On failing in front of the team you lead

11 min read

In my head, I had this! I was gonna be AWESOME!

We have a distributed team. Eleven of us are spread across seven different cities. If I haven’t mentioned it before I’m a HUGE fan of distributed teams. They work extremely well and even better if they get together from time to time. We’ve taken a lot of plays out of Scott Berkun’s book The Year Without Pants. The book blends product development and working in a distributed team. It’s one of the best business books I’ve read in a long time.

So, to kick off 2017, and for the second time in 6-months, we pulled the whole team together. On day one we talked about our finances and strategy. How did we do in 2016? Why were we successful? What should our strategy be for 2017? Does it make sense? How should we measure our effectiveness?

On day two we talked about tactical matters. How should/do we sell more? What’s our process? What are our core messages? It was all very focused. On day three we had a half day scheduled before our team outing. We started with a statistics lesson from Will and then got highly tactical. What’s our approach to social media? How do we monitor and prioritize our dev pipeline?

And then…it was time for some fun

In advance of the retreat we’d sent out a “rank your preferences” survey to the team of fun things we could do. To my chagrin, ice skating and axe throwing went down in flames. Indoor skydiving was it! We booked one hour of indoor skydiving at iFly.

iFly has locations all over. It’s essentially a big vertical wind tunnel. Flyers get a lesson on proper skydiving positioning and then suit-up and into the tunnel you go one by one. There’s an instructor next to you (or nearby) the whole time. The team was pumped and only Kevin had done it before.

Success in the wind-tunnel comes from being relaxed and not fighting the air but rather working with it. The clearer your mind, the more successful you’ll be and the more fun you’ll have. Perhaps you can see where this is going.

This was a new experience for everyone and we couldn’t wait to get at it. We broke into two groups and had three turns each of one, one-and-a-half, and two minutes. As the founder and owner of VetSuccess, I wanted to watch the team enjoy themselves and volunteered to be in the second group and go last.

As mentioned, Kevin had done this before. He stepped in and was quickly on his own turning left, turning right, going up, going down. He had this. My hypothesis is that the rest of our millennial teammates have relatively few cares in life. At least they sure seem to know how to relax. All smiles, Nada, Will, and Anthea stepped up and crushed it. Sally and Linda looked like kids. They had the biggest smiles and figured this thing out quickly. Karyn, Jess and Dan were impressive. They listened and were quickly on their own.

And then it was my turn

Zen is not a word used to describe me. I run pretty hard and fast and unplug infrequently. It’s just my nature. I clear my mind and am most focused when I’m pushing super-hard on a spin bike, not in a yoga class. If I need to relax and clear my mind, the worst thing you can do is tell me to relax and clear my mind. My iFly experience brought this home to roost. As I mentioned up front…in my head, I HAD this! No problem. I clearly hadn’t thought this through.

The wind-tunnel fired up and Ryan, the instructor, motioned me to lean in. I was lost. Disoriented. I couldn’t get my body to do what it was supposed to do. I didn’t understand the mechanics of it. Against all improbable odds, with wind velocity pushing against me, I crashed to the netting and stared directly down to the fans 42-feet below.

Try again

I rolled over and tried to pay attention to Ryan but my body fought the wind the whole way. “Relax!” he signalled. Maybe begged. Relax! Yeah, right. This was not going well. The long and the short of it was that for each of my successively longer three turns in the tunnel I tried to get the hang of this and just couldn’t do it. I had moments but they were brief. All the while everyone of my direct reports, my teammates, my friends were watching. To add insult to injury, of the ten of us that went flying that day, I was the only one that the instructor didn’t feel comfortable taking on a short, guided flight forty feet up the wind tunnel. It looked like fun. I’ll never know.

Being an entrepreneur/business owner is hard. Being a leader is hard. The risk of failure is present every day. My iFly experience reminded me of two things:

Stay humble

We all have things that we’re really really good at. Relish that. Celebrate that. Nurture that. But it’s important to remember there are things we’re not good at, too and that’s OK. Trying new things is great because they remind us that the world is made up of so many different skills and abilities and we can’t possess them all. Without a whole lot of (very unlikely) work I will never be a great skydiver. You can replace the word “skydiver” with lots of other words too (artist, software programmer, scientist, academic, and many, many more). I’m at peace with that.

Surround Yourself with Generous People

I talk about this a lot. If there’s one thing we’ve focused on at VetSuccess it’s been building the very best team for whatever’s in front of us at the time. To a person our team is highly talented, engaged and generous.

I had a tough day at iFly. I literally flopped. But my direct reports? My teammates? My friends? They cheered me on and wanted me to do well. Not because I’m their boss but because to a person they’re generous and want each of us to be successful.

I probably won’t go back to iFly again soon. I’m going to let others be great at skydiving. But I sure am glad I went. It was a memorable and thought-provoking day.

, Martin Traub-Werner

, Martin Traub-Werner

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