How to Mentor Effectively

As a mentor or advisor to a new business, your job is to help the team win*. How do you do that as effectively and efficiently as possible?  While other folks may have different approaches, I have the following critical to make mentoring work for both the mentor and the founders:

  1. Create the right setting to meet.  It takes up to an hour to really dig in and talk in detail about a business.  Best is a closed-door meeting with no distractions.  Meeting over a meal sucks because you’ll spend half the time talking about how you like your steak cooked and some jackass is always asking if you want more bread.

2) Understand what problem they’re solving first.  I find the best way to do this is to ask a bunch of questions.  The first question is always:

“What customer problem are you solving?”

If a founder can’t answer this one, we have an issue.  I’m quick to interrupt to put us back on track, especially if they ramble.  The second question is usually, “How big is the pain you’re trying to solve?”

3) Understand the proposed solution. What is it? How are you going to market it? How are you going to sell it?  Why are you the right team for this?  This last question is often the toughest to tackle: telling a team that they’re not the right people to build the product they envision.

  1. Explain** your motivation. **I make it very clear I’m cheerleader #1 for someone doing a startup. I want them to win and am volunteering my time to help them do so. There’s no concern that I may have ulterior motives.

5) Separate the idea from the person. Ideas are cheap. Mentors should be clear they totally support the effort to start a company.  If I rag on the idea, that’s not a personal attack. In fact, it’s the opposite — mentors are hard on ideas because they want the entrepreneur to succeed.  If a team arranges eight hours of mentor meetings such that they change their approach for the better or pick a new problem to solve, that’s better than wasting six months building something doomed from the start.

  1. Be focused.  One experienced mentor told me that in a first meeting with a team he wants to leave them with one suggestion.  No more, no less.  I’ve seen mentors give a dozen recommendations in rapid succession.  The teams have a shell-shocked look and get little out of those meetings.  Mentors should pick their battle(s) and keep the number of takeaways given to the team at the three most important course corrections.  If possible, pick two or even one.  It’s a good idea to repeat your takeaways multiple times, too.

7) Say the ugly things (…as nicely as possible.)  The ugly things about a business is what a mentor is supposed to focus on.  The art is being nice while talking about it.   A more experienced mentor advised me:

“Just tell them what you think.  Don’t hold back or you’re wasting their time.”

I had a mentor meeting where I asked the team “Why are you doing a startup?” and got three contradictory answers.  I told them very plainly (and hopefully nicely) that this lack of alignment is a huge risk.  They told me I “just didn’t get it” which is the mentoring equivalent of a team calling you a chump.  (While I wish I had been wrong, the startup broke up six months later.)

  1. **Be persistent.  **I met with a team comprised of 20-something hipsters who had recently shifted their target market to 40-something soccer moms. I had a concern that the team didn’t truly understand their customer.  I said this was the most important thing for them to consider. I explained my concern the first time and they gave me blank looks. They were ready to move on to discuss funnel optimization or some other detail but I kept at it and explained it several more ways. Attempt number four worked and while they may not have agreed with me, they understood the criticism they’d heard from me and other mentors.

  2. Timing is everything.  In schoolwork, the best tutors know not only what to say, but when to say it.  They drip-feed the knowledge based upon their ability to follow the thought process of the student, allowing them to make progress one step at a time.  In my experience, this is what sets apart the good mentors from the great ones.

10) **Suggest they get other opinions. **Your average founder is a stubborn sucker. I’ve seen teams have to hear the same contrary opinion dozens of times before changing their direction. Some are so stubborn that they still don’t change! So, if I’m the first mentor to poop on an aspect of the business, they often need to hear it from a few more times to get the picture. And, as a mentor, it’s very possible I’m wrong.

11)** Let go. It’s their company**.  I had three meetings over six months with a particular startup where I said that they should pursue another problem+solution suggested by a potential customer.  The founders had no interest in this new market despite a handful of customers begging for it.  They pretty much ignored my advice for that six months. That’s cool. It’s their company.  In talking with current CEOs/Founders who mentor, this is the hardest thing to do when one goes from a “boss” mindset to a “mentor.”  Early startups belong to the founders.  Mentors must be OK with their strongly held opinions being ignored.  (This particular startup eventually pivoted and it seems to be paying off.)

12) Leave on a High Note. I learned this watching a very experienced mentor. Founders always left his office smiling and energized even though he’d spent 30 minutes crushing their business. So, don’t forget to cheerlead – this startup shit is hard.

Former or current founders/CEOs often find that advising companies is really hard so they often avoid it.  That’s too bad because mentoring is a way to give back and makes the mentor better in their own business.  The good news is that mentoring is a learned skill just like building a company or learning software development.  With practice and study, it’s something every current or former entrepreneur can learn.

** A mentor or friendly meeting is different than an investor meeting.  Investors top priority is answering the question: “Should I put money into this?”  So, most don’t tell teams when their idea sucks because it’s not a good use of their time.  If someone is soliciting investment, I have a discussion with them to decide whether this is an investor meeting or a mentor meeting.*

Thanks to Cole Wollak, Ryan Tanner, Mike Troy, Richard Ortega and Matt Egan for reading drafts of this.

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