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A few questions will help re-engage your chronic complainer

A chronic complainer can suck the life out of you and your team and make everyone want to quit. But your complainer can also have valuable insights and likely doesn’t feel heard. When you lead them out of their complaint spiral, they’ll be more effective and the team will benefit from their insights.

“He’s Bad…”

“I’ve got to warn you about Phil.”

The HR Director of a large engineering firm where I (David) was about to start a day-long workshop had taken me aside to warn me. “He’s bad.”

“What does ‘bad’ look like?”

“He is so cynical and complained so much during yesterday’s session that the facilitator quit and left at the break halfway through the program.”


Chronic complainers and cynics have that effect on people. Fortunately, you can use a few straightforward questions to help address your complainer and help them be a positive, contributing force. (And if you’re frequently on the receiving end of feedback telling YOU that you’re too negative or complain too much, be sure to check out How to Be Less Negative – and Still Be Yourself.)

Dealing with a Complainer Who’s Never Happy

There are two types of chronic complainers. Knowing which one you’re dealing with is crucial for a productive conversation (and your own sanity). The first type of complainer is the person who’s just never happy. They can be at a five-star resort with someone massaging their fingers with coconut oil and they’ll find something to complain about. “It’s too hot in here. I can hear you breathing. This coconut oil smells too much like coconut.” Nothing is actually wrong, concerning, or threatening. They complain because it somehow makes them feel better.

This first type of complainer can be a huge drain on your time and energy. You can use Powerful Phrases to address the behavior and disengage from unproductive discussions.

“In the last hour, I’ve heard you mention that you’re unhappy about when we’re meeting, the decision we have to make, and the meeting software we’re using. What’s going on?”

Use a neutral, non-judgmental, curious tone here. When you call attention to someone you suspect is an “I’m never happy” chronic complainer’s behavior, they’ll often tone it down. With this approach, you genuinely check to see if there’s a problem or something deeper happening. You’re not ignoring them, but neither are you amping up their negative energy.

If there’s something legitimate in their grumbling, you can listen, reflect to connect (Goat #11), and try to move them to take action:

“That does sound frustrating. Do you want to make it better?”

This Powerful Phrase helps you know if you’re talking to a “never happy” complainer. If they answer “Yes, I do want to make it better,” then skip ahead to the next section phrases to continue the conversation. But if they defer and say something like, “Nah, it’s not worth it. Nothing ever changes” then it’s time to end the conversation.

You can’t care more than they do. If they’re not invested in doing anything differently, it’s time to extract yourself from the conversation:

“That’s tough. Well, I’m up against a deadline here and have to get back to it. Hope you have a better day.”

How to Approach Your Chronic Complainer Who Cares

The second type of chronic complainer is someone who genuinely cares about the team and the work you’re doing, but it can be hard to see that caring because it’s hidden under a veneer of cynicism. As you prepare to deal with a chronic complainer or cynic who cares, it can help to understand what’s happening for them. Some people have a naturally cautious or self-protective way of approaching life. It’s kept them safe or avoided disaster (or at least feels that way).

If you tell this person that they’re being negative or that they’re a “complainer,” they’ll respond honestly, “No, I’m not, I’m trying to prevent a problem, avoid needless frustration, and keep us on track.” And their analytic, skeptical way of looking at things can be a real asset as you make decisions. The challenge is to help them add that value without dragging you down in a vortex of cynicism and complaints.

Besides understanding their general approach, it’s also helpful to understand where the “chronic” part comes from. Most of the time, when someone is complaining frequently, it’s because they don’t feel heard or seen. They’ve been dismissed as “negative” and watched people roll their eyes, and their skepticism gets worse – and the complaining spirals. A few powerful phrases can help redirect that energy to more positive outcomes. Curiosity and connection will work wonders.

Powerful Phrases for Dealing with Chronic Complainers and Cynics

“It sounds like you’re concerned about…?”

When your complainer raises an issue, avoid the temptation to shut them down. Use this question to Check for Understanding. If they’re really worked up, grab a pen and paper and start writing what they say. Just the act of taking them seriously eases some of the pressure that’s built up for them.

“And what else?”

This is a power-packed question when talking to a chronic complainer. You’ve listened intently. You’ve written what they said. Now, when you ask, “And what else?” it creates a pause. A moment of reflection. It gets them out of the autopilot “no-one-ever-listens-so-I’ll-keep-talking” mode and gets them thinking critically about the issue. If there is more, keep listening and taking notes. You might need one more “And what else” before they’ve got out all their concerns.

“What do you see as the consequences if…?”

This Powerful Phrase helps both of you get perspective. Sometimes your complainer will answer this question with, “Hmm, I guess the consequences aren’t all that big, really.” And they’re ready to move on. But when they do see significant concerns, you can continue with:

“What would it feel like if we could solve that?”

Chronic complainers have been cynical for so long that it’s sometimes hard for them to envision that things can actually get better. When you invite them to consider how it would feel, it opens the door to solutions.

“How do you think we can address this?”

With this question, you shift the conversation to solutions. They may have a few and you can explore them together. But sometimes, they’ll reply with “I don’t know.” When that happens, try this:

“What would you say if you did know?”

This odd-sounding question helps someone who’s stuck move through their stuckness. (It can be very helpful in your leadership coaching conversations.) Often, we do know, we have ideas, but are reluctant to speak them. We don’t want to look dumb, disappoint someone, or use energy to think more deeply. When you introduce this conditional language of “what would you say if you did…” it makes it safe to bypass all those mental brakes and get talking.

For a chronic complainer, another way to break the “I don’t know what to do” impasse is with:

“If you could snap your fingers and create a solution, what would you like to see happen?”

Of course, their solution might not be immediately practical, but it gives them a place to either start taking action or understand that the situation isn’t as bad as they thought.

“It sounds like you want to…”

As you recap the conversation, focus on what action they want to take next. (And if they truly couldn’t come up with a practical way forward, you might suggest monitoring the situation for a month and seeing if anything changes.)

“I’m glad we had this conversation…”

At some point, you need to help the chronic complainer get moving (and get back to your work). This Powerful Phrase emphasizes that you’ve “had” – past tense—the conversation. You might need to pair it with a follow up “I need to get back to…”

Your Turn

It turned out that Phil wasn’t nearly as troublesome as the HR Director had feared. He had genuine, valid concerns that no one fielded. After listening to his questions and giving him truthful answers (even when they weren’t always the answers he wanted), Phil became an advocate for the program. And you’ll be able to help your chronic complainers too, when you use these powerful phrases and genuinely listen.

We’d love to hear from you: how do you help your chronic complainers avoid getting stuck or dragging down the team while benefitting from their concerns?

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Want more human-centered leaders in the workplace? Share this today!

Want more human-centered leaders in the workplace? Share this today!

1 Comment

  1. Benson waema

    This is a very straight to the point article.


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Karin Hurt and David Dye

Karin Hurt and David Dye help human-centered leaders find clarity in uncertainty, drive innovation, and achieve breakthrough results. As CEO and President of Let’s Grow Leaders, they are known for practical tools and leadership development programs that stick. Karin and David are the award-winning authors of five books including, Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and Powerful Phrases for Dealing with Workplace Conflict. A former Verizon Wireless executive, Karin was named to Inc. Magazine’s list of great leadership speakers. David Dye is a former executive and elected official. Karin and David are committed to their philanthropic initiative, Winning Wells – building clean water wells for the people of Cambodia.

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7 Practical Ways to be a Bit More Daring

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