Mentors ask questions to help founders find answers

8 questions

I learned how to use the Socratic method in management from Wayne Oler, then president of Addison-Wesley Publishing Company, where I was General Manager of the Educational Software Division. Wayne rarely made a statement. Even if you were clearly in the wrong he wouldn’t say so. For example, I remember being in one meeting where an executive used the term “budget” when he clearly mean “forecast.” Instead of correcting him Wayne sort of cocked his head and said, “Do you mean “budget” or do you mean “forecast”? The executive quickly corrected himself and the meeting moved on. Coming from a very hypercritical family this was a real lesson for me. Don’t point out people’s errors. Help them discover them. And maybe they aren’t even errors! By asking questions you may find out you were operating under the wrong assumption and the other person was in fact correct. And mentoring is about being right, it’s about helping the entrepreneur get to the answer that’s right for them and their venture.

And mentoring isn’t about right or wrong, it’s about learning. And the best way to learn is to ask questions. I try to model that behavior with my mentees. I was pleased to see the articleThe Best Mentors Ask These 8 Questions – an essential part of being a good mentor is asking the right questions by Gwen Moran in Fast Company.  These questions come from Lisa Z. Fain, CEO of The Center for Mentoring Excellence, a mentoring consultancy and coaching organization. “For mentors, the most important thing, really, is to ask questions, to be this guide on the side, rather than the sage on the stage,” she says.  Here are eight questions good mentors ask according to her. Per usual I’ll list the question but add my own comments.


This question is ok, and perhaps it’s intentionally vague, but I prefer a question more like, “How will you measure success?” or “How will you know when you are successful?” Measurement of success is important to founders in at least three different ways: in their own company, in strategic alliances, and with customers. Teaching them to understand what success means and how you measure it by asking this question as a mentor helps founders learn this technique to use themselves, including how they will mentor their staff.


I always tell founders that we can’t help them unless we know where trying to get to. I use the old saying, “If you don’t know where you are going, any road will take you there.” This is a very important question for ventures with more than one founder. The outcomes, whether it’s going public, getting acquired, or creating a lifestyle business must be congruent amongst the founders or conflicts will arise from the get-go. It is surprising how little thought early stage founders give to this. See my post Product or Company? for a bit more on this subject. Whether you want to build an app and sell it ASAP or try to build a company like IBM that lasts for 100 years, doesn’t matter. And it doesn’t matter if you decide to change that goal. What matters is complete alignment of the organization behind the vision and the goal. That’s job one for a CEO.


Business plans used to ask for 5-year projections but I doubt that many do today. Things are just moving too fast. Five years ago a tiny fraction of entrepreneurs even knew what a blockchain was. Now it’s hard to find a startup that doesn’t include blockchain in their product plans. So asking what you want to be different in five years may stimulate the founder to think about their aspirations, but perhaps it’s the very pragmatic stance of MIT’s Venture Mentoring Service where I’ve volunteered for going on 9 years, but I find three years out to be a more reasonable time frame.


I have a somewhat different way of asking this question, “What’s keeping you up at night?” Either way it is important for mentors to get good answers to this question so that we can use the very limited time we have – a typical meeting is 90 minutes and we might have one or two meetings a month at most – to prioritize the areas where we try to provide advice, feedback, and guidance.


I’ve never heard this question asked! I think it would steal time away from asking the above question. But I just might try it to see what kinds of answers it elicits. As you’ll see if you read the original article, this question seems more appropriate for mentoring someone inside a corporation rather than a founder of a startup.


I like to go beyond this question to getting the founder to list the pros and cons of each option. So for example, if they are having difficulty gaining customers fast enough, one option might be to lower the price. This might have the pros of getting more customers to buy the product but the con of reducing cash flow and profitability. One can get more sophisticated still in asking the mentee to work through the repercussions of each option by developing decision trees. See my postHow do you make decisions?


This one’s right out of a Rogerian therapists playbook! And that’s a playbook worth stealing from. Mentors aren’t therapists, but we do need empathy with our founders and there are other similarities. When there’s more than one founder in the mentoring session this question can be addressed to a different founder to see how their perspectives may differ.


This is a good way to get to know someone and also a way to suggest books or articles that we might want to recommend to a founder. I haven’t used this one, but again, it’s a question I might try if I can fit it into our time slot.

Questions tend to get people to open up, to reflect, to think. Statements can often make people feel defensive talked down or come across as too didactic and to close down. On the other hand sometimes a statement is the shortest route to providing good advice. For example, a founder starting a service that provides health care options to the elderly should definitely look in to liability insurance. You don’t need to have a conversation or discussion on something like that. But of course you can always phrase a statement as a question, “Have you looked into acquiring liability insurance yet?”

And here’s one question an experienced mentor always asks during the session, “Are we bring helpful?” Mentors need feedback too!

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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