Mentors 15/18: Be Optimistic

Last month I took two weeks completely off the grid. As part of it, I spent some time working on my next book, Give First. As part of that, I finished up the sections on Deconstructing the Techstars Mentor Manifesto. While I wrote a draft of this post over a month ago, It felt appropriate to publish this, and the next few Mentor Manifesto posts, after a wave of Techstars Demo Days that just happened.

#15 is “Be Optimistic.” It sounds simple, but it can be incredibly difficult.

As a mentor, your job is not to solve a founder’s problem. It’s to help. It’s to listen. It’s to provide feedback and data from your experience.

You can do this from many different perspectives. However, given the stress on a founder, it’s best to do this from an optimistic frame of reference.

Here’s an example of the challenge. You are a mentor to Maria, who is struggling with her co-founder Stephan, who has become unpredictable, inconsistent, and subdued. Maria feels alone, both on a day to day basis as well as in dealing with Stephan (there are only two founders in this case.)

As a mentor, you had a difficult co-founder experience in your last company. While the dynamics were different, it ended poorly with your co-founder leaving the company. While you haven’t spoken since you split up, your business was successful and acquired for a life-changing sum of money for each of you.

Your co-founder struggle is one that didn’t work out between you and your co-founder but was ultimately financially rewarding for each of you. You carry around this conflict in your head. On the one hand, you are pessimistic about where things between Maria and Stephan will end up. On the other, you know that even if their relationship fails, the company can still be a success.

You also learned a lot from your experience with your co-founder. Each of you made mistakes in approaching things during your conflict period. This hurt both of you and negatively impacted the company for a while. Your struggle with each other was public, and it ruined several other relationships with people who felt like they needed to choose sides.

Being optimistic in this context is difficult. But it can be done. Start from a positive frame of reference. Talk openly with Maria about the things that you and your co-founder did wrong as you tried to address your conflict. Be clear about how things could have turned out differently. Be introspective in your discussion and speak from experience, instead of giving advice. Remember to reinforce that even though your relationship with your co-founder ended up failing, your business was successful.

Let Maria have her experience as she tries to resolve things with Stephan. Try to be a positive influence in the mix to encourage her to do the work involved, even if they end up parting ways.


Also published on Medium.

  • Great point to remember, good advice delivered with a negative vibe is not going to help specially someone whose under pressure. Just sharing the past experience as u mention would be great, co-founder issues are tough!

  • Bikerwithnoname

    This is well said – thank you for posting this. I’m going to be on a panel soon about mentoring and will mention this article – all with proper attribution of course!

  • Daniel Kraft

    A good leader will figure things out and a positive spirit accelerates to find that path. That is what a mentor is for: bring you onto the right path.

  • panterosa,

    “Speak from experience, instead of giving advice” is perfect advice, but probably hard to follow. A great example when talking about yourself is the answer.