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?

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:
Connect:
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.
- Know everyone’s growth goals.
- Know everyone’s career goals.
- Align challenge with growth and career goals.

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.
- Share opportunities.
- Listen to employees.
- 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.
I think that there is a bit of an elephant in this room. In most organisations, the degree of depersonalization means that individuals’ growth and career goals are irrelevant. The conversation goes “We are going to grow the organisation and this is what you’re going to do…”
In over 35 years in my industry, I have never been asked my career or growth goals. Those questions were asked of people who had been picked out in the leaders’ image for “Bigger Things”. For everybody else, you get what you’re given and like it.
I have been known to tell folks working for me: “I am about to throw you into the deep end. I will be standing here with a life preserver. But I doubt I’ll need it, because you are ready for this.”
Because a challenge that I overcome for you isn’t really a challenge.
How might managers challenge people and help them thrive at the same time?
Managers need to start by explaining the demands that are happening in the marketplace. Customers are demanding. They want more, better, and faster. They want better and better products, services, and experiences. The competition keeps improving. It’s a demanding business environment.
The challenges that managers present to their employees needs to tie to what happening in the marketplace. “Our products, or lead-times, or services must improve because the customer is demanding it.”
Help people thrive. Performance is a function of Knowledge/Skills + Motivation + Resources – Interference. The manager needs to diagnose what the employee needs to thrive. Each employee is unique. Some need skills, others need more motivation or better resources etc. Sometimes the manager needs to remove the roadblock that is holding the person back.
Great post, Dan! I love how you mention CONNECT as the first thing under how-to.
It’s so very important for any leader to connect with each person they’re leading. When I observe a new manager struggling or who just doesn’t seem to “get it”, not having made good connections with their direct reports (and often not with others either) is usually at least part of the issue. A manager who fails to make people connections will be just another not-so-great manager in a vast ocean of them.
Nobody wants to be not-so-great. If your own immediate leader/superior isn’t helping you grow as a leader, then drive your own destiny by connecting with others who can help you become a better leader. You need to make it happen so you can create more positive impact in the future, especially for your direct reports who deserve a good leader to help them grow.
The team around you is the secret to your success. Connect with each person, learn what makes them tick, help them grow in their desired career direction and commit to helping them be successful now and in the future. IMO the best feeling as a leader is to know in your heart that you helped another person be successful. Nobody else even has to know, but you knowing it in your heart makes it real. Their success is how you achieve success.