The Hardest Choices

7. Hardest Choices.jpg

This post was written a few months ago so don’t pay too much attention to time references. I kept them to maintain the essence, the immediacy of the post. As always, thank you for reading.


Yesterday marked one of the hardest days I’ve ever experienced professional. I had to lay off a long-time employee, friend, and an individual I respect enormously.

One of my advisers made a comment to me that I will always remember - that as founder and CEO of Covo, I made this choice long before yesterday: I opted for the glory as well as the trauma of leading a company.

But while he’s exactly right, these situations are not the ones you think about when you begin. We thought we had run through all possible worst-case-scenarios in developing our founding team, making sure we were on the same page. But somehow, layoffs never made it onto the table.

Someone once told me and I completely agree, that entrepreneurship requires a lot of confidence and a heavy dose of unreality. You know it’s going to be hard, full of difficult challenges and unforeseen obstacles. In retrospect needing to let people go is one of the most common challenges a company faces. I don’t know why it never occurred to me, but it really didn’t.

That’s not to say I hadn’t been in similar positions before - I have had to fire people on numerous occasions. It’s certainly not fun, but in every instance it has been necessary. Necessary because, before getting to that point, I have done everything possible to retain the person: develop their abilities, change their responsibilities, give them time, tough love, and empathy as needed. At the end of the day, those who get to the point of being let go have essentially fired themselves, so I have been able to minimize the guilt. 

This time was different. I feel immensely guilty for not recognizing earlier that we were heading for a rough patch. My attention was focused elsewhere, but that is not at all an acceptable excuse. I dropped the ball on being on top of our finances, and in doing so neglected the most important part of my role. There is a very good chance that I could have averted this had I been paying better attention. So on top of letting go of a valued team member, I also carry a heavy load of guilt and regret.

We both cried in the meeting, and the employee told me that it didn’t feel right, in line with our values, and that they had lost a lot of respect for me. I know part of this reaction was due to surprise, part down to taking the situation personally, part hurt and anger. But even knowing these things in my head doesn’t help me avoid the ache in my heart.

Could I have done this better? Was their feedback accurate? My confidence is shaken, my workload increased, and the rest of my team needs me more than ever to be warm, confident and strong; to provide the resilient backbone of the company that is such an important part of my role. I always try to lead from a place of transparency and authenticity, which means that while my team does need me to be strong, faking strength is not the answer.

Writing about this experience is one way I can process my mourning. And, maybe, hopefully, help someone else going through a similar situation feel less alone.

Author’s note: Rereading and finishing this post months later for publication, I remember this raw emotion and feeling of inadequacy. I'm so glad I captured these feelings right off, and am publishing almost exactly what I wrote initially, because there is value in full transparency. I'm pleased to share that my feelings have changed and evolved since this low point. I wasn't sure it was the right move and felt my hands were tied. I now believe it was for the best for a number of reasons, and am pleased with the results. 

Letting go of this employee has forced me into more day to day operations, and led to more creative and strategic membership recruitment, improved community management and better attended member events. The team is thriving and working more efficiently. I still miss this team member, but no longer agonize about it being the right choice or a huge mistake.