How Executives Master the Art of Productive Complaining | Issue 4

How do we, as leaders, navigate complaining and complaints effectively? Can complaining actually be a tool for growth, or is it always a productivity drain?

Before I was part of the C-Suite, I once had a boss on the executive team who would complain relentlessly about the CEO. The first time they did it, I thought, “Ah, they’re being transparent with us and vulnerable!” A month in, however, I started losing respect for them and over time, I lost confidence that I could affect change at the company. If this executive is walking around with their hands tied, what about the rest of us?

Is Complaining Productive?

As a recovering complainer, I want to make one thing clear: Complaining isn’t, in and of itself, bad.

Complaining is a natural human response to frustration, anger, or disappointment. Short bursts of complaints, like venting, help those built-up feelings escape so they don’t escalate. This act of commiseration, even if sometimes misguided, also offers a way to forge social connections. 

Perhaps more meaningfully, complaining—when done right—can serve as a catalyst for change. It highlights a snag in the system—an area where things could be better. It brings attention to something that needs to be addressed. 

But there's a tipping point. 

Frequent complaining can negatively impact mental health and meaningful relationships. And when complaining becomes truly excessive, it can cultivate a helpless, victim mentality.

So it’s unsurprising that so many executives are left to wonder: “Am I allowed to complain?” 

Certainly, we’re all human, and it’s bound to happen now and then. However, it’s a leaders’ job to fix problems, not pile on. Given their reach, complaints from an executive quickly seep into company culture and exacerbate the amount of frustration and malaise—or, worse, toxicity—in the workplace. 

So, when is complaining problematic? 

A complaint is effective when it provides awareness that something is wrong, but complaining ad nauseam is a sign that no one is working to make it right. When you’ve repeated the complaint two, three, or more times and have not gotten any closer to solving the issue, it’s time to either drop the complaint or take action. 

The Art of Effective Complaining

The most impactful complaints are those that spark action. They don't dwell on the problem—they pave the way for a solution. 

Remember that classic YouTube video of people stuck on a broken escalator? Yelling for help, complaining about their situation, and waiting for action. The answer is right there. They can simply step off! The key lies in recognizing when change is within your control or not.

As an executive, you have the power to turn complaints into positive change. If you worry you may be teetering on the edge of complaining, consider one of these tactics:

1. Break the Cycle

Notice when venting or seemingly harmless catharsis over a situation isn’t enough—when there’s a real problem that needs solving. If it's you complaining, ask yourself why it’s bugging you—is it related to jealousy, trust, productivity, or performance, for instance? What’s truly in your control? If it's someone else complaining, acknowledge their feelings in the moment, determine if it’s a problem that has a path forward worth pursuing, and if so, nudge them towards Step 2.

2. Find the Fixer

Complaining to the wrong person can be detrimental, and sometimes turns toxic if circling the same group of people who have no power or resources to change the situation. If you personally can’t fix the problem, the next step is for the complainer to seek out someone who can. As I often say, if you’ve complained about it a few times, take that as a sign you aren’t telling the right person. 

3. Avoid Absolutes

Often, complaining breeds extremism. We believe there’s nothing that can change for the better. “Our CEO is never going to launch this.” “The board always shuts down these ideas.”

Words like those don’t easily allow for change. I’ve seen execs get to this point of no return—they are so frustrated with the organization that they’ve convinced themselves nothing will improve the situation. Why bother?

Often, they’re so committed to this story that there’s no room for another to exist. Sometimes, their feelings are valid: They tried 100 different ways, and it truly never worked. In these cases, it might be time for them to move on from the issue or if warranted, the organization. But, for most people, it’s less extreme. It’s more like often than always. And we can work with often!

4. Focus on the Future

Shifting from complaining to problem-solving is moving from focusing on the past issue to gravitating towards the future state. Shift from reflecting on what isn’t to focusing on what could be. Instead of, “It sucks that X isn’t happening,” or “We’re totally going to miss the deadline,” take a  constructive approach: “Given the delayed deadline, let’s discuss how to adjust the plan.” It doesn’t mean we ignore consequences for missing goals, but it does mean we care more about what we’re going to do that’s in our control than what has already happened.

And often, the perspective of time can help gain perspective on the actual size of the problem. Ask yourself, “How big will this problem be in a month, a quarter, or a year?”

5. Surface Issues Early

When possible, encouraging open dialogue can surface issues before they become major complaints. Ask employees questions like: “What’s something I should know about but don’t seem aware of?” “What would you fix if you had one free focus day/week/month?” “What’s something bothering you that doesn’t seem important enough to mention yet?” Not all employees will talk, but even small discoveries can prevent major complaints in the future. If employees are open in their complaints with you, coach them about what’s in their control (and what’s not). Often, a simple nudge in the right direction can go a long way to turn a complaint into a solution.

Remember, you set the tone. Acknowledging complaints empathetically while focusing on solutions within our control, fosters a culture of ownership and problem-solving within your team.

6. Turn the Tables

To shift a culture of complaining, adapt the advice from Deb Liu, CEO of Ancestry.com. She recommends an unconventional approach in her latest Perspectives newsletter: Put the person who keeps complaining in charge of keeping other people from complaining. Suddenly, the offender becomes the enforcer, dramatically shifting the group dynamic by giving the complainer a new role and an opportunity for a new narrative to emerge.  

7. Replace with Gratitude

The next time you find yourself complaining, try swapping the complaint for gratitude. Research suggests people who practice gratitude report lower stress, stronger relationships, and more life satisfaction. For example, instead of “Working together is frustrating,” try “I appreciate perspectives that push me to think outside the box.” Or instead of “These meetings are soooo long,” try “I’m grateful we are gathering everyone’s input now to avoid miscommunications later.”  That way, instead of seeing the gaps, you build the muscles to focus on how far you’ve come.

Did you enjoy this edition of The Left-Hand Column newsletter? Don’t miss out on other insights from my practice, including:

• The importance of shining a light on the questions we hesitate to ask.

• How to be a better listener in three key steps.

• Practical ways to create more curiosity in your day-to-day conversations.

Keep reading, keep leading,
Jess

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