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.


  • Another great post Nic. There are serious shortcomings in the way that startup advice is doled out. The challenge is that delivering advice is actually an art, and it takes a long time to learn how to do it well and not confuse the person on the receiving end. This is why parachuting random Mentors in can be dangerous (but that’s another subject). A basic coach-approach works very well:

    G – what’s the Goal of the conversation?
    R – what’s the Reality of the current situation?
    O – what are the Founders current Options (this is where an advisor brings personal experience)?
    W – what Will the Founder do?

    Leaving Founders empowered with an ability to make their own decisions and judgement is what builds future CEOs. Simply telling people what you think they should do based on your own experiences unfortunately does not. As you point out, via Phin Barnes from FirstRound “I’ve seen this before + instinct = decision” is not helpful! I’m no psychologist but I know from ten year’s consulting experience that if the client feels that they have come to their own conclusions, then they’ll feel far more positive about executing than if they’ve just been told what to do.

    Finally, there’s a big difference between ‘giving advice’ and ‘giving advice effectively’. The Trusted Advisor is the book I recommend to anyone wanting to build their own skills in this space: There’s a whole chunk of the book devoted to the discipline.

  • I like that GROW framework. Thank you.

  • Good points … yes this is not about the advisor living through the entrepreneur but about creating options that the entrepreneur can and wants to execute, the best advisor should have no axe to grind.

  • YES! Flipping that round, if you have an axe to grind you should think twice about being an advisor, or maybe better, qualify your advice as coming from a biased position.

  • Pingback: Advice for Startup Advisors - Richard Hughes-Jones()