The Boat: The Tough Call That Speeds Everybody Up

Ever feel that gut twist when you realize someone on your team isn’t rowing in the same direction? It’s a tough spot. Letting people go is rarely fun, but it can be the best way to speed everyone else up.

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1. The Rowers Who Slow You Down

I talked with a technical CEO a while ago who had to let go of an underperforming dev team. All of them. They held on for too long, hoping things would change. Yet day after day, deadlines were missed, frustrations rose, and trust eroded. Once the CEO finally made the call, the rest of the company moved faster than ever. Smaller boat, faster speed.

2. Culture Clashes Are Real

Another founder I know brought in a new leadership team to “shake things up.” That shake-up, though, led to significant culture conflicts. The new leaders had a different view of growth and a different style of management. Divergent visions tore at the core of the startup. Ultimately, the founder had to part ways with that leadership team. Painful? Yes. It restored alignment and returned to the original mission that inspired employees.

3. Founders Who Drift Apart

Misalignment can happen even at the highest levels. I’ve seen promising startups where co-founders begin with excitement and big dreams. Over time, one founder sees the product going one way. The other imagines it differently. Once it’s clear that neither side is willing to meet in the middle, parting ways is often the only path. The earlier you address it, the less damage it does to morale and momentum.

4. Spotting Problems Early

Short, weekly sprints make issues obvious. When tasks are broken into 1- to 3-day chunks, you immediately see who’s delivering and who’s stuck. If someone isn’t getting things done, it’s wise to ask:

• Is there a personal issue?
• Do they lack a needed skill or resource?
• Are they no longer interested in the mission?

Sometimes, the problem is temporary and easy to fix. Other times, it’s a deeper mismatch. The worst thing you can do is ignore it. The team usually knows something’s off and wonders why nothing is changing.

5. Why Letting Go Feels Right (After the Fact)

Often, the remaining team feels relief. They were carrying the weight of the misaligned member, and they wanted to move fast again. When someone breaks trust or is constantly combative, the cost to the rest of the team is enormous. Removing the friction points keeps everyone else engaged and enthusiastic.

P.S. In Case You Missed It

• Travel Tips: A recent issue covered how I plan and streamline my trips. If you’re new here, it’s one of my most-read newsletters. Skim through it for tips on hacking travel details without getting lost in the process.
• Weight Loss and Health: My recent email on weight loss got lots of feedback. One frequent question was about the apps I use. For food pics, use estimated calories -> CalAI.app. It’s not perfect, but it saves me a ton of time to get an idea. For menu scanning, I use the ChatGPT mobile app.
• Run a 10k Using ChatGPT: Last weekend at SXSW, my friend Jason said he needed to run a 10k for his marathon training. I'm not a runner. I did a few sprint triathlons, but those were 5k, and that was more than 15 years ago. I was like, let's try it, and I trusted ChatGPT to guide me. Woke up at 6am - Here’s a bullet list of all the prompts before and after the run:
  • "I don’t really run much let alone hit 10k steps each day. Going on a 10k run with a friend in an hour. Give me what I should do and a stretch and warm up routine"
  • "Would taking two Advil before help or be advised"
  • "Is coffee ok to wake up before run"
  • "Here are the run stats. How did I do?" (Attached an image of run stats)
  • "What should I order. I want lots of protein" (Attached an image of a smoothie menu)
  • "Day after a bit sore. Give me stretches to recover"

Thanks for reading. Making tough choices, like letting someone go or changing a founder relationship, helps you move forward. The boat moves faster when everyone rows in sync.

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