Recently, we shared how the creators of Vinyl Me, Please were helped by mentors in starting and growing their company. I like the way their approach to seeking mentor-wisdom is different from the way tech-startup media portray mentors as personal Obi-Wan Kenobi’s, all-knowing experts on everything who devotes themselves to training Jedi knight entrepreneurs.

Why several special situation advisors can be better than one dedicated mentor

Don’t get me wrong. I’m all in favor of having personal mentors, coaches, etc., just like I’m in favor of personal trainers for losing weight and getting in shape. The concept is great if you have a specific goal in mind and you have the money, time and discipline to follow the professional trainer’s (or mentor’s) program. However, there are lots of situations that come up that can be easier to address with a special situation solution, not a commitment to a professional trainer and a program.

Typically, those who start a business have experience in–or an understanding of, or a passion for–the specific industry and type of business they start. Or perhaps all the right stars of an opportunity lined up at the perfect time. Rarely does a first time business owner (or a veteran one, for that matter) have such vertical knowledge (the knowledge of a business vertical, say, being an expert chef,  florist, or computer programmer) while simultaneously being an expert in the horizontal skills necessary to operate a business (knowledge of finance, marketing, operations, etc.).

New business owners face a challenge that is similar to the famous (or, depending on your point-of-view, infamous) answer Secretary of Defense Donald Rumsfield gave reporters in 2002 about linking the terrorist attacks of 9/11/2001 with Iraq:

“As we know, there are known knowns; there are things we know we know. We also know there are known unknowns; that is to say we know there are some things we do not know. But there are also unknown unknowns — the ones we don’t know we don’t know. And if one looks throughout the history of our country and other free countries, it is the latter category that tend to be the difficult ones.”

Learning to run a business is using what we know (the known knowns) and then realizing (and accepting) that there are plenty of things we know we don’t know (the known unknowns). And then, the biggest hurdle we face is coming to grips with the reality that running a business hinges on knowing how to handle something you never even knew was possible before about five seconds ago (the unknown unknowns).

What is the role of a special situation advisor?

The role of a special situation advisor is like a “lifeline” on Who Wants to be a Millionaire. It’s a lifeline for when you encounter an unknown. (Don’t waste it on something less.)

How does the interaction between a business owner and a special situation advisor work?

You may never call on a special situation advisor. Indeed, there are some that you hope not to need. For example, those that involve you needing to know what lawyer to hire.

But if you need one, here’s the heart of your exchange. (Anything beyond this is nice, but nothing more than chit-chat.) In a concise, articulate way, you explain the situation in a way that enables the advisor to project it back to a personal experience they may have had. Then, in as precise a way as possible, say something like the following that relates to the situation: “I know this is something I have to decide on my own. But I’ve never encountered anything like this and I know with your experience, you must have seen everything. So I’m really just asking if there are any thoughts you might have or people you might suggest who could help me address it.”

Again, don’t say anything that makes them feel like you want them to solve your problem. Likewise, don’t use up this lifeline on a trivial matter that you should be able to solve yourself. Word your request in a way that makes it  easy for them to understand why you are contacting them and not someone else.


Make sure your advisors know they’ll never have to attend a meeting. (Image via

A few examples of the types of special situation advisors you should line up

  • One who can tell you if a tech issue is hardware or software and who to call for more specific advice
  • One who knows what lawyer you should turn to the first time someone uses the word “sue” in a threatening way.
  • One who is the Kevin Bacon (as in, “six degrees of Kevin Bacon“) of your community or industry.
  • One who has failed in business but then succeeded.
  • One who is your customer or client, and really gets what you are trying to accomplish
  • One who was doing what you do before you were born.
  • One who is far younger than you

How to recruit a special situation advisor

The key to recruiting special situation advisors is to anticipate the types of problems that you may encounter for which you have would need a lifeline.

Make a list of such situations and beside each item, list a few names of people in your town or industry who you think know enough about the topic to point you in the right direction if the situation arises.

In an informal way, say, you run into a potential advisor on your list at your daughter’s soccer game, say something like the following: “Hey, I’ve been thinking about you lately. Our business is doing great, but I worry about ______ happening and, frankly, know nothing about it. I know you’re an expert and I would never want to take up any of your time trying to ask you work questions at a soccer game. But in the future, if ______ ever becomes an issue, would it be okay if I called you so you could head me in the right direction.”

  • Make it clear you aren’t asking them to do anything beyond answering your phone call.
  • Don’t use any titles like “mentor” or “advisor.”
  • Ask for their help long before you need it. Don’t wait until the situation occurs and your voice is full of panic.
  • Don’t be shy.
  • Have a script and stick with it.
  • Good luck, and may the Force be with you.

Feature image: Illustration by from a photo by randychiu via Flickr, (CC BY 2.0)

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