A few years back, I was running businesses that spanned all of the Americas. I was traveling constantly — Vancouver one week, São Paulo the next, back to Toronto, then down to the US. I was often in the air or in meetings or genuinely unreachable.
And something interesting happened.
People stopped waiting for me.
Not because I’d trained them explicitly. Not because I’d run a delegation workshop. But because I physically wasn’t there to hand things off to, so they had to figure it out themselves. And they did. Almost every time.
I was on the Unscripted Small Business Podcast recently with Jeremy Rivera, and when this came up, he said something that landed cleanly: don’t delegate tasks, delegate outcomes. That’s the short version of what I’d been accidentally discovering over years of being unavailable.
The Second Email Rule
One of the 52 articles in my book — the one the book is named after — is built around a simple observation from my corporate years.
When I was genuinely busy working on something that mattered, and someone who wasn’t my boss or a direct report came to me with a request, I’d let it sit. Not out of disrespect. Just because I was swamped and their request wasn’t urgent enough to interrupt what I was doing.
What I noticed: most of the time, the second email never came.
The problem had resolved itself. They found another way. They figured it out. Someone else helped. It turned out not to be as pressing as it seemed when they first sent it. Any number of things.
That’s the title of the book. Most problems solve themselves. And while that sounds like permission to ignore things, it’s actually a framework for understanding where your attention genuinely needs to go — and where it’s just been pulled by habit, or by someone who found it easier to ask you than to think.
“Most problems solve themselves. And the ones that don’t are the ones that actually need your attention.”
— Brad Poulos
The Vancouver Test
Here’s the thing I’d actually do in practice.
When someone came to me with a problem, instead of solving it, I’d ask: ‘Last week I was in Vancouver. What would you have done?’
They’d tell me. And almost always, their answer was exactly what I would have done. Sometimes it was better. Occasionally I’d push back and explain a different approach. But the key move was putting the decision back on them — not to dodge responsibility, but to show them something important.
I wrote about this in the autonomy context in my post on what actually motivates people. Autonomy — real control over how you do your work — is one of the most powerful drivers of engagement and retention. You can’t give people autonomy and then take it back every time things get hard. Autonomy has to be structural.
A Players vs B Players — And Why You Need Both
Jeremy made a distinction during our conversation that I think is worth pulling out.
He talked about managing a team of twelve, and the difference between people who can own an outcome and people who need a checklist. He compared it to AI tools that will do exactly what you say, exactly how you say it, and nothing more — without any thought for what comes next. ‘Turn the pipe seven times. Done.’ Even when turning the pipe seven times was only meaningful because of what was supposed to happen after.
That’s not a bad employee. That’s an employee in the wrong seat.
I’ve written about this distinction before — the organic vs. mechanistic organization framework captures part of it. Some roles in your business are genuinely designed for consistent, reliable execution. Others need people who can own outcomes and figure out the path themselves. The mistake is treating both types of roles identically.
- Organic roles: give the person an outcome, get out of the way. Check in on results, not method.
- Mechanistic roles: give clear tasks, define standards, measure consistency. Hire for reliability.
The McDonald’s fry cook example is my go-to here. The fries are figured out. You don’t want an entrepreneurial person in that role telling you a better way to cook the fries. You want someone who cooks them the same way every time, in Toronto and in Shanghai. That’s not a lower-tier hire — it’s the right hire for that seat.
What Gets in the Way
Most business owners know this intellectually. They’d agree with everything above if you asked them. So why does the bottleneck persist?
Three reasons, in my experience:
- Speed: It’s faster to do it yourself. The first time, and the second time, and the fifth time. Until suddenly you’re the only person who knows how.
- Quality anxiety: You’re worried it won’t be done to your standard. Which is a legitimate concern that should be addressed through clear outcome definition and feedback — not by never delegating.
- Identity: The problem-solving is part of how you see yourself in the business. If you’re not the person everyone comes to, who are you? This one is harder to fix, but it’s worth examining.
The fix for all three is the same: define the outcome clearly, give the person the authority to achieve it, set a check-in rhythm that catches problems before they compound, and then get out of the way. My planning system at Confident Operator is built around exactly this — helping business owners install the structure that makes delegation actually stick.
The Payoff
When you get this right — when you have a team that can own outcomes, that’s structured correctly for the type of work each role requires, that doesn’t need you to be the answer to every question — you get the thing most business owners say they want but rarely actually build.
You get the Barbados option.
Not that you’ll necessarily take it. But you could. And that’s what separates owning a business from owning a job.
Full conversation with Jeremy Rivera: Unscripted Small Business Podcast · Watch on YouTube.
You might also like my post on building resilient companies that never have to bet the farm — the delegation question and the resilience question are deeply connected.
