Tag: leadership

Anchors and Sails

I have to credit John Cena for this one. I heard him on Amy Poehler’s podcast this week talking about anchors and sails, and I haven’t stopped thinking about it, because it describes every team I’ve ever worked with. I love John Cena, by the way. He was a neighbor of mine for many years, and he’s exactly what you would expect. Funny, sincere, friendly, and kind.

So, yes…anchors and sails. Every team has both.

Sails catch wind. They propel the team toward the mission. Anchors hold the team right where it is.

And the anchors? Almost never the people who don’t care. Usually it’s the opposite. They care so much about the mission, and about their own piece of it, that they get stuck. I’ve watched brilliant people sit on work that was ready weeks ago. Stall on a decision because getting it wrong felt unforgivable. That was never apathy. It was fear. Fear of letting the team down. Fear that the work isn’t good enough.

Anyway…sails don’t have to be perfect. A patched sail with a few holes still catches wind. The boat doesn’t need your work to be flawless. It needs your work to move it.

Perfectionism paralysis is one common anchor behavior. Another is paralyzing the team with endless questions before executing. Analysis paralysis. Usually these are good and valid questions. But in technology, you very rarely have all the answers. We’re often inventing something new. You have to make your best guess with the information you have, and you execute. Challenge your thinking regularly, absolutely. But move forward. Waiting for all the answers ensures you’re not creating anything new. You find the answers on the journey.

Anyway, I love this simple concept, anchors and sails, but don’t use this as a label to bludgeon team members. Use this as a question. When someone’s ruminating on everything that can go wrong: okay, great points. Solid red teaming. Now how do we turn this into forward movement? Or when someone is desperately seeking to exhaust all unknowns from the domain space — often impossible — thank them for their thoughtful questions and challenge them to turn this into forward movement, even if it means inferring answers. How do we turn this into a sail and not an anchor? When someone’s been polishing the same deliverable for weeks, ask them, no accusation in it: are you being a sail or an anchor right now? No reason to get defensive; we’ve all been an anchor at times. The question assumes they care. It just asks where that care is pointed.

Caring about the mission means moving it. Ship the patched sail.

Thanks, John. I’d say it to your face, but I moved out of the old neighborhood, and it was always hard to see you anyway.

When Your Integrity Crashes Into Your Ego: A Lesson in Revolutionary Positivity

I’m going to share something embarrassing because the lesson is worth the cringe.

Several years back, I was leading a business unit that was absolutely crushing it. It was growing sixteen times faster than any previous unit in company history. It improved Net Promoter Score (NPS) and helped other divisions hit their numbers by increasing their Net Retention Rates. The math was irrefutable.

Yet somehow, we became a political piñata. Some executives questioned the data. Peers cherry-picked our results to make them seem less impressive. People who didn’t know my technical background attacked my technical competence. They criticized my vision. At the same time, they tried to absorb parts of our product into their portfolios.

Here’s where it gets ugly: I got swept up in the negativity. Started talking shit in backchannels. Being snarky. Acting like the very people I was frustrated with. Then, through my own stupidity, one of those backchannel conversations went public. The worst part? My snark was aimed at someone who hadn’t even done anything wrong. I was venting sideways.

The hypocrisy hit me like a stink I couldn’t wash off. There I was, compromising my integrity while complaining about others’ lack of integrity.

I wasn’t maintaining my form. I was fracturing under pressure, becoming someone I didn’t recognize. I was already feeling terrible, and then my leader delayed a promotion I’d been promised. But it wasn’t losing the promotion that hurt. To be honest, that actually made me feel a little better since it was establishing a cultural boundary. It was the realization that I’d violated my core values, and my actions hurt others. That pain hit deeper than any career setback. Still does when I think about it.

During this transformation—while rebuilding my integrity—I found this Epictetus quote that became something I would refer to often:

“If you are ever tempted to look for outside approval, realize that you have compromised your integrity. If you need a witness, be your own.”

Most people think integrity means obeying a moral code. But the word comes from the Latin integer—whole, complete, untouched. It’s about maintaining your form under stress, much like we discuss structural integrity in engineering. Yes, it’s also about behaving morally as we know it today. However, there’s this lovely aspect of the word that is about authenticity and honoring your values. Being your whole self. I had allowed the disapproval and behaviors of others to compromise my integrity. To be clear, this is not an excuse for my behavior. That was entirely on me. But it helped me understand the absurdity of my behavior and get to the root cause.

Another helpful phrase came from my leader at that time. He said, “What people say about you behind your back is none of your business.” This guy has an incredible ability to elevate himself above the nonsense. I learned a lot from him.

I started coaching myself and my team on what I called ‘polite, positive, persistent pressure.’ When someone questioned third-party data in a meeting—objective numbers from an independent source—we didn’t get defensive. We’d say ‘Let’s dig into those numbers together.’ When denigration reached our ears: ‘That’s none of my business.’ Present solutions, not problems. Share credit, own failures. Show up prepared, stay relentlessly positive.

Here’s the thing about cynicism—it metastasizes like cancer. It’s toxic and justifies mediocrity and inaction. Sometimes, you’re not in a position to affect change. You must not allow this to drag you into the morass of negativity. And in these situations: Remaining positive in the face of overwhelming negativity isn’t weakness. It’s rebellion.

It’s punk rock in a polo shirt.

Growing up on a farm taught me this: When operating heavy machinery, you have three options. You can run it, you can trust the operator, or you can get the hell out of the way. Standing around complaining achieves nothing useful, but it could well get you maimed.

Business is the same. You can’t control the cynics. You can only model something better. And when that fails? Avoid their machinery. They’ll crash it on their own schedule, and you don’t want to be nearby when they do.

Our unit kept growing. The cynics kept talking. But here’s what I noticed: Positive teams ship. Cynical teams bitch.

I’m not naturally someone who seeks praise—it actually makes me uncomfortable. But I care deeply about the mission. When negativity threatens the mission, that’s when integrity demands we do something different.

And sometimes, the most revolutionary act is simply refusing to join the mob or trying to fight the mob.

Choosing positivity isn’t about being soft. It’s about being effective. It’s about maintaining your structural integrity when others are fracturing. It’s about being your own witness when the gallery is full of critics.

In our current climate—whether in business, politics, or culture—cynicism feels like the smart play. But cynicism is just fear dressed up as intelligence.

The real punk move? Building something extraordinary while others are busy tearing things down.

Be your own witness. Maintain your integrity. And when the negativity comes—because it always does—remember that your polite, positive persistence isn’t just personal development.

It’s revolution.