We’re taught not to complain.
It’s unproductive, they say. It’s immature, they say. It’s tilting at windmills, the English majors might add.
I used to subscribe to this theory.
No longer.
In Defense of Complaining
We aren’t meant to be buttoned up all the time, holding our emotions in check, letting only the most polished, edited, digestible commentary reach the people around us.
Life gets hard. People get sick. Things we pray for don’t work out. A massive undertaking falls flat. It’s just life.
I get the idea of gritting it out, picking yourself back up, and moving on.
That’s how I live. It’s how I coach my founders to live too.
But refusing to pause and say, “You know what? This sucks,” denies the part of us that feels that way. It denies our humanity.
Sometimes we just want to bitch and complain.
So complain, I say. Bitch out loud. Be selfish, momentarily narcissistic, childish.
Vent until the venting is done. Get it all out, then move on.
Companies should do the same.
I built a new offsite exercise and recently ran it with one of our companies. I call it the Productive Complaint Session. Colloquially known as the Whining and Bitching Session.
At any given time, your company is doing stupid things. It can’t help it. Work piles up that is inefficient, redundant, or flat-out ineffective. It shows up in how you run meetings, build product, capture knowledge, and engage customers.
Complaining gets a bad rap, as if the act itself is evil. It isn’t. There’s a way to complain productively. Venting, getting it all out, and airing your concerns work, provided someone is listening, and action awaits on the other side.
That’s the whole point of this exercise. Get the eye rolls out of people’s heads and onto paper. Then put those same people to work fixing what they’ve named.
How to Air Grievances Productively
Step 1: Allow everyone to write privately
Give the whole company 30 minutes of quiet time and a frame for the exercise. It can be narrow, like how you run customer deployments or onboard a new hire, or it can be as broad as the company itself.
The instruction is simple. List everything that makes you roll your eyes. Everything that feels dumb, duplicative, needlessly manual, slow, or just plain ineffective. Everything that takes too much coordination to get done.
One gripe per Post-it.
No self-editing. Nobody is grading this; just get it all down.
Step 2: Match like with like
Put every Post-it on a board and group them. A digital board works too, though it’s less fun. (LLMs are particularly good at this part.)
However you do it, the goal is to collapse dozens of individual gripes into their underlying categories. Some people will need to explain what they meant by their scribble. Let them. It’s usually funny.
By the end, you’ll have a short list: the same handful of things everyone has been quietly complaining about for a long time.
Step 3: Decide how many to tackle, then switch modes
First, decide how many topics the group can realistically address. Time and priorities will mostly make that call for you.
Then shift from complaining to solving.
Ask people to self-select into the complaint area they feel most drawn to. Let them work on what energizes them, or on what has caused them the most pain. Some problems are real but still bore the people looking at them.
Match people to juice, not to their place in the org chart.
Step 4: Build solutions in small groups
Standard brainstorming rules apply. No bad ideas at this stage. Get the full range of solutions onto the table before anyone starts filtering them.
Then plot the solutions on a two-by-two matrix: ease of execution against potential impact. You’re hunting for the greatest gain with the least effort.
Step 5: Write one-page briefs, then red-team them
Each group picks a small subset of solutions and writes a one-page brief for each. Give them an hour.
The brief covers:
- The complaint, defined.
- Why it causes the organization pain.
- The proposed solution.
- The specific work required to test it.
- How the world looks different if it works.
Each group names one person to present their briefs. Everyone else in the room has a job: red-team them.
Poke holes. Pressure-test. Make them better.
Step 6: Assign owners and make agreements
The most senior person in the room decides which briefs become commitments.
Most of them won’t be fully baked. That’s OK. This is the starting point, not the finish line.
What matters is that every commitment has a named owner and an agreed-upon deadline for turning the brief into a complete plan that includes a definition of success and the resources required to achieve it.
So founders, hear me out: Here’s the uncomfortable truth. Your company is doing things deserving of complaints. Your people are already whining about them. They’re just not doing it in front of you. And that’s not helping anyone.
So invite the complaints into the room! Don’t be afraid. And definitely don’t be defensive. Just bask in the glow of a flaming dumpster full of whining. And then use that flame to fuel collective action. There will always be complaining. Might as well make it useful.