask yourself- did I run too long? (I already had this feeling after one week) or did I run too short? (I didn’t get enough data).