The Dive
A customer threatened to leave. In the same week, a brand-new customer came on and broke everything. Two fires, same week.
The founder I was working with told me straight: that's the week I knew I couldn't grow this alone.
She'd built the company doing every job herself, sales, marketing, product, all of it. That instinct got her here. Her company is right at the 30-to-50-person mark, the exact point Molly Graham (who scaled teams at Google, Facebook, and Quip) says is where a company stops being a family and starts being a company. Graham has a name for what happens next: giving away your Legos. Her line: "As you add people, you go through this roller coaster of, 'Wait, is that new person taking my job?'"
This founder wasn't worried about losing her job. She was worried about giving away decisions, budget, and judgment calls to people who hadn't earned her trust yet, because they hadn't had the chance to.
That's not a confidence problem. It's a skill nobody teaches you until a bad week forces the issue.
MIT Sloan's Elsbeth Johnson, on a Harvard Business Review podcast last year, put a name to the test I use with founders in this exact spot: "Am I the best, cheapest person to do this work?" If the answer is no, it's a candidate for giving away, whether or not it feels like it right now.
The Save
Here's the process I actually walk founders through when a week like that hits:
Run the job fully yourself, first. You can't hand off what you've never done end to end. Step into it completely before you give it away, so you know exactly what you're asking someone else to carry.
Build a trust profile, not a job description. A job description lists tasks. A trust profile answers the real question: what judgment does this person need on day one versus month six?
Lean on the peers of the role. People already doing this job well somewhere else know the actual workflow and the landmines better than you can guess from the outside.
Ask the role question before the hiring question. Is this a genuinely new role, or work already happening in your org without the authority to do it well?
Giving the job away isn't just a handoff. It's a sale, you're selling the person taking it on the vision for what it becomes in their hands, the same way you'd sell a customer or an investor. That's the same thread running through Everyone Sells: the skill isn't confined to a sales team, and it shows up here too, in the moment you hand someone your Legos and need them to believe in the tower as much as you did.
30-to-50 is one inflection point. Graham's map has three more after it (50-200, 200-750, 750+), each with its own version of this same problem. It doesn't go away by hiring faster. It goes away by giving things away on purpose, before a bad week forces it.
Who's the one person on your team right now who wouldn't leave for another job, because you gave them the chance to grow into this one? Reply and tell me. I read every one.
Talk soon, Anita
This is Issue 10 of Live Wire, a weekly jolt of candid thinking for CEOs, founders, and people leaders who know culture isn't a side project, it's how a business performs. I'm building this alongside Everyone Sells. If this landed, forward it to a founder having one of those weeks.