How to Handle Employees Who Challenge Everything

Every manager encounters them: the direct report who finds fault with every idea, decision, or initiative. While healthy debate strengthens teams, chronic challenging without openness to constructive discussion can derail progress and damage relationships.

The key question is how the manager can shift the conversation from criticism to collaboration. This process begins with the manager regulating their own emotions around the situation and behavior. This is required, because part of the solution starts with the manager.

Basic Tools

Acknowledge the employee’s analytical strengths. These employees often spot genuine risks others miss. However, make it clear that their insight into problems is part of the equation.

Investigate the reason for their approach. Frame it positively: "I value your critical thinking, and notice that your feedback is often negative. Have you noticed this? Is there something going on that drives this response.” Be specific about behavioral changes you want to see, “I need you to be open to brainstorming to help us find positive solutions."

Get curious. When they raise objections, respond with "Yes, I hear your concern about X, and what solutions do you propose?" This pivot forces them to think beyond critique toward constructive problem-solving. Set the expectation that every challenge requires them and everyone on the team to own the challenge and consider potential solutions.

Include them in the front end of the decision-making process. Collect input from all those involved and potentially affected, including your challenging team member. Then make your decision.

Use the Lead Boldly© Why, Why Not, What’s In It For You framework. First, after you’ve collected input and made a decision, return to those who provided input and explain your reasoning with radical transparency. Second, clearly articulate the risks of not taking this path, both to the organization and to them personally. Third, identify and share what's in it for the team and for them individually, highlighting specific benefits they'll gain.

This inclusive approach transforms resistance into engagement. When people understand the "why" behind decisions and see personal benefits, chronic challengers can become advocates.

If the behavior persists despite clear expectations, the employee’s approach may not be the fundamental challenge. Perhaps, it is you.

Self-Reflection

Before implementing any strategy, pause for honest self-reflection. When you ask the team for input are you genuinely seeking input, or simply looking for validation of pre-made decisions? Some "chronic challengers" emerge when managers do not seek input, consistently ignore feedback, or fail to communicate the “why” behind decisions. Consider whether your communication style invites collaboration or creates defensive responses.

Sometimes what appears as chronic challenging is an employee's frustrated attempt to contribute meaningfully to discussions where they feel unheard. How as their leader can you adjust your approach to meet them where they are?

Also, consider capabilities and capacity, which may be affecting their behavior. Are they overloaded with competing priorities? Do they have expertise you're overlooking?

The Reality

Be realistic about the time investment required for the three-part inclusive decision-making approach. This isn't a quick fix. Meaningful change in team dynamics requires consistent effort over time. It is not an on/off switch. You'll need to budget extra time for collecting input, crafting transparent explanations, and having individual conversations about benefits and risks.

Initially, this process may slow decision-making as you establish new patterns. However, short term sacrifice will result in long term rewards in reduced resistance, stronger buy-in, and more thoughtful solutions. Plan for this transition period and communicate timeline expectations to stakeholders who might question the pace.

Remember, the goal isn't to silence dissent but to make it productive. With genuine self-reflection and the right approach your biggest critic can become a valuable collaborator.