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Earl R. Smith II, PhD

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A Lesson Learned

I don't believe that someone who has not had a series of superlative mentors can be a mentor. You have to be on the receiving end of mentoring before you can start giving back. That is why, after I came to learn this very important lesson, I spent a lot of time with each potential mentor asking about the mentors in their life. That time and effort always paid off.

There are five very good reasons why I believe that to be the case. The first is that good mentors are always grateful for what they have received from their own guides. I have not found that gratitude in people posing as mentors who have not had good mentoring. Second, good mentors are engaged in passing on knowledge and understanding. They see themselves as conduits rather than prophets. Third, good mentors are compassionate rather then ideologically dogmatic - they are not selling a method or approach but engaging on a human-to-human basis to help another fellow traveler. Fourth, good mentors are fearless when it comes to interpersonal interaction - what I call adult conversations - and have a low tolerance to wasting their time and effort. Finally, good mentors are not selling solutions or quick fixes. Each engagement is unique and tailored to the person being mentored.

Here is an example of that I mean from my own experience with one of my most important mentors and the impact it had on others.

Many years ago, while I was working on Wall Street, I had the great good fortune of having a mentor who took the time to explain the world as he understood it. At the time, I was focused on evaluating companies and management teams as candidates for inward investment and/or potential acquisition by clients of the firm I was working for.

One of my tasks was to meet with and evaluate senior management teams. My mentor would often sit in on the interviews and then ask me about what I had observed and what conclusions I had come to. After one such interview, I was very impressed by the people I met and offered a fairly glowing assessment of their capabilities. He smiled, shook his head and said,

“Leaders have a vision, managers have to-do lists. You just spent an hour with a manager.”

Now, before you start objecting and pointing out that leaders also have to-do lists or go on about how managers need teams, I suggest you try to understand what he was really getting it. His point was that visionary leaders begin by thinking strategically and build towards the tactical while managers tend to think tactically and seldom move very far towards the strategic. Leaders assume the burden of generating a vision while managers tend to outsource that burden to others.

As the years have passed, the gift I received so many years ago has served as the foundation of a deeper understanding of how management teams work and how to evaluate them. The patterns are very clear if you know how to look for them. If you miss them, the experience can be very expensive.

Telling the Difference

Recently I was asked to assess a number of management teams for a venture capital firm. My task was to determine which of them presented the best opportunity for further investment. I’ll heavily sanitize my descriptions of two of the companies but hope that they will help you understand a bit of what I’m getting at.

The first company was based upon a disruptive technology. The technology wasn’t purely cutting-edge but it was pretty close. The management team was led by technologists who had participated in the development of a product.

When we sat down, I ask her what she was working on and what major challenges she faced. Her response took me back to Manhattan and my mentor. Her life was busy with details and she had a very extensive to-do list. She was covering everything from banking relationships to corporate filings. When I asked her about her vision for the company, all I heard was a rote repetition of the summary description of her company; a description which I strongly suspected someone else had written.

I then turned to the question of her leadership approach. To describe hers as laissez-faire would be an understatement. It would be more accurate to say that she had no leadership philosophy at all. She simply hadn't thought about it. The same was true of her approach to evaluating the performance of her team members. She assumed that they were all doing their best and that was all she could expect.

Company number two was a spinoff of a larger corporation. The investment was made at the time of the spinoff. Where I had expected to find a visionary leader in company number one, I expected to find program managers in this company. But, as another mentor was fond of observing, “Assumption is the mother of all misunderstanding.”

When I asked the senior team member about his day, I received a very different answer. “I spend most of my time worrying that we don’t have the right value proposition, the right team, the right tasking, the right performance metrics and the right vision for our company”. When I pressed him on what he meant, it was clear that he was thinking strategically rather than tactically about the company.

To be sure, part of his day was taken up with the mundane but he tended to see that activity as necessary but not as important as his role as a visionary and a leader. He knew that the burden of communicating a vision and holding his people accountable rested on his shoulders and should not be avoided. His management style was to set the vision, tone and pace by his own actions, teach his people how to implement his vision and monitor progress towards realizing his vision of the company.

I had long ago learned that entrepreneurs who merely have visions are as dangerous and expensive as those who don’t. In this case, I had found one who had a vision and was aggressively implementing it.

Acting on the Difference

In my report to the venture capitalist, I recommended that company number two was a good candidate for additional investment while company number one needed an overhaul of the management team. To be clear, I suggested changes in both teams. With company two, I suggested that the CEO receive additional support. We needed to take the day-to-day issues off his desk in order to free him up to spend more time in his role as a visionary leader. With company number one, I suggested that a new CEO was required and that the present senior team member assume the role of COO.

A Success Story

In my mentoring work, I often begin by asking how a client spends their day and what takes their attention and time. I focus on the challenges that they see themselves facing and how they approach overcoming them. I pay particular attention to these questions when the person I’m working with is the senior member of a management team. I have found that this approach can generate huge advances in the area of self-understanding. I’ll give you an example of what I mean.

Alice had been brought in to take over the management team of a company which was making and distributing a relatively commoditized product. The angel investors who had provided the initial investment had lost confidence in the present CEO. Her approach to assuming the leadership position in the company was instructive. Prior to even going to the company’s offices or having her appointment announced, she spent the better part of three months researching the space that the company operated in.

My involvement predated her appointment and so I was able to observe her preparation from the very beginning. Like most of us, when facing a somewhat daunting challenge, she began by making lists of things to do. During one of our sessions, she showed me the lists. They were very extensive. I had the feeling she was preparing for an exam of some sort.

I suggested that she might take a different approach. Why not concentrate on her core vision for the company? After all, she wasn’t being brought in for her ability to generate and follow extensive to-do lists but for her ability to develop and implement a vision for the company. That session turned out to be a true turning point. She put her lists aside and began to think about her vision for the company. The result was that, when she finally assumed the position of CEO, her vision was well developed and ready to be communicated to the team.

I also suggested that she spend some time thinking about how she was going to lead the team. One of the problems with the prior CEO was that he was unable to specifically task team members and then hold them accountable for their performance. Over a few weeks, we worked on a statement of expectations which would guide her as the CEO. We also spent a significant amount of time with the angel investors discussing the various team members, their strengths and weaknesses and how they would be best managed. The result was that, by the time she finally sat in the seat, she had a very clear idea of how she was going to lead the team, set expectations and hold people accountable.


I hope these examples have given you some insight into what I’m getting at. It’s okay to be a manager and focus on your to do lists. The world needs far more managers than it needs visionary leaders. And, if you are one of those people who finds life difficult without making lists, you can save yourself a lot of angst by accepting who you are and seeking out roles that allow you to excel. You see, the key question is not whether you are or are not a visionary leader. The key question is, “How well do you know yourself and how well do you select opportunities that allow you to be yourself?”

The best tool available is the mirror and the most effective approach is honest self reflection. If you decide to assume the role of a visionary leader, you must accept the responsibility to think strategically. If you choose the first and don't deliver on the second, you will end up damaging the lives of all of those people who were dependent upon you.

If you choose to be a visionary leader, you must accept the responsibility of leadership. If you don't provide leadership, you will end up with a gaggle rather than a team. Being a leader means leading.

Preparation is an often overlooked necessity and precursor of success. At the temple at Delphi, there were two inscriptions. The first, roughly translated, was "nothing too much". The second, and likely more relevant here, was "know thyself". Well? How well do you know thyself?

© Dr Earl R Smith II

I look back on the first three months of my work with Dr. Smith with wonder. My journal reflects a journey of self-discovery so vast that I hardly recognize the person who wrote the first entries. It's been a year now and I am happier now than I have ever been.

PJ, Mentoring Client

"It's the most amazing experience I have ever had. I needed to find a new path. A friend recommended Dr. Smith. What was most amazing was the wisdom and perception that he brought. New vistas have opened up and, as a result, a new chapter in my life. There's no way that I could put a value on what he has contributed to my life."

Mentoring Client, CEO and Serial Entrepreneur

"Chief - that's how Dr.Smith was introduced to me and, based on our work together, I have come to understand why - helped me focus on the possibilities that I had been missing in my life. He guided through developing a new vision for my life. My life is richer because of working with him."

Mentoring Client

"Earl is a wise mentor with lots of experience. He has a great way of explaining things and getting you to look at them from another perspective. Dr. Smith is a tough mentor, but, if you can learn just some of what he knows, your life will change forever."

Mentoring Client, Deloitte

“Dr. Smith is a very different kind of mentor. If you’re looking for a warm and fuzzy adviser, this is the wrong guy for you. But if you are dedicated to change and want to be challenged by a very experienced mentor Earl may be just what you are looking for.”

CEO of Croix Connect and Host of ABC Radio’s ‘Taking Care of Business’

“Dr. Smith's mentorship has been of great value and inspiration to my personal and professional development. I felt the need to take a new direction. He helped me sort out the possibilities and showed me ones that I never considered. Working with him has been a truly life-changing experience.”

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