A Trap for Leaders: Don’t Let Your Team Delegate Their Thinking To You

Annette Court has extensive experience as a CEO of major insurance companies – Direct Line Group and Zurich FS – and she is currently chairman of Admiral Insurance. She’s also a colleague of mine at Merryck & Co., where we mentor senior executives and work with leadership teams. In our conversation, she shared smart insights about the challenges that she sees often in her work with leaders.

Q. What are the most common themes that come up in your mentoring work?

A. One is around how people are using their time, particularly about how much time they’re spending thinking about short-term stuff versus longer-term strategy, and how much time they’re spending doing the things they should personally be doing compared to doing their people’s jobs.

It’s very easy to get pulled into the day-to-day issues without standing back and examining what’s really important ⁠— what are my real responsibilities, what do I really need to achieve, and what are my key objectives? – and whether I’m spending sufficient time on those.

Another is how people think about their teams and how good they are. When I ask people about their team, they’ll usually say, “My team’s great, they’re fantastic, I’m really happy with my team.”

    “After that exercise, they often say that maybe their team isn’t as good as they thought.”

But then I’ll ask them to go through each member of the team on a flip chart, in terms of their performance, their potential, and then we put a check mark or a cross or a question mark after their name. After that exercise, they often say that maybe their team isn’t as good as they thought.

Q. That must be a tough moment. What do you advise them at that point?

A. I’ll ask, “What were the times in your career when you had the most energy, you felt most excited?” The common theme is that it’s usually the times when they were given a big new responsibility, they were on a massive learning curve, and they were given a lot of autonomy. So I’ll say, “Think about that when it comes to how you’re leading your people. You need to be giving them those kind of opportunities, that space to learn and develop.”

Q. Back to your earlier point about time management, what are the traps people fall into?

A. People are completely flooded with e-mails and feel like they need to go through them before they move on to anything else, rather than saying, what are the times of day when I have the most energy to tackle the really big meaty things?

The analogy I use – and I didn’t invent this – is of a jar with pebbles and sand. If you’ve got a jar and you fill it up with sand, the pebbles won’t all fit in the remaining space. But if you put in the pebbles first and then put in the sand around it, it will all fit. In this analogy, the pebbles are the big things and the grains of sand are the e-mails and smaller tasks.

Another time challenge for leaders, particularly for the CEO, is understanding that when leading change, you need to communicate the same message again and again and again. Some people think, “Well, I said that, I told them that, so let’s move on.” They underestimate how much they need to continuously send the message.

The other challenge I work on with executives is getting them to really listen. Sometimes leaders who have been given greater responsibility feel that the onus is on them to be more directive and to show how much knowledge they have about something, rather than encouraging their people to come up with ideas. So people end up delegating their thinking up to the leader, rather than the leader delegating to their team.

Q. What are some of the most important leadership lessons you’ve learned in your own career?

A. I feel very lucky that people have spotted things in me that I haven’t known myself, and encouraged me to take on big responsibilities. I wrestled with the imposter syndrome at times – thinking, “Are you sure? I don’t know any of this stuff?” – but you learn. So I always try to help other people take those risks, as well, and get the fears behind them.

Q. In all your years of hiring, what’s the approach you’ve developed?

A. I ask them about their biggest learning experience. So much has changed in the world of work, and I want people who can continue to adapt and change and learn.

Q. And in your work on boards, you’re now assessing CEO candidates. What is the X-factor you’re looking for from those leaders?

A. To me, the X factor is whether people really want to work for that leader, and how good they are at developing their people. So I ask them about their teams and the people they’ve led, and I’ll ask them, “Why should people be led by you?” I’ll also ask them about key decisions they’ve made and how they made those decisions. I’m listening for whether they were involving others in making those decisions.

Q. What were some other early influences for you?

A. I learned a lot from my grandfather and what he achieved. He started off in a company in the early part of the last century as a typesetter and ended up being a director of the company, and he got that through working hard. He would say to me, “If you work hard, you can achieve anything,” and that instilled in me a real work ethic. He also instilled in me a real curiosity about things and a real desire to learn, to push yourself and to try stuff.

    “I assumed that being a woman in a leadership position was just normal.”

The other interesting thing was that his boss was a woman, and that was extremely unusual in those days. But I didn’t know that was unusual. I just knew that his boss was a woman. I met her and she was a kind of role model in my life, and I assumed that being a woman in a leadership position was just normal. It wasn’t until later that I understood how unusual that was.

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