Mentoring Entrepreneurs And Developers

Screen Shot 2016-06-16 at 12.51.01 PMIn the past six years I had the pleasure to mentor hundreds of entrepreneurs and developers. For some, as an investor and for others as an external advisor or a domain expert. These days I’m doing it mostly as my day job which is really fun!

Here are some of the lessons learned over time.

If you are an entrepreneur who is asking:
“Why do I need someone to mentor me?”
Well, there are many good reasons, but check the graph below.


I know it’s far from being a perfect study, but it does tell a story.
So how to be a better mentor? Read on.

Before the meeting

Learn on the startup you are about to meet.
Make it clear to yourself:

  1. What is the current state? Try to see where they are standing right now. What are the main challenges?
    Product market fit? monetization? growth?
  2. Do they have a certain weakness? competitors? strengths?
  3. What others (e.g. investors, mentors) are saying about them?
    If you can, go the extra mile and talk with few of them.
    You will learn a lot from their insights. Especially on the strengths and weaknesses.

During the meeting

The rule here is to listen for at least half of the time.Turn it into discussion, not a lecture. I know you will feel that you have a ton of things to say, and that is great, but wait and let them talk. Not easy, but very helpful. Other points I found useful:

  1. Do a quick round of personal presentations. No slides – just a quick overview on each one.
    • Be the first (lead by example) and keep it short and on the point. Think of it as a tool to teach others about you and your added value.
    • Ask each person to take 1-2 minutes and to follow you. It’s always good to learn who is sitting with you. Plus, it will melt the ice quicker.
  2. Take next five minutes to set up expectations for the meeting.
    • Ask for their wishes from the meeting.
    • Try to make it as clear as possible what you will do and more importantly, what you will not do.
    • Give someone the role to take notes and share them with everyone after the meeting.
    • You will be surprise how effective it can be to have a summary of the meeting and its action items. A summary that all parties can go back and refresh their memory.
  3. In many cases, it will be better to focus on challenges and not to dive into specific solution. It’s ok to set a new meeting in order to focus on a specific problem.
  4. You should challenge their ‘knows’ and unknowns. Conviction that is being led only by passion is an awful combination.
  5. Try to teach them how to think and leverage your knowledge/experience in order to find the answers later on their own. Try to give them examples from your real world experience. In most cases, this is a better way to drive your points home.
  6. Encourage them to talk and more importantly to disagree with you. This is a powerful tool! Try to create an atmosphere that will encourage them do it.
  7. Ask a lot of questions (the 5 whys)  in order to do #4 – Sometimes you think you know what they mean, but you missing it. More questions will push them to elaborate and experiment. This will be very helpful.


After the meeting

  1. The last 5-10 minutes of the meeting should be devoted to a summary and a wrap-up.
    • Make sure the person that took the notes had the chance to capture everything important.
    • Look at what she wrote as action items – This is critical in order to keep everyone on the same page.
    • Follow up on their progress vis a vis the action items you all agreed on. In cases where you wish to get involved, try to set a monthly (or weekly) updates about their progress.
  2. Ask for their feedback. After all, you should debrief yourself in order to improve, no?


Misc Stuff


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