Cheryl Black | Crain's

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Cheryl Black


YOU Technology, owned by The Kroger Co., delivers custom digital grocery coupons to millions of households.

The Mistake: 

I was 29 and a relatively new manager. I was managing a small software engineering team at a company called Cullinet, one of the early startups. Cullinet and IBM had two of the only database management systems. At the time, they were one of the early success stories of the industry—until all of a sudden we were being leapfrogged. A new database technology was coming on the scene. 

I found out that we’d be laying people off on a Friday, and we had training for it that afternoon. But we wouldn’t be doing the layoffs until Monday morning, so I had the whole weekend to worry about it.  

I had two gentlemen to tell. One of them was quite a bit older than me, and one was a Marine. And then there was my friend, who was nine months pregnant.  

We had been working together for three years. There were a few of us who hung out, all female software engineers—a little bit of a rarity at the time—and we all had small children or went through pregnancies. I was six months pregnant myself. My friend was a primary breadwinner, and she had a young child already. I was also worried about how my other friends would react to me laying her off, even if it wasn’t my decision. Many of them worked with both of us, so I couldn’t tell anyone before Monday. 

The layoffs started first thing in the morning. We had boxes of Kleenex on the desks. We were told to deliver the news without emotion, to let them have their moments. So, I went to each of them and said, “I need to speak with you.”  

The older gentleman, he took the news quite well, and didn’t really have that many questions. A bit better than I expected. The second gentleman—he did not get angry, but he was quite upset, because he had a young family he was supporting. I think it made me even more nervous for my friend. I had built it up through the whole weekend. I had only talked to my husband—I talked about it as much as I could with him, but I mostly just worried and thought about how I would feel if that were me. 

I had to go get her from her desk, but by that point everyone knew layoffs were happening. I asked her to come into my office. 

I think the first thing I said was, “I am so sorry to tell you this,” which is exactly what they tell you not to do. And then I lost it. I began to choke up—I told her how badly I felt, in essence making it about me. The box of Kleenex on my desk was being used by me, and not her. She was giving me hugs. 

Then I told her the terms. It was a ridiculously large amount of severance. With her maternity, it was almost a year of paid leave. She could stay home with her new daughter, and she helped her husband launch a new business. I felt like a huge weight had been lifted off me. I helped my friend pack her desk, and we talked to our friends who were concerned, and it almost felt like a party. 

When letting someone go for performance reasons ... sever the business relationship with respect and without a lot of fanfare. 

The Lesson: 

Ever since then, I have still cared about whatever impact the layoff or firing is going to have on a person’s life, but I’ve acknowledged I can’t predict what it will do. And while it is never easy, it has never been as hard as that first time. I’ve come to understand that, especially when letting someone go for performance reasons, it is always better for all parties involved to sever the business relationship with respect and without a lot of fanfare.  

The worry – I put that on hold, because it will inevitably turn out different than I imagine.

Pictured: Cheryl Black. | Photo courtesy of You Technology.

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