How to Challenge Confident Creatives

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Dear Dan,

I manage a large team of creatives who range from 20 to 70 years of age. I fall in the earlier category.

Part of my job is to lift the quality of their work for consumers. That means pushing back and providing constructive criticism and or feedback wherever I can.

I fear that every time I push back it falls on deaf ears because we coddle a lot of the time.

I usually ask:

  • Is this your first idea?
  • Do you believe this is the best work you can produce?

I have an incredibly confident and assertive team who always say their work is their best it can be. They seem to value their peers opinions above me. I’m starting to question my value even though I know I’m good at what I do.

My question is, are there better ways to get greater performance out of creatives when you have far less experience than they do?


Starting to Doubt

Dear Starting,

Congratulations on leading a team of diverse creatives. I’m going to jump right in.

#1. Don’t be coy about your intentions.

“This is creative work. Let’s discuss how we might make it even more creative.”

#2. Explore ways to ‘pull with’ rather than ‘push back’.

Push back applies when others do something wrong. Your situation is about improving something that is already good.

  1. Use ‘we’. How could we take this to the next level?
  2. Leverage creative colleagues.
    • Ask them to seek input on improvements from someone on the team. Who might make this even better?
    • Ask, “If you encouraged someone on the team to take this to the next level, what would you say?”
  3. Leverage the team. Bring a project to the team and ask for suggestions and improvements. Do this in a positive way, not as punishment. Make it fun.

#3. Improve your questions.

The questions in your email call for ‘yes or no’ responses. Ask questions that invite conversation.

  1. What if …? (You were designing this for children? (Insert gender, race, ethnicity, age, education, handicap, or industry.)
  2. In what ways might we …?
  3. I love how you did this. What might you add to that?
  4. What would you do if the budget for this project was cut in half?
  5. If you could make this even more creative, what would you do? (Emphasize, IF YOU COULD.)
  6. What are some dumb ways to improve this?
  7. If you were just starting this project, what would you do?

#4. Don’t use the same questions every time.

#5. Try a directive approach.

“Take this project to (name a team member). Tell them they have 15 minutes to suggest 5 improvements.”

Strategies that include others are given with three assumptions.

  1. The team believes in reaching high.
  2. Team members trust each other.
  3. Seeking suggestions from others is valued.

#6. Ask team members how you might best challenge them to take their work to the next level.

“You are all really creative. I’m looking for creative ways to help us all bring our best to the work we do. I want to respectfully challenge. What are five ways I might respectfully challenge you?”

You might ask, “How can we make it fun to make improvements on our work?”

#7. Ask them to teach you.

Bonus: Ask team members how they might challenge themselves to take their work to the next level.

You have my best,


How might leaders challenge confident creatives?