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What have you been thinking, but not saying?

Posted on August 1, 2023August 22, 2025 by admin

What have you been thinking, but not saying?

I love this question when I coach cofounders or leadership teams, as it gets at the heart of any issues in the relationship. It takes effort to withhold your thoughts, so if you are feeling the tension of not saying something, that is energy that could be used for something more productive once it is addressed.

It’s scary, though. The reason we don’t feel comfortable bringing up certain topics is a complex melange of our previous experiences with the topic (when we’ve been told this isn’t a big deal in the past) and with the other person (feeling that we will get shut down), so it feels easier to withhold. But the cost of that tension can build up cumulative resentment until it damages the relationship.

Say the thing you don’t think you can say. Have the difficult conversation. Avoiding the topic will only raise the stakes and make it harder in the future.

Even in the worst case scenario, where your concerns are dismissed, you will have learned something about the other person, and you can decide whether you still want to be in relationship with somebody that dismisses your concerns.

Note that everything I wrote above also applies to personal relationships. I feel so much better when I share something with my wife, rather than withhold it for fear of a fight.

What is your experience with such #difficultconversations?

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