The Best Mentor/Advisor Question I’ve Ever Been Asked

Building great mentor relationships requires intention on both sides. Here's the best question a mentee has ever asked.
Sue Heilbronner
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December 13, 2017
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Mentoring
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Today I met with Devon Tivona, CEO of travel startup Pana. I’ve known Devon for almost four years. We met during his senior year of college at the University of Colorado. I was an ad hoc mentor for his company during the school’s New Venture Challenge, a competition that Devon and Pana ultimately won. You can listen to an intimate conversation between Devon and me on the Real Leaders Podcast if you want more background.

Devon Tivona, Founder & CEO of Pana

I’ve been working with the Pana team since we met in a range of capacities, including mentor, executive coach, informal mediator, and friend. I’m an investor personally, and the MergeLane Fund also is a two-time investor. This relationship has been one of the most enjoyable of my career.

I met with Devon today to touch base on this thinking as the company is moving solidly on a trajectory toward raising a Series A investment. He’s always a few steps ahead, and he wanted to get input on how his close advisors think about this transition for him, the company, and the use of his advisory circle. I could stop there, and I’d observe that his attention to these questions alone is fantastic.  But he went further.

To advance his learning at this stage, he’s assembled a group of four CEOs who have had experience managing a company post-Series A. I could, again, stop there. That’s just fantastic. The group has met once, and they assigned homework. Devon has a few things to tackle, one of which is building out a two- to five-year strategy for the company.  He wanted to use our time together to dig into this assignment.

He told me that in order to flesh that out, he wanted to connect his desired outcomes over that timeframe to strategic building blocks he’d need to establish over the next one to two years. Awesome. The lens he wanted to use for our discussion was, without a doubt, the best mentor/advisor question I’ve ever been asked or had the pleasure to answer:

"Knowing me as well as you do, I’d like to use you as a mirror. Based on what you’ve seen, what do you imagine I would most like to create over the next five years?"

That is a money question at so many levels that I wanted to share it. I think this query works well for businesses, intimate relationships, or parent-child interactions.

Here’s why I like it:

  • The person who asks this question conveys tremendous respect for the person he is asking.
  • The person being asked gets to feel the value being conferred and engage in genuine reflection about what she has learned about the person asking the question.
  • The conversation is definitionally intimate. The person answering gets an opportunity to show that she has been paying attention, whether her judgments are “right” or not (because, of course, there is no “right” here). Both players get vulnerable in this question, quickly.
  • There’s a natural opportunity for projections in this question, and an aware person answering gets to own her own stuff in offering her thoughts. I often say that with feedback that contains projections (as almost all feedback does), there is enormous value for the speaker and the listener.
  • The person asking the question gets phenomenal feedback. Devon asked me and a couple others to share their reflections, and being the analytical (and creative) guy he is, he will merge all these insights, find patterns, compare the his own opinions on the question, and integrate this exercise into his homework.
  • The person asking the question gets to put himself into a real “beginner’s mind.” Somehow when Devon asks questions that show this much openness and curiosity, I ascribe it to his self-awareness but also his young age. I realized today that’s implied judgment on my part; CEOs or people of any age or experience could garner enormous value from a question like this. I also notice that I only want to spend time with people of every age who are willing to ask and answer wonder questions like this.

I shared my responses, which integrated personal and professional ideas about Devon and the company. After I took my shot -- only tossing in about 50 disclaimers “I’m not right, I’m just sharing my gut as you asked” -- Devon shared with me the thoughts of a Pana board member and friend Nicole Glaros of Techstars. He shared some common themes, some places of departure. And that was enlightening as well.

Five years ago when I started my coaching and consulting company, ten dear friends and colleagues of mine offered to join me for a day to serve as my “Board of Directors.” This was an extraordinary gift to me, and much of the session revolved around them sharing with me what they believed was the intersection of what would most light me up and what would create marketable and meaningful value in the world. Conclusions emerged from this session that govern how and with whom I work. There is also a taut thread between this session and the subsequent founding of MergeLane.

Looking for insight on what your “Zones of Genius” are? Wanting to suss out the big vision for you, your company, or your relationship with someone whom you value. Ask this one question, then let me know what happens.

Sue Heilbronner

Sue Heilbronner is the CEO of MergeLane and a Conscious Leadership executive coach and consultant.

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