3 Essential Habits for Advising Entrepreneurs


Why are some people truly amazing mentors while others -- even with years of experience -- fail to contribute? I believe that anyone can be a great mentor, so read on for three ways you can become the mentor that entrepreneurs dream of.

1. Provide Questions, Not Answers

A lazy mentor gives their mentee answers. A truly great one gives their mentee questions.

As an entrepreneur myself, I remember struggling with a number of difficult decisions, all of which felt tougher because I couldn't pull myself out of the weeds in order to see the big picture. If all you do as a mentor is help an entrepreneur see the (possible) answer, you are robbing her of exploring the journey to get there herself.

In sessions where I am now advising entrepreneurs, whenever I feel the urge to give an answer, I instead force myself to ask a question to encourage the entrepreneur to delve deeper. It's an approach championed by the community benefit organization 'Creating the Future.' Not sure which questions to ask? Here are a few favorites:

  • What's the highest potential outcome of this situation?
  • What will that make possible?
  • How will you know if this endeavor is successful?
  • What will it take to get there?
  • What resources will be required?
  • Imagine you didn't have any constraints -- what would you do then?
  • What's the hardest part about this?
  • What's holding you back from doing this now?
  • And if these questions don't feel right, then use my favorite question of all: why? Ask why enough times and you'll find yourself at the core, and from there the answers will start getting much clearer.

I've found a good rule of thumb to be that the entrepreneur should be speaking 90% of the time. If you find yourself speaking more than 10%, you may be providing too many answers and not enough probing questions.

And finally, embrace silence -- those perceived awkward pauses in-between thoughts are where the magic happens.

2. You're Always Right. And You're Always Wrong

Remember that any advice that you give based on your own experience is simultaneously completely correct, and completely incorrect. It's correct in that you lived it -- you made it, you lived it, and you dealt with its consequences. This outcome-driven advice is also incorrect because your experience was just that -- yours. While it may seem analogous to an entrepreneur's decision today, she is making a decision in a completely different context -- a different time, a different place, a different culture, with different people, technologies and other variables.

This shouldn't stop you from sharing your stories. On the contrary, you should absolutely share your valuable experience. But instead of focusing on the outcome of your decision, emphasize your decision-making process -- the variables you weighed, the values you applied, and the approach that you took.

When telling your story about how you selected Windows 95 as the best operating system for your company, the outcome of your past decision is already dated and can't possibly help a developer choosing between Android and iOS. But the approach you took -- weighing market size vs. risk, stability vs. opportunity, how you engaged key stakeholders, and how you made sense of disparate pieces of information -- is what will be useful to an entrepreneur. Not the end result. Sharing your approach and thought process is what will empower an entrepreneur to make his own decisions, with the benefit of your insights. And don't be surprised if they don't choose Windows 95 themselves.

3. Be a Connector

In Adam Grant's brilliant book 'Give and Take,' he talks about the power of the '5 minute favor.' One extremely valuable favor is connecting two people who would benefit from knowing one another.

Beyond asking questions and sharing stories, connecting an entrepreneur to someone else you know can often be the most useful. You can't possibly support an entrepreneur with everything, but chances are someone in your network can.

The best mentors are ones who, instead of guarding their contacts, are constantly asking themselves 'who do I know who could also help?' Challenge yourself to make one connection and introduction per meeting -- whether that is a talented project manager you know who is looking for work, a possible partner, or another potential advisor to support a new challenge.


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