It is the trials, tribulations, and just plain stupid mistakes we go through as managers that create indelible lessons in leadership. The “how could I possibly be that dumb” moments we all share. Publicly and privately. To set the stage, I bring you two tweetstorms from Ali Partovi who had startup twitter madly liking and retweeting these last couple weeks with a couple painful career memories:

First this one:

As the world celebrated Steve Jobs’s life last week, I recalled a lesson he taught me. My one meeting with Steve didn’t end well. It’s one of my most painful memories, and a warning to startup CEOs about the danger of taking hype too far. Here’s the story. (1/n)

— Ali Partovi (@apartovi) October 10, 2021

Summary: he asked for too much money, was deemed to be dishonest, and lost the deal

And then this one:

I once killed a $125 million deal by being “too honest.” There are many ways to lose deals, lest you think last week’s story was my only painful blunder. This one hinged on a fateful encounter with Jerry Yang and involved Paul Graham (@paulg). Here’s what happened…. (1/n)

— Ali Partovi (@apartovi) October 17, 2021

Summary: he was radically transparent on the verge of closing a life changing acquisition and his honesty caused it to fall apart

Go ahead and read those threads. Your first thought might be “What is up with this guy!” “He’s blowing it all over the place!!” I think it’s admirable of Ali to publicly share these extremely expensive failures. However, before we go feeling too bad for Ali, I went over to his personal website and it appears he has invested in Airbnb, Dropbox, Facebook, and Uber. So clearly he figured it out and is doing just fine! Phew.

It did get me thinking though. What were some of my painful management failures? There are a bunch. There are a few formative, but much lower stake stories, that jumped out:

The Slow Play Departure
There was a member of my team who just wasn’t getting the job done. Let’s call him John. Their teammate who we’ll call Scott called it out and I didn’t take it seriously enough. I listened to some client calls. I didn’t hear him speak.. When I brought it up John said he was just on mute and I took him at his word. But was he even on the call? Soon after Scott left the company. He was frustrated that I hadn’t dealt with the situation. I’d slow played it. I wasn’t sure or confident enough in my judgment to make the tough call. One year later? I was back where I started with the same performance challenges. You can guess where things went from there and a couple months later John was gone. But I’d let it go way too long. Too conservative and too “busy” to do the hard thing when it was most needed.

Compensation Transparency
Has anyone had training on how to give compensation updates to members of their team? I certainly didn’t. But I was excited to give my first raise out and I really wanted to get it right. So I thought, what would I want from my manager? Transparency. Yes! Members of my team would be excited when they heard how I’d fought for them and gotten near top of range adjustments. So it’s 1×1 time with one of my harder to please team members. We’ll call him Chris. “Chris, I’m excited to share that on your yearly anniversary we’re going to give you an 8% raise. This is a really strong raise near the top of our 0-10% scale!”. Boom! Strong ass raise near the top of the scale. How bout that?? Silence. “Why didn’t I get the full 10%?” came the reply. Shit. I don’t remember what I mumbled out next but it wasn’t good. Or strong. Long story short I crawled back to HR and got 2% more for Chris. That was a lot of extra grief in the name of “transparency”. Rookie move. Learning the ins and outs of compensation takes time. That much I’ve learned.

Should They Stay or Should They Go
She’d been at the company a year. She worked really hard and carried a lot of responsibility on the team. She had management aspirations. Let’s call her Meredith. Then she came into our 1×1 one day and opened up with “I got an offer to join another company. I’d really like to stay but they offered me more. Is there anything you can do to help me with my decision?” What’s the move here? If her heart isn’t in it should I let Meredith leave? We’d worked hard to get her and she was producing. Maybe we could fast track her management responsibilities? We did. She stayed. But guess what? A year later (almost to the day) she left for the same thing. More money, maybe slightly more responsibility but it was pretty comparable. I was dealing with a job hopping pro but I didn’t know it! Was it the right decision to keep Meredith another year? Maybe, maybe not. But I knew then that when those conversations happen it wasn’t a matter of if, but when, she was going to leave.

There are more..I’ve just suppressed those stories better. Additionally, there might be this:

Uncomfortable truth: Vulnerability is only rewarded once you're seen to have made it.

— Dr. Julie Gurner (@drgurner) October 17, 2021

Maybe so Dr. Julie. Hopefully not but something to keep in mind and perhaps explore another week. Ali isn’t alone in his F ups. Neither am I. And neither are you. We gotta keep carrying on, lessons of failure in hand.