I think it is important to have a bias for action. Like anything else, this is something you can make a habit of. Moving forward allows you to make progress. I don’t know about you, but I’ve frozen up in the past not knowing what the right path was for me. Moving forward, even the smallest possible step, helped break that stasis.

One habit I like is to ask for no, not yes. Note that this is based on my experience at small companies (< 200 employees) where a lot of my experience has been. I’m not sure how it’d work in a big company, non-profit, or government.

When you have something you want to do and that you feel is in scope for your position, but you want a bit of reassurance or to let the boss know what you are up to, it’s common to reach out and ask them for permission. Don’t. Don’t ask for a yes. Instead, offer a chance to say no, but with a deadline.

Let’s see how this works.

Suppose I want to set up a new GitHub action that I feel will really improve the quality of our software. This isn’t whimsy, I’ve done some research and tested it locally. I may have even asked a former colleague how they used this GitHub action.

But I’m not quite sure. I want to let my boss know that I’ll be modifying the repository.

I could say “hey, boss, can we install action X? It’ll help with the XYZ problems we’ve been having.”

If you have a busy boss (and most people do), this is going to require a bit of work on their part to say “yes”.

They’ll want to review the XYZ problem, think about how X will solve it and maybe do some thinking or prioritization about how this fits in with other work. Or maybe they’ll want you to share what you know. It may fall off their plate. You will probably have to remind them a few times to get around to saying “yes”. It might be a more pressing issue for you

Now, let’s take the alternative approach.”Hey, boss, I am going to install action X, which should solve the XYZ problems we’ve been having. Will take care of this on Monday unless I hear differently from you.”

Do you see the change in tone?

You are saying (without being explicit) that you “got it” and are going to handle this issue. The boss can still weigh in if they want to, but they don’t have to. If they forget about it or other issues pop up, you still proceed. This lets you keep moving forward and solving problems while keeping the boss informed and allowing them to add their two cents if it is important enough.

You can also use this approach with a group of people.

By the way, the deadline is critical too. Which would you respond to more quickly, if it was Jan 15, all other things being equal and assuming a response was needed?

• “I’m going to do task X.”
• “I’m going to do task X on Jan 17.”
• “I’m going to do task X on Feb 15.”

I would respond to the second one, which has a deadline in the near future. I think that is the way most folks work.

Again, pursue this approach for problems you feel are in the scope of your role but that you want to inform the boss about. It’s great when you want to offer a chance for feedback, but you are confident enough in the course of action that you don’t need feedback.