Most of us have been taught that being easy to work with is a leadership strength. Don’t create conflict. Don’t question the plan. And definitely don’t challenge your boss.
But new Zenger Folkman research tells a very different story.
In this episode of 90th Percentile Leadership, BreAnne Okoren and Joe Folkman examine data from 139,267 managers, each rated by an average of 13 people across 60 leadership behaviors. The finding surprised even us: the leaders who constructively challenge others the most are also rated as the most effective—and the data showed no point where constructive challenge became “too much.”
But there’s an important distinction between being a constructive challenger and simply being critical.
BreAnne and Joe explore what separates the two, why intent and timing matter, how to challenge a boss without damaging the relationship, and why the best challengers leave people with more energy—not less.
Because extraordinary leaders aren’t the people who agree with every idea.
They’re the people who know how to make good ideas better.
1. Constructive challenge is strongly connected to leadership effectiveness.
The research found no ceiling: as leaders became better at constructively challenging others, their overall leadership effectiveness continued to rise.
2. Challenging isn’t the same as criticizing.
Destructive challengers focus on what’s wrong. Constructive challengers look for what’s possible. The difference often comes down to whether you’re trying to improve the idea or prove that you’re right.
3. The best challengers create energy rather than drain it.
Questions like “How could we make this stronger?” or “Have we considered another approach?” invite people into better thinking instead of putting them on the defensive.
4. You can challenge your boss without undermining them.
Timing, tone, and setting matter. Constructive challenge isn’t about embarrassing someone or demonstrating how smart you are. It’s about improving the outcome.
5. Don’t just point out the problem—offer a better possibility.
This week’s 90th Percentile Practice is simple: in your next meeting, replace “I don’t think this will work” with “Here’s another approach we might consider.” Small shifts in language can change how people experience your challenge.
Would you rather work for a leader who never challenged a bad decision—or one who respectfully challenged ideas that could make the team better?
Why?
We want to hear what you think. Email your answer to info@zfco.com. We may feature some of our favorite responses in an upcoming episode.
And here’s another question we’re curious about: Have you ever challenged a boss and had it go well—or badly? What made the difference?
Send us your story at info@zfco.com. We’d love to hear it.
Interested in bringing Extraordinary You to your organization?
Visit Zenger Folkman to learn how Extraordinary You helps individual contributors identify their strengths, accelerate their development, and make a greater impact—long before they step into formal leadership roles.
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BreAnne
Most leaders think being easy to work with is a strength.
They avoid conflict.
They don’t question decisions.
They smile in meetings and save their opinions for the parking lot afterward.
But Joe…your newest research says that may actually be one of the biggest mistakes leaders make.
In fact…
The leaders who challenge others the most are also rated as the most effective leaders.
That feels completely backwards.
Are we telling people they should become more argumentative?
Joe
Not at all.
I think most people have been taught that great leaders create harmony.
They don’t rock the boat.
They don’t make people uncomfortable.
Especially if they’re challenging their boss.
Most people assume:
“If I disagree, I’ll damage the relationship.”
“If I question the plan, I’ll look negative.”
“If I challenge my manager, it could hurt my career.”
Those fears aren’t irrational.
We’ve all seen people who challenge everything.
Nobody enjoys working with them.
So, people conclude…
“It’s safer to stay quiet.”
BreAnne
Exactly.
I think most listeners are probably picturing that one person in every meeting.
Before anyone finishes a sentence they’re already saying…
“That won’t work.”
Nobody wants to become THAT person.
So is your research really saying…
Challenge people more?
Joe
No.
It’s saying something much more nuanced.
It isn’t about challenging more.
It’s about challenging differently.
BreAnne
So let’s get into the research.
What did you actually study?
Joe
We looked at 139,267 managers, each rated by an average of 13 different people, and measured overall effectiveness across 60 leadership behaviors.
The question was surprisingly simple.
Can leaders challenge too much?
Would there be a point where challenging people starts hurting effectiveness?
BreAnne
I actually would have guessed yes.
Too much challenge sounds exhausting.
Joe
That’s exactly what we expected.
Instead…
We found no ceiling.
As leaders became stronger at constructively challenging others…
their overall leadership effectiveness continued climbing.
Every step.
There wasn’t a point where it leveled off.
There wasn’t a point where it became annoying.
It just kept increasing.
BreAnne
That’s fascinating.
Because I think listeners hear that and immediately picture someone who’s constantly criticizing everyone.
But that’s not what you’re measuring.
Joe
Exactly.
The key word is constructively.
Constructive challengers ask…
“How could we make this better?”
Destructive challengers say…
“That will never work.”
Those sound similar…
but emotionally they’re worlds apart.
BreAnne
So it’s less about disagreement…
and more about intent.
Joe
Exactly.
One person is trying to improve the idea.
The other person is trying to win.
People feel that difference almost instantly.
BreAnne
One thing I loved from your article was this idea that constructive challengers actually leave the room with more energy, not less.
That’s such a different picture than the stereotypical devil’s advocate.
Joe
Yes.
Because the goal isn’t proving someone wrong.
The goal is making the idea stronger.
The best challengers ask questions like:
“Have we considered another approach?”
“What’s another possibility?”
“What if we looked at this differently?”
Instead of…
“Why would anyone do that?”
BreAnne
Okay…
I’m going to push back.
Let’s say I’m an HR executive listening.
I completely agree with the research…
but I also know there are organizations where challenging your boss really can hurt your career.
What would you say?
Joe
I’d say the fear is real.
But the research suggests something interesting.
When challenging comes from genuine intent to improve outcomes…
people generally see it as engagement—not insubordination.
BreAnne
But timing matters, right?
You don’t interrupt your CEO in front of 500 employees.
Joe
Exactly.
Constructive challenging isn’t about embarrassing people.
It’s about helping them.
Sometimes that’s in the meeting.
Sometimes it’s afterward.
Sometimes it’s through questions instead of statements.
BreAnne
I also think there’s a misconception that challenging means having all the answers.
Sometimes it’s simply saying…
“I don’t think we’ve thought through this risk.”
Joe
Exactly.
Great challengers aren’t always the smartest person.
They’re often just the person willing to ask the question everyone else is thinking.
BreAnne
Here’s another concern.
Couldn’t people hear this episode and think…
“Great. I have permission to criticize everything.”
Joe
That’s why intent matters.
Ask yourself:
Am I trying to improve the outcome…
or prove I’m smarter?
Those are completely different motivations.
BreAnne
That’s probably the easiest self-test.
If people leave the conversation feeling energized…
you’re probably doing it well.
If they leave feeling smaller…
you’re probably not.
BreAnne
Let’s finish with this week’s 90th Percentile Practice.
What’s one thing listeners can actually try this week?
Joe
Here’s a simple challenge.
In your next meeting…
Don’t identify a problem.
Identify one better possibility.
Instead of saying…
“I don’t think this will work.”
Try saying…
“Here’s another approach we might consider.”
Or ask…
“How could we make this even stronger?”
That subtle shift changes everything.
Over time, people stop seeing you as a critic.
They start seeing you as someone who improves ideas.
BreAnne
I love that because anyone can try it today.
You don’t need a new title.
You don’t need permission.
You just need a better question.
BreAnne
We’ll leave you with today’s 90th Percentile Question.
Would you rather work for a leader who never challenged a bad decision…or one who respectfully challenged ideas that could make the team better?
Tell us why.
We’ll feature some of our favorite responses in next week’s episode.
