KEY Lessons From Training, Coaching and Leading High Performers | #LatimerAt20

This is the sixth and final short essay written by CEO and Founder Dean Brenner to commemorate the 20th anniversary of The Latimer Group. In this series, Dean has been sharing his reflections on, and learnings from, the last two decades.

In today’s essay, Dean shares the lessons and learnings that have had the most profound impact on the way he thinks, leads and serves our clients. 

The world has changed significantly over these last two decades, in more ways than I can count. And so has our company. Now, with a much more complicated business and organization in place around me, I look back on many things with a perspective that can only come with time and experience. And over the last few months, I have tried to capture the lessons that have been most impactful on me.

This reflection has been a powerful process for me, and I hope you find value in these lessons as well.
And perhaps this will inspire you to do the same for yourself. Because the world is changing rapidly around us, and leaders need to be in an almost constant state of learning and change. Self-reflection is required for ongoing success.

Lessons About Business Communication

When I first started this business, I focused almost entirely on coaching for business communication outputs – what my clients said, how they spoke, how they built slides, etc. And without a doubt, all of these things are just as important now as ever, and still a major part of our work. 

But over these last twenty years, and especially in the last ten, I have developed a much more profound understanding of how the communication inputs – the information we take in through our awareness, listening and questions – impact our skills as communicators. The outputs are what people typically see and hear and feel, and those are critical. But the inputs are the foundation of those outputs. 

At its core, therefore, great business communication requires attention and care to make space for and absorb those inputs. As I have grown as a coach and a leader, the skills I pay much more attention to – in myself, my colleagues and the people I coach – are listening, empathy, and understanding. These are at the core of human connection, and if there is no connection, then it won’t matter how polished and strong the outputs are. 

Don’t ignore the inputs. 

Lessons About Leading Strong Performers

In the early days of Latimer, I had some valuable experience leading teams of strong performers, mostly from my life with the US Olympic Sailing Program. But I still had a lot to learn about leading teams in a business context, because there are some significant differences. 

As I started to build this company into a real “group,” I became a student of what would be required to build a great organization. And one thing that every great organization has in common is the quality of the people involved. Great organizations are not made up of drones, people just punching in and punching out. Great organizations are filled with people who are committed to the group, the goal and the outcome. And those kinds of people will bring their own experiences, ambitions and opinions to the organization with them – which means they will add big value. AND it will also mean that there will some unique challenges in keeping them aligned. 

As this company has enjoyed significant growth, my understanding of the importance of building team alignment has undergone similar growth. Creating alignment, especially among the most influential members of your team, is mission critical to any successful business outcome and will be among the most important things a leader must be able to do. When I have focused on building deep alignment on a direction we are taking, the outcomes are almost always powerful. And when I have skipped, or short-changed, this step, I have almost always come to regret it.

Strong, experienced, talented performers won’t just fall in line because they were told to do so. If you want to build an organization or a team that performs at a high level, you need high-level performers. That comes with lots of benefits. But building alignment among a group of talented performers is no easy task. 

And, finally, every leader must be ready to act when the alignment is not happening. This is most challenging when you have a strong performer who can’t, or won’t, get aligned with the rest of the group. When we come to a crossroad with a strong performer who is not aligned, make sure to examine both sides of the ledger of the impact. Because that lack of alignment might be causing problems that cancel out the otherwise strong performance. Eventually their positive value may be diminished. Thus, there is a constant cost-benefit analysis that must occur, measuring the value of the strong performer vs the cost of the lack of alignment. Good team leadership requires a constant accounting of this ledger, and perhaps a healthy dose of creative conflict resolution. There may be some creative ways to bridge the lack of alignment, if we make ourselves open to it. 

Don’t ignore the importance of alignment. 

Lessons About Hard Choices and Scrutiny

Leadership is often about dealing with difficult choices, because the only choices that end up on the leader’s desk ARE the hard ones. The easy ones, where all or most of the variables point towards the same choice, get made somewhere else on the organizational chart. And with these difficult choices, there will always be competing needs, perspectives, opinions, and risks that must be balanced. 

“Balance” is a word that I think about much more often now. Leaders need to be constantly balancing variables that might not align. And because leaders are constantly balancing competing needs and interests, by definition, in almost every decision a leader makes, someone is likely to disagree or be disappointed. Someone is likely to think you made a terrible choice. Someone is likely to question your leadership. This is inevitable. For many leaders, when they are new in the role, this is a major challenge… especially so for those leaders (like me) who care a lot about the people that they lead. (More on that in the next section.) 

In a world that seemingly becomes more opinionated by the day… where the exchange of information and those opinions is easier, faster and more acceptable than ever before… where there is more data or “proof” on which people can base their strong opinions… in a world where all of these things are true, every leader must know that creating alignment and building consensus is of critical importance, usually not easy, and eventual scrutiny is inevitable.

BUT… the ability to align a team and lead it to great heights creates a sense of great satisfaction for many people. I know it has for me. And I am glad that I have stuck with it, and remained focused on building the team that I have. The scrutiny and the size of the challenge did not deter me.

Don’t let the scrutiny deter you.

Lessons For My Former Self

Sometimes it can be helpful (and a little fun) to imagine ourselves as time travelers, who can go back and give advice to former versions of ourselves. And over these last few months, the opportunity to reflect on the last twenty years to examine what I have learned has been immensely valuable for me. I realized where some of the biggest missteps occurred, and all those missteps, the big and the small, give me great perspective today. 

So, if I could go back in time and give some advice to my 2002 self, I would share the following:

  1. The biggest roadblocks you will encounter will be external initially, and internal eventually. In the early days of many startups, there is a ton of energy spent on products, services, delivery systems, pricing, etc, etc, etc. And that’s all critical. The early energy must be focused on the marketplace around you, because those external forces will be unforgiving. But eventually, the bigger roadblocks inevitably become self-imposed and largely internal. The bigger the organization becomes, the harder to build alignment, the harder to plan, the slower the organizational reaction time. And while an external focus should never go away, over time more focus needs to be paid to the internal.  I wish I had a greater sense of this reality in the early days.
  1. Always treat your employees with the utmost care and understanding. But also know that in some cases, it might not be enough. The first part, I have always known. But the second part has been a harder lesson for me. Because no matter how hard you try, your care might not cause every situation to end well. Market realities, life realities, differing goals or ambitions, widening personality differences… any or all of these can create complications that make certain situations untenable… no matter how hard you try. I knew this in 2002…sort of. I realize it a lot more now.
  1. You will make bad choices along the way. Everyone does. Don’t beat yourself up. This one is hard for goal-oriented, achievement-oriented people. But when you are moving fast, examining multiple fields of information, and navigating a rapidly-changing competitive environment, bad choices will be made. I definitely knew that in 2002. But when you experience it in real time, the tendency for lots of leaders is to feel a healthy ration of regret. Some of that is OK and inevitable. But the key is to let yourself off the hook as quickly as possible. I know I struggle with this, and often live with the regret longer than I should. And most of the people I coach do also. But if we live too long in the regret, we slow down the learning process. Nothing good comes from excessive regret. Make the mistake, learn from it, move on.

Twenty years is a long time. And it creates a lot of opportunity for learning and growth.

I hope this has been helpful for you. I know it has for me. Thanks for following along.

As we continue to share our #LatimerAt20 insights on a weekly basis, you can access the full anniversary series here.


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Dean Brenner

A book about change

The Latimer Group’s CEO Dean Brenner is a noted keynote speaker and author on the subject of persuasive communication. He has written three books, including Persuaded, in which he details how communication can transform organizations into highly effective, creative, transparent environments that succeed at every level.