30 years, 30 lessons in Leadership

I love leading teams. I love the idea of figuring out how you motivate and inspire a group of people to achieve big audacious goals. I love helping to create a culture where people feel empowered and supported and inspired to do their work. I love creating an environment where people can think creatively and critically and feel safe expressing their ideas and putting them into action. I love getting to know my teams, what makes each individual tick and helping them develop, grow and achieve their dreams. Leading is tough, it’s challenging, it can be lonely and thankless at times, but it’s also incredibly rewarding and fulfilling when done right.

I’ve been lucky enough to lead teams for a long time now. I can trace my leadership beginnings to roles in student government and athletics back in Middle School and High School. My training and experience continued to a variety of leadership opportunities at the Naval Academy and then numerous management positions over the course of 11+ years in the Navy. Over the past 15 years since leaving the Navy, I’ve had the privilege of leading a variety of teams and groups in the Tech Industry.

I have learned that leadership is as much an art as it is a science. As such, it’s something you never really stop learning about. Every experience has taught me new lessons and new ideas and new techniques.

I’ve tried to capture the most important lessons I’ve learned and have written them down in a Google doc. I usually add a new lesson every year. And often I share this doc with other managers and individual contributors who are learning to lead. I figured I’d finally try to share these lessons more broadly than my own personal network by publishing on Medium. The complete list is shown below. Believe it or not, it’s actually condensed from its original form, but it’s still long. Hopefully, this is something that people can reference from time to time and come back to when they have a free moment.

I would love to hear your thoughts and comments and certainly would enjoy hearing about leadership lessons you have learned via your own experiences that I haven’t captured here in this list.

  1. Integrity is the fundamental building block of leadership. Without integrity, you simply cannot lead. Do the right thing. Always.
  2. Your leadership philosophy should be clear, concise and easy to communicate. Here’s mine in two basic steps: define the mission, determine the path and set the objectives for and with your team. Then take care of your people and they’ll take care of the rest.
  3. Care …. deeply about your people. To lead your team, you need the trust of your team. To earn that trust you must show you care. So, to lead effectively, you must care. You can’t fake caring. They’ll know it. If they know you don’t care, they won’t trust you. If they don’t trust you, you can’t inspire them and if you can’t inspire, you cannot lead them. So if you don’t care, you can’t lead.
  4. Lead by example. On the surface, this seems simple……always always always lead by example! Dig a little deeper and you’ll find some complexity. Part of leading effectively is having the respect of your team. It’s very hard to gain or maintain that respect if you don’t set the right example and lead from the front across 3 important areas: technical competency, effort, & behavior. On behavior — remember that as a leader you are always on duty! Everything you do, everything you say on the job or off, is setting a leadership example for your people.
  5. To build a high performing team, you must be maniacal about: Hiring — who you hire, how you hire. Training — new hire training, ongoing training, skills training, leadership training. Learning — creating a learning culture where feedback and improvement are desired and expected. This is an incredibly important subject and I wrote a series of Medium articles about it a couple of years ago.
  6. High performing teams also place tremendous value and emphasis on: Leadership, Transparency, Accountability, and Balance. Leadership Development — hiring, training, developing, and promoting managers who know how to lead through inspiration, motivation, and empathy. Transparent Communication — clear, honest, transparent communication as well as a culture where everyone is expected to think creatively and critically and can safely express their opinions. Accountability — devising plans, setting goals and holding everyone accountable on a regular basis. Balance — keeping things in perspective and making sure everyone can balance work and life. Achieving big goals is always difficult. It’s easy to get lost in the intensity of the work. But it’s important that people can sustain their performance over the long run and keep work and life balanced. As a leader — you need to ensure you create a culture that allows for balance.
  7. Sweat more in peace, bleed less in war. Practice, prepare and train harder than the real deal. Training hard makes any “real-life” engagement easier. Practice, train, and debrief. Then do it again. And remember that to create a high performing team you need to create a learning organization.
  8. Repetition won’t spoil the prayer when communicating with your team. You need to keep everyone going in the same direction. The entire team needs to know and understand what they’re doing and why they’re doing it. Defining the mission, the goals, the objectives, and the path will help you keep everyone moving together. But once you define those points, you need to repeatedly communicate them all to the team over and over and over again to make sure it’s fully understood, remembered and kept front of mind. You can’t do it just once a year. Do it once a month!
  9. Your people need an individual approach. You can’t treat them all the same. You can’t expect the same thing of every person. Figure out what each person’s strengths and weaknesses are. Figure out what makes them tick and adjust your style and approach to meet their needs as well as your expectations when it comes to evaluating them.
  10. Listen more than you speak. Good leaders often use their ears more than their mouth. Active listening means that you really pay attention to what’s being said before you form your response. Listen to what people are saying (and not saying). Focus on the message, on the intent and the perspective. This will not only give you critical information to help you make decisions, but it will also help you build relationships (through trust)
  11. Laugh. As much as possible as often as possible. Life is short and if you can’t have fun, you’re probably doing something wrong. Your teams should be having FUN and laughter should be a regular part of that.
  12. Praise in public as often as possible, but upbraid in private…. always.
  13. Leadership takes ENERGY. As a leader, you are always ON. You have to set the pace and fuel the team with your energy and your mood. You have to learn to compartmentalize your bad days and put your game face on every time you walk through the door. Your team will follow your lead and the op-tempo you set. And remember, that you still have to take care of your people no matter how you feel about things. Eat last, sleep last, wake up first. Always put your people and your team first.
  14. Don’t talk crap about your boss(es) or the organization, you’ll erode everyone’s confidence in you as well as them.
  15. You have to walk the deck to know the state of the ship. You can’t possibly understand how things are going if you don’t get out there and literally spend time w/ your people. You’re probably incredibly busy and in meetings all day. Take charge of your calendar and schedule time to sit with your team. Every day, every other day. More than once a week!
  16. Say good morning and goodnight to your team every day. They’ll notice and it’ll mean a lot to the team. It’s all of the little things that add up to greatness.
  17. Show you care by investing in your people and their development. Remember, you need to earn their trust to lead them and caring is a great start. So, make career development a priority. Help them define their path and follow it. Better yet, help them define their dreams and inspire them to have the courage to GO FOR IT.
  18. Debate is a good thing! Your team should feel comfortable debating, disagreeing and even arguing with you from time to time. To be an effective leader you need accurate information, honest opinions and clear thoughts and feedback from your team. To get that from your people, you need an open environment where people feel safe disagreeing w/ your opinions. You are the boss, so don’t assume that you are doing things properly or making the right decisions just because people agree with you. They may just be afraid to speak their minds. One incredibly important measure of the culture of my teams is how easily my direct reports are willing to disagree and debate with me.
  19. Pull don’t push! Lead people with inspiration and motivation. Avoid having to push and direct.
  20. Set a high bar, challenge people to meet it, help them when they need it, but don’t lower it. People don’t want a push-over for a boss. They want to perform for someone that inspires them to reach further, faster and higher than they thought they could.
  21. Remember that a small problem to you may seem like a big problem to your team. Know and understand the issues your team faces and give them proper weight and attention. Don’t assume that they understand your perspective or have the context you have. A common mistake that managers make is to dismiss a problem that they perceive is small, when it’s actually a big deal to their team
  22. You’ve gotta have a plan! Carve out time for you and your team to create a simple and actionable plan for achieving your goals. And then track your progress by checking-in regularly. If you don’t have a plan, you and your team will wander aimlessly, reacting to whatever pops up. Sounds simple and it is. But people don’t always do it completely and correctly.
  23. You rarely hear about the good stuff. As a dedicated and driven leader, you’re going to pour your heart, soul and everything you’ve got into your role. If you’re a good leader, you’re going to be open to and will receive lots of feedback. But the vast majority of that feedback will be “constructive” i.e. stuff you could be doing better. Don’t get discouraged by this. It’s the nature of the role. You just won’t hear about all the things that are going well. You’ll only hear about the stuff that folks think can be better. Leadership is lonely, so get used to it. Rank has its privileges and its responsibilities!
  24. Power doesn’t actually give you the ability to influence. It’s your ability to influence that truly gives you the power to get things done.
  25. If your org chart doesn’t make sense, then most likely….. neither does your org. And don’t optimize your org for one or two people and de-optimize it for everyone else. Set things up in a clear way that optimizes for performance and growth of the entire organization.
  26. Make sure your people have as much context as you have whenever possible. You may understand an issue because you have more information and context. But if they don’t have all of the same background and context, then your team won’t understand the problem, the issue or your proposed solutions.
  27. When facing challenges, problems, and compromises, there are times when making incremental progress is important. Moving in the right direction keeps people motivated and bought in. However, there are other times, when accepting a half step forward will make it harder to ultimately solve the problem down the road because stakeholders may not want to re-engage. The trick as a leader is to learn when to accept incremental progress and when to push for the complete solution.
  28. Learn to lead with data, not just instinct. You need to be good at gathering the right sets of data and using it to make informed decisions. Leaders can’t just operate on instinct. Conversely, don’t be paralyzed by collecting and analyzing data. It’s important to make decisions and often to make them quickly. Gather as much information and data as possible, analyze it, and make the call based on the information you have. Remember that an imperfect plan executed with energy and conviction TODAY is better than a perfect plan executed too LATE.
  29. You don’t always win by winning. Sometimes you win by losing. Learn to negotiate, influence and compromise. It’s not always about winning and losing anyway, most of the time, the best outcome is when everyone gets what they need.
  30. Integrity is the fundamental building block of leadership. Without integrity, you simply cannot lead. Do the right thing. Always. (yes this is a repeat of lesson #1 ;-)

Father, Son & Husband. Aviation, Car, & sports enthusiast. Tweep, Googler, Aviator & Sailor.