6 Painful Management Lessons

By Jenn Steele - Jun. 25, 2014
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On Tuesday, we posted Paul’s top 8 “aha” moments. We figured that we’d also give you a few more valuable lessons that I learned from my experiences as a new manager years ago. If you’ve ever been a new manager, you can probably relate to some of these, too!

If you haven’t been a new manager, then I strongly encourage you to learn from my 6 lessons. Seriously. They were painful enough for one person!

1. “No” Is a Strong Word

When I first became a manager, I was in charge of a small IT department. The first thing I had to do was move a 125-person company into a new office space, complete with a new systems buildout. Shortly after accomplishing this, the HR Manager asked me to come into her office.

“You need to not say ‘no,’” she said.

I was confused. People were asking the impossible and I couldn’t say “no”? That made no sense, and I told her that.

Her response? “Well, maybe you shouldn’t say it as firmly.”

From there, we worked on ways for me to say “no” without pissing people off. It’s something that has helped me countless times in my career, and I’m grateful that I learned it early.

2. Show Some Humanity

My first employee (well, the one I didn’t fire) had been working with me for a year when I mentioned that my husband and I were going out to dinner that night. And I mentioned my husband by name.

He gave me a blank look.

“That’s my husband,” I said.

“Oh, you’ve never used his name before.”

And I realized I hadn’t. I had worked very closely with this person for a year and had never used my husband’s name. That was when I realized that I needed to talk about things other than work occasionally, and when I did, morale instantly lifted.

Maybe it feels frivolous to show that “human” side sometimes, but it’s a key part of building a strong team.

3. Asking Is Okay

When I first started as a manager, I never asked for anything from our Executive Director. I’d never ask for anything for my team unless they pushed me really hard. And then I’d complain about how my team got passed over for bonuses or I’d wonder why I was always the first manager to lose headcount.

I was complaining about this to one of my mentors when he turned to me and said, “Jenn, if you don’t ask, you don’t get.”

So I asked for headcount, bonuses, and budget. Guess what happened?

4. The Extrovert’s Curse

I am a pretty classic extrovert (as long as you don’t count my hobbies of wine and science fiction). And, as such, I suffer from what I call the “Extrovert’s Curse.” This is where things just fly out of your mouth without actually touching your brain. This definitely can get in the way of management.

I’ve stuck my foot in my mouth in pretty much every way imaginable. Finally, I asked advice from my team about how they wanted me to deal with it when I said something dumb. Their unanimous response surprised me: own it. When I said something stupid, they wanted me to just admit to it and apologise. Not to try to justify it. Not to try to mitigate it.

Since I haven’t stopped regularly putting my foot in my mouth, learning to own the things I say has helped me through a lot of embarrassing moments.

5. Be Very Careful with Assumptions

Although I was on the management team at my firm, I didn’t always know about benefits and other policies that were about to come out. My firm put out a memo about new benefits and cost structure that really pissed off my staff, because the employee cost was going up. They all marched into my office to complain.

After listening to their complaints about how evil the firm must be to raise healthcare costs for its employees, I said, “I’m sure the firm isn’t explicitly screwing over employees. I’ll bet they’re paying more, too!” And then I pulled up my computer and did the math right in front of them.

And… the firm wasn’t paying as much this year. It had quite explicitly passed more costs to employees. I was stunned speechless and had to slink into the HR Manager’s office to explain that I’d messed up in representing the firm to my staff.

Oops. I check now before doing math in public!

6. Play the “Get out of Conversation Free” Card

Underwear. Wedding nights. Sex lives. Skirt lengths. Rear (ahem) views. What do all of these have in common? They’re all topics I NEVER wanted to discuss with my staff!

When these would come up early in my career, I’d stand there and turn purple. Or quickly try to change the subject. It got to the point that I felt like I couldn’t even have a simple conversation with my staff without turning funny colors or wanting to crawl under the desk.

Then I started using what I called the “Get out of Conversation Free” card. When things got awkward, I’d say, “I’m playing the card now” and walk into my office (and close the door if I needed to laugh myself silly). This was an easy way for me to get out of risky conversations while still having fun with my team.

I still keep the card handy!


Paul & I can’t be the only one with (somewhat) painful “Aha” moments – what are yours?


Jenn Steele

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