“Guess what I’m thinking” management

This happens most often in the creative field.

A manager gives a designer or writer an assignment. The designer or writer, or team, go away to work on the assignment. When they think it’s ready, they present their work to their manager, only to hear:

“Ummm, I don’t think it’s quite there, yet.”

There’s nothing actionable about that feedback. All it tells your people is that whatever they produced, it isn’t something you like. It doesn’t give them any guidance they can use. It doesn’t tell them the tone is too lighthearted, or the copy is too conversational or you’re concerned it may not resonate with the target audience because they tend to be “this” way and the piece is kind of “that” way.

Working for managers like this can be very frustrating because you have to keep coming back to them until you a) luck into getting it right, b) they’re finally able to tell you something you can work with, or c) they end up doing it themselves (which happens far more often than you would expect).

As a manager, a good way around this is to give your team a problem to solve and give them the freedom to solve it.

Don’t have any preconceived notions about how you want the problem solved, and keep an open mind about what is presented to you. There are many ways to solve a single problem, and you have to be prepared to be shown something you had never considered.

The freedom to solve a problem also comes with the freedom to fail. Not everything works. A good manager will understand the context of the assignment and whether it’s an opportunity to try something innovative that may fall flat or whether it calls for a more conservative approach. If there’s room to fail, it’s important to let the team know it’s OK to take a chance.

Either way, if you let the team develop and execute a solution, or a few solutions, they will be more invested in the outcome, which will usually lead to more research and better work because it represents them – not their execution of your idea.

If you need to stay close, a few well-placed check-ins will tell you if they’re on the right path. If not, you’ll still have plenty of time to course correct.

If you’re going to hand an assignment to a team, and you’re not on it, then you have to realize you’re handing over the keys. This means it’s your responsibility to provide as much clarity and background around the problem as you can so you give the team the best chance to develop a good solution.


If you don’t trust your team to do it, then you should just do it yourself.

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