Leadership Lessons Learned from 40 Years in Tech

Alan Gilbert
3 min readDec 30, 2022


I’ve been fortunate to have an amazing 40-year career (so far!) in tech, going back to my first co-op job in 1983. I’ve worked for big companies and small companies, and been part of the most successful tech exit in Ohio history. This summer, I rode my bicycle across the United States and had a lot of time to think. One of the topics I pondered was all of the great leaders I have worked with, and for, in my career and what I learned from them about building great organizations and companies. I learned both what you should do and what you should not do. When I got home, I did a big brain dump on my white board. Now I’ve decided to organize and share what I’ve learned with a series of blog posts. I’ve found that the lessons fall into two general categories:

  • Lessons learned in building a great company
  • Lessons learned in becoming a great leader

My hope is that, in sharing this knowledge, I will help current or aspiring leaders build better organizations that are both great places to work and more successful businesses. This is by no means a comprehensive guide on how to build a great company or be a great leader. Rather, it is what I consider to be the most interesting lessons that I have been fortunate enough to learn. And of course, there is a strong bias towards my experience, which is that of a technical leader in technical companies. So without further ado…

Here are my favorite lessons learned from great leaders on building great companies:

Here are my favorite lessons learned on being a great leader:

In the coming months, I will write blog posts on each of these, expanding on the lessons learned, how I lived them in my career, and how they can help you, your organization, and your company.