There’s a weekly report I used to dread.
Not because it was complicated. Because it was slow. Every week, I’d sit down and spend at least an hour pulling it together. When I was done, it was fine. Complete. Professional.
But fine and complete are not the same as great.
A few weeks ago, I produced that same report in 15 minutes. And here’s the part that stopped me: the 15-minute version was better. It had more depth. It surfaced risks I hadn’t even identified on my own.
The difference? One hour with the right person.
But I almost let two months go by before I made that call.
I want to say something that doesn’t get said enough in business circles. Especially among owners who’ve been at this for a long time.
Asking for help is hard.
Not logistically. Emotionally.
When you’ve spent years building expertise, building a reputation, building a business, there’s something that feels almost backwards about reaching out to someone significantly younger than you and saying, “I need your help with this.”
That resistance is real. And for a lot of business owners, it’s quietly costing them.
It was quietly costing me.
I knew I needed to implement some new AI functionality. I could see how it would make me more efficient. I could see how it would help me lead better. I’d even tried setting it up myself a couple of times and kept running into technical issues I couldn’t resolve.
I had plenty of reasons to keep pushing it off. Executive calls. Staffing decisions. Customer escalations. Financial reviews. The list was real and it was long.
What I didn’t want to admit was the other reason. The one underneath all of that.
I didn’t want to be the one who didn’t know.
Then I remembered a book.
Who Not How by Dan Sullivan and Dr. Benjamin Hardy makes a simple but disruptive argument: when you’re facing a challenge, your first question shouldn’t be “how do I figure this out?” It should be “who already knows how to do this?”
That reframe changes everything.
I set up a one-hour Zoom with a junior colleague who’s an expert in AI tooling. He’s relatively early in his career. I have two decades of leadership experience.
And in 60 minutes, he changed the way I work.
He didn’t just help me get set up generically. He configured everything with the specific context of the program I’m leading. That context was the difference between a tool that kind of works and a tool that actually works for me. We ran example prompts together while he was still on the call. I could ask questions in real time. I could see what worked and understand why.
That’s a different kind of learning than reading documentation alone at 10pm and hoping something clicks.
By the end of the call, I had something I hadn’t expected going in: a documented, step-by-step process that I, or anyone on my team, can follow each week to produce that status report in the same format, pulling the latest information every time.
Not a one-time fix. A system.
Here’s what that one hour actually cost me: one hour. And a bit of humility.
Here’s what it’s returning: 45 minutes back every single week, on a report that’s better than the one I was grinding out on my own.
Run that math over six months. That’s 18 hours returned to the work only I can do.
But there’s something else I don’t want to skip over.
My colleague walked away from that call better too.
He got to be the expert in the room. He saw how the AI tooling could be applied far beyond software development, which is where he’d mostly been using it. And the two of us, who had never had a one-on-one despite working on the same large program, built a real working relationship in that one hour.
When you reach out to someone for help, you’re not burdening them. In most cases, you’re giving them something. A chance to contribute, to teach, to grow beyond their current lane.
That’s not a small thing.
Now let’s talk about you.
I used an AI example because that’s where this showed up in my world this week. But the pattern isn’t really about AI. It shows up everywhere in a small business.
It shows up in the marketing you keep meaning to get to. The bookkeeping system that still isn’t quite right. The proposals you’re rebuilding from scratch every time when a solid template could cut that work in half. The process that only exists in your head because you’ve never had time to write it down. The financial picture you’re navigating on gut feel when a simple dashboard would tell you everything you need to know.
Somewhere in your business right now, there is something you’ve been white-knuckling alone.
And somewhere around you, there is a “who.”
That who might be a team member who knows more about a specific tool than you do. It might be a vendor who can show you a shortcut in 30 minutes that would take you three hours to find on your own. It might be someone in your network who’s already solved the exact problem you’re stuck on.
Here’s what I want you to sit with: how long have you been asking “how” when you should have been asking “who?”
Two months is how long I waited. Two months of one-hour reports, when the 15-minute version was sitting right there.
Here’s what I want to say directly to the owners who’ve been in the game for a long time.
There is no shame in learning from someone younger than you. None.
The willingness to do exactly that is one of the clearest signs of a strong leader. It takes more confidence to say “you know more about this than I do” than it does to stay stuck behind a wall of self-sufficiency.
And here’s the urgency: AI is accelerating this faster than most of us expected.
The business owners who are reluctant to ask for help, who feel like they should be figuring this out on their own, are going to find themselves working harder and falling further behind at the same time. That’s a brutal combination.
The ones who will move forward are the ones who get strategic about who they surround themselves with. Who stay humble enough to be the student sometimes. Who understand that asking for help isn’t a weakness in your leadership. It’s evidence of it.
Not how. Who.
If something in this article landed, that’s your signal to start somewhere.
The F.O.R.W.A.R.D. Framework Self-Audit is a free 12-question diagnostic that takes about 10 minutes. It helps you see clearly where the friction is in your business so you know exactly where to focus next. That clarity is usually the first thing that breaks the cycle of staying stuck.
Take the Self-Audit here: brian-rapier.mykajabi.com/free-self-audit
If you want to go deeper, the F.O.R.W.A.R.D. Framework Workbook is a 50+ page guide that walks you through building a business that doesn’t require you to be the answer to every question.
And if you’re ready to have a real conversation about where you are and what’s possible, a free 45-minute Business Strategy Call is available at freebusinessstrategycall.com.
You’ve been doing this long enough.
Stop asking how. Start asking who.