How does Shailesh juggle keeping the big picture together with appreciating the smaller things?
He puts a framework in place from the planning stage itself, specifically when he's going from strategy to execution.
When people are strategizing, they choose one path and when they are walking the path, they completely forget the strategy itself. They continue down the path and as they run into the roadblocks, they spend and waste so much time in getting the roadblocks off, and then after a reasonable amount of time, they think of going back or see if there is another way to go around.
Many teams end up spending a lot of time on this. To avoid this from happening, keep a framework in mind and do periodic check-ins. Even if you've missed it, the very simple rule of thumb that you can keep for yourself when you're fighting a problem is to ask if the problem is even worth fighting for.
Another piece of advice from Shailesh is to acknowledge the fact that there are people who are smarter than you and have done what you are trying to do. So, collaborate. Ask questions. Don't be shy. There is no stupid question. Go around and find it out.
There are a lot of good people who have gone through what you are going through, and they'll be more than happy to provide some ideas and suggestions. Go ask them.