Over the years I’ve been asked several times to mentor an entrepreneur. Assuming there’s a good personality fit, I always start with a quick meeting at my office or over lunch. My goal is to get a better understanding of the entrepreneur’s past, present, and desired future. My tendency is to be a problem solver such that I gather as much information as possible and then start looking for solutions, which isn’t always the best course of action.
Here are a few thoughts on making a mentor relationship work:
- Design a rhythm of interaction (e.g. a bi-monthly lunch or quarterly phone call)
- Outline the goals and metrics both parties care about
- Consider overall commitment period (e.g. let’s try this for a year and re-evaluate)
- Look for coordinated mentoring arrangements in a professional group (e.g. YPO has a program with mentors from WPO)
The best mentor relationships happen when both parties are actively engaged and adding value. Mentor relationships take time and effort to be most valuable.
What else? What are some other thoughts on making a mentor relationship work?
David Cummings on Startups 
My mentoring relationships have always arisen organically. I’m always on the lookout for those I can help and for those that I think that can help me. So a mentoring relationship can span one interaction as far as I’m concerned. I have a question or dilemma and I ask it of someone I respect.
I’ve never had the occassion to formalize a relationship, other than my marriage or business endeavors, so its a strange concept.
I always like to mentor people that I know, or have seen progress in the industry and feel that they are not only impressive at what they do but have put a lot of sweat equity into their career, concept, and have seen them grind through start up hurdles, in addition to making life sacrifices where their focus is completely on being successful to the point of obsession. Sometimes, I like to reach out to them and sometimes they reach out to me. Also, I get requested to help someone – coffee, lunch, etc. These random requests come at such high frequency that if they are not a friend, connected through a close relationship that can vouch for them, or doing something really interesting, generally I try to avoid these meetings. Whether you realize it or not my time is valuable, at least $500 per hour but including opportunity costs place it closer to $1000 as this is what I get paid as an expert when executives are looking for a briefing to best understand current industry trends, real time updates, etc. So, once the first meeting is set, I like to tell the entrepreneur to expect what I like to refer to as a business concept sparring session. In essence, I am going to dig I to the concept, the value prop, the competition, key points of differentiation, the financing needs, the people/partners, the industry, and in every area keep beating it up and see how the entrepreneur responds, as I really try to assess strengths and weaknesses not only in the concept but also the entrepreneur as I quickly try to assess the quality of the concept and entrepreneur. I tell the entrepreneur to be ready for tough questions as well as transparency in my thinking – which wont all be positive and want to see how they handle not only a tough exchange but also the tough reality that the concept has weaknesses. At the end if this session, I try to quickly assess my interest in helping further and also give the entrepreneur feedback on both him/her and the concepts as well as 3-5 key action items that I want them to do before meeting with me again. Then, from that point forward, I expect regular updates – calls to update on progress as well as any major issues/hurdles encountered. For me, there is a formula that I have found works and by involving myself with the entrepreneur and by being tough with them, I can usually help them get the business off the ground more quickly, ensure they have the best alignment of their skills/passions with the concept as well as proper market positioning, and I give them the hard reality of what it is like to be an entrepreneur and expect that they take this path – sacrifice, focus, and a sheer sense of will and determination that can motivate them through any hurdle they are confronted with. If I don’t see the willingness to sacrifice it all, work harder than ever in their lives, or not react favorably to the tough discussion and feedback, I typically won’t proceed with committing any more time to the entrepreneur. The reality is I don’t have time to work with people that I don’t feel have what it takes to be a bootstrapping entrepreneur as that is what I know and who I like working with. Unfortunately, in my mind you either have it or you don’t and I can spot it quickly. Early in my career I helped people because I liked them, and I found this to be frustrating to give someone everything you’ve got and then not to see the outcome, follow through, or unwillingness to grind or pivot from a model that just was not working. I studied business in college and in grad school, and this training was invaluable, but until you apply these skills in the real world and in a start up, you quickly learn that many of these teachings are just that teachings but may not always apply or even not work completely. I believe that the best way to learn is by doing and which is why I recommend – get a little big company experience to understand how they work and how miserable it can be – then use this experience and big company mediocrity – to motivate you to never want to return and work harder then you have ever worked before as the sheer thought of returning is almost like a death sentence. Then, when you start your company, do it with your own money and grind until you have refined your concept, see a real need in the market for it based on discussions with target customers and even ideally get a small initial contract to allow you to continuously refine, improve, and understand the real need. Additionally, during this process, I like to see all corporate details are adhered to such as the type of corporation, operating agreement with partner provisions, accounting records recorded and stored to allow for easy review in the future, and industry experts working on these items for you. In Atlanta, many of you are quick to ask for this from others and almost discount the value or even what is required for success. I like to pick my jockeys carefully and hope that my experience will be that slight bit of inspiration or knowledge that helps them dodge failures or capitalize on that opportunity and at that time our work has best put the entrepreneur in a position to capitalize when those moments occur where preparation meets opportunity. It is at these moments that will eventually define the success of the business and entrepreneur. And, as we all know no one or business is always successful. So I try to help then see these issues (icebergs) from a distance and help guide/ navigate the best path. As entrepreneurs, I expect you to take risk and I expect you to fail as well as learn, but what I try to advise is to never take a risk so big that you put the corporation at risk of bankruptcy as then your journey has ended. Even some of the greatest companies and smartest people in the world have made these mistakes – Wachivia, Arthur Andersson, and the list goes on. So, I know that was a mouthful, but the key takeaway is that entrepreneurship will be one of if not the hardest thing you have ever done in your life. It will also be one of the most rewarding. So like anything. Don’t treat it lightly and be prepared to work harder than you ever have, for very day to be a roller coaster of sheer joy and even sadness, but you know what? If it weren’t for all of this, the sacrifice, the emotional journey, the highs and the lows, there would not be the reward that accompanies the success that follows. If this is not what you were thinking, don’t be an evtrepreneur. Go to work for someone else. Put on your suit each morning. Eat your lunch each day for an hour. And, come home in time for dinner with your wife and family. Best of luck in your life journey, apply yourself, take it seriously, work your assign, and even if you fail you will gain a whole new appreciation for a paycheck abs be that much better because if it. Yours truly, Dave Williams
* please excuse typos, run ons, etc as this was produced from my iPhone device.
Like most any relationship, I have found in my mentoring engagements that its key to discuss and discover three things:
1. how deep is their knowledge of the customer – what they want, need and how to serve them
2. what factors constitute success (and keep sight of those ongoing)
3. what is their personal vision and commitment to their endeavor