Thinking to become

Reflecting on my top 40 lessons learned while operating

Experience is hard to compress but time alone put to good use affords the opportunity to reflect. I recently considered lessons learned while operating in Tech.

Many were learned in the company of others wiser and more experienced. Some are deeply personal.

Look into their minds, at what the wise do and what they don’t. — IV. 38

These are my top 40:

1. It’s often better to be non-consensus right than consensus right¹.

2. Products should force choices² not comparisons.

3. One of the most important questions to ask your customers is how disappointed they would be without your product³.

4. Storytelling⁴ is under-learned but a most powerful skill in business.

5. Living in the future is the most effective—but difficult—way to generate ideas that create the most change.

6. Willingness to pay⁵ is chronically understudied/under-optimized in enterprises— existing price anchors makes this hard.

7. The most important question to align on is what problem you’re solving for and what you’re not.

8. Deprecating products and features should be done much more often—by extension subtraction should be valued more closely to addition.

9. Corollary: there are two types of systems— deprecated and those that will be deprecated⁶.

10. Much software doesn’t do what it says on the tin and most companies don’t actually use much of the software they buy.

11. Counterintuitively: product usage in enterprise software is not always the largest driver of retention.

12. Focusing myopically on process leads to the death of outcomes.

13. Product-market-fit is second fiddle to product-market annealing⁷.

14. Code is often not nearly as important as it’s architecture, the infrastructure and skill to run it.

15. Functional incentives lead to solving for local maxima despite many business opportunities being inherently cross functional.

16. Corollary 1: More MBOs for organizations that have them should be wholly shared.

17. Corollary 2: More GMs of Business Units could yield better results despite the model largely falling out of favor

18. Planning product development cycles — not objectives — beyond a half is planning to fail.

19. We still haven’t figured out the most effective way to incentivize non-sales performance.

20. We don’t consider incentives in aggregate nearly enough.

21. OKRs should not be used for individuals.

22. Engagement surveys fail most companies in their intended purpose because of limited / non-existent follow up loops.

23. Recruiting shouldn’t start when you need a role and curiosity, enthusiasm and attitude often trump experience.

24. Many companies benchmark and copy organizational structures and funding levels of others to their detriment.

25. Organizational structures being reset too often leads to “ripple through” chaos.

26. More ICs should shadow leaders⁸ and vice versa.

27. Leaders should consistently share what is on their mind more frequently— writing is one of the highest leverage ways to do this.

28. A company’s ability to innovate is inversely proportional to its size: zone to win.

29. Repositioning incumbent strengths as weaknesses is potent⁹.

30. The essential questions sales must answer: what is it, why is it different and why now.

31. Corollary: Product teams need to understand what inflection leads to what insight leads to what mobilized idea.

32. Corollary 2: Are we building the right thing, are we building it right and can we sustain building also remain standout questions.

33. Companies would be better off openly diagnosing themselves more often and sharing this in an unvarnished way.

34. Corollary: Authentic transparency about your faults and where you come up short is key to building customer trust¹⁰.

35. The founder’s story isn’t nearly as important as framing the hero’s journey for your audience that will result from their involvement in the thing.

36. Luck vs. skill is chronically under-appreciated— grinding through high variance activities helps root it out.

37. “Successful failures” of calculated risks that don’t pay off should be celebrated more often.

38. Nearly all data is subjective¹¹ despite our assumptions about “objectivity”. This doesn’t make it bad.

39. There is no better way to rally a group than to end with positive affirmations.

40. Happiness is positive cash flow¹².

1. Another way to think about being differentiated and good.

2. Arnold’s quote in Terminator 2 captures the essence: “Come with me if you want to live”

3. This is far more powerful than asking them how satisfied they are (e.g. CSAT, NPS).

4. A good story always has a character and a problem. A great story sees a plot develop alongside that character’s internal struggle or “third rail” which drives the plot to the story’s conclusion.

5. This is fundamental to value based pricing and price based costing.

6. This was first impressed on me during my time at Google and stuck.

7. A deeper understanding can be gained here.

8. Here’s an open sourced guide on how to do it.

9. A the key to counter positioning. See here for an overview of Helmer’s 7 powers.

10. Caponi’s book on the topic is a real gem.

11. Consider product telemetry you might use in your organization: what unit was chosen to be logged, at what interval, on what scale? All of this is subjective.

12. In Carl Icahn’s documentary he has a pillow with this phrase on it. I agree. You can buy yours here like I did.