some embarrassing news to share here, but no one taught me how to lead.

not in school. not in past jobs. not in the early years of running a business.

and if you’re reading this? maybe you might be in the same spot …

drinking a late night bourbon on the couch recovering from a tough employee interaction or asking ChatGPT how to handle the latest process issue.

trying to grow the business and the team that helps you do it.

trying to delegate without micromanaging.

trying to show up for people, even when you’re tired, even when you’re unsure.

learning as you go.

the good news? when we have the right people, the ones who want to be coached and want to grow … it gets easier. not easy. but easier.

am I authorized to write this? probably not. but recently I’ve been testing out some strategies with our team and they might inspire you. I’m not going to be perfect. chances are you aren’t either. but I am committed to progress, to showing up for my team, and to being someone they can grow with not just report to.

1. 📚 book club

we’re not reading 50 pages a week or analyzing like it’s AP english.

we pick one book that helps us reframe how we lead, communicate, or give feedback and we talk about it for an hour.

it’s a low-lift way to start building shared language and expectations. it can be getting smart on your market, the overall industry, or in our case – leadership. especially if your team hasn’t led before either.

run the first one, then assign the next one to someone in the group.

(by the way … stay tuned for a book report from team sweb)

2. 👂 team gut checks

every so often, I ask:

• what’s feeling unclear right now?
• where can I support you more?
• what would help you optimize productivity?

it’s not formal. it’s not feedback week. it’s just listening without immediately solving.

3. 📅 monthly power hours

these are short, but structured. oftentimes they’re informed by the gut checks or taking notes on scenarios where I can tell the team needs some more reps.

what do they look like?

• a sent-ahead agenda (so no one shows up unsure)
• real role plays (client convos, hard feedback moments, internal misalignment)
• and most importantly – takeaway guides so the learning doesn’t die in the conference room or Zoom

we use this time to build muscle memory and confidence.

and sometimes, it’s clear there should be a round 2.

4. 📩 recapping opportunities

when something goes wrong, don’t just fix it. document it.

I’m starting to send a short note or audit with points to consider when certain scenarios or teachable moments occur.

misfire with a client or customer?

• what happened
• what did we discuss on how to handle it
• a hit list for next time

sales pipeline or outreach email?

• send a short audit.
• what did they nail?
• what are some pro tips to consider before the next send?

this way the lesson isn’t just in the moment, but instead it’s something we can file away and build on. even use for future team members.

5. 🤝 join a group, phone a friend, and no matter what don’t lead alone.

being the boss is lonely unless you make sure it isn’t.

this year, I’ve asked for more help than ever from peers, other founders, and Vistage (or whatever group fits your world)

sometimes the best advice isn’t from a book or a course, but it’s from the person who’s two steps ahead and still remembers what this part feels like.

you can’t lead well if you’re still doing everyone’s job. but you also can’t lead well if you expect yourself to know how, without ever being taught.

maybe this helped, maybe this was just a CEO dear diary. but if you want to trade notes or peek at some of our internal guides, reply. happy to share what’s worked for us.

🥡 the real takeaway: marketing strategy rarely stays in the marketing lane.

if a client can’t delegate, if the team is unclear, if decisions are stuck in midnight review purgatory … even the best idea in the world won’t get you the results you’re looking for.