How to Challenge People

Every manager wants to know how to challenge people.

Competitive business environments require greater productivity and efficiency. High expectations are table stakes.

But how might you challenge people and create an environment where they thrive?

How to challenge people. Image of a giraffe reaching high.

Challenge and growth:

When Julie Winkle Giulioni asks managers about their growth experiences, she often hears about being thrown into the ‘deep end of the pool’ and learning how to swim.

It’s hard to imagine growth apart from challenge.

Think of your growth experiences. How many of them involved challenge?

How to challenge people:


Don’t randomly challenge people. No one wants to improve today if tomorrow you simply demand more. We’re all sick of the lousy managers who constantly pressure people for more. Exasperated employees think, “It doesn’t matter what I do, it’s never enough.”

Any fool can yell, “Work harder.”

Connect challenge to something relevant to an employee.

Everyone wants to grow. If you can help someone get better at something that matters to them, you’re a hero. People who don’t want to grow belong in jobs where growth doesn’t matter.

Link challenge to growth.

  1. Know everyone’s growth goals.
  2. Know everyone’s career goals.
  3. Align challenge with growth and career goals.
Image of a man pointing and yelling. Any fool can yell, "Work harder."

How to find linkage:

Effective challenge is a two-sided conversation, not a one-sided command.

“Even your best managerial intentions aren’t transmitted telepathically to your employees.” Julie Winkle Giulioni from, Promotions are So Yesterday.

  1. Share opportunities.
  2. Listen to employees.
  3. Collaborate on plans.

“Make challenge feel like an invitation, not an imposition.”

“Greater velocity, volume, and accuracy isn’t squeezing more work out of people. It’s squeezing more development out of work.” Guilioni

How might managers challenge people and help them thrive at the same time?

In her own words:

Author’s note: This post is based on Julie Winkle Guilioni’s new book, Promotions are So Yesterday, and our conversation.