I think I’ve been bitten by a bug and have a disease. It’s the entrepreneurial bug and I can’t quit dreaming and thinking about starting new ventures. This is, in part, due to the fact that I’ve been completely freed from the operations side of my current enterprises thanks to hiring Keith Foster as our new COO. If you haven’t read my previous columns about what a game-changer that has been, I encourage you to check them out.
Another contributing factor is a show I binged over the past couple of days called Undercover Billionaire. The basic premise is a billionaire is dropped in an unfamiliar city, given $100, an old truck and a challenge: Launch a business in 90 days that will be valued at $1 million. Otherwise, he has to invest $1 million of his own money into the venture. It got me back in touch with the early days of launching our shops. It also made me think about what my dad did almost 50 years ago to get our family into this industry. The grit and grind of being a startup entrepreneur is both terrifying and exhilarating. In my last column I talked about a new venture I’m starting with my son. This month, I want to go even further out on the entrepreneurial limb and share another idea I want to launch later this year. But first, some context.
Two Bosses, Two Styles
As a young man, I had two very different bosses. Let’s call this “The Tale of Two Bosses.” The first boss I worked for was what you might call autocratic. His style was militant, very top-down. He set the agenda—I executed his plan, his way. I was rewarded for being a good follower who didn’t ask many questions, other than to clarify anything I didn’t understand about his assignments or his way of doing things.
The other boss was very collegial. When we worked together on projects he asked what I thought and he genuinely wanted to know. We discussed projects together. We planned it out and decided as a team who would tackle what. He cared for me personally. He was genuinely interested in my development, both professionally and personally. It mattered to him that I was not only accomplishing tasks but growing in the process.
Now, it’s important to say at this point that both of those are valid styles and have their place. In fact, I’m not going to pit one against the other. It’s more subtle than that. It has to do with circumstances and the person who we’re leading. What style do they need at this moment, under these circumstances? It’s truly situational. When a business is in crisis, being a strong, commanding leader is needed to bring confidence and comfort to the team. Forming a committee and listening to everyone’s feelings is not only not helpful—it can be dangerous.
Leading in Uncertain Times
Imagine an immediate crisis like a fire. Would we want the firefighters to make sure that everyone was emotionally comfortable before they executed the evacuation plan? “Hey everyone, let’s gather around and see how you’re processing your feelings about this fire, and when we’re all on the same page and agree on the plan, we can start to evacuate.” No thanks! I want my firemen and firewomen to be decisive and just tell me when, where, and how to get out safely.
But then, afterward, when people are dealing with the trauma of going through a fire, we likely don’t need someone to come up to us and say, “Just get over it and move on! You’re fine now, just forget about it.” That’s actually a time when we might need to process a bit. This is where the “soft skills” of active listening, empathy, and care come in. And I agree with Brene Brown, who says, “If you want to call these ‘soft skills’ after you've tried putting them into practice—go for it. I dare you. Until then, find a home for your armor, and I'll see you in the arena.” Soft skills are far from easy and not for the weak. They can actually be much tougher to develop, requiring lots of time and practice.
This is why later this year I want to launch another enterprise that helps train leaders in the skills of coaching. Seasoned coaches, whether in sports or business, know when to be direct and commanding and when to have a more collaborative approach.
We all have a leadership style preference. That’s our natural default. We’re typically good at one or the other. The challenge and the opportunity for all of us lies in developing our weak side so we can respond to the complex and exhilarating world of leading in uncertain times.
