5 Things You Need to Know If You Want to Be The Boss: Advice From an Insurance CEO

5 Things You Need to Know If You Want to Be The Boss: Advice From an Insurance CEO

To paraphrase Benjamin Graham, the former chairman of GEICO, you should avoid endeavors in which you have much to lose and little to gain. The insurance business is all about calculating risks and life is all about taking calculated risks. I probably know more than most about both, as well as how the two intersect in ourselves. It’s true that fortune favors the bold but as a CEO, I’ve learned that you won’t get anywhere if no one is following you. Here’s five maxims I’ve learned climbing the corporate ladder to the top while staying true to myself.

1. Don’t micromanage

We can’t control everything that happens in our lives, but it’s wonderful–and productive–to stop pretending that we can. When you have thousands of clients and dozens of employees, you learn that being the boss doesn’t mean bossing everyone around as much as it does enabling a productive, rewarding and inclusive workplace. If you can inspire people to work together and then step out of their way, great things will happen.

2. Be approachable

It’s easy to have an open door policy if your employees are too scared to step into your office. If you’re not approachable, you’ll probably end up only getting advice from sycophants or else people who are extraordinarily confident of their own opinions.

Working in a conservative industry, as I do, toeing the line usually means not hearing from progressive voices, which I would find unacceptable and unwise. Of course, employees should remember that their bosses may not be who they think they are–take it from me! I recently saw a memo from Tesla’s CEO Elon Musk, who happens to be the world’s richest human being and among the smartest, to his employees where Musk admitted that he was often wrong. Humility and a sense of humor both go a long way.

3. Be open to new ideas and encourage your people to challenge you.

There’s a big difference between insubordination and constructive criticism. Sadly, a lot of managers don’t know the difference. If you want to be the CEO, you’d better figure this one out, soon! You’ll also be better off having experience doing the jobs of the people you lead, so when they pose a challenging question or thought, you can give them a constructive answer.

 4. Don’t be afraid to get your hands dirty.

You’d be amazed how many billionaires wash their own dishes. Maybe that example is a little too on the nose for your taste, but successful executives and founders actively seek out ways to stay grounded in their lives and in their careers. Not only will doing rudimentary tasks get your head out of the C-suite, literally and otherwise, but getting your hands dirty shows your people that you’re a team player and that you know how to work! I guess a lot of executives are afraid that if they do anything but make decisions all day long, they’ll seem less leaderlike. I’ve found the opposite to be true.

5. Practice what you preach

There are so many cliches about being consistent that I won’t bother to repeat them here. However, it’s worth saying that if you want people to trust you, they cannot perceive you as being a hypocrite–or even as being dishonest with yourself. When I came out to my employees and clients as a trasngender woman, plenty of people thought that our business would suffer. Instead, our revenues increased 20% in less than three years and the bonds that I’d built with my best clients became even stronger. Trust me that your people respect integrity more than pandering.

Wynne Nowland is Chief Executive Officer of Bradley & Parker, an insurance firm based in Melville, New York.

John Norwood
John Norwood is best known as a technology journalist, currently at Ziddu where he focuses on tech startups, companies, and products.