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  • Writer's pictureJenny Kosek

What the James Lipton Challenge Teaches Managers

Updated: Oct 18, 2020

With the news that legendary interviewer James Lipton has passed away, my Facebook friends are currently passing around the James Lipton Challenge, where us common-folk get the opportunity to answer the thoughtful personal questions Lipton would pose to celebrities on his popular show, “Inside the Actor’s Studio.” One of Lipton’s questions is particularly interesting to me as a supervisor. Lipton would ask, “What profession other than your own would you like to attempt?”

It has been interesting, and surprising, to see how far from their current occupations so many of my friends would like to go. There’s an instructional designer who would pursue being an aesthetician. There’s a baker who would like to be a writer; a wildlife rescuer who would be a dialect coach; and a  social media manager who would rather be a freshwater lake tour boat guide (actually, that’s me).

Lipton’s question is ideal to ask during stay interviews or annual conversations, and I've done so. It helps gauge career goals, professional development needs, professional vision, and job and organizational satisfaction in one go. It’s an invaluable way to gain insight into your employees’ professional contentment and future aspirations. And however they respond, this question provides guidance for managers on shaping employees' development and growth. All of us daydream about tackling a new profession and the ones that interest us reveal a great deal about what we seek in our professional life. Few of us are going to abandon ship (a phrase I may need if I do pursue that tour boat guide life) and make a major career leap. But we can all reflect on what we need to be satisfied in our jobs, and we as managers can help ensure our people are receiving as much fulfillment as we can provide.

If asked this question, many people may answer that they would continue doing the same type of work, and that’s not a bad thing. If they have a true passion for the work and really love their job, that’s awesome. However, if they are in a professional rut, managers need to get to the bottom of why they feel stuck and figure out how to get them out of those work doldrums.  If they are in a professional rut and are fine staying in that rut because they never want to try anything new, we need to push them out of their box, for both of our benefits.

The employees who express interest in a total career shift are the most interesting, and should not be written off. When I have asked this question to my direct reports, many have surprised and delighted me by admitting that they would seek a position entirely different from their current role: the music educator who wanted to enroll in culinary school, the sales rep who wanted to become a repair technician, the administrator with aspirations to do marketing – these are the employees I was able to see in a new light. These are the employees with passion, and if they want to change career tracks entirely, managers shouldn’t see this as a negative. Passion is a fantastic quality to have in an employee, and failure to nurture a passion in the workplace always ends badly. Forcing these employees to keep doing the same rote tasks, day in, day out, will lead them to boredom, disillusion, and even toxicity. That employee’s passion can often be fed internally with a little creativity, increasing our chances of keeping that employee for years to come.

Listen carefully to the employees who see something different for themselves, and think long and hard about what that reveals about their professional needs. Then, get creative about providing it. In the twenty-first century, that’s easier than ever to do, because successful organizational structures no longer support black and white, linear career trajectories. Today, career paths can be horizontal; they can loop back on themselves, go diagonally, or even simply blur. Twenty-first century organizations are responding to workers’ needs and aspirations by being flexible to the notion of creating new positions, allowing more hybrid roles, and being more fluid and responsive with cross-training opportunities.

For example, if asked what career she would attempt other than her own, an AR rep responds with, “I’d apply for marketing jobs,” she is telling me she wants more opportunities to be creative and work on more public-facing projects. Well, why can’t she? If her plate is overflowing with AR tasks, maybe there’s an opportunity to delegate some of her projects to a junior finance employee. That could free up a few hours a week for this employee to collaborate with a PIO and stretch her creative muscles. She’ll be more fulfilled and more likely to stay, and the junior employee will have an opportunity to step up; literally, everyone wins. Let’s not get hung up on job descriptions here – job descriptions can be changed if needed, and “other duties as assigned” certainly covers projects outside of their department that an employee might be excited to tackle if the organization will benefit from improved retention and higher job satisfaction.

My baker friend who wants to write more could be composing content for his company’s website. The instructional designer with aesthetician aspirations is obviously interested in health and wellness, so get her on the company’s wellness program committee. Regardless of how far-fetched the career shift seems, the employee is dreaming of it because there’s something about it that really excites them. How can that excitement be leveraged in their current role? Ultimately, good managers aren’t only leaders, but supporters, shapers, and guides. Ask your employees James Lipton’s question this week, and then ask yourself: what are you doing to keep your employees fulfilled?


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