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33 Lessons About Scaling Companies - Learnings From Coaching CEOs

  • May 26
  • 2 min read

  1. $5M problems > $50 problems. Spend your time wisely.

  2. Common sense is not that common. 

  3. Your leadership team has ‘lead’ in their name for a reason. 

  4. No strategy, no OKRs. No amount of OKRs can make up for the lack of strategy. 

  5. Often co-founders fall out of love, and that’s ok. Divorce gracefully. 

  6. Money talks, bullsh*t walks. The rest is smoke & mirrors. 

  7. Not every CEO likes the job post seriesA, and that is ok. Don’t force it. 

  8. Just because your roommate, friend, relative, fill in the blank was there at the beginning, it doesn’t mean they are the right fit for the job. 

  9. The quality of leadership depends on the quality of the questions asked.

  10. Impostor syndrome is normal and more common than you think. 

  11. Find your ‘zone of genius’ and shrink your ‘zone of competence’. 

  12. Let people fail. And watch what they do about it. 

  13. Strategy is not a pretty powerpoint with big statements and fancy visuals. 

  14. Just because you have had a few sales, it doesn’t mean you have PMF.

  15. Giving tough feedback and having hard conversations are skills you can learn. 

  16. Fear and anger are the worst advisors. 

  17. Experience > Advice and opinions 

  18. Just because you understand your strategy, it doesn’t mean that the rest of the team does too. Most likely they don’t. 

  19. How your company operates is the direct reflection of how you operate.

  20. Aim for an A-team, not a team full of A-players. 

  21. OKRs is a framework to facilitate leadership, not to replace it. 

  22. Systematic solutions > Ad hoc putting off fires 

  23. What you struggle with in your personal relationships, you will struggle with in your professional ones. 

  24. Don’t give out ‘Chief’ titles too early. Use ‘Head of’ instead. 

  25. The company offsite doesn’t replace your personal vacation. You need both.

  26. Even when you start to scale, still hire slow & fire fast. Especially execs. 

  27. ‘Radical candor’ doesn’t mean you can be rude in the name of ‘being candid’.

  28. Get a coach or a therapist (or both) way before you think you need one. 

  29. You can’t outsource ‘culture’ to the Head of People. 

  30. Being a founder and being a CEO are two entirely different things. 

  31. Just because Amazon, Spotify, Google, etc. have done it one way, it doesn’t mean you should too. 

  32. That said, some things are called ‘best practice’ for a reason. Don’t be arrogant. 

  33. It’s not cute to live in chaos anymore, like in the early days. 

 
 
 

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