Un-Stuffing the Stuffed Shirts

Un-Stuffing the Stuffed Shirts

It’s lonely at the top.

Or, so I’ve heard. And the reason is that senior executives are often viewed as unapproachable and impersonal. And in a military setting where officers have to send troops into deadly combat, that irreproachable stature is probably necessary. But in a business environment, it can do more harm than good. Executives not viewed as accessible to the organization often find it more difficult to lead.

And that was the situation for a senior executive we’ll call “Carol.” Carol was a director at a global Fortune 500 company and part of the company’s strategy leadership team reporting directly to the global strategy officer (GSO), Ben.

She was incredibly bright, hardworking, and ambitious. But to a lot of people she was intimidating. And that was a problem. Because success in her role required influencing thousands of managers in the company to adopt the new business models she and her team were developing. And deploying those new tools meant traveling around the globe to regional offices teaching the local business teams how to use them.

One Night on the Company Plane

Well, on one particular trip, it was the journey back, and not the training session itself, that made the biggest impact on the GSO’s team and its ability to lead in the organization.

As a senior officer of the company, Ben was afforded one of the most visible trappings of high office in the corporate world—access to the company plane. Instead of flying on a commercial airline, these executives, and anyone they choose to bring with them, fly in style on a Gulfstream G-4 corporate jet.

This particular trip was overseas to the company’s European headquarters. The topic was a controversial one, so they were all nervous going in. But by the end of the day, it was obvious the training was a huge success. The feedback was phenomenal, and all the trainers got high praise.

Well, that night, Carol and her three peers decided to celebrate their success with a night on the town. They stayed up half the night gambling at the hotel casino and enjoying the finest French wines. So, morning came early. As they settled into their comfortable seats on the jet for the flight home, Ben wanted to debrief the prior day’s training. He hadn’t noticed the telltale signs of a hangover on the faces of his team. So, they had to tell him:

Ben, we can’t do that now. We’re exhausted, and we won’t do a quality job of it. Can we do it tomorrow in the office?”

Now, to some, that refusal would have bordered on insubordination. But his team had done a good job, and Ben graciously agreed. So, shortly after takeoff, the four night owls were sound asleep, while the boss stayed up to work. Halfway through the return flight home, the plane stopped for fuel. After the second takeoff, it was Ben who was ready for a nap, while the other four were just waking up.

And here’s where the hierarchy is important. The company plane is an asset at the disposal of the company officer high enough to warrant it—in this case, the global strategy officer. Anyone else on board is a guest. If the boss wants to sleep on his plane, protocol dictates you let him sleep in peace. But Ben’s guests were now wide awake and were still feeling the lure of the casino from the night before. So they decided to continue their celebration with a game of poker—a loud game of poker.

Despite his restless sleep, Ben never complained or even said a word about it. But his four direct reports had plenty to say about it. Word spread quickly of their night at the casino and the flight home—how they respectfully declined Ben’s request for a debrief, and then probably kept him awake with their boisterous card game.

The Lesson

The story conveyed three key messages to the organization:

First, it showed the four senior leaders as regular people, with the same desires and frailties as anyone else. They were no longer stuffed-shirt corporate types. It humanized them.

Second, it showed them treating their boss respectfully, but no differently than they would have treated anyone else. If four people want to play poker while one wants to sleep, they play poker. Majority rules.

Third, Ben let them treat him as an equal and didn’t complain or hand out any consequences for it.

In short, that one story reframed the equity of those intimidating strategy gurus into a fun, approachable group that didn’t take themselves too seriously. Other managers were quicker to want to work with them and accept their guidance and counsel. They couldn’t have crafted a better message if they’d tried—which is actually the point.


You don’t need to stage situations like the one just described. They’ll happen naturally. The point is that when they do, tell people about them. There were only five passengers on that plane, and Ben certainly wasn’t telling this story to anyone. It got out because the other four must have. But imagine if they hadn’t. Imagine if through their own sense of decorum, they’d kept their evening’s excursion and airborne nap a secret. The story would never have gotten out, and their entire department might still be viewed as a haven for unapproachable corporate elite instead of a collaborative place to get some great strategy advice.

Yes, corporate hierarchy is based on a rigid military structure. But with stories like these, yours doesn’t have to feel like it.

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Source: Lead with a Story: How to Craft Business Narratives that Captivate, Convince, and Inspire, by Paul Smith.

Paul Smith is one of the world’s leading experts on business storytelling. He’s a keynote speaker, storytelling coach, and bestselling author of the books Lead with a StoryParenting with a Story, and Sell with a Story.

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