Can mentorship be learned?

The following post is from Richard C. Harris, PhD and is the first in a series on mentoring start-ups.

If the recently-held Angel Investor Bootcamp, held in Cambridge, Mass on June 1st is any indication, there is a rising interest among angel investors in all aspects of the angel’s role, including the role of mentoring. Reddit co-founder Alexis Ohanian captured the spirit of the discussion when he argued that entrepreneurs are not just interested in an angel’s money alone. They want to tap the angel’s experience as well. Besides, he concluded, it’s fun to help (see entire talk here). Dharmesh Shah offered this counterpoint, however, “I suck at mentoring. I don’t do it.” (see entire talk here) Let’s give Shah points for candor, but methinks he protests too much.

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I’d have to say that I’m in Ohanian’s camp. Having been around start up service businesses my whole career, I get a certain rush out of helping a next-generation leader avoid a problem that I can see coming. There’s also a practical issue for angels. All mistakes are potential learning experiences. But those street MBAs don’t always come cheap.

Ah, but there’s the rub. How do well intentioned angel investors provide the right kind of help…and at the right time? If you’ve ever tried to help a friend break a habit, you’ll know that quality advice doesn’t always get a good hearing.

Q: How many psychologists it takes to change a light bulb?

A: One, but the bulb has really got to want to change.

So how do you provide the right help at the right time that motivates the entrepreneur to use your advice? Can you learn to be a better mentor? I think you can, but it won’t be from taking a course in Mentorship 101…or even 201.

3 Suggestions

Here are three suggestions to help you raise your game as a mentor. The first requires learning about yourself; the second requires learning about the entrepreneur and the type of relationship you need to have; and the third requires skill development.

  1. Know what you have to offer in addition to money. Deep domain knowledge? Financial acumen? Talent spotter? Market trend setter? Or maybe it’s something other than business discipline…something like wisdom, or perspective. You can’t possibly meet all the needs an entrepreneur will have, so get clear in your own mind about what you can offer. That way, you can move quickly to mobilize help for issues that are beyond your scope. Think of yourself as a family doctor that specializes in one thing, say internal medicine. If one of your patients comes to you with a skin rash, you bring in the dermatologist. You’re an investor and a mentor, not a magician. Save the hero stuff. You’ll only dig a big hole for both you and the entrepreneur you’re trying to help.
  2. Find out what the entrepreneur is looking for in your mentoring role. Some mentors are experts. Others act as a sounding board, or a tough-love observer, or confidant, or door opener to other members of their network. It’s hard to play all these roles at once, so it’s important for both of you to understand which role you’re playing. If you’re giving tough feedback to somebody who just wants you to listen while they try to think through a problem, you’re not helping. It might be therapeutic for you to get it off your chest, but it’s not mentoring.
  3. Develop your 1:1 coaching skills. Coaching skills are a judicious blend of questioning and giving advice. Even if you decide that the major way you can help an entrepreneur is by sharing your experience in a specific area…and even if you’ve negotiated your role to provide expert advice in that area, you’ll still find yourself needing to ask questions to clarify the situation. On the other hand, if you’ve negotiated the role of sounding board, then after hearing the entrepreneur out, there will probably be an ideal opportunity to inject some of your expertise into the situation. Questioning, advocating, and knowing when to switch from one to the other are communication skills that professional business coaches work on constantly. It makes for much stronger mentoring relationships.

A final word of caution…watch out for mentoris overloadus. This condition takes on two forms. If you find yourself spending a lot of time with the entrepreneur, remind yourself that the reason you invested in this person was so that he or she could build a company. No matter how insightful your mentoring advice, you need to be aware that you could be getting in the way. If you’re spending a lot of time on your investment, maybe it’s time you started to look for your next CEO job. The second form of mentoring overload occurs in syndicated investments where there is only one entrepreneur to help and several investors are lined up to give advice. Somebody’s got to act as the gate keeper here before the interesting-conversations-to-tangible-results ratio gets out of whack.

One of the perks of being an angel investor is that it allows you to live vicariously through the eyes of another entrepreneur—all the thrills, but none of the lost sleep. But the rising interest in the role of mentor among angels suggests that there’s scope for a much bigger contribution. As investors get smarter about all aspects of angel investing, one of those aspects—mentoring—will make them better at helping entrepreneurs build stronger companies—companies that make a real difference to customers, employees, and markets.

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  1. […] Mentors and coaches have been a hot topic in corporate learning for a while but the formalized programs and corporate-minded approaches have seen limited success. You may know, a month or so ago I launched a blog about the corporate learning space as a means of collaborating with some of the industry’s brightest and to catalyze a long overdue discussion on the industry (my industry rant here). We are underway with our work on a “lean learning” approach and now  the topic of start-up mentorship is in our sights! I am collaborating with Rick Harris (@rchphd LinkedIn) a long-time friend, one-time colleague and really big brain, to lead the charge on mentoring. Our energetic offline discussions on this topic made it clear that there was some cool new work to be done on helping angels and start-ups optimize this important element of the start-up equation.  Over the next few weeks we will be posting our learnings and looking for your feedback on the Learning Hacks blog.  You can see Rick’s kick-off blog on mentors here. […]

  2. […] investor and the access to other resources that the investor provides. I wrote recently about the mentorship role that angel investors play. An investor can offer a lot more than money, but both founder and funder need to be clear what […]

  3. […] month I wrote about what angel investors need to learn in order to become better mentors. A recent blog post by Fred Wilson raises the mirror-opposite question: can entrepreneurs learn how […]



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