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Leadership lessons learned from a 40-year business career

Know your people, know your message, know yourself, and the rest will come together

It was Friday, March 19, 1982. The day was overcast, as I recall, with a cool dampness that’s common for Knoxville at that time of year. This date will live in infamy for me, as this was the date I was graduated from the University of Tennessee with a B.S. in Business Administration and a concentration in Management.

That was 41 years, 1 month and 10 days ago to the day I’m writing these words.

The following Monday, I began my business career at a printing company in Nashville. I was 22 years old and was thoroughly convinced that I would be a millionaire within five years. Boy, was I misguided.

I did eventually become a millionaire, though. In fact, I have been blessed to become a multi-millionaire, which is — unsurprisingly — not important to me now.

What is important are the lessons I have learned and the people I have helped — and been helped by — along the way.

Within a year of graduating, I launched a commercial printing company with my father, which we sold in 1988. That was what started me on an entrepreneurial journey that led to the founding or co-founding of six more companies.

I suppose that makes me what some business schools would call a “serial entrepreneur.”

All but two of those startups were positive experiences, with those outliers being solid and humbling financial defeats. In fact, I have failed financially numerous times, and always with numerous zeros attached to the cost of the losses.

By far though, the most rewarding experience has been Benchmark Realty, which is now part of the 5th-largest real estate brokerage in the country, United Real Estate.

Still, the universe has taught me many hard lessons since that overcast day in 1982. Some are best forgotten, as they were caused by my own stupidity.

But some of them are good lessons worth passing along to those who come behind me. Perhaps this will help others avoid some of the landmines that I stepped on.

Or, perhaps I’m writing this down simply due to the realization I am closer to the end of my career than the beginning. Age has that impact.

Leadership lessons from a 40-year career

In this 40-year business career, I have encountered many people during my 40-year business career who responded to, and reciprocated, the loyalty and generosity I have always tried to extend to every member of an organization where I’m in a leadership role. I am forever grateful for those relationships.

It is just a basic best practice to find, cultivate, and continuously nurture the people you know will have your back, no matter the circumstances. Had I realized the critical importance of a support ecosystem earlier in my career, my tribe would be much larger today — that’s for sure.

Still, I have also encountered those who, either due to having no personal mission or lack a self-defined direction, absorbed my loyalty without reciprocating — until (as Jim Collins describes it) “the next glittery object” came along. When that happened, they did the dump and run, chasing after something that appeared beneficial, but in the end held much less value for them or their families.

It is sad to see and sadder to confess that I have encountered exponentially more of this sort than the loyal sort. That’s OK – it’s on them, not on me, which, by the way, is a very important attitude for a leader to develop. A leader must be at peace with the idea that not everyone will like them. Human relations is not a popularity contest.

In my experience, leadership is not about keeping score. It’s about service to others. Just as the key to every successful business lies in the philosophy of under-promising and over-delivering on service, the same is true with leading people.

A leader must come to grips with the idea that less than one-quarter of the people you pour your heart and soul into daily will really latch onto what you are offering. I do not believe it is their intention to be ungrateful. It’s just that the inescapable noise of modern society competes, almost to the point of drowning out the leadership message at times.

And, what I have also come to understand is that this one-quarter rotates, meaning it’s not the same quarter that catches every offering. One offering will garner attention from one group, while the next lesson will garner the attention of a different group — and so on. This results in a need for the leader to keep pounding the message, over and over again.

Here is the problem, though. Once a leader comes to realize that only 25% of their audience is paying attention at any given time, frustration can arise. If allowed to grow, that frustration can creep into the leader’s mindset and turn into discouragement.

That’s the danger zone.

Without careful thought management, this can result in a belief that no one is listening — a truly dangerous place to be in your head. What you tell yourself matters immensely. Remember, no one hears what you say to yourself any louder than you do.

With the realization that this audience is rotating, it appears to me that the message eventually moves through about 85-90% of the organization. That means that over time, you will have communicated your service offering to most of the organization.

Being a realist, I also know that there are about 10-15% that pay attention to nothing you say or do as a company because they are consumed with something else or have a lack of genuine care about excelling in their career.

In turn, a leader must be careful about sacrificing high quality service to the 85-90% simply because they are overly intent on pursuing that 10-15%. It is a trap to be aware of, particularly in the real estate brokerage world, where I exist among independent contractors.

While the ratios may be off here, it would be helpful to remember the principles. The leader must know and accept that some are unreachable. Again, that’s on them – not on you.

The solution for me has been to develop a mindset of: “I’m going to do the very best I can every single day, and they will either get it or they won’t.”

What I mean by this is that I employ a constant quest to over-deliver on value, even if that value is not perceived by all who are exposed to it — and never let up that quest or let the frustration creep into my head.

Acres of diamonds

What comes to mind is a speech given by Richard Conwell over 5,000 times between 1900 and 1925, titled “Acres of Diamonds.” It has little to do with leadership skills, but accurately characterizes many of the personalities that we lead today.

A brief summary of the speech is that a man owns a beautiful farm in Africa with a river running through it. Frustrated by his lack of success, he learns from a local priest that there is a special river somewhere that contains diamonds – so numerous, in fact, that they could not be counted.

The farmer so desperately wants to become rich that he quickly sells his farm to rid himself of the burden of running it, using the money from the sale to travel across the continent in search of this special river. After years of fruitless searching, and his funds exhausted, he finds himself on a distant shore, sick and completely impoverished. In total despair, he throws himself into the sea, taking his own life.

Meanwhile, the man who purchased the farm for very little money is out grazing his livestock one day alongside the river running through the property. One of his animals kicks over a rock, which turns out to be the largest diamond ever discovered. With further investigation, the new owner discovers that the entire farm is literally covered in acres of diamonds buried just under the surface.

The moral of the story is this: Had the original farmer simply focused on what was right in front of him, and fully explored what was within his grasp, he would have achieved his goals and dreams. But instead, he sacrificed all of it for some far-off promise, suffering tremendous pain and despair in the process.

Such stories accurately portray the human condition with always wanting something that appears just out of reach, often when the most valuable thing is right there in front of us.

Realizing that this is the paradigm of most people who comprise our organizations is critically important for leaders to grasp.

Know your people, know your message, know yourself, and the rest of the world will come together as it should.

I hope you find these words encouraging. Now put your big pants on and go lead your team.

Phillip Cantrell is the CEO and Founder of Nashville-based Benchmark Realty. United Real Estate – a division of United Real Estate Group – announced its merger with Benchmark Realty, LLC in 2020.

This column does not necessarily reflect the opinion of RealTrends’ editorial department and its owners.

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Phillip Cantrell at

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