Leadership Lessons Learned from 40 Years in Tech

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:

• Study your competition and take them seriously
• Every important result should have one, and only one, directly responsible individual, especially when it comes to product
• Don’t let stable become stale
• Ruthlessly prioritize and get used to saying “no” or “wait” to important things, so that you can say “yes” to the most important things
• Ready, aim, fire — in that order
• Venture capital is frequently a trap and incentivizes bad habits
• Attention to detail and high standards matter
• Don’t rush core values
• Don’t be tempted by the Dark Side of motivation — fear and blame-avoidance
• Getting meetings right is enormously important
• Build a culture where it is more important to win than to be right

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

• Speak and write with purpose, always
• Guide, but don’t force
• Be an exceptional listener
• Make the right way the easy way (by managing meta-work in your organization)
• Make and execute high-level, strategic decisions that make it easier for everyone else in your organization to win
• Cultivate leadership throughout your organization as a key component of every career track, even for non-managers
• Provide unique perspective and challenge assumptions and thinking, even if it runs counter to the the consensus of everyone else in the room
• Understand that people don’t like surprises, unless they result in bigger paychecks
• Take the time to provide balanced feedback to people and avoid the temptation to simply complain about things that aren’t going well
• Make sure to spend time and energy evolving and growing yourself as your organization grows

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.