How Business Mentors Work

By: Dave Roos
Two men talking.
No man -- not even your boss -- is an island. Everyone needs a little advice on the way to the executive suite.

One of the greatest myths of entrepreneurship is that it's a one-man show. We tell and re-tell stories about successful companies launched in garages by lone geniuses. We like to read about CEOs who pulled themselves up by their bootstraps to become billionaires solely by the power of their personalities and the clarity of their corporate vision. What we don't hear enough about are the influential people behind the scenes whose timely advice and counsel helped shepherd the legendary entrepreneurs in the right direction.

Mentors are essential to the success of a new business. A mentor is an experienced businessperson who has already navigated the treacherous waters of launching and sustaining a profitable enterprise -- including everything from soliciting investors to designing a marketing campaign to going public. But success is not the only qualification for a good mentor. A mentor must have a strong desire to share his or her accumulated wisdom and to give something back to the professional community.


Finding the right business mentor is a long process, and it should be. Think of it like dating. You shouldn't settle for the first silver-haired, six-figure executive that comes along. You need to find an experienced, trustworthy individual who has both the time and inclination to invest in your success. For that to happen, both sides need to get something positive out of the mentoring relationship. You get sage advice, and your mentor gets the satisfaction of grooming the next generation of entrepreneurs.

A good mentor is more professional than a friend, but more friendly than a paid life coach. Needless to say, quality mentors don't grow on magic retired executive trees. You'll need to leverage your network and kiss a lot of proverbial frogs in suits before you find the perfect match. Find out more about choosing a business mentor on the next page.


Choosing a Mentor

The best way to find a business mentor is to get out there and network. Start by combing through your connections on LinkedIn or searching the online alumni directory at your alma mater [source: Hughes]. You'll have a better chance of making a solid connection if you already have friends, colleagues or colleges in common. Local mentors are best, so consider joining the local chapter of the Rotary Club, Toastmasters International or Entrepreneurs' Organization [source: Lowe]. Attend some meetings, identify potential candidates, and start asking people out to lunch or coffee.

There are also national small business organizations designed to help connect entrepreneurs with resources and mentors. The National Association of Women Business Owners and the National Federation of Independent Business are good places to start. The U.S. Small Business Administration partners with a Web site called, which connects small business owners with online mentors. There are also regional SCORE offices across the country where you can seek out offline mentoring relationships.


What characteristics should you look for in a potential business mentor? First, your mentor needs to have experience with your exact business situation. If you're trying to raise venture capital for a tech start-up, find someone who's successfully funded and launched a profitable start-up (or six). The important thing is that your mentor has done what you want to do and gone where you want to go [source: BusinessWeek]. Otherwise, you might get a lot of good general business advice, but nothing you can apply directly to your current situation.

Secondly, your mentor should have an established network of industry contacts. This is one of the greatest benefits of having a mentor -- instant access to a Rolodex of savvy investors, trustworthy vendors and potential partners. For this reason, a business mentor doesn't necessarily have to be older. It's his or her years of experience in your field that matter most.

Thirdly, your mentor should actually care about you. Your mentor needs to be someone who is deeply invested in your success; not financially, but intellectually and emotionally. If your mentor truly cares about your success, he or she will be more committed to regularly scheduled meetings, feedback and networking on your behalf. Of course, a crucial aspect of caring is honesty. The best mentor shouldn't be worried about hurting your feelings. Your mentor should tell it like it is, pointing out the weak parts of your business plan along with the strengths.

Now let's look at the flip side of the mentoring relationship. Do you think you're experienced and knowledgeable enough to be a mentor yourself? Read more about becoming a mentor on the next page.


Becoming a Business Mentor

Two men reading together.
If you want to be a mentor, you have to make yourself available -- physically and emotionally.

You've worked hard for your success. After years of maxing out credit cards and clocking 70-hour workweeks, you're finally seeing the fruits of your labor. Profits are up, customers are happy and investors are knocking at your door for once. Now that you have time, you can reflect on the circumstances that brought you here. Perhaps there were some influential people along the way who gave you critical counsel and opened doors to important business contacts. Wouldn't it feel good to have that same influence on the next generation of entrepreneurs?

First, you need to find some potential mentees. If you haven't been approached by entrepreneurs in your community, make it clear that you're available. Contact local colleges and universities and ask if there are any established mentoring programs in which you can participate [source: Misner]. Your LinkedIn profile should show that you're interested in mentoring opportunities. Join your local chapter of the Rotary Club or other business organization where you can meet young people who might be looking for an experienced ally just like yourself.


A successful mentorship is built on trust and mutual interest. This won't happen overnight. Take time to get to know your mentee and his or her business goals. Harvard Business Review blogger Anthony Tjan suggests that you start by asking these five questions:

  1. What is it that you really want to be and do?
  2. What are you doing really well that is helping you get there?
  3. What are you not doing well that is preventing you from getting there?
  4. What will you do differently tomorrow to meet those challenges?
  5. How can I help/where do you need the most help? [source: Tjan]

Once you have a firm grasp of your mentees goals, strengths and weaknesses, make yourself available through regularly scheduled meetings. Be prepared to act as a sounding board for new ideas and a confidante in harder times [source: Hart]. Actively advocate for your mentee by introducing him or her to members of your professional network or championing your protégé's ideas with potential investors. You have the power to open doors that your mentee didn't even know existed.

In the next section, we'll look at the most effective questions to ask a mentor.


Questions to Ask a Mentor

A business mentor can be an incredible resource for a young entrepreneur -- but only if you ask the right questions. If there's one cardinal rule for getting the best advice from a business mentor, it's "be specific." Mentors are very busy people who are dealing with their own set of critical business decisions. Signing up to be your mentor means they're happy to help, but they can't make every decision for you. Instead, they can offer an experienced perspective on current issues and future plans.

The specific questions you ask your mentor depend on your career status. If you're just starting out and still drafting your business plan, you might ask your mentor to see a copy of hers to use as a guide. That's something easy for your mentor to share and hugely valuable to you as a real-world resource. Once you've drafted your plan, ask your mentor to read it. Don't expect a line-by-line critique, but encourage him or her to highlight any areas that need work or to suggest alternative ideas.


If you already have a business plan and are looking for potential investors, ask your mentor to suggest some contacts in his or her network. If your mentor believes strongly in your business, ask him or her to call some investors personally to make the initial contact, and then let you follow up to make the pitch. Again, it's a service that's relatively easy for the mentor to perform, but something that would have been very difficult for you to do alone.

At various points in the development of your business, you'll arrive at a crossroads. If you choose the wrong path, it could be costly. Before you invest in expensive equipment, take on new partners or make any other long-term decisions, consult your mentor first. Ask what he or she would do in the situation. Ask about any risks or benefits that you haven't considered.

Lastly, remember to ask, "How can I help you?" A mentoring relationship shouldn't be a one-way street. Just because you're new to the business, it doesn't mean that you have nothing to offer. Maybe you have a special skill -- Web design, social networking or lawn care -- that would be valuable to an older professional. Make a specific offer. "Hey, would you like me to create a Facebook page for your company?" Even small gestures will help balance the relationship.

Still not sure what a mentor can do for you? We'll outline the top benefits on the next page.


Benefits of Having a Business Mentor

Man looking sad as another looks on.
One of the greatest benefits of having a mentor is a steady dose of tough love -- whether you want it or not.

For a young entrepreneur, a close mentoring relationship is like having a big brother in the office. The big brother knows the ropes, has a large network of friends and is bigger than the bullies. There are countless benefits of having an experienced, fully engaged business mentor on your team. Here are a few of the highlights.

First of all, if you can find an experienced mentor in your field, then you'll gain access to that person's extensive network of contacts. Building an effective professional network is still one of the hardest parts of starting a new enterprise, even with social networking Web sites like LinkedIn. If you're looking for a vendor, supplier or investor, the mentor knows exactly who to call. And unlike you, his call will actually be returned. That's priceless.


If you can establish a trusting and mutually beneficial mentor relationship, your mentor will not only share his or her Rolodex, but also a long and valuable list of "lessons learned." Mistakes are a great way to learn, but some are so costly and time-consuming that it's best to let someone else do the ""learning"" for you. By analyzing your business plan and keeping track of your major upcoming decisions, a good mentor will help you steer clear of the biggest blunders.

A healthy mentor relationship is really an informal education. You can learn a lot in an MBA program, but there are some lessons that can only be gleaned from real-world experience. In an Inc. magazine article from 2000, a small-town businessman named Kent Sutherland described the unique mentoring relationship he shared with billionaire and Wal-Mart founder Sam Walton. Sutherland met Walton as a 23-year-old salesman peddling health-care products for a national supplier. Even though Sutherland never worked for Wal-Mart, CEO Walton took the young man under his ample wing. When Sutherland talks about the benefits of the relationship, he cherishes the nuggets of common sense wisdom -- like "always diversify" -- that helped him make a small fortune in unglamorous businesses like insurance, storage units and mortgage brokerages [source: Welles].

Keep reading for links to lots more information about professional development and reaching career goals.


Lots More Information

Related HowStuffWorks Articles


  • Bloomberg BusinessWeek. "Why You Need a Mentor." Winter 2007 (Sept. 10, 2010)
  • Hart, E. Wayne. "Seven Ways to Be an Effective Mentor." June 30, 2010 (Sept. 10, 2010)
  • Hughes, Ivy. Entrepreneur. "Meet Your Mentor." September 2010 (Sept. 11, 2010)
  • Lowe, Keith. "Finding a Business Mentor." October 1, 2001. (Sept. 9, 2010)
  • Misner, Ivan. "Become a Networking Mentor." April 22, 2009. (Sept. 10, 2010)
  • Tjan, Anthony. Harvard Business Review Blog. "Five Questions Every Mentor Must Ask." March 25, 2009. (Sept. 9, 2010
  • Welles, Edward O. "The Mentors." Inc. June 1, 2000. (Sept. 9, 2010)