Lesson Learned: Ready, aim, fire. In that order.

Alan Gilbert
3 min readFeb 6


This blog post is part of a series of leadership lessons that I have learned from 40 years in tech.

Ready, aim, fire. In that order. I know this sounds contrary to a lot of conventional startup wisdom and the tropes we all like to glorify, like moving fast and breaking things. It also, to some degree, can be at odds with the valued leadership practice of making decisions and acting with incomplete information, with a bias towards action, and failing fast and learning. But there are two sides to that coin.

Every great leader I’ve worked with was driven, impatient, and aggressive. And those attributes, which I happen to share, were essential to their success. The lesson I learned is to not let those attributes dominate to the point where you thrash and wear out your employees, and lose their trust and confidence. Sometimes the desire to act, or react, in the moment is overpowering. You have an irresistible drive to immediately act on the insight, or jump on the new opportunity, or make the new problem that recently appeared just as quickly go away. But I learned that when you let those instincts dominate too much, bad things happen, like:

  • Having to walk back plans once you realize the new thing contradicts with other existing plans or strategy.
  • Causing your team to become confused on priorities. Is this new thing the top priority or the thing that was super important yesterday?
  • Disengaged, exasperated employees, who end up leaving, or worse, staying and dragging down the culture.
  • Loss of credibility, where people don’t act because you have a track record of changing your mind or coming in with a different plan tomorrow.
Photo by The New York Public Library on Unsplash

One piece of feedback I received from a wise and trusted mentor, when my impetuous nature caused a combination of the above side-effects, was “you are too much fire, ready, aim.” It was hard to hear and I wanted to dismiss the feedback as “well, that’s my super power and the downside is worth the benefits.” But it was really great advice. I worked (not always successfully, to this day) to recognize when I was in that mode, slow down, take a step back, and consider the broader picture. Sometimes I would draft an email or write out my plan and then just set it aside, waiting until the next morning to see if it still seemed like the right answer. Or at least take a walk or otherwise create some space to gain perspective before I forged ahead. Or run ideas by trusted colleagues to get feedback before I went broad with them. I found a few — up, down, and across — who I trusted to give me candid feedback with no strings attached. It was amazing to me how much creating a little space improved my perspective and I’d like to think it helped me make better decisions and avoid bad side-effects.



Alan Gilbert

I build teams that build things.