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3 Questions for Mentors and Advisors in Small Business

A very healthy trend in small business management is in retaining talented advisors to offer guidance and accountability.

In your search for talent for your small business you are prepared to ask and answer many questions. For both your employees and for your ‘boss.’ A ‘boss’ in the form of a wise old man or woman who is not intimidated by your hard charging spirit.

There are questions you should be prepared to ask. Questions for your possible new ‘boss.’ And not just the trite and true, “Tell Me How You Came To Build XYZ Corp.” My questions are to (dis)qualify him. You may not want to ‘work’ for him. And if you really, really need the advisor, you at least won’t be blind-sided. Look for Love, Strategy, Tactics.

1) Love. Does he love me? I was humbled to have Jesse Brown, the former Veteran’s Administration Secretary for Bill Clinton, as a business partner.

“Does he love me?” was Jesse’s one rule for taking on a new client or a new board seat. “If the love’s there, all else will fall in.” Look for; get the feel for the love. Yes, yes, I know it’s an emotion. But so is misery. Look for the love.

The Honorable
Jesse Brown

Jesse was an honorary campaign manager for the Al Gore presidential race. Which meant he was a $100K contributor. And could have any job he wanted. So I asked him why he gave the money since he wasn’t going to take a position in a new administration. “I wanted to help my friends get jobs.” He didn’t need anything for himself; he sincerely wanted to help others. Including nobodies like Your Business Blogger.

2) Strategy. What would you do if you hit the lottery? Or the IPO is really successful?. What would your potential ‘boss’ do if he had a sudden windfall of a nine-figure pile of cash? I asked that question in an interview where I was looking for board members for my thinly capitalized start-up. And I was surprised. The former CEO, an avid sailor, leaned back, and with a far away look in his eye talked about opening up a chain of marinas. His big dream. His big dream was not in my building and I wasn’t a part of it. I didn’t feel the love.


JJ Abrams with Tom Cruise
Credit: Stephen Vaughan

The right answer is seen in JJ Abrams, the director of Mission Impossible III with Tom Cruise. He was recently asked what he did with all his money and about his work,

Next up for Abrams is a “Star Trek” movie, now in pre-production, which will unleash his inner geek as never before. He’ll also be working on “Lost,” trying to ensure the show doesn’t splinter into so many directions that it chokes on itself or stops moving.

There’s not a lot of talk from him about downtime.

Asked if he has any plans for his money, he seems confused.

“What money?”

You know, the money you get paid for all this incredibly lucrative work.

He thinks for a moment, then tilts his head and points to his locks.

“Hair care,” he says.

The reporter’s question was met with a joke. JJ Abrams really didn’t think about the money, didn’t think about the stuff it could buy. Or taking long vacations. He was consumed with his passion of making movies. The Love.

If you had the wealth of Solomon you should be doing exactly what you are doing now. The right answer from your potential advisor or mentor is, “If I struck oil in my front yard, I’d still be doing what I’m doing now.” And he is really saying, “I love your work and I want to help you.”

3) Tactics. What classes are you taking now? Continuous learning is, well, continuous. Life-long-learning is the hallmark of leaders.


Benjamin Franklin [1]

“An investment in knowledge pays the best interest,” said Benjamin Franklin. An outstanding prospective ‘boss’ is reading a compelling book, just finished a seminar on international business etiquette, or studied overseas strategies for a board of directors’ meeting. She is always learning something.

Education and continuous improvement is the one thing every ‘boss’ should care about.

I was surprised to learn this. It’s the one thing everyone in the organization wants.

Your Business Blogger once acted as the COO of a Fortune 350 size organization. In my first meeting with the human resource directors, I asked them what was the one benefit our employees wanted.

I thought it would be more money. More time off. Vacations days. Sick leave. The typical union demands.

Nope. The nine HR professionals, who happened to all be women said, unanimously, education. More budget and time for improving knowlege, skills and abilities. More opportunities for studies and credentials. (Then they’d clamor for increased pay based on increased efficiency. Clever buggers.)

So we opened attendance for adult education programs at local universities and community colleges. And squeezed out budgets for fancy business consultants to teach advanced management skills. Everyone was happy. Our employee retention rate improved.

If your new board member or advisor doesn’t care about adult education for himself, he won’t care about improvement for you or your team.

So you are now armed with three qualifying questions to test your next ‘boss.’ Or try them on your current board if you are looking for an excuse to ask them to leave [2].

And let me know how it goes. I might learn something.

Jesse Brown passed away 4 years ago this month. I still miss him. My inaugural post was dedicated to him.