Risk Taking and Team Building; It’s a Balancing Act

December 23, 2019

By Art Wittmann, editor of Brainyard(opens in new tab) 
5-minute read

This is "The Art of Growth," Art Wittmann's new column for Grow Wire. Read the first installment here(opens in new tab).

There are certain academic disciplines that drill into practitioners’ heads the paramount importance of being right. You hope, for instance, that medical professionals have a strong bias toward precision. (“Appendix? We thought you needed a tonsillectomy!”)

Even outside STEM, our education system values accuracy. No one gets a perfect score on the SAT by being theoretically correct. We judge misspellings harshly, even if we can easily see what the author meant. Being right matters, a lot.

I studied electrical engineering when it was extremely popular — which is to say, a while ago. At the time, the brightest lights in the Silicon Valley firmament were HP, Sun Microsystems, Cisco, Intel ... companies that made great hardware. Electrical engineers got paid a lot out of school, and the servers, switches and storage arrays they helped build were the transformational technologies of the day. 

As often happens with ‘it’ majors,(opens in new tab) more students wanted to study EE than colleges could accommodate, so “weeder classes” popped up to thin the herd. In my case, it was a difficult circuits class, usually taken the first or second semester of sophomore year, in which everything came down to writing and solving second-order differential equations in a very proceduralized way. Awesome.

We took our first test a few weeks in, and when we got the 10-question paper back, there was universal shock and dismay that grades came in increments of 10: 100, 90, 80 and so on. No partial credit, very few high scorers. I stared at a big, red 60 wondering how I was going to survive this class. 

The kid next to me mused, to no one in particular, “Why did they even bother giving us room to show our work?”

The instructor, who’d taught circuits for 30 years, let us stew for awhile. Finally, one of the brighter and more intrepid kids marched up and waved his paper. 

“I got this right,” he complained. “I just missed a minus sign here!”

The instructor conjured up his best look of disdain and replied loudly: “Oh, you ‘just’ missed a minus sign?” He flailed his arms a bit and continued, “And the space shuttle misses the moon and flies off into the sun!” 


Now, clearly, NASA triple checks the numbers on critical aerospace calculations, but the point was made. Get the answer right, or get nothing. After three more years of engineering studies, it was firmly ingrained in my head: Find the right answer. Always.

Flash forward 10 years to me in couples therapy talking about a contested decision that was wreaking havoc on my relationship. After explaining how I’d methodically reasoned out the correct answer, I was sure the therapist would turn to my partner and explain that I was clearly right. Because I was.

Instead, he studied me for a minute, and then asked, “Would you rather be right, or would you rather have this relationship?” 

As the color drained from my face, I realized this was an aha moment. In my mind, I was trying to get our space shuttle safely to its destination. The concept of picking my battles didn’t come naturally, but you can bet I learned that lesson quickly. 

Business is all about picking your fights. Hopefully that’s not a revelation, though given the trend of engineers founding companies(opens in new tab), I worry it might be. For leaders with clear visions of how not to fly into the sun, it can be exceptionally hard to approve a decision you know is suboptimal for the sake of team morale. 

Business is all about picking your fights. Hopefully that’s not a revelation.  


What’s the Worst That Can Happen?

In my last job, the financial overlords expected gross margins in the 70-80% range on events in my portfolio.(opens in new tab) That meant new products had to produce margins of about 50% out of the gate or I’d hear from bosses. 

Our sales team at the time was young and full of big ideas — most of which I had to shoot down, either because they’d been tried elsewhere and failed or clearly would never make the minimum margin. 

There was one concept in particular the team was really big on and had pitched several times. They were sure they could get at least 10 sponsors to buy in. I knew they needed me to greenlight this event, lest they think I’d never say yes to anything and give up trying to pitch me. 

So, because they were so excited, and because I calculated we would at least break even financially, I said yes to the event — with conditions: Get buy-in from the audience marketing team, because having a sellable idea is one thing; getting busy attendees to show up is another. Get at least six sponsors by a certain date, and get the operations team to agree it had the bandwidth to create what amounted to a new sub-event. 

We got the six sponsors, and operations did its thing. The room looked great. DJ, open bar, carving stations, mood lighting.

I’ve rarely wished harder to be wrong, but I wasn’t. We got only one-third of the audience needed to call the event a success. We had created a product that our attendees didn’t want. We didn’t lose money, but we didn’t delight our sponsors either, and that was an important lesson for the sales team. Just because you can sell it doesn’t mean we can create an expectation-beating product. Particularly in media and events, it’s easy for sales to think a lot about what its clients want and not enough about whether there’s an audience for those products. 

But that’s a topic for another column. 

Bottom line: As long as the worst case isn’t all that catastrophic, leaders need to let their people fly — even if they’re pretty sure the idea will miss the mark. 

As long as the worst case isn’t all that catastrophic, leaders need to let their people fly — even if they’re pretty sure the idea will miss the mark. 


The first reason to do so: You might be wrong. Perhaps you’re missing an opportunity that the team sees. If right, it’s a teachable moment for the team. What went south? How should we think about our customers, our opportunities and long-term success?

Allowing your team to miss the mark is also a chance to help them grasp what you were saying that they weren’t hearing, and in so doing, gain respect for your process and improve how they vet ideas. In this case, approving that tenuous event helped a young team mature quickly. There’s nothing like standing on stage talking to a room that’s one-quarter filled to focus the mind on exactly how one landed in that position. You can bet I made sure the team members who wanted this product were on stage. No hiding behind the DJ.

Fortunately, this was a limited misstep in the context of a very successful event. While the product didn’t come close to making margin, the situation led to more nuanced discussions going forward. 

Controlled failures teach us a lot, at every point in our lives. They are the course corrections we remember. Leaders sometimes protect their people too much. Dare to let your team learn the hard way.

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