5 Ways to Find and Keep a Mentor

One of the biggest needs in the world of entrepreneurship is the need for a successful mentoring relationship. But far too often, I see entrepreneurs asking to meet with mentors only to brashly discard the priceless wise counsel shared by mentors. I have been in countless meetings where I sat down with a company for a few hours, listened to where they are as an organization, and offered some observations, suggestions and guidance (free consulting, FTW!). After leaving a seemingly positive meeting where the founders have taken copious notes, talked about next steps and felt more confident than ever that they are going to change the world, I am astounded by how often I never hear back from these companies! There is no follow through, no implementation of the ideas we discussed and I, along with many other mentors, find ourselves frustrated and confused that our time was not valued and our counsel not heeded.

And yet, I constantly hear of startups and entrepreneurs searching for mentors and a relationship with people who are experts in their respective fields! So, just to make it amply clear and easy for entrepreneurs, I’m writing about an approach that will help create a mutually beneficial relationship between mentor and mentee.

Before I do, here’s a quick reality check from a mentor’s perspective. We are all busy and we don’t have time to do all of the work we have on our own plate, much less take on someone else’s problems. We fight a daily battle of trying to accomplish all of our own to-do lists without having to worry about the weight of another startup or entrepreneurs’ business on our shoulders. However, almost all of us realize that we have had someone who took time to invest in us when we were getting started and we would not be where we are today without that influence and relationship.

Without further ado, here are the 5 key steps to finding, and more importantly, keeping a mentor. Remember, the key for a healthy mentoring relationship is effective use of the time and resources of the mentor.

1. Ask the Mentor to Participate

You do not have, because you do not ask. First identify the type of person you would like to mentor you — this should be either an expert in your field or someone who would be a good personal fit for you. Then ask!

A word of warning though. If you are starting a new restaurant, Mark Cuban is not necessarily going to best the best person for you to approach to mentor you. Be ambitious but realistic. I am all for showing initiative and trying to get the best mentor possible, but make sure you are approaching someone that you have an existing relationship with or a realistic connection to. Find someone located in your city, someone you can meet with once a month. It helps in developing a long-term relationship.

2. Present the Mentor with a Plan

Come with a plan. Sounds simple enough, but you have no idea how often this is ignored by entrepreneurs who just walk into the room with little or no preparation.

When you approach a prospective mentor, present them a short one-page bullet point proposal on what you are asking of them and what you are committing to do from your side. And you’ll hear me say this all the time — “make your ask palatable”. Do not ask to meet with your mentor once a week or for three phone calls a month. My recommendation is that you ask to take them to breakfast, lunch, dinner, or drinks or coffee once a month for an hour. The word ‘mentorship’ conjures a commitment far greater than we would like to agree to, so if you are specific with what you are asking you are far more likely to get one of us to agree to participate.

By being very clear that you are asking for advice on specific things and by making your ask palatable, you will be able to convince the mentor that they actually do have time for this relationship. Some people suggest having an informal contract just for the sake of accountability, but I recommend you submit a signed proposal so the mentor can see what you are explicitly agreeing to do. Asking them to sign may be asking for too much.

3. Prepare the Mentor for the Meeting

Once you have gotten the mentor to agree to this relationship, you need to do your best to make the most out of each meeting.

Prior to your monthly meeting, send the mentor three questions or topics that you would like to discuss with them. Don’t be vague with questions like “how do I get rich” or “tell me how to be successful”. Rather, ask specific questions like “what are three ways in which I can motivate my sales team” or “how much transparency do I need to have with my staff” (see related blog post on the need for transparency in the workplace). This gives them a framework for the discussion and these are the questions they can answer well with little or no preparation. I would encourage you to make this email short and to the point (no more than a couple of paragraphs and only a few sentences per paragraph). Set up the meeting including time, date and location and mention the action items from your previous meeting that you will update them on. Make sure you have planned out before the meeting how you can keep yourself on track to get the agenda accomplished in the time frame allotted. If you agreed on a 1-hr meeting, respect it and make sure you are done within the hour. If the mentor wants to spend more time with you, that’s great, but make sure to say “I want to be respectful of your time, the hour we had scheduled for is up” and give them the chance to wrap the meeting.

4. Ask for Homework

This may sound a bit silly, but do ask your mentor for homework. Ask questions like “what can I do to prepare for our next meeting”. You can also recap the advice and counsel you were given in that day’s meeting and convert them into action items that you would want to update the mentor on in your next meeting. It demonstrates that you were indeed listening to their advice, and are committed to not only hearing but also acting on their advice. In the follow up meeting, make sure to let the mentor know that you have executed on your action items by giving a brief synopsis of results achieved by acting on suggestions from the previous meeting. Remember, a mentor will be more interested and engaged with you if you show them that you are taking an active part and value the relationship.

5. Deliver on the Advice from the Mentor

DO what you say you are going to DO. This is the most important component of cultivating a mentor relationship. Having been a mentor to both for-profit and non-profit organizations for the last 10 years, the one thing I always encourage companies and founders to do is deliver on what they have committed to in the last meeting. You obviously value the opinion of mentors, so do both them and yourself the favor by implementing things that they have advised you to so and you have agreed to do. There is nothing that will endear a mentor to you more than you doing what they are asking you to do. My experience has been that the more you do, the more advice and time a mentor is willing to spend with you.

This last thing that I would like to say is not as much a suggestion for developing the mentor relationship, but rather a mandate to each of you looking for mentors. Don’t ask someone to spend time, effort and resources on you if you are not willing to do the same for someone else. Return the favor. Seek out and find people who are a few years behind you and who might be able to learn from your experience. A wise person once said you were born with two arms — one for reaching up to pull yourself to the next level and the other for pulling someone up to where you are. So please go out there and mentor others while you are searching for someone else to mentor you. I think at the core, we all want to help others. We are willing to go the extra mile to share experiences, advice and counsel. The key is to letting us help you is to convince us that you are going to do something worthwhile with that help and advice.

So now I ask you, what are some interesting stories from mentoring relationships that you have had in the past? What were things you did that worked, what were things you did that didn’t work? And then give this method a try and let me know if you see the same results that we have over the years.

This post was republished with permission from Trey Bowles. Read more on his blog, Jump Right In.

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