Managing Resistance: How to Reset Expectations With Challenging Direct Reports

Edited By Brandi Neal, Radical Candor podcast writer and producer, and director of content creation for Radical Candor. This article about how to reset expectations with challenging direct reports has been adapted from the Radical Candor podcast S7, Ep. 8 transcript about the same topic.

Managing a resistant direct report can be one of the most frustrating challenges for a leader. When someone consistently resists engagement, questions every directive, and undermines leadership, every interaction can feel like an uphill battle.

Kim Scott, author and co-founder of Radical Candor, and Amy Sandler, principal coach and podcast host at Radical Candor, recently received a question from a manager facing this exact dilemma.

Listen to the episode to hear Kim and Amy roleplay solutions for managing a challenging direct report.

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Table of Contents

How to Reset Expectations with Challenging Direct Reports

The Question:

I have a team of 40 people. I've done all the usual things to engage my team — weekly 1:1s, praise publicly/ challenge privately, been approachable, arranged team events, given people opportunities to step up, provide feedback and encourage the team to give me feedback and most of the team love it. I get fantastic engagement scores.

But, one of my managers is a young manager in their early 30s and they will just not engage and as a result their team is siloed. I've tried talking to this person, providing gentle coaching and very direct feedback and they will not listen, and actively undermines me and other members of the management team.

I've offered mentors, training, including this person in decisions, and leaving them be. I've given them direct instructions which they question in detail "just so they understand." They're intelligent. They certainly understand exactly what they’re doing.

The manager blames me for two team members leaving. One of whom was good but didn't want to do the job and had a tantrum when they didn't get the promotion they thought they were entitled to, and the other we had many complaints about. I honestly don't know what to do. This manager is like a cancer and I know it will make my life an absolute misery if I try to put them on a performance plan. Please help — I'm at my wits' end.

Their advice? Resetting expectations by practicing the principles of Radical Candor.

“I’ll make a few assumptions based on the description: 1) They’ve already tried multiple approaches over a reasonable period of time 2) The manager’s behavior is having a negative impact on team dynamics and results 3) They have have documented evidence of the issues described,” Scott said.

“First, let’s acknowledge that this situation is affecting them personally — being ‘at your wits’ end’ is a clear sign that this needs to be addressed, not just for the team’s sake, but for this person’s wellbeing too.”

However, she added that it’s important to remain centered and approach this situation with clarity, focus, and a plan for a path forward.

Step 1: Solicit Feedback First

Before jumping to conclusions, Scott emphasized the importance of first understanding the root of the issue.

“One thing that could be going on is that [the direct report] has some criticism for [their boss] and the leadership of this company, and that criticism might be worth hearing,” she noted. Encouraging direct reports to voice concerns fosters an environment of trust and transparency.

To open the conversation, Scott suggested a direct approach: “I feel like you don’t respect me and you don’t respect the other managers at this company. And it’s really hard to move forward. I want to know what I have done to earn this.”

Sandler added that when managers become frustrated, they risk assuming negative intent. “When we feel so frustrated, we might start making assumptions about intentions,” she said, highlighting the importance of maintaining an open mindset.

Step 2: Identify Whether the Problem Is Salvageable

Once feedback is solicited, the next step is to assess whether the issues can be addressed. Scott outlined three potential scenarios:

Legitimate Criticism – The direct report has valid concerns about management decisions, which, if addressed, could improve engagement.
Authority Issues – The individual has unresolved issues with authority and may be unwilling to cooperate.
Toxic Behavior – If the person is actively undermining leadership and harming the team, corrective action is necessary.

When someone isn’t hearing feedback, Radical Candor teaches us to move further out on the Challenge Directly dimension while maintaining Care Personally. The fact that this manager questions instructions “just so they understand” suggests they’re not actually listening to understand, but rather to find ways to resist or undermine.

“If this person is just an asshole,” Scott said bluntly, “it’s better to have a hole than an asshole.” This means potentially firing the person.

Step 3: Establish Clear Expectations and Consequences

If a direct report continues to challenge authority in a destructive way, managers must shift from coaching to accountability. “If we can’t get back on track, we’re going to have to make some changes,” Scott advised.

She suggested the leader have a direct conversation using the CORE feedback model. For example: start by citing the specific context (e.g., “When you question instructions in detail”), make your observation (“you often end up not implementing what was agreed”), describe the result (“this creates silos in the team and undermines the management team’s effectiveness”), and state your expected next steps (“I need you to either commit to implementing our agreed approaches or openly share your concerns so we can address them together”).

If they continue to resist after this clear feedback, it’s time to move to more formal performance management. This may involve putting the employee on a Performance Improvement Plan (PIP) to document behavioral expectations and consequences. A PIP isn’t meant to be punitive — it’s meant to provide absolute clarity about what needs to change and by when.

And while the person asking for help said putting this manager on a PIP “will make my life an absolute misery,” avoiding it is actually going to make everyone’s lives more miserable in the long run.

When implementing the PIP, be sure to:

Document specific instances of the behavior and its impact
Set clear, measurable expectations for improvement
Provide a reasonable timeline for change
Outline specific consequences if improvement isn’t made
Keep HR informed throughout the process

Step 4: Create a Culture of ‘Listen, Challenge, Commit’

For teams to function effectively, employees must be encouraged to challenge decisions but ultimately commit to them. “Listen, challenge, commit,” Scott explained.

“It’s your job to listen and understand a decision well enough that you can explain the reasons for it to others, even if you disagree. Then, challenge it directly with your boss. And finally, commit to the decision once it’s made.”

Sandler reinforced that an anti-authoritarian stance alone isn’t necessarily a problem—some of the best employees push back against authority. However, there’s a difference between healthy skepticism and toxic resistance.

“You can be skeptical of authority and still maintain common human decency and respect,” she said.

Step 5: Know When It’s Time to Move On

If a direct report refuses to engage productively despite clear expectations and consequences, it may be time to part ways.

By allowing this behavior to continue, the boss is potentially doing a disservice to everyone else who is engaging positively and contributing to the team’s success.

“There comes a moment on too many teams when the jerks begin to win,” Scott warned. “And that’s the moment when the culture begins to lose.”

By fostering a culture of Radical Candor—caring personally while challenging directly—leaders can navigate these difficult situations with confidence, ensuring both their teams and their company thrive.

Need more advice? Join our Radical Candor Community, or email us at advice@radicalcandor.com.

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