Tips for productive advisor-entrepreneur conversations – argue intelligently and criticise kindly

A couple of days ago I wrote that startup advice should focus on the ‘why’ and the ‘what’. Today I’m going to write more about how to do that.

A common pattern is for advisors to pattern match with something they’ve seen before and come quickly to a piece of advice that feels right to them. That’s great and hugely valuable when it chimes with the entrepreneurs intuition, but when it doesn’t the dialogue can deteriorate to brute force persuasion and sullen acceptance or passive resistance.

Focusing on ‘why’ the advice is appropriate is a big help, as I wrote about last time, but getting into the right frame of mind emotionally and attitudinally is also a big deal:

  • Think of areas of disagreement as opportunities to learn. Don’t avoid difficult conversations for fear of getting advice you don’t wan’t to implement or having your advice ignored.
  • Make it your goal to find the best solution, not to win the debate.
  • Listen first and then debate second. If you can summarise what you’ve heard in words the other side would use, list your points of agreement, and note anything you’ve learned before you go to say your piece.

Not every conversation can end productively, but the hit rate can be increased, and with that comes learning, better insight and ultimately business success.

This post was inspired by a summary of philosopher Daniel Dennett’s thinking about arguing intelligently and criticising kindly.