A Good Mentor Can Help Limit the Uncertainty in Your Business

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Founder and CEO of Boxbee
6 min read
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Being an is one of those few jobs where your path is not charted out for you. No one cares about your past experience, no one will hold your hand when things get difficult and no one will sugar coat their belief in your potential failure.

For some, the constant reminders of limited runway and odds being stacked against them unravel their sense of certainty and cause second guessing. Others overconfidently march forward, without paying respect to the mines hidden in their path.

A great mentor is the solution to help illuminate the path while alerting you to unforeseen dangers.

Related: Why Would a Successful Entrepreneur Hire a Coach?

One of the few certainties in the entrepreneurial journey is that you don’t know what you don’t know. At Boxbee, we had several of the common problems that startups eventually encounter: scaling, hiring, competitive threats, etc., but we have dealt with them because they were anticipated.

The items we were blind to: our initially incorrect positioning in the market, the time it would take to actually establish operational efficiency and how our metrics would fair in the changing venture capital landscape, were anticipated from our mentors after they took an unbiased look at the from the outside. Without them, we would not have anticipated these dangerous obstacles that could have caused the company to go under.

How to identify a mentor.

Being able to accept that you will need some guidance is the first step to growing your company with certainty and an anticipation of risks. Entrepreneurs too often try to reinvent the wheel and ignore guidance from experts. There’s a tendency to believe that a technology-enabled service or product is original and even revolutionary, when in reality, components of the problem have been solved in some way or another in the past, and there’s a mentor to help you avoid predictable mistakes.

Logistics/supply chain-intensive companies such as and have solved much of Boxbee’s logistical, supply chain and labor challenges, which is why we sought out mentors such as FedEx’s cofounder, Roger Frock, and Apple’s former vice president of the online store, Mike Janes. Both have helped us anticipate obstacles in our business model and operations.

Research related, successful organizations and find someone you respect and that fits your criteria, someone who has done what you’re going through. Identify multiple mentors, as one mentor will not have encountered all the same problems you are bound to run into.

How to approach a potential mentor.

The reason many entrepreneurs miss out on having great mentors is because they are afraid to simply reach out to the person. Most people don’t do this because they’re concerned that these people are too busy and important to consistently donate time, but you’ll find that they’re flattered you’ve asked them for help and would relish at being partially responsible for your success.

Ask your mentor prospects for a meeting, whether in an office environment, over drinks or at a coffee shop. Communicate your goals for the meeting and identify some key areas in which you wish to seek their advice. Flattery will also go a long way -- mention why you admire them and why you feel they would suit you as a mentor. Don’t be discouraged if someone says no to your first request. Great mentors are pursued, not found.

Related: What Happens When Startup Advisors Advise the Whole Team

Questions to ask a mentor.

Once you have a mentor in place, you’ll want to prepare for your first meeting so you don't waste their time. Prepare a list of questions, topics or subject matters that would be good conversation starters and help cover what you’re hoping to learn.

Here are a few questions to get you started:

1. How would you handle [insert subject here] scenario?

2. What is the most important thing I should be doing that I’m not doing now?

3. What are the critical things we need to get right?

4. What are the big risks that we should anticipate?

5. Do I have the right team?

6. How do you spend most of your time?

7. What are your most successful habits?

8. Who else should I be surrounding myself with?

Pay attention.

The great advice you are going to get from your mentor can come from your questions, but much of what you learn from them will be through absorption of their habits and mannerisms.

Being closely surrounded with mentors has changed how I approach all sorts of situations: what to say to the top executives to guarantee a meeting, how to build a strong network and use it regularly to strategically grow the company, how to start every day by visualizing and rehearsing events, how to constantly push everyone around me to their full potential, how to maintain confidence and cope with tremendous uncertainty and bad news, and on and on.

These are not things that one learns from management books or exercises. You must surround yourself with people frequently and consistently enough to a point where you naturally absorb these behaviors. 

It’s important to remember that mentors will not solve problems for you. A true mentor will cause you to ask the right questions that help you get to where you want to be and they’ll call you out when they know you’re accepting less of yourself, your vision or your team. They’ll help you frame your problem and they’ll help you check the assumptions and belief systems that are holding you back so you spend less time spinning your wheels and wasting precious capital.

So get out there, accept criticism, ask questions, absorb new habits and take business advice from seasoned vets. You’ll be thankful you did.

Related: Even Warren Buffett Relied on a Mentor

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