Creative team managers: ask this one critical question to help employees solve problems

Photo by Austin Distel on Unsplash

At my first “real” job out of college, someone gave me a piece of advice that’s stuck with me ever since.

“If you need to go to your manager with a problem,” they said, “bring at least one idea for a solution. Even better if you can bring three solutions.”

I was floored. Wasn’t solving problems my manager’s job?

After grudgingly taking their advice, I began to learn the sometimes-difficult steps that lead to independence and deeper responsibility.

But it wasn’t until many years later that I recognized the wisdom in this tactic. So many people believe, as I did, that a manager’s sole responsibility is to solve problems for their team. And it is—to an extent.

A creative individual solves problems every day

A creative team, like a team of writers, is made up of people whose daily lives are all about solving problems.

All writing is ultimately a question of solving a problem.

William Zinsser

Writers—copywriters, UX writers, technical writers, novelists, journalists, medical writers—spend entire days, years, and lifetimes solving problems of communication, information, structure, hierarchy, word choice, tone, readability, discipline, inspiration, motivation, entertainment, comprehension, and, of course, metrics.

Learning to creatively solve problems—or come up with ideas that could potentially solve problems—is one of the most critical skills a creative person can nurture in their career.

How can managers of creative ICs (individual contributors) develop this skill in their team members?

One approach could be to tell your employees that they can’t come to you with a problem unless they have a solution. The downside to this approach is that it’s inherently un-empathetic and potentially cruel. I would never recommend doing this.

Another approach—which I strongly prefer—is to ask good questions that can help guide your ICs to develop their creative problem-solving skills themselves.

Here’s one seemingly simple question you can start with.

I was introduced to this question in the book The Coaching Habit by Michael Bungay Stanier (not an affiliate link). The book is an absolute gem for any manager, but some of the tactics he provides completely changed my life.

This one stands out, in particular, for the way it encourages the employee to think about the heart of the problem that needs to be solved.

What’s the real challenge here for you?

The best thing about this question is that it removes from the conversation any preconceived ideas you (as a manager) might have about the situation.

For example, say you manage a writer. This person comes to you complaining about a project they’re working on. They say they’re getting tough feedback that they can’t interpret correctly, their product partner wants to do all of the writing themselves, and none of their work seems to suit the needs of the project itself.

Your first thought might be that the project team needs to work on making sure the brief or project doc is comprehensive before the project kicks off, so the whole team can make sure they’re working toward the same goal.

But after asking, What’s the real challenge here for you?, you might come to understand a different situation. Turns out the individual is feeling stuck because their product partner pointed out that the writing had typos.

“But it was just the first draft!” the writer exclaims. “They should know they were supposed to review for messaging, not final copy!”

Ah-ha. The real challenge for this person isn’t that their goals are different from their project partner’s goals. The real challenge here is the review cycle hasn’t been clearly defined for the writing.

Maybe the next step is for the writer to define the goals of each review. Maybe it’s up to you as a manager to establish guidelines for reviews in the first place. Maybe all that needs to happen is a 10-minute sync with the project manager to re-align on what each stage of the review cycle means.

Work at it, together

When you start with the intent to discover the real challenge for your employees, you can work with them to get to the real heart of the problem that needs to be solved. Allowing your employee to first consider the depth of the problem at hand can put them on the right path to solving it gracefully.

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