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Try this: log on to and search the term “leadership.” When I was working on this article, that search yielded 116,863 hits. So what does Gary Kaplan have to add to all that?

There’s not a whole lot new in the world of leadership ideas. And I’m probably not going to tell you anything you haven’t heard already. But here’s what’s really valuable about those Amazon books and this article, too: Proven Success.

Becoming a leader can be a little scary. If you’re new to a leadership role, you might not know exactly what’s expected of you. And even if you’re a leader with years of experience, you’ll undoubtedly find yourself in unfamiliar situations where your personal experience can’t help you.

Leadership isn’t automatic. Becoming a leader is an iterative process. You have to take chances and get outside your comfort zone, so you can acquire, practice and demonstrate leadership skills.

And that’s where those 116,863 or so authors and I come in. We’ve been there and maybe there are some helpful things you can learn from that collective wisdom, experience and even the screw-ups.

I’ve been in this business a long time. In that time, I’ve encountered a lot of leaders. They were bosses, heads of corporations, clients and brokers. I saw a great T-shirt once. It read: “If you can’t be an example, be a warning.” I followed the examples and paid close attention to the warnings. By observation and trial and error, I developed my own leadership style. That style is the sum total of my professional experience, which includes a fair amount of calculated risk-taking. The style I’ve developed is based on what I believe are the 7 critical skill sets all good leaders must have. Here are my thoughts on each.

Building Trust & Accountability

This is probably the number one thing to be a successful leader. Your people need to trust you. When your people trust you, their engagement increases. They also are more willing to go above and beyond to get the job done. With trust, you’ll be more effective in facilitating cooperation and building relationships. More important, building trust is the foundation for establishing accountability and successful delegation. There’s no secret formula for developing trust, but there are certain characteristics that positively influence it:

  • Be Authentic. People can spot a phony. Be yourself (unless you are a phony, that is). That’s also why you have to adopt only those leadership teachings that fit with who you are. Otherwise, it just won’t work.
  • Have a Sense of Humor. This doesn’t mean be a jokester. It does mean don’t take yourself too seriously and be able to laugh at yourself.
  • Be Enthusiastic. Don’t just go through the motions. Approach your job with gusto. Enthusiasm is contagious.
  • Commit Fully. Give 100% to everything and let it show.
  • Be Positive. Like enthusiasm, a smile is contagious. You and your people will be more productive if you’re not a miserable person.
  • Be Honest. One of the fastest ways to destroy trust is to lie. It’s also just plain wrong.

Developing a staff of people who are accountable for their actions starts at the top. Be accountable for your shortcomings and own up to mistakes. Allow your people to take the necessary risks to deliver their best performance and outcomes; they’ll take those risks if you establish trust. Give yourself and your people permission to make mistakes. Just be sure you learn from them and make the necessary corrections to avoid making the same mistakes down the road.


Every leader needs a team. And if you have a team, you need to delegate. Delegation takes practice. If you’ve built trust and accountability, delegation becomes easier and more effective. Sometimes we want to hold onto particular projects or tasks because we’ve always done them or because we enjoy them. But those projects or tasks might not be the best use of your time. It may be holding you back from taking on more leadership opportunities. And, besides, by delegating a project or a task to a team member, you might also be giving that person the opportunity to develop skills or gain visibility in your organization.

Project & Change Management

If you’ve been to a conference anytime in the last decade, you’ve probably heard a speaker say this: the current rate of change (technological and otherwise) is so fast that we are unable to keep up. Well, it’s true and it’s only getting worse. Change is a fact of life in our industry. Whether it’s a big change like a merger or a smaller one, like a departmental reorganization, you’re going to encounter change.

Your people react to any size change in pretty much the same way—they don’t like it. It’s natural. Humans simply don’t like change. As a leader, it’s your job to manage that change. Not just the big strategic pieces, either, but helping your people understand and adapt to the change. I think the best book I’ve read on this subject is Leading Change by John Kotter. Add that one to your library.

Project management is another thing that never goes away. As a leader in your organization, not only do you have your own projects, but you also need to oversee the projects of both individuals and teams. You need rock solid project management skills, that’s a given.

One very effective way of managing large or small projects is by using sponsorship. Here’s basiccally how it works. You, as the project sponsor, create a charter for your team. In that document, you outline:

  • Project purpose/background (What’s the challenge to the team?)
  • Project goals (Help the team set a stretch goal)
  • Deliverables (What kind of results are you looking for?)
  • Deadline (When do you need to see results?)

Then provide coaching along the way. Set up regular intervals to check in with your team to keep things on track, make needed adjustments and provide guidance. If you are put in charge of a project and you don’t get a sponsorship statement, ask for one. Getting the important project components in writing before you start saves time and money. It’s not a stretch to say it can save a career, depending on the complexity and scope of the project.

To learn more about project management, Execution: the Discipline of Getting Things Done by Larry Bossidy and Ram Charan is another book I highly recommend.


Not all decisions are created equal. That means you shouldn’t spend the same amount of time and/or energy when making them; adjust your decision-making style based on urgency. Remember, too, there are some decisions you probably shouldn’t be making anyway (remember why we delegate?). Make low-stakes or time-sensitive decisions quickly and move on. If you have more time, seek additional input from your team and others in your organization.

And when all is said and done, one of the most important things you can do when making decisions is to make sure your team knows why you made a particular decision. You don’t have to justify, but the people who look to you as a leader will appreciate knowing why you did what you did.


This is such a critical skill for leaders. This is especially true when you’re trying to get people to follow you or buy in to your vision or a new or risky idea. Here again, there are so many books on the subject of communication in the business world. But here are some things I’ve found to be particularly important:

  • Mechanics. There’s communicating and then there’s communicating. For me, the best messages are the ones that are clear and have passion. A good, clear message connects the dots for the audience (charts are really helpful). But almost more important is that those messages are delivered with passion. After all, if you don’t seem to believe in or care about your message, why should the people listening to you? Don’t forget about body language. You can ruin an otherwise powerful presentation with weak body language.
  • Style. Great communicators have their own styles. Ronald Reagan and Bill Clinton are both examples of great communicators. Each one had a different style. Reagan was really strong when it came to delivering a vision and talking about big ideas. Clinton was particularly good at engaging people and getting them involved in his message. Watch other speakers and take note of what they do well (and not-so-well). Identify your own strengths and build on those.
  • Practice. Have a colleague record you while you give a presentation (use that Smart Phone). Then really study it. You’ll be amazed at what you learn.
  • Listening. The most critical communication skill is listening. It’s especially important when you’re working with your team. You have to be able to listen to know what your people are thinking, how they’re feeling. And active listening is really important. Here are some tips: Avoid Distractions. Put your mobile device away. Turn off your computer monitor. Forward your phone to voicemail. Close your door if you still have one. Take Notes. Writing things down will help you focus on what’s really important. Repeat. Another way to focus is to repeat back key ideas. It also helps you validate what the other person is saying.
  • Confidence. When you communicate, what you say is only part of the process. How you say it is every bit as important as (maybe even more important than) what you say. Remember body language? It’s a big factor in communicating with confidence.

Strategic Direction & Prioritization

Strategic thinking is hard work. You need the time to think. Figure out the best time for you. It might be in the gym. Or doing yoga. Or running. For me it was in my car on a long commute or on a plane. The key is to write it down! Make sure you have the ability to get your ideas down on paper or a text message. Something! I used to keep a tape recorder with me so I could capture my thoughts safely while I was driving or sitting in traffic. Of course, now we have Siri, but she doesn’t seem to be able to understand my Chicago accent.

And you need to take that strategic thinking and create workable operational plans. But before you even start to plan, you have to set priorities. I use a simple 2x2 matrix for establishing priorities, balancing importance/value with urgency. Once you map it out and assign priorities, you’ve taken an important step toward creating your plans. Remember that a matrix like that should be a living document. Move things around or delete items as priorities change and communicate with your team. And don’t forget to check things off as they’re completed and then celebrate your success!

Acquiring, Developing & Retaining Talent

To be a successful leader, you need to surround yourself with talented, empowered (and ultimately, happy) people. Here are some important things to remember:

  • The No-A**hole Rule. This isn’t my term. But it’s true and it works. I made sure everyone knew about this rule when we were building out our new team at XL. It became a part of our culture. In fact, I’ve had to reconsider hiring decisions when I learned a candidate would violate the rule. To learn more about this rule, just search Robert I. Sutton, PhD on
  • Showcase Your Talent. Let your people shine. Don’t be that person that takes credit for the work of your team. When a team member comes up with an idea or leads an initiative, let him or her get in front of upper management whenever there’s an appropriate occasion. Not only is this a great growth and development opportunity, but also a way to provide recognition for your people. It also helps build that all-important trust.
  • One-on-One Time. The annual review shouldn’t be the only time you talk with your people. Schedule one-on-one face time with each of your team members. It gives you the opportunity to make sure projects are on course and (more importantly), it gives each of your people a chance to share ideas and concerns directly with you (remember to listen).

And one more thing. Have Fun. Nobody ever said business has to be serious 100% of the time. Find ways to have fun with your teams. Hold teamwork exercises. Throw a party. Create interesting project names. Incorporate team building into your meetings.

So, you still want to be a leader? Here are some steps you can take that will help you along the way to help you be seen as a leader and to position you for future success in that role:chart for leadership article by Gary Kaplan

Leadership is trial by fire. You learn by observing, reading and trying things for yourself. If you remember only one thing from this article, remember this: the key thing to being a good leader is authenticity. So, you have to use the advice that works with your personal style and ignore the advice that doesn’t. Hopefully one or two things in this article will help.

About the Author

 Gary Kaplan  is President of XL Group’s North America Construction team, and by all accounts, a great leader. He has also served as an interim leader for the environmental group and the distribution management teams of XL Group’s insurance segment. Gary can be contacted at



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