Criticism & Ruinous Empathy

When bosses care too much about hurting their employees’ feelings, they will avoid giving criticism. Eventually, it becomes too late to fix this Ruinously Empathetic situation.

Here’s an example:

Bob joined Kim’s team at a software startup with glowing references, an amazing career at two of the world’s greatest technology companies, and a quirky, charming personality.

There was just one problem: Bob’s work was terrible. After a few weeks of working diligently, he finally made a presentation that was essentially a “jargon salad.” His slides were riddled with sloppy mistakes — whole sections were cut and pasted, and he hadn’t even bothered to make the fonts consistent.

Kim didn’t say a word to him after he showed it to her because she was so mad she was afraid she might say something “mean”. So she procrastinated. For ten months. It got so bad that several of her best employees said they’d quit if Kim didn’t fire Bob.

Kim scheduled a meeting, took a deep breath and told him, as gently as she could, that she was firing him. She was so gentle as to be incoherent. Bob sensed something was wrong, but mostly looked puzzled. He reassured Kim he was going to buckle down and work harder, how he would focus on making fewer sloppy mistakes.

“No, no, you don’t understand. It’s too late to fix,” Kim said.

He reassured her that he loved the company, that he had never seen a product he was more excited about, that he was committed to our collective success. Kim was trying to fire him, but there he was talking about love and commitment. She felt terrible.

To try to make things clear, Kim described not only what was wrong with Bob’s projects, but how his bad results had caused the whole team to lose faith in him. She explained that his poor work had cost the company months, and that now they would have to raise more money from VCs, diluting everyone’s stock and bringing them one big step closer to failure.

Again, he didn’t seem to understand. He was busy sketching out on a napkin an aggressive plan to address his many delayed projects.

Kim realized she was going to have to be much, much more direct. “Bob, today is your last day. I am firing you.”

He shoved his chair back from the table with a screech that made everyone look up from their steaming mugs.

“Why didn’t you tell me?” The question rolled around in my head slowly and heavily, with no good answer. “Why didn’t anyone tell me what I was doing wrong?”

He was right. Part of a boss’s job is to give guidance. Kim’s silence had hurt Bob much worse than any criticism could have. Even if Kim had been too upset at the time to phrase it artfully, if she’d told him what she really thought of his first presentation, he would have had two options. Either he could have fixed the problem and kept his job, or he could have moved on to a job that was a better fit. Instead, he’d wasted ten months of his career in a job where he was slowly failing.

Also, by letting his poor performance slide for so long, Kim had hurt company's odds of success and been unfair to everyone on the team who was doing truly amazing work. Kim thought her silence made her “nice,” but in reality her empathy made her a ruinously bad boss.

Kim realized that she always needed to Challenge Directly the people who worked for her, no matter how much it stung. It was her job, her moral obligation even.

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More about this story and others is included in “Radical Candor: Be a Kickass Boss Without Losing Your Humanity,” published by St. Martin’s Press. Learn more