When Things Go Wrong

Earlier this summer I had a tough meeting with one of my work teams. We had a project that was giving us a lot of trouble. The technology was more complex than we originally thought, the requirements weren’t as clear as we would like. Most of the people around the table — including me — hadn’t been involved when the key decisions has been made. I had been asking for an updated timeline for at least a month and no one could give it to me.

Sitting in the room, with everyone telling me that it would take another six to eight weeks to just assess how long the project would take to deliver, I could feel the weight pulling the team down. They needed a way to put a win on the board and there I was, asking harder and harder questions. I took a deep breath and tried to give them a hand up.

“I hear you saying that you can’t do it any faster, but what if we took a new approach? If I could eliminate any other work from your calendar for 24 hours, what could you do?”

For me, one of the biggest challenges of leadership is not in leading in time of success, but rather leading in times of failure. When everything is going well, nearly any leader can motivate their teams and help them to do good work. Companies delivering big market share and profits can invest and provide generous benefits; sports teams who are the top of their league can easily recruit and create a legacy.

Success is self-fulfilling and empowering.

It’s harder when things go wrong. In his TED talk, Stanley McChrystal said something I really liked. “Leaders can let you fail and yet not let you be a failure.” No person or team that tries to do anything amazing ever gets there without stumbles. I’ve written in the past about my own misses and the fact that those moments have helped me grow into the leader that I am. I understand the sinking feeling in one’s center when you know that your talent, intent and focus isn’t enough. The feeling that you won’t be able to meet the expectations of those who count on you (or worse yet yourself) sucks. And if you aren’t careful it sucks you into a slime-filled pit without a handhold for escape.

Failure is exhausting.

Two days later, after putting aside all other work and focusing simply on the question of how long it would take to get to the finish line, we came back together. The answer was grim, the timeline was far longer (and the project far more expensive) than anyone had predicted. They were disappointed and they knew I would be disappointed. In my heart I knew that if I reacted with any of the fear, the frustration or the fury that I was feeling I could never expect them to tackle an assignment like that again. They would seek out easy assignments and — if they did take on hard work — I couldn’t count on them to tell me the whole truth when things were bleak. In a millisecond I knew there was only one thing I could do.

I thanked them for delivering a timeline that — only days earlier — they had told me couldn’t be done in less than six weeks.

What followed after that was a focus on the path forward. I reiterated that even though none of us were happy, we were in a better place with an aligned foundation for improvement. I asked them about their assumptions and what changes were possible to shorten the timeline. I reminded them of the business risk inherent in the timeline and our shared accountability to deliver the functionality. I asked for commitment on next steps, ownership, and our plan to communicate our status transparently to the broader team. And, I thanked them again for the good work they had done.

Later that week, I had a one-on-one discussion with a middle manager on the team. He had been part of the meeting and expressed surprise at how I had reacted to the news. Wasn’t I worried? He noted that I had actually seemed pleased in the meeting and he didn’t understand how that was possible. Looking across the desk between us I explained my thinking. I assured him yes, of course I was worried. But I was happy that we had arrived at an answer, even if I wasn’t happy with the answer itself. We had a start.

The best leaders that I have worked for, the ones I aspire to emulate, have reacted the same way. In the times when I found myself standing in the slime pit, dejected and without any clear path out, they have climbed in. Bracing their backs against the slippery wall, they have interlaced their fingers and formed a step for me to climb. Putting my feet in their hands I was able to grab the ledge and painstakingly pull myself out. It was never easy, but it was possible. That is what I want to give my team; not a way to avoid the pit, but a way to climb out of it.

And, if I’ve done it right they’ll pull me out, too.

Learning from Failure

As we ended 2016, a 29-year old woman went to work and had a really bad night. A lot of people have bad shifts, but I'm willing to bet she was probably the only one that night who did it in front of more than 18,500 people with millions more watching live at home or bars. Traditional and social media covered it within minutes showing pictures and videos of her beaten face, describing her 48-second destruction and calling for her immediate retirement. Articles noted her previous suicide attempt and hoped that she would pull through the devastating loss.

I'm not a fan of mixed martial arts, but at the time my heart went out to Ronda Rousey.

In that moment I started and abandoned a blog post. For more than a month she was silent in social media as everyone sat on the sidelines of her life and speculated about her next steps. Tonight I sat down to write and thought, hmmm, I wonder whether she has found her way out yet? A quick Google search revealed that just yesterday she emerged with a single quote on her Instagram account.

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I hope the post means that she's finding a way to pull herself back up, to recognize that her worth as a human being will not be defined by a single night. I hope so.

Our culture is framed in a ridiculous binary where the people either win and get everything or lose and have nothing. I cringe every time I hear phrases like "second place is first loser" or "to the victor go the spoils" because they reinforce the idea that if you can't win you shouldn't play. It's like every dystopian novel, filled with triumphant winners and cringing losers.

That's a load of crap.

It's not that I'm against winning. Everyone who knows me knows that I am a feisty competitor and I like a medal or an "A" as much as the next guy. It's just that I haven't learned a damn thing about living from my wins. Every single worthwhile story in my life is built around a loss. The time when I fell just yards from the line at states. The time when I swung for the fences applying to graduate school and got rejected. The time when I tried to do a no-win job and failed. Losing has helped me recognize the value of a life well-lived, relish my diversity of experiences and create a community of support. Winning I was a cocky entitled pain in the ass. Losing taught me grace.

We don't celebrate failure (or more importantly the growth that comes from failure) often enough. Look, I get it. Success is sexy and failure is messy. Failure requires a good hard look inside yourself to ask painful questions. Did I try as hard as I could? Was I as prepared as I could have been? Was I in over my head? Who did I harm? Can I try again? Should I?

Some days I think it's easier to just win, but easier isn't better.

So, I'm pulling for Ms. Rousey. I hope that she's finding a way to look inside herself and find a woman that she respects and loves. I hope she recognizes that whether she continues to fight or never steps into the arena again she has value and can contribute to the world. Sure, I'm an out of shape middle-aged desk jockey, but if I could I would sit down with her and assure her that nothing about her life is predetermined at 29. I would look into her eyes, thankful to be sitting with her and not the winner, and I would ask her one question.

What did you learn?

The Undo Button

I hate that moment. You know, the one where your stomach drops and you are sure you have made absolutely the wrong call. You zigged instead of zagging. You opened your mouth when it should have stayed closed, or closed it when you should have said something. You stepped out on the ledge, or stayed in the fort. You didn’t make that left turn at Albuquerque.

Whenever I find myself in those moments I mentally reach for an undo button, like the one I use so frequently in Excel. The button that allows me to quickly get back on track and leave that misguided moment behind. The button that lets me try things without consequences. To say, “well that didn’t work the way I thought” or “hmmm, maybe there’s a better way”. Click, click, click and you’re right back where you started, ready to try it over again. Do over — no harm, no foul.

Unfortunately, life doesn’t have an undo button, it just has an “I’ll learn from it” button. The “I’ll learn from it” button feels crappy to press it because nothing really happens. You only feel better about pushing it years later with some time and tears behind you, when you’re talking to someone considering the same choice and you can say, “It’s up to you, but if I had it to do over again…”

But, I’ve found one thing I hate more than going through that moment: watching someone I love go through that moment.

Nothing prepares you for the out of body experience of watching someone you love make the wrong call. Seeing them realize they can’t change it and struggle with how to address it. Holding them through their tears and fears as their brain cycles through the what-ifs and the should’ve-beens trying to get everything back to where it was before. Reaching with them to try to click the undo button.

Click. Click. Click. But, the undo button doesn’t work any better when two people try to click it.

Harder still, I’m not sure you can give someone an “I’ll learn from it” button — I’m pretty sure you have to pick that one up for yourself. And, I recall that it took me several futile attempts to find an undo button before I bought into mine.

Of course, making the wrong call is a part of life. With time and space, I can’t think of any wrong calls in my life that haven’t turned into learning moments. I’m very comfortable with that. I just wasn’t prepared for the fact that I’m not comfortable yet watching the people I love struggle through it.

So, where’s the button for that?