Stop Asking “How”—Start Asking “Who”

The other day, I chatted with a woman who wanted to enroll in a construction technology program at a local community college. Her goal was not a career in construction—she just wanted to learn how to build her own house. On the one hand, that level of initiative is admirable. On the other hand, it made me pause.

Not because she couldn’t learn construction. But because I’ve seen this pattern before—especially among self-starters, solopreneurs, and ambitious doers. We’re taught that doing things ourselves is a virtue. That if we want something done right, we should roll up our sleeves and figure it out.

But what if that mindset is actually holding us back?

The Dangerous Habit of Asking “How?”

Dan Sullivan, in his book Who Not How, puts it simply: stop asking “How can I do this?” and start asking “Who can do this for me?”

This isn’t about laziness. It’s about leverage. About getting out of your own way.

The traditional path—figuring out how to do everything yourself—is slow, exhausting, and often counterproductive. Sure, you might learn some new skills. But at what cost? Your time, energy, and focus are limited. Every hour spent learning a new “how” is an hour not spent growing, creating, or leading.

Related Post: Why You Need to Always Assess Opportunity Cost

Take websites, for example. I constantly hear from business owners who spend weeks—sometimes months—trying to build their own site from scratch. They wrestle with templates, plugins, SEO tools, and tech jargon, all in an effort to save money. But here’s the truth: it’s often far more efficient—and more affordable—to hire a skilled developer from India, Pakistan, or Bangladesh. These developers are pros. They work with go-fast tools, know the shortcuts you don’t, and charge a fraction of what a local agency would.

You not only save time but also gain insight. These professionals bring years of specialized experience to the table, often surfacing ideas or best practices you’d never discover unless you made web development your full-time job. Imagine what you could do with that time saved. You could land another client, develop a new product, or finally tackle that strategic initiative you’ve been putting off. That’s the real ROI of hiring a “Who.”

Yet so many of us default to “how.” And it’s no mystery why.

School Trained Us to Think This Way

Think about it. From a young age, we’re taught that doing our own work is required. School drilled into us the idea that asking for help—or worse, collaborating—is a form of cheating. We’re evaluated on process over outcome. Following instructions becomes more important than solving real problems.

But here’s the thing: in the real world, no one cares how you got there. You’re measured by results. Did you solve the problem? Did you create value? Did you deliver?

In business and life, outcomes matter more than the path. Yet we’re hardwired to obsess over the “how” because that’s what we were rewarded for during our formative years.

No wonder it feels unnatural to delegate. No wonder hiring someone to do something we could figure out ourselves feels like “cheating.” It’s not. It’s smart.

“Who Not How” in Practice

Reading Sullivan’s book was like putting language to a principle I’d practiced subconsciously for years. I’ve always been the kind of entrepreneur who learns just enough about a topic to identify the right expert—then steps aside and lets them run with it.

A recent project really drove this home for me. I’ve spent years building an extensive business blog—over a thousand posts deep. With AI evolving rapidly, I realized there was an opportunity to turn that content into a custom chatbot to assist small business owners. Cool idea, right?

I explored the tools. I got my hands a little dirty. I learned enough about GPT customization to understand the potential. But then I stopped. I knew I could spend the next few weeks (or months) learning how to wire it all together, but I also knew that wasn’t the best use of my time.

So, I posted a job on Upwork. Found someone with the technical chops. Shared my vision. Outlined the success criteria. Then stepped back.

I didn’t micromanage. I didn’t need to. Because I found the right “Who.”

And guess what? The project turned out better—and faster—than if I had tried to piece it together myself.

The Power of the Impact Filter™

One of the tools recommended by Dan Sullivan to ensure the success of this approach is the Impact Filter™ . Think of it as a one-page blueprint for your “Who.” It spells out the What and the Why—so they can handle the How. 

Here’s what’s on the form:

Purpose of the project: Why are you doing this?

Importance: Why does it matter?

Ideal outcome: What does success look like?

Worst-case scenario: What happens if it fails?

Success criteria: What must be true for this to be a win?

It forces clarity. You can’t hand off a project unless you’re clear on what you want and why it matters. The Impact Filter™ helps you articulate that without needing to define every step in the process.

If you want to explore the original Impact Filter™ tool that inspired this process, you can download Dan Sullivan’s Impact Filter™ here.

Related Post: Why You Need a Project Clarity Brief Before You Hire a Freelancer

Know What to Keep—and What to Hand Off

This is where it gets nuanced. Not everything can—or should—be delegated to a “Who.” Sullivan draws a useful distinction between technical and adaptive challenges.

Technical challenges have known solutions. They can be easily outsourced. These are tasks like building a website, setting up your email list, editing a video, or customizing an AI chatbot. There’s a process, a skillset, and someone out there who already has it.

Adaptive challenges are more complex. They require insight, judgment, or a shift in mindset. These are things like deciding which business model to pursue, crafting your brand voice, or leading your team through a major change. Adaptive work is messy, human, and personal.

Here’s the rule of thumb: delegate the technical; own the adaptive. You can’t outsource leadership, vision, or culture. But you can stop spending half your day googling how to set up a CRM.

Many of my clients—especially those with already successful businesses—tell me they’re exhausted. They’re clocking 60+ hour weeks and still feel like they’re falling behind. The grind never seems to end. What they’re really looking for isn’t just more efficiency—it’s relief.

This is where finding a “Who” becomes transformational.

By offloading technical tasks instead of trying to master every tool or platform themselves, these business owners can reclaim significant blocks of time. The time they can then reinvest in navigating adaptive challenges—the kind of work that unlocks new opportunities, brings greater clarity, and ultimately, saves time and provides financial freedom.

This shift doesn’t just create better businesses—it creates better lives.

The Real ROI: Time, Energy, and Momentum

When you adopt the “Who Not How” mindset, you start to see a compound return on your time. You gain:

Speed: Your project moves faster because you’re not bottlenecking progress.

Quality: Your “Who” is probably better at it than you will ever be.

Focus: You stay in your zone of genius—doing what only you can do.

Freedom: You have time to think, lead, and grow your business.

It’s not about hiring a big team or abdicating responsibility. It’s about intentionally choosing where your time goes. And today, with platforms like Upwork, Freelancer, or Toptal, it’s easier than ever to find fractional or project-based experts who can knock out your “how” without long-term commitments. Whether you need a developer, designer, copywriter, or analyst, you can tap into global talent on demand. Every “how” you hold onto is a tax on your time. Every “Who” you find—especially through these platforms—is an investment in your momentum.

Related Post: How to Use Upwork.com to Find, Hire, and Manage Talent

What You Can Do Today

If this concept resonates with you, here are three simple actions to take:

Audit your to-do list. Circle the things that feel like technical tasks. Ask: “Is there a Who who could do this better and faster?”

Download and complete an Impact Filter™ or my Project Clarity Brief for your next project. Even if you’re not delegating yet, this will clarify your thinking.

Give yourself permission to let go of the school-conditioned guilt around “doing your own work.” In entrepreneurship, collaboration isn’t cheating—it’s winning.

Final Thought

You don’t need to be the hero who knows everything. You need to be the leader who surrounds yourself with the right Whos.

That’s how you move faster, avoid burnout, and build something that lasts.

So next time you catch yourself asking, “How do I do this?”—stop. Take a breath. And ask, “Who can do this for me?”

That’s not weakness. That’s wisdom.

What is one task that you could hand off to a “Who” today?