Lesson Learned: Build a culture where it is more important to win than to be right.

Alan Gilbert
2 min readMar 28, 2023

This blog post is part of a series of leadership lessons that I have learned from 40 years in tech. This is the last post focusing on building a great company. Next week I will start to focus on lessons learned in becoming a great leader.

One of the best cultural attributes I’ve experienced in great companies is when people are more interested in winning than being right. What I mean by this is that everyone in the company is comfortable, secure, and empowered enough such that they can put the greater good of the company, and fulfilling their mission, ahead of their own ego. Getting to this state is not easy because it runs counter to human nature. People are naturally protective of their own ideas and want to see them flourish. They gain a sense of self-worth and accomplishment if their ideas are adopted, and they feel regret when their ideas are rejected.

The key to winning is to create a culture, promulgated by the leaders, that encourages and rewards people to:

  • See beyond their localized (personal or team) concerns and biases, and instead internalize and focus on the big picture (company and mission)
  • Put forth bold ideas and suggestions and be unafraid to let them go if they don’t catch on
  • Express concerns, but then be mature enough to listen to and understand counterpoints
  • Focus on the harder and riskier work of advocating solutions instead of taking the easier and safer, but less productive route, of just pointing out problems with others’ ideas
  • See the forest for the trees and let go of and live with a problem, even though they are “right” in identifying the problem, in favor of a more impactful greater good that requires everyone to accept compromises

I saw this in action a few years back, in an engineering team meeting, with a co-founder and CEO. He was advocating for a reorganization that would benefit the business and our customers, but presented a challenge for the engineers, because the lines of code responsibility would not be as clear. (Multiple teams would be in the same code base.) One of the engineering managers correctly pointed out this problem, but could not seem to get past it to consider the larger benefit. After about 15 minutes of frustrating conversation, the CEO looked at him and said “It’s not your job to be right… It’s your job for us to win.” That left an impression on me that ultimately inspired this blog post. The key takeaway is being “right” and winning are not always the same thing. Sometimes you have to be “wrong” on a smaller thing, and find a way to live with it, to get a bigger win.