How to fail at managing an executive
Before we started Textio, I considered myself a strong manager. My teams at Microsoft and Amazon consistently had the highest employee engagement scores. We delivered results and were widely seen as high-performing. I have great relationships with many people who worked for me, and in several cases, have gone on to hire them again.
For a while at Textio, I continued to feel confident in my management skills. I hired excellent people, team engagement and delivery were very strong, and the company grew and grew.
However, at some point a few years in, I found myself in much harder management situations. Practically overnight, I was leading very senior executives in disciplines where my main personal exposure was having duct-taped stuff together as a startup founder. It was obvious, to me and surely to others as well, that I didn't know what I was doing.
I've talked a lot about management learnings and mistakes, but I haven't said much about managing executives. My experience leading execs cuts much closer to home. In the interest of transparency, here are five things I wish I'd known about managing execs before doing it.
#1: Unless you're a hell yes, you're a no
50-70% of exec hires fail in their first 18 months on the job. If you hire the wrong person in the first place, they never even stand a chance.
Every exec I've ever hired is a highly capable professional, but they weren't all right for the job I hired them for. For every one that didn't work out, if you'd asked me during the interview process about the top risk factor in hiring them, I could have told you immediately. In every single case, 1) I was right, and 2) I ignored my doubts and hired them anyway.
If you have doubts about the hire, don't make the hire. Execs are major trajectory-changers for your business, good or bad. Don't go into it with hesitation. Same is true for the exec considering a new role: if you have major doubts before taking the job, listen to those doubts.
#2: Micromanagement guarantees failure
Earlier this year, I had a conversation with a CEO who was struggling with their new sales leader. "What are they accountable for?" I asked the CEO.
The CEO didn't hesitate. "Hitting their number."
"What leading indicator activities are they responsible for?" I asked.
"One of them is producing a weekly forecast," the CEO replied. "And I don't like how they approach it."
"Are their forecasts accurate?" I asked.
"So far they have been, yes," the CEO admitted. "But I disagree with the methodology for building it, and eventually it's going to fail. Our forecast needs to be constructed differently."
Unsurprisingly, the sales leader exited a few months later. The CEO didn't trust the leader they'd hired, and they micromanaged tasks so closely that the exec never had a chance to prove them wrong.
Don't micromanage. Trust the person you've hired or ask them to leave. Micromanagement serves no one.
#3: If you find yourself swooping, you're both failing
I thoroughly enjoyed leading Textio when it was an early-stage startup. I love being in the details and making stuff, and it was valuable and fun to learn about new areas of the business by diving in directly. My generalist tendencies made me a strong early-stage founder. They also made me difficult to work for as the company scaled.
When I first hired growth-stage execs, if an exec wasn't as close to the details as I wanted them to be, I didn't hold them accountable for the gaps. Instead, I leaned on my early-stage skills and swooped in from above to provide direction to people on the team myself. I'll give you one guess how much my exec team enjoyed this.
If you find yourself swooping in, you undermine the exec and make it impossible for them to get closer to the work. Failure is inevitable.
#4: Managing up is not the same as being a good executive
I love a good 1-1. As a CEO, there was almost nothing I found as fun as spending an hour or two with a curious and ambitious exec who brought great topics forward for discussion. A good exec uses their 1-1 time with the CEO to share insights that will shape the CEO's thinking and to get context that only the CEO can provide.
However, the real work for the exec comes not just in hanging out with the CEO, but in using these conversations to drive real results. Just because an exec shows up for their CEO doesn't mean they're effectively leading their team.
More than once, I've mistaken an exec who is great at managing up with one who is great at the rest of their job. It's fun to discuss and brainstorm! But that's a very small part of a good exec's work.
#5: If you're not a hell yes, then you're a no (part 2)
Every time I've managed an exec who didn't work out, things were rocky for months before we decided to part ways. I knew it. The exec knew it. So why didn't either of us take action sooner?
People don't reach exec levels without having built significant skills along the way. Even exec hires that don't work out typically have positive impact on the organization before leaving. When an exec is contributing good work alongside the misses, it's common for both the exec and their boss to minimize the misses. Hope springs eternal, at least for a while.
Maybe these situations sometimes work out? I've never seen one, including among all the CEOs and execs I have coached. If both parties are having consistent, serious doubts, you're on borrowed time.
The bottom line
I've hired, managed, promoted, and/or fired many leaders over the years. In every case, even the successful ones, I wish I'd been a better manager.
I'm grateful for the lessons, but learning them hasn't always been fun. My own coach Carole Robin calls these experiences AFOGs: Another F***ing Opportunity for Growth. As Textio grew, I became a better manager for execs than I had been in the beginning. But not without a whole lot of AFOGs along the way.
What do you think?
Thanks for reading!
Kieran
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