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How to Work With a Mentor

How to Work With a Mentor

You know why you need a mentor. You took the time and energy to find one. If you haven’t yet: take your list of dreams, goals and aspirations for your personal life, find someone who has achieved the bulk of them in your industry (or if there are none, consider changing industry) and grab their coat tails and never let go. A bit of elbow grease and a whole lot of patience and interviewing will do the trick. So, now that you have a mentor, what the heck do you do?

Be Open

When I mess up, I want to fix it and make myself look better. No one wants to look like an ass. When you are out in the world, there are things you share and things you don’t. When you work with your mentor, they need the hard facts. If they don’t know the truth, they can’t guide you. That extends beyond the daily business of your company. It includes your health, you marriage, and everything else that has significant impact on your life. It takes courage to share weakness. In the book Good to Great, they discuss the Stockdale Paradox – the idea that you can be brutally frank about your situation while maintaining a positive vision for the future. That is the goal of your relationship with your mentor.

Ask The Question

My mentor Tom taught me to ask a question. It is the first and last question I ask every time we meet.

“What do you know about my business that I don’t which would make the greatest difference?”

This is such a powerful question. It gives your mentor permission to be honest and share what they see. You may not like or understand the answer, but you will gain value from it if you listen. We sometimes get so focused on the minutia of the business, we loose track of the big picture. Sometimes we are focused in the wrong place. Sometimes we ignore something we decided was irrelevant, only to have our mentor carefully point out that we absolutely can’t ignore it.

A great example of such a talk (not with Tom) was the post I wrote on “Managing the Explosion“. Not the most pleasant talk, but the right one at the right time.

Your Goals & Organization Chart

Always have your list of goals for the company present when you are going to meet with your mentor. You should also bring your list of personal goals. Your company is simply a vehicle to accomplish your life goals and your mentor may be in a position to help you bridge the gap. With a list of where you think you are headed, you mentor can help you prioritize your goals based upon your current situation. If you are growing a team, bring your organizational chart with you and be prepared to discuss what everyone is doing, their performance and any issues you are dealing with.

Your Financial Statement

Have a profit and loss and an income and expenses statement for the current month, quarter and year with you. You may not use them, but if you need to discuss strategy, these two financial reports help give you the pulse of a business. If you have not created these and do not review them consistently, you are essentially flying blind.

Your Activity Sheet

Your daily habits form the foundation of your longer term results. You will work with your mentor to identify places in which you personally need to grow and improve. Tom and I worked out a list of 6 things I had to do every day that would have the most impact on my business. My daily list includes the following:

  • Meet a new person
  • Read from a business book for 15 minutes
  • Create a list every night on what I need to accomplish tomorrow in order of priority
  • Check in with everyone on my team
  • Listen voicemail morning and evening
  • Give Julie 30 minutes of focused listening

Most of these may seem basic, but they are the habits that we determined together would make the greatest difference in my life. Though I admit I do not always pull them off, especially the first, I continue to do them day in day out.

A List of Questions

Come with a list of questions. You may not get to them, but it is good to come with a desire to learn. If time allows, then you can work on your questions. Don’t expect their answers to be the ones you want. I remember a great story I heard a few years ago by a business man I’ve often had the chance to hear speak at events. After achieving significant results in his industry, he went back to his mentor and asked him why he never gave him any answers. His mentor laughed and said “I was giving you answers. You were just asking the wrong questions. You were constantly asking about the technical details of your business, when you should have been asking questions like, ‘how can I be more relatable?’ That is what you needed to work on and that is where I was giving you advice.”


Your relationship with your mentor is much like your relationship with a business partner. It requires patience, work, and a willingness to be wrong. One of my biggest struggles is putting people on a pedestal (like my parents) and finding myself disappointed when they are just human. They may have been further down the road than you did, but they have the same human failings we all do. Treasure their advice and forgive their mistakes.