ISSUE #036 | THE LEADERSHIP CONTRARIAN
They set a plate of carved meat down between the seven of us that somebody nicknamed the Beef Charcuterie Board. It was glorious.
We sat there for over two hours. Eating, laughing, going deep on what we were grateful for this year and what we'd learned the hard way. The conversation bounced everywhere, giving each other a hard time about nothing, then getting quiet enough to talk about the wins we were still excited about and the hard things we're still walking through.
I'll tell you why that dinner mattered so much in a minute. But first you need to know what the two days before it looked like.
Last week Kathryn and I were in Austin with a group of business founders we gather with three or four times a year. About two hundred of us in a room for two days learning, catching up with old friends, and making new ones.
If you've read the last couple issues of TLC, you know I've been circling something: the human side of leadership, and how much we need each other to survive it. This week didn't change my mind. It proved it.
I want to tell you about three wins and one painful loss, all inside about 36 hours. Here's the thing nobody tells you about business at this level: the wins and the losses don't take turns. They stack on top of each other, sometimes in the same afternoon, and you're supposed to keep functioning through all of it.
It's like a roller coaster at Six Flags - except you're blindfolded. Up, down, left, then upside down, then a full 360, and you never see any of it coming. (The fancy term for this is volatility. We've covered that one before.)
You don't get through a ride like that by being tougher. You get through it because of who's sitting next to you, and sometimes you sit next to them before you even know you need them.
That's the whole issue in a nutshell. Here's how it played out.
Being back in a room full of founders was super refreshing. Old friends, big smiles, warm hugs. We even made a new friend who turned out to know half the same people we do, from all over North America.
I was late to lunch the first day because I got caught up talking to people, which is no surprise to most of you. Walking through the buffet line, I ended up next to a woman who's the COO of a large organization here in California, one that offers services to tens of thousands of employees across the state.
Small talk turned into real talk fast. She found out we do leadership work and lit up - she loves the topic, and she's wrestling with real challenges of her own. Then we found out we share the same faith, which made the conversation even easier. And then she told me they have a real gap in what they offer: leadership development coaching for their people. Would we be interested?
That's a significant opportunity. As of today, it's still just that, an opportunity that could go either way, but I'm grateful for every conversation about how we can help.
Here's the lesson I don't want to lose: I wasn't working the buffet line or the room. I was just being present with people, genuinely interested in them. Opportunities like that don't show up because you chased them down. They show up because leaders want to work with people who actually care, and who can solve their problems.
Highs and lows can sit closer together than you'd like. That's the part of the roller coaster nobody warns you about - you don't get a slow climb back up before the next drop.
Day two, lunch again, everyone was still riding the high from the morning session, and then word came that one of our best clients of three years was leaving. Taking their marketing and leadership work in-house. They'd grown enough to handle it, and at the same time they'd taken a hit over the last five months that had them cutting corners everywhere.
We were shocked. Crushed, honestly. I'll admit fear grabbed hold of me for a minute. We tried to respond the way you're supposed to in the moment, with grace and maturity, and then Kathryn and I went back to our hotel room and let ourselves actually feel it. Shock. Tears. Fear. All of it, at the same time, while still choosing to remind each other that God has been with us through every storm before this one, and He hasn't left now.
That doesn't make it easy. I also know putting that on paper is vulnerable, and for some of you reading this, it's more than you wanted to know. For most of you, it isn't, because I've sat across the table from a lot of you when life got hard for you. So thank you for being a safe place to share. That's not a small thing.
Ninety minutes after that startling news, I had plans to catch up with a longtime friend. His life has been chaotic on a personal level for a while, and I'd promised him this trip that we'd sit down and catch up. I went into it fully intending not to mention what had just happened to Kathryn and me. This was supposed to be about him.
We found two chairs by a big bay window with a beautiful view. Three sentences of small talk in, he asked how I was doing.
That was it. My eyes welled up, my face gave me away, and all my friend wanted to do was be there for me.
Which, in the end, was a gift.
For the next hour he asked good questions, told me some of his own story, admitted this had likely been the hardest month of his life personally, and that he was more convinced than ever of God's goodness in the middle of it. Then, with a big grin, he turned around and encouraged me. Because he's sharp and a genuinely excellent business leader, he saw things in my situation I couldn't see myself. Before we parted, he made me promise we'd talk again soon.
The lesson: one-on-one time with another leader or founder who actually cares about you matters more than we realize or will admit to. And when you need it, you want to already have been that kind of friend to another leader. There's an old saying: dig your wells before you're thirsty. Investing in people pays out a relational ROI you can't get any other way, and you usually collect on it exactly when you need it most.
Now you know what was going on with us before we ever got to that charcuterie board of delicious meat.
The conference had just ended. The afternoon had given us whiplash, and without any of us announcing it, we ended up surrounded by people who wanted to encourage us, pray for us, and just be present with us.
Kathryn and I figured we'd end up alone that night, crying into a glass of wine. Instead, we landed at a spontaneous dinner with people who turned into exactly what we needed. A couple of folks in our group almost skipped it to go "get more work done." They were glad they didn't.
The apostle Peter, writing to people going through their own hard season, put it this way: "So I will always remind you of these things, even though you know them and are firmly established in the truth you now have" (2 Peter 1:12).
If you're reading this newsletter, you're already a solid leader who cares about growing or you wouldn't put up with me week after week. So take this as a reminder, not new information: find your community, keep meeting with your peers, or get back to it, and protect it.
If you’re looking for your community or need help in any way, will you reach out and let us know?
Until next time,
Keep learning.
Keep growing.
And God bless,
Michael Redman
Half a Bubble Out (HaBO)
Business Consulting | Leadership Coaching