What Happened
ClickUp, a project management software company, recently cut roughly 22 percent of its workforce. The CEO framed the layoffs as preparation for an AI-driven future and sweetened the announcement by promising seven-figure salaries for the employees who remain. The move follows a now-familiar pattern: gut your headcount, invoke AI as justification, and dangle big money to keep the survivors from walking out the door.
The Communication Angle
Here is the lesson. When you announce pain, lead with truth. Do not lead with spin. ClickUp's CEO did the opposite, and it will cost them more than the severance checks.
Wrapping layoffs in the language of "AI readiness" is not strategy. It is a costume. Employees are not fooled by it. Neither is the press. When you fire one in five people and the headline out of The Register reads "survivors of a 22 percent staff purge," you have already lost the narrative. The word "purge" does not appear in a favorable story. That language comes directly from how the announcement felt to the people reading it: cold, corporate, and dishonest about its real purpose.
The seven-figure salary promise is where things get genuinely interesting, and genuinely problematic. On the surface, it looks like generosity. In practice, it is a distraction technique. You are asking the audience to look at the shiny object (big paychecks) instead of the uncomfortable reality (hundreds of people just lost their jobs). Audiences see through this. The people who were let go are not comforted by what the survivors will earn. The people who stayed are now anxious, not grateful. Anxiety and gratitude do not live in the same room.
What should the CEO have done? Three things. First, say the real reason plainly. "We grew too fast and need to be smaller to be profitable" lands harder but cleaner than "we are optimizing for an AI future." People respect directness even when they dislike the news. Second, separate the bad news from the good news. Do not announce layoffs and bonuses in the same breath. The juxtaposition is tone-deaf. Let the hard news breathe before you pivot to anything that sounds like a celebration. Third, speak to the people who were let go before you speak to anyone else. Your first public statement should acknowledge their contribution, specifically, not generically. "These were talented people" is a throwaway line. Name what they built. Name what they gave.
The underlying communication failure here is sequencing. ClickUp got the order wrong. They led with positioning (AI future), buried the human cost, and tried to close with a motivational hook (big salaries). That sequence works in a product launch. It is a disaster in a layoff announcement.
This is exactly the kind of scenario I break down in Say It Right Every Time. The chapter on delivering bad news gives you a framework for sequencing difficult messages so that your audience feels respected rather than managed. The difference between those two outcomes is not about softening the blow. It is about the order in which you give people information and what you choose to prioritize in the first thirty seconds of communication.
Never Be Lost
for Words Again
Get word‑for‑word scripts for the conversations that shape your life, from job interviews and negotiations to difficult talks with family and partners, so you always know exactly what to say and how to say it.
Never Be Lost
for Words Again
Get word‑for‑word scripts for the conversations that shape your life, from job interviews and negotiations to difficult talks with family and partners, so you always know exactly what to say and how to say it.
Key Takeaway
Before your next difficult announcement, write this sentence and do not move forward until you can complete it honestly: "The real reason we are doing this is..." If your completed sentence sounds nothing like your planned public statement, rewrite the public statement. The gap between those two things is where trust dies.
