I had the alternating pleasure and horror of managing people for 17 years, and can honestly say that most of the horrible parts were brought on by myself… conversations I didn’t have and actions I didn’t take, rather than regretful things I did say or do. Now that the post-traumatic stress of management has subsided (I’m kidding about the PTSD; managing people was 97% pure pleasure and 3% shit show), I’ve had a lot of time to reflect on what worked and what didn’t in the four years it’s been since I’ve had to manage anyone other than our cat sitter once a month.
Working with leaders in the work I do also provides constant fodder for reflection. As Jim works through how to how to let his assistant go, for example, I think back (in my head) to how I handled that same situation. As Kerri contemplates how to restructure her team, I recall what I said and did back in the day, and what I didn’t say and do. My mistakes are that much clearer to me now that I’ve stepped outside of the circus ring, and maybe some of my missteps can help you make better choices as a leader.


I caught one of my salespeople in a classic fib – Kim said she was at the dentist, and I somehow found out she was really out at an interview. (I may or may not have gained access to her schedule to determine this, something I’m not proud of if I’m remembering that part correctly. *Cringe.*)  I get it – people make things up when they’re interviewing – I’d never let someone go for the tried-and-true dentist appointment ruse. When Kim came back from her appointment and pretended to have her mouth frozen for several hours, to the point where she was willing to drool a little bit, well, that’s where things went awry for me. She metamorphosed her rather innocent fib into a lie that forced me to question her integrity – a non-negotiable quality for a salesperson, right?
I approached her about her possible future as an actress (maybe not that directly), and while we worked things out (likely a reasonable exit strategy where I probably counseled her on where to work next), I didn’t make it clear that I felt lied to, that that wasn’t acceptable, and that her taken-too-far actions compromised her ability to work on my team. I missed the chance to show every valuable team member around me exactly how much integrity mattered, in the face of drool. I wish I had said a firm yet fair goodbye to Kim that day.

“I want you to be prepared for the future.”

I had the displeasure of letting a lot of people go over the years, as a result of a series of layoffs not so successfully disguised as optimization projects and “rightsizing.” In this example, I knew that a termination wave was on the horizon, and ever the dutiful soldier, I didn’t tell a soul about the pending doomsday. I don’t regret that — the show must go on — and people think they want to know the bad news in advance, but don’t always appreciate being terminated in a whisper seven weeks before they’re officially terminated with HR in the room. What I do regret is that I didn’t give a “professional heads up” to one woman, in particular, a 20+ year veteran who was blindsided by her layoff. He job was restructured right out from underneath her, which made her angry and resentful.
What could I have done, within the parameters of being a responsible leader? I wish I had sat with her in the months preceding her restructuring, to talk about what might be in store for her if things were to change. I could have alluded to the fact that times were uncertain and that I wanted her to be prepared for the future, whatever that might look like. I wish I had been more of a compassionate human than responsible corporate robot.

“This isn’t looking good, is it?”

Putting a team member on a performance improvement plan is never something to look forward to, especially when it’s a friend who happens to work with/for you (the kind of friend who attended your really small wedding). This talented woman was in a professional rut and needed to either get back in gear or move on to greener pastures, so the 60-day plan was put in place. She was a champ during the initial conversation – she got it, she wanted to do better, she was going to try. We got through the discomfort of the chat. We laughed. The plan was in motion. And in classic conflict-avoidant behavior, I let business be as usual between us for the next 59 days, even as her performance failed to improve ­– until that last day when I said a professional and awkward goodbye. It was obvious, right? She had missed her targets and we agreed that meant this goodbye was going to happen, right? Technically, yes.
What I wish I had said was a whole lot more along the way, like “How else can I support you? What are your thoughts about your results this month so far? I wish this was turning out differently,” and “This isn’t looking like you’re going to make your goals this month, is it?” Really, anything. I wish I hadn’t let my own discomfort of having to say goodbye to a friend get in the way of a process that would have been a lot fairer if I’d checked in regularly. She’d have been a lot less surprised that I meant it when I said she’d have to go by day 60 if she didn’t meet her goals, and I’d have kept a funny and smart friend.
Don’t be shy – share the things you wish you had said as a manager with me at Jodi@happyspectacular.com, and I’ll publish them anonymously to help others get better. I have enough content of my own to keep this going for years to come, mind you…

Jodi Wellman

Jodi is a co-founder of Happy Work Spectacular Life, loves red Skittles (maybe too much) and finally got a Happy Spectacular logo tattoo.