Thread by @ryan_caldbeck

1/ Persistence is such a double edged sword. I’ve always thought it’s the most important trait an entrepreneur can have. But another key one is knowing when to not keep pushing.

-when should you not keep pushing your point in a meeting?

2/ -when should you not be persistent with current strategy and pivot the co?
-when should you not be push hard on a new hire that is on the fence? Is “convincing them” to join always/ever a good thing?

3/ -when should you stop trying to help an employee meet the performance bar, and just recognize they need to move on?
-when should the CEO say that a board relationship just isn’t working and move to end it?
-when does the current product not really need that "one more feature"

4/ I've struggled with all of these questions. My persistence, a trait I take a lot of pride in, has likely hurt me in these situations. But it's really hard to know when I should try and flip that switch off.

5/ In the most vulnerable conversations with other CEOs I hear consistent themes about this topic.

Knowing when to not keep pushing is something I, and many other CEOs, struggle with daily on issues big & small.