How to Pick the Best Mentors & Advisors

How to Pick the Best Mentors & Advisors

Posted by: Anne Kennedy on Wednesday, April 5, 2017 at 12:00:00 am

Let’s talk about mentors, and advisors and what the connection is between the two. We do a lot of mentoring, to individuals and to companies in our portfolio. We also sit on several boards of advisors, each of us individually and together as Outlines Venture Group.

Remember Dear Abby? Ann Landers? Advising is an old art, probably back to ancient Greek oracles or the like. People want and need advice, and ask for it. In start ups it seems to be especially welcome if it’s free. More about that later.

Okay, that was advice. We’re talking about mentoring. What is the difference?

Today we have mentors. Everyone is advised they can go farther, faster and higher with the right mentors. There are myriad articles on why and how to find good ones. Much of the advice on mentors talks about mentors for your career. That said, such advice is equally true for startup founders.

Look, you probably started your company because you had a great idea for a product, or a service that will make modern life and work better, or you saw a need to be filled. Most likely the last thing you have is knowledge of how to build a company around your idea, especially if it is your first time. That’s where a mentor can be your indispensable guide through the woods.

In deed, many angel and seed investors – indeed, the best ones – provide solid mentoring to optimize the impact of their investments.

What the Best Mentors Do

Successful people always refer to their mentors as key to their success. Sometimes that person was a coach or teacher while they were in school. Sometimes the mentor arrived as they began their careers. My mentor in PR was Bob Davis, who started at Warner Brothers just in time to make Anne Baxter famous for her role in ‘All About Eve’, and then went on to Parker Pens, and wrote a little book “Do’s and Don’ts Around the World’ just as American businesses were beginning to expand across borders. Kind of like the book I wrote about International advertising!

The best mentors bring wisdom, contacts and context for all that information coming at you.

Wharton’s Adam Grant says mentors are the ones that make an activity so much fun that you willingly invest enough time to master it.

Seems like sometimes they are much the same, mentors and advisors.

Should mentors be compensated? Josh Maher in ‘Startup Wealth’ says this is inconsistent with the ethics of mentoring. We love Josh and his work, but do we agree with him on this? There are certainly different levels of involvement for mentors, including a perspective in which ‘skin in the the game’ provides a deeper level of involvement.

Last, the best mentoring works two ways; I derive as much from the young women I mentor as I hear them say they do from me.

How do you mentor effectively? For example, less talk, more projects: Some mentor relationships involve mostly talking. That’s fine if all you need is a sounding board. Good mentors will bring their experience to support your startup.  A Better mentoring relationship will challenge you to achieve landmarks – perhaps with specific tasks or even exercises to tackle and report back. Or more specifically, help you set, measure and track KPI’s.

Gillian and I are mentoring the founders of the startups we invest in. Sometimes they need a lot of hand holding and careful guidance. Sometimes, just a check-in from time to time to bounce ideas off of us.

The best mentors advise you for the long game, as well as help you over short-term speed bumps.

Your Board of Advisors

How do you build a good board of advisors? Who belongs on it?  You’ll want to seek different types of expertise, for example, to fill in what you don’t have. And note, it’s very important to know your own strengths and weaknesses – you can’t be or do it all.  Then find advisors who complement your skill sets.

Amy Chang, from Google Analytics and now at data company Accompany, says “Being a founder is perpetually needing more expertise than you could ever possibly accrue as an individual. Mentors give you a way to get close.”

Chang divides advisors in two groups: ‘Light advisors’ who are available for an occasional 20-minute call to gut check, and ‘board advisors’, her ‘go-to’ people. And indication of a great advisor, she says, is: Every time you walk away or hang up the phone, you feel like you need to spend more time with them.

How do you ask someone to be your mentor an advisor to your company? Be direct. Define the scope of the commitment, and the compensation. Listen patiently to their response. Express gratitude with enthusiasm if they say ‘yes’.

 Tips for Finding Mentors & Advisors

  1. Get an Agreement in place – use 500 Startups Standard Advisory Form
  2. Work efficiently with your advisory board
  3. Report to advisors – and ask for their help on specific items every quarter


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