How to become the most interesting person in the room

9/10/2020
 

I was talking to a client who is currently a c-suite executive in a Fortune 500 company. As often happens in large political environments, there has been a major restructure, and after discussions, she decided her best move was to leave.

My client, I’ll call her Laura, is fortunate that she has a strong track record of successes and a financial cushion. That gives her the luxury of time to think about her next chapter. She doesn’t know exactly what she wants to do next, but she knows categorically what she doesn’t want to do: more of the same.

She asked me what she should do: Work on her resume? Call a headhunter?

As an executive coach, I have helped many clients through various career transitions. My advice surprised her and it may surprise you: become an exponentially more interesting person.

Successful executives tend to follow the well-trod path up the career ladder. As you get more senior, you naturally shed many things you consider superfluous. Your professional and personal networks narrow and you end up knowing mostly people from your industry. As you get busy with work and family responsibilities, external interests and hobbies fade.

So at a certain point in your career, you’re simply single-threaded. And you are very good at the things you’re very good at, so of course, executive recruiters will call you for the jobs that require those things. And since you enjoy being successful and having all the right answers – who can blame you? – You’ll be tempted to go after and then accept that same old job.

Resist the temptation. Take the time to refresh your perspective. When your inputs are the same, your outputs are the same. So if you want different outputs, find fresh inputs. Focusing on becoming exponentially more interesting will mean different things to different people, but it definitely won’t mean more of the same.

Here are some ideas to help you get more interesting.

1) Proactively find new hobbies. Many of my clients are very successful startup founders or C-Suite executives in Fortune 500 companies. Their most common answers to the question “what are your hobbies?” is “work is my hobby” or “my kids are my hobby” or simply “between work and family I don’t have time for hobbies.”

I’m sympathetic. But if you’re trying to get exponentially more interesting, it’s essential that you have things to talk about besides work. Hobbies give you that. They also help you open yourself up, build your skills in, well, building new skills, and help you make connections between disparate ideas.

Do something you’ve never considered before or scratch an itch by finally taking up the activity you’ve been putting off. Try something like archery, bird-watching, bee-keeping. Train for a 10K or decide to do the 30-day happiness challenge. Take up a musical instrument or find a meditation group, even if it’s virtual for now.

Hobbies stretch your mind, which helps you with lateral thinking. New pastimes also give you something interesting to think about and talk about, so you have a new reservoir of stories at the ready - you will never know who else is into axe-throwing or CrossFit until you start talking about it.

2) Build a broad network. When was the last time you had a deep conversation with someone who was completely outside of your field? If you’re a business executive you may have never met an opera singer, a storm chaser, or an astronaut.

I’m not suggesting that you will suddenly discover a singing voice that you had been hiding from yourself and the world or drop everything to prepare for your NASA physical. But meeting people very different from yourself exposes you to a distinctive worldview. New people tell you new stories. New people know different people. Ultimately, having a variety of people in your network helps you connect the dots in a different way, and all of that makes you more interesting.

You can find new people by asking your friends to connect you to the most interesting people they know. Be explicit that you are not asking to network to find a new job. You just want to expand your horizons.

Certainly, when you take up your new hobbies, you will also meet interesting people. For example, I know the CEO of a media company who is in the process of learning to be a pilot, something that has been on his bucket list for a long time. Not only is he stretching himself, but he is also connecting with people around the world who are also pilots. Through these contacts, he’s learned a lot more about flying as well as about other cultures and attitudes.

3) Date new jobs. Many people assume that when changing careers they should take a few months off, find their new full-time position, and start. Instead, consider experimenting with a few different opportunities and create a portfolio. This approach has multiple benefits. It allows you to try new things without committing fully to any of them. It allows you to build new skills that can help fill in your gaps and also give you compelling things to talk about.

Another benefit to this is that it takes the pressure off of finding your passion or your dream job. Having a portfolio sets up everything as an experiment. Your focus can be on learning and growing rather than hitting the ground running.

My client Rebecca did this when she retired as the CFO of her tech company. She was tempted to take the first offer she got as the CFO of a private equity-backed company. Instead, she decided to serve on a non-profit board, fill in part-time as the CEO of an animal shelter she supported, and did some consulting on corporate strategy. As a result of her new experiences and the people she met, within 18 months she became the CEO of a fast-growing health-care startup and landed a board seat. She did not take a linear journey and her choices came with some risk. Unlike the initial CFO role, which was predictable, she didn’t know where her choices would take her, but ultimately they led her to much better career adventures.

4) Read widely. Reading new things helps you think differently. If you normally read fiction, try history. If you normally read business books, how about self-help? You can go through a list of classics or school yourself in science fiction.

Expand your definition of “reading” to include audiobooks and podcasts. Either way, expose yourself to new information.

Once you do that, find a way to exchange ideas with others. Join a book club or start one. A colleague of mine has a group that reads ten pages per week of an interesting but difficult book – very manageable – and then gets on a zoom call together Sunday evenings to discuss it. That helps them mine the ideas in the book, and the discussion helps them get to know new people and develop lateral thinking.

5) Find out what’s interesting in others. You become more captivating when you pull out what’s engaging in other people. You do that when you are direct in complimenting them, talking about their interests, and using what they say to find points of commonality.

Ask people deep questions and listen to the answers. For ideas of interesting questions, you can download my list here. Also, follow your curiosity and don’t be afraid to ask someone a question that is more personal. I once asked someone how she met her husband and it turned a stiff conversation in an open discussion.

Then, to be really captivating, make a note to follow up on what they told you the next time you interact. People love feeling seen, and you remembering the conversation will go a long way towards you being memorable.

Thinking about ways to make yourself exponentially more interesting will lead you to a richer life. It will also help you generate new ideas and open up new pathways for your life and career.

 
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