The best lessons I’ve learned from 2 years of executive coaching in a 5 minute read

business Leadership Personal Development

I’ve been privileged to have been engaged with executive coaching for over 2 years now. It’s been absolutely transformative. I’ve taken meticulous notes in the last 2 years to really distill the key takeaways. I’ve distilled the highest leverage takeaways.

Some of these are frustratingly simple and easy to skim past — that actually might be a sign there the ones you might be neglecting. I can’t tell you how many times I scrolled past articles describing the impact of sleep on productivity until I actually did the work to stop abusing caffeine and actually sleep and saw incredible results in my live. 

here we go:

Breathe — Take time to be healthy.

If you aren’t healthy you can’t be effective. Sleep. Diet. Exercise. Mental Health. These things are real and have quantitative impact on your business results. If you can’t get this one down you’ll see significantly less impact regardless of how much you can move the other topics in this outline. I was at best scoring B- in every one of these categories, the last 2 years have been a huge transformation for my business and my own self.

Run your life. Get your personal “operating model” clean.

Connected to taking time to be healthy but deeper. This is about making sure you are in the driver’s seat of your life, effective in the basics and you aren’t letting the company run you.

Start with your calendar. Your time and attention is your only irreplaceable asset. If you aren’t happy with your calendar fix it. Say no more. Make sure your default week has some margin and you are really working on what matters. Move on to your Workspace, effective task management, good meeting hygiene, time for thinking and breathing.

You have to let go of your ego, but not your ambition or conviction.

As a leader you need to be very ready to let go of your own ego and be very wrong, make mistakes, have bad ideas. It’s really essential to always be the biggest person in the room, focused on results over being right. However, it can be easy to over-correct and let your ambition or conviction be silenced. There’s a difference between arrogance and confidence you have to accept that sometimes it’s a blurry line. Focus on getting results over being right. Focus on letting the best ideas win. But also don’t loose your confidence or convictions to ask questions until you are satisfied.

Know your numbers.

You need to find the key metrics that matter, build a system to track it, measure them consistently. Find the most essential 7 numbers (plus or minus 2) that give you clarity if you are making progress or not. Don’t overcomplicate it. It’s more important that you are looking at the numbers than it is you go standing up fancy business intelligence software. You should know your numbers, what inputs drive them and which are interdependent better than any of your reports.

Don’t take the Monkey. (Don’t do other people’s work for them).

3 out of 3 of my executive coaches have referred back to the HBR classic “Who’s Got the Monkey?” If you haven’t read it. Read it. Then make sure you are honest about not doing other people’s work. It’s very easy to fall into patterns of just making all the decisions and solving all the problems. But the more you step back and truly let people do their jobs the more effective the organization can be.

Ask questions until you are satisfied.

If you feel like a number or a process or an answer isn’t right. Ask questions until you are satisfied. Not out of combativeness or bullying the other person into compliance but out of genuine curiosity to understand more. The more understanding and context you can gain the more empathy and nuanced understanding you have as a leader.

Give others space. Talk less.

I think most of us need improvement here. There needs to be dead air in more of our meetings. Space for others. Reading this book on Active Listening was mind blowing realizing how bad of a job I was doing. It can be exhausting at times, but letting people finish their sentences and taking the extra few minutes to actually understand others perspectives has truly paid dividends for me. Without dead air in meetings you are just reinforcing the loudest people in the room and the more it’s rewarded the more it drowns any other voice, which often times is the more thoughtful and well reasoned voice in the room.

Set and keep boundaries — don’t permit bad behavior.

There’s a big difference between giving someone autonomy and space and letting them run unmanaged. It’s important to literally define the boundaries of company values, authority, role, budgets and enforce them. If people are breaking your boundaries you need to keep them accountable to those expectations.

Example: We have a company Value of “We act with Kindness and Respect.” I had a former manager on our team who was consistently acting with over-aggressive behavior, cursing, publicly shaming people. I didn’t and you can’t let bad behavior persist. This turns into a negative spiral very quickly if not dealt with.

Self Awareness through objective assessment is essential.

I didn’t realize how much I needed to talk less, give others space until I got back a 360 assessment from my team. I had tons of blindspots on my own self-awareness. Both negative and positive. There were many areas I had deep insecurities around where my team’s perception of me were the opposite, and other areas I thought were strong where I was really missing the mark. This kind of objective clarity has gone a long way to make me a better person. Find a way to get 360 assessments from your peers and team and take the time to understand the results and help that guide your self-improvement moving forward.

“The opposite of doing too much is not doing nothing“

In the desire to give space and autonomy it’s easy to over-correct and get too hands off or uninvolved. I’ve found this concept to be really empowering for myself to remember to not overcorrect to be too hands off as a leader.

Share the burden: “People would be happy to fail with you”

In running this startup I found myself constantly wanting to shelter the team from the responsibility or stress of the stakes of the work we are doing. The risk and possibility of failure. Some of this is good but it’s easy to overcorrect here. In most cases people join a startup knowing failure is a possibility, and they actually would way rather be involved. In a way “Happy to fail with you” it’s incredibly empowering to have a team that understand the risks and shares the burdens of the stakes of the day to day work.

“The business is running me” is not an option.

You have to run your business. You have to make the hard calls, let go where needed, until you get to a point that you are in the drivers seat. “The business is running me” is an absolute recipe for complete disaster and burnout.

“Slow is smooth and smooth is fast”

There’s a big difference between moving quickly with intention and downright thrash. Especially if you have a team (even a small team). You need to make sure you have clarity of thought to have things operating smoothly. You’ll end up accomplishing more with clarity on shared goals and initiatives. A little goes a long way with good systems to keep everything running. Don’t neglect planning, you should have really clear priorities for the next 60 days and be re-looking at them with rigor every few weeks.

The key to changing your own behavior is slowing down.

Unfortunately your own personal behavior can be a significantly limiting factor in your business. So understanding how to not only identify your shortcomings but actually change your behavior for the better is really important. I’ve found that one of the most powerful things you can do is to slow down. When you are looking back thinking about a behavior that you didn’t like think about the trigger, what thought did it trigger and what action did you take? If the earlier in that chain you can disrupt the behavior the more likely you will see change.

Be mindful of False Collaboration.

if you actually know what you want, then the collaboration feels off. “Were going to go into a strategy session and dance around it for 3 hours”. I’ve made this mistake with my team. It sucks for them. If you really know what you want have the nerve to just say it outright.

Bring others along

If you really want collaborators who understand your thinking, motivations and goals you need to take the time to “bring others along”. This means writing out your final thinking clearly and then justifying it with the right context, allowing others to ask questions to clarify. Take the time to bring others along it’s worth it.

The best kind of leader is a coach.

You like me probably talk way too much. If you lead others if you talk a lot then in reality you are likely doing their job. If you are providing every prompt and solution and specific direction then you aren’t really growing beyond yourself. Working to talk less has been hard but really fruitful. A great book on this is the Coaching Habit.

Understand your Saboteurs

Saboteurs are the voices in your head, the ones that create negatively and stress in the way you handle work and life. They sabotage your potential for both happiness and performance. Foe example: I have tendencies of a hyper-achiever, restless controller. Being aware of these negative tenancies (saboteurs) and learning about them has helped me avoid sabotaging myself. Learn more about saboteurs and take the assessment from positive intelligence.

“Never Complain, Never Explain”

This phrase has had a radical impact in my work and marriage. It feels good in the moment to complain about this or that, or when pushed on an action you made to try to make excuses and justifications. In the end it doesn’t accomplish anything. Many times this can alienate those around you. Especially when it comes to explanations or justifications, it often times puts you into a worse light that the potential negative assumption the other person had about you. I could have avoided so much frustration if I was just willing to accept that I can’t change the way others perceive me.

In closing — I’d challenge you to revise the simplest or most trivial of these principles that you may have previously overlooked. I’ve found that getting these simple basics right have actually had the biggest impact in my life: Sleep, Diet, Exercise. Start here if you haven’t pushed these.

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