3 habits I worked on to become a better mentor

David Kenney
5 min readDec 26, 2019

I’ve always felt a little uncomfortable with the title Mentor. Eight years ago I joined a group of extremely smart and accomplished people. Many of them now dear friends, had built and sold a business.

Initially, I felt awkward. Helping build cohorts of high growth companies and their founders was a huge challenge, I took quite seriously. By then I had advised on hundreds of business sales. But felt out of my depth. I did a lot of listening, sat next to smart people (always) and asked a lot of questions.

2020 will mark 25 years of advising Entrepreneurs. Curiosity, patience, insatiable learning and giving away my time to so many who actually taught me in return is its own reward.

Why even become a Mentor?

Approaching a problem with a mindset of not knowing. Every new piece of knowledge gained is a thrill. Discovering the truth is intoxicating.

Unlike most sports, determining your progress or any clue of your score in this regard is complex. Growth and Start-up companies are my obsession, passion, and challenge. So the score doesn’t matter, it’s the people around me and how they score that is reason enough.

My calling was never ‘the numbers’. It was always going to be about what ‘the inputs’ are towards building exceptional entrepreneurs. The companies they lead are better for them learning about the levers and which inputs matter most.

By ‘inputs’ I mean the capital you allocate to solve any problem. Time and money are your levers. But the knowledge is understanding the value and return on investment when you allocate capital like a magician. The outputs are more or less based on the quality of the inputs.

Developing culture, aligning your values for how you will treat your team and your customers is a key input too.

The ‘levers’ in a business must be found, established and systemized. The usual example given is a dashboard. A dashboard integrating your CRM and capital allocation can demonstrate a lot more than your CAC. It informs how well your company understands your customers and is a useful tool in discovering Product-Market Fit.

A great Mentor understands that business units, Sales, Marketing, Operations, and Product should all be measured in the same way. What Capital allocation does each department really deserve judging its allocation by return on investment? Can you help a company become more proficient better at predicting this?

What does a good mentor do?

In sitting through over 1,000 pitch sessions, advisory board meetings, on judging panels, Mastermind sessions, hot seats, and 1:1 meetings. I have attempted to narrow it down to these three principles and picking three was tough.

1. Don’t tell

Resist the urge to tell people what someone should do.

It is human nature that people like to revere as an expert.

Unfortunately, for those with any level of experience in building a company to eight figures will identify with the truth that what has worked in another situation may not be applicable in the current one. Unconscious biases and impatience is the enemy. There is no substitute in business for doing the necessary work to make better and faster decisions.

If you could choose between 2 superpowers, would you choose to be?

a) An amazing solution provider or
b) A brilliant question asker?

The nature of mentoring is developing the founder. Bringing out solutions by asking better questions is a framework you can develop.

A problem-solving framework is a gift you can provide to anyone. As the expression goes, ‘give a man a fish…or teach them to fish’ makes the difference in solving a problem versus developing someone’s potential. If even only by percent.

2. Listen and develop deeper thinking

The most valuable meetings I have ever been part of with a founder, I would estimate the listening to speaking ratio would be around 80:20.

Mentoring is essentially helping founders develop deeper thinking. That can result in ‘compressing time’. By way of example, if a Mentor is able to help a Founder solve a problem with hiring talent, product development or resource management that allows them to achieve 3 years' growth in less than 1. Great outcome. If you listen intently, you will often hear things the founders aren’t saying, which are often the cause of the problem being encountered. Body language, vulnerability, and openness to other possibilities only come from listening intently.

3. Tease out where or what the founder is blocked on

Whatever you want to do, a framework helps.

The biggest question anyone really ever has in the business, is what do I do next?

Should I focus on product, team, customers, revenue, raising capital or how do I go from six figures to seven and then to an eight-figure business?

Many times people get too close to the problem. They can be limited by the diversity of their team and its experience. Or possess bias or preconceived notion which can block a breakthrough. I find that borrowing a solution that has worked in another application or market often has great utility. Mother Nature too has a library of solutions on show. These have evolved over thousands of years and more often the perfect playbook to reach into.

If all a mentor does for you is connect you to people, further your knowledge and acts as a champion of your cause you are one lucky person.

I use a process of asking several questions which usually get to the root cause of issues.

If you can get to the truth, or even distill the problem into smaller elements that are a good starting point. If you can then examine the goal and the data you will often see an answer appear and compress the time taken to reach any and every goal.

My own framework continues to evolve. If you would like to participate in a free workshop with world-class entrepreneurs who can only be accessed through the connections I am referring to why not check out www.insanegrowth.com/mastermind

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David Kenney
David Kenney

Written by David Kenney

Author, Founder, Mentor Ask me for a free chapter https://www.amazon.com.au

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