The More You Complain, The More You Complain
When I teach my Leading with Empathy workshop, we do an exercise where people break into pairs:
Think of someone with whom you often feel empathy.
What helps you feel empathy for them?
What are some of the ingredients?
Now think of someone with whom it's difficult to feel empathy.
What does that feel like?
What are some of the challenges?
Invariably, a large portion of the class comes back with some version of the same line: I struggle to feel empathy for someone who only complains and doesn't try to do anything about it.
Then we move into active listening: reflecting what you're hearing, and following up with curious, open-ended questions. All of it meant to really hear someone, understand what's going on, and maybe even help them solve their problem.
And then, invariably, someone asks: "Okay, but what about the person you've done all of this with a hundred times, and they're still in your ear the next day with the same complaint?"
I've probably run fifty of these workshops by now, and every single time, someone asks about the chronic complainer. (Or, if you're my nana, the kvetcher. Oy vey).
I define the chronic complainer as someone more invested in complaining than in progress. The complaining itself has become what sustains them, and a change in circumstances might actually be worse for them. They might not even know how to be successful if they couldn’t endlessly complain about what’s wrong.
When workshop attendees ask that question, what they're really saying is: “I've used all the tools you recommended, but nothing is working. What do I do now?”
A Word in Defense of Complaining
Before we go deeper into chronic complaining, it’s important to note that complaining isn't inherently a problem. Sometimes it's a release valve. You let a little steam out before the pressure has to go somewhere worse. Sometimes it's connection. “You too?” can be a surprisingly powerful form of camaraderie. And sometimes people just want to know they’ve been heard before they can let something go.
An occasional complaint, even a pointed one, doesn’t necessarily mean dysfunction. It's often just being human at work. But what we’re talking about here is different. The persistent complaining being called out in my workshops can be a hindrance to work culture and sometimes a distraction from a real problem that needs addressing. Differentiating between complaining for complaining’s sake and a real problem is step one.
Before You Call Someone a ‘Chronic Complainer’
Take a minute to gut-check a couple of things before assigning labels.
First, and most importantly, are you sure you're seeing the whole picture? Someone who keeps raising the same issue may not be a chronic complainer at all. They might be experiencing bias, or a microaggression that you're simply not positioned to see. Just because you hear something over and over again doesn't mean it’s unfounded.
If someone has a different lived experience than you, the “same complaint” you’ve heard five times might be the fifth instance of a real pattern. Try enlisting a different perspective or trusted peer to make sure your bias or blindspots aren’t getting in the way.
Secondly, have you identified and tried to solve the problem, or are you just tired of hearing about it? Those are two very different situations, and only one of them is actually about the other person.
For example, if someone is constantly complaining about how hot it is in the dining room, and it is, in fact, hot in the dining room, that’s not complaining for complaining’s sake; that’s a problem with a cause that hasn’t been addressed.
If you’ve done the real work: the gut-check, private conversation, the reflective listening, the curious open-ended questions, reviewing your own blind spots, and it still hasn’t moved the needle, here's a technique I borrow from mediation.
Enter the Future
In mediation, when we have a complicated, deeply rooted case, we can spend a lot of time listening to century-old gripes. I like to say you start out thinking everyone is there to talk about Dad's inheritance, and an hour later one sibling is reminding the other about the time they hid their teddy bear in the microwave when they were nine.
You're still mad about that??
When mediation hits an impasse, and we’re hearing the same rehashed, yet often valid, complaint, we’ve got a few tricks. One of my favorites is reflecting the present, shifting toward the future.
Asking about the future moves people away from rigid positions and helps them look at practical solutions instead of repeating old hurts.
It lowers anger. Looking back can keep people angry; looking forward helps instill some optimism.
It changes the view. A hard wall becomes a problem to solve together.
It builds hope. Small steps for next week feel easier than fixing the whole past (let’s leave teddy in the microwave).
It’s a simple practice:
Reflect what you're hearing them say. Then ask a curious, future-focused question.
Instead of, "Why do you keep bringing this up?"
Try, "You've mentioned X a few times now. We've tried Y and Z to address it. I hear that this is still bothering you. What would a successful outcome actually look like to you?"
Sometimes it works, and you get a real answer, but other times you just get more of the same. If that’s the case, it may mean that you've reached the edge of what reflection, coaching, and good questions can do for this particular person, in this particular situation.
When It’s Clear a Workable Future May Not Be Possible
You’ve exhausted all the tools at your disposal, and still no change. This suggests you may not be dealing with someone who wants a solution, but instead with someone for whom complaining IS the solution.
While it’s important to note that this person may not have always been this way, at some point, a manager’s job isn’t to keep helping someone process the problem but to be clear about what happens next.
If there is no workable outcome you can identify together, give yourself the permission to shift from solving their complaint to addressing their complainING. That may mean that this particular role, company, or work environment is no longer a good match.
Only then might you arrive at the harder truth: sometimes the healthiest move isn’t one more conversation, but recognizing that the circumstances (or the relationship to them) are not going to change here. Sometimes an employee decides that for themselves, and sometimes, after a fair and clear process, their leader has to.
I’m not even going to ask if you have a chronic complainer in your midst because I know you do. If you’re not sure whether you’ve effectively exhausted all your tools or you’re at the decision stage and need a second set of eyes. I’m here for you.
And one more thing before I let you go. It was my favorite cousin who hid my teddy, not in the microwave but under the guest room mattress. And, yes, I have forgiven her, but Sharon, I see you! I now know what you’re capable of.
For those who haven’t taken one of my workshops, you can find more information on ‘the real work’ in the previous newsletters or get in touch directly.
