How to be a Leader: Perspectives in Leadership - Pluralsight

James Caplin spends a great deal of time thinking about leadership. His thoughtful nature becomes immediately apparent when you speak with him, especially about interpersonal communication and the qualities that improve organizational culture. James’ career as a coach and mentor for executives at organizations of all sizes has helped him understand better than most what makes a good leader. The takeaway? There is no one way to succeed as a leader.

James joined our Perspectives in Leadership podcast for a long conversation about ways leaders can improve and how first-time leaders can set themselves up for success and healthy communication with their teams.

What follows is a shortened version of that podcast episode. 

*Answers have been edited for length and clarity.

The Great Resignation has led to so much transition in organizations across all industries, and this transition is leading to a number of people becoming leaders for the first time. In our initial conversation, I asked you to share best practices for first-time leaders, and you joked that those don’t exist. Would you like to speak on this more to open our discussion?

When you do what I do for a living—consulting and coaching, that is—you come across leaders from all walks of life and every industry. That is one of the reasons why executives hire coaches so frequently. We have seen countless examples of leadership, which enables us to best form a plan for our clients. I create the space for people to do their best thinking, which is an extremely delicate task. I have a coach and a supervisor, and I do training courses every year. And the reason for all these tools I access is to be prepared to help leaders think through what will work best for them and their team.

Even the advice I give will be different from my colleagues because, truly, there is no single way to be a leader. That's why we get different people as presidents or elected officials. Some of them are awful, and some of them are quite good, and some of them seem utterly mad, and some of them seem quite respectable. 

What President Obama said about leadership was very wise. He said, by definition, every decision that lands on the leader's desk is a difficult one. If it wasn’t, it wouldn’t land on your desk. All of my clients are faced with this. The question is how, as a new leader, do you manage? The thing I've noticed about the people who are the best leaders is they learn to be generous and kind, but they don’t get taken advantage of. This is essential. So, while there isn’t a single set of tools to be a successful leader, a key starting point is to understand that difficult decisions will be placed in front of you, and you need to have generosity and kindness at the forefront while creating a fair and impactful decision. 

You discuss a great deal about the need for leaders to look inward and be reflective about what is the best version of themselves. What type of leader they can be and what type of leader their team needs. Given that understanding others starts by better understanding yourself, do you have suggestions for ways that people can better get to know themselves? 

Looking into yourself is a useless activity done by itself. What a good leader does is create space, trust and safety for their teams, centering around thoughtful conversations. You begin to know yourself by watching your impact on others. That tells you much more about who you are. 

Becoming interested in your own impact on others helps you better see who you are as well. Being on the spectrum personally, I don't often notice the way I can upset other people. So the people I work best with are people who understand people much better than me. Seeing my effect on others helped me to better see myself. Getting to know yourself is complicated, but it is extremely beneficial to do, especially when thinking about how you interact with your team collectively and one on one.

You spend a great deal of time building out boss “boot camps,” where you guide organizations through courses, discussion and examples of successful leadership. Can you walk us through that experience?

We delve into the four main things I think that you need as a leader, but it's a description, not a prescription. It's what you need, not how to do it. The boot camp itself is the beginning of the leadership program. I've noticed a whole set of things that, unless they can start doing them better, they don't have the space to be their best selves. We tackle the fundamental skills of the workplace that don’t usually get talked about. How do you really do prioritization so that it really works for you and you don't just get swamped? That's a skill. 

We examine listening. How do you listen? How do you listen properly? We focus on listening because it’s the best way for you to learn what your employees want to do and what they thrive at. When you look at some people working and you think, “Oh, they work a particular way and excel at these types of projects,” then you understand the tasks you can give them. That's proper and healthy delegation. That's noticing how other people operate. 

Learning to do these things organically can take a long time, so our boot camp aims to accelerate people along that curve. 

One of the reasons I love talking about leadership so much is one of the same reasons that I love talking about mental health so much. It’s because I think it's important for people to realize that there's no finish line. There's no final boss in leadership where you conquer it, and you put your initials in the high score at the end of the day. 

If you can cultivate that feeling, then you will become—in my world, anyway—a lifelong winner. Saying there is no finish line might lead people to believe that achieving in both leadership and mental health is impossible. I think the exact opposite. If you understand that life and leadership are about ongoing improvement, a continuous state of upskilling yourself, then you will improve and “win” every day.

What's a bit of advice pertaining to leadership that you really take to heart.

Cultivate your inner kindness. If you cultivate your generosity as a leader, you can't go wrong.