Valuable tips on how to how to handle conversations


Mentoring has three main activities: presentations, product demos, and conversations. I’ve written a lot about presentations and a post on and a few posts about demos, but given that conversations – talking and listening – make up the bulk of a mentoring session. There are plenty of takeaways for both mentors and founders from the Wall Street Journal article by Celeste Headlee The Right Way to Have Difficult Conversations. These tips apply to the many conversations a founder will be part of not only with mentors but with investors, with job candidates, with partners, and of course, with co-founders and colleagues.

Headlee describes the value of conversation as the power of conversation between people who are willing to listen to each other and learn.

Here are the crucial insights and tips excepted from her article:

  • Resist the impulse to constantly decide whether you agree with what someone else is saying. The purpose of listening is to understand, not to determine whether someone else is right or wrong, an ally or an opponent.
  • Beware of bias. We all have them. When we approve of some salient quality of another person, we are more likely to judge them positively in other respects. The opposite is true as well.
  • Show respect at all times.
  • Empathize. Try to remember that everyone is trying to accomplish something that they think will improve their lives and the lives of the people they love.
  • Stick it out. Grit and persistence are of course key elements to any founder’s success but persistence pays off in conversations as well.
  • Talking through tough issues can be awkward and painful, but try to avoid getting frustrated and walking away.
  • Silence is preferable to avoiding confrontation. If you have nothing to say, just listen. Silence is a powerful tool in any conversation. Avoid the tendency to just jump into a conversation for the sake of participating, or worse yet, hearing the sound of your own voice.
  • If you say something you shouldn’t, apologize immediately. Acknowledge that you said something hurtful or wrong and make no excuses. Then you can put the mistake behind you and move forward.
  • End the conversation in a friendly and gracious way. That sets the groundwork and tone for future conversations.

This article is based on the book We Need to Talk How to Have Conversations That Matter by Ms. Headlee.  It will be published September 19th. I’ve got it on my reading list, you may want to add it to yours.


Author: Mentorphile

Mentor, coach, and advisor to entrepreneurs, small businesses, and non-profit organizations. General manager with significant experience in both for-profit and non-profit organizations. Focus on media and information. On founding team of four venture-backed companies. Currently Chairman of Popsleuth, Inc., maker of the Endorfyn app for keeping fans updated on new stuff from their favorite artists.

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