Welcome back to Little Leadership Lessons, my newsletter highlighting short but powerful insights to help you lead with confidence and create lasting results. These lessons come directly from my research, interviews, and coaching work with six- and seven-figure creator-founders.
Hope you have something both enjoyable and restorative planned for this weekend.
In my world things are busier than I’d like them to be during this time of year. There are many irons in the fire in my business and each is asking of my time.
Whenever I start feeling this way I try to remember: I have agency. I am choosing each of my current commitments. And I can choose differently at any time.
My inner peace is not dependent on anyone or anything but me.
Let’s get to it!
A Beautiful Photo to Quiet Your Body and Mind
As a reminder, each edition of this newsletter is the direct learning from a $1,500 coaching session translated to you and your business in 10 minutes or less. Here’s this week’s…
The Situation
As we were standing in line for coffee last week, a friend leaned in and said:
“I need your take on something. I know you try not to coach me but right now I want you to.”
“Hit me with it. What’s up?” I said.
“I think I have a sales problem. We’re launching a high-ticket program this fall, and I have the capacity to fill it. All the sales depend on my right now.”
I asked if his current salesperson could help.
“He runs sales for a different program—lower ticket. I can’t give this one to him.”
We sat with that. I asked a few more questions—what made this new offer different? What would have to be true for him to hand off sales for the new program?
After some back and forth, my friend paused and dropped his head into his hands.
“Shit. I know what the actual problem is. It’s not that we can’t fill the program—it’s that my salesperson isn’t the right person to sell it.”
There it was. It wasn’t a sales issue. It was a people issue. And more than that—it was an avoidance issue.
The Emotional Blocker
This is where a lot of smart entrepreneurs get stuck.
They don’t get stuck on the decision.
They get stuck on the emotional weight of making it.
Because letting go of someone you care about—someone who’s loyal, who’s done good work—hurts. It brings up guilt. Grief. Doubt.
So rather than tackling it head on, we reframe the issue in our minds. We call it a “capacity problem” or a “strategic question.”
But really:
It’s not that you don’t know what to do. It’s that you don’t want to pay the emotional cost of doing it.
The Breakthrough
Every growing business eventually outgrows some members of the team. That’s not a failure—it’s a sign of progress.
But when you ignore it? You stall your momentum. You cover for people. You carry work you shouldn’t. And you put your loyalty to individuals ahead of your vision and responsibility to the rest of the team.
Just because your current team can’t do the job doesn’t mean the job can’t be done.
And the longer you avoid facing that truth, the more it costs you.
It’s not about being harsh. It’s about being honest.
And honesty is what creates the conditions for real growth.
And in this case, my friend didn’t have a sales problem. He had a people problem. Once that became clear, he knew what to do.
Coaching Questions to Apply This to Your Business
- What is every problem in your business that you believe “can’t be handed off?”
- Which of those problems are you labeling as strategic or tactical when it’s actually an emotional problem?
- Who on your team are you afraid or sad to outgrow? Who have you already outgrown?
- If you acknowledge the sadness and let yourself feel it, what decisions or next steps become clear?
Don’t confuse your current team’s capacity with what’s possible.
You might not have the right person… yet. But that’s a different problem from “it can’t be done.”
Make sure you’re solving the right problem.
Much love and respect,
