The most important question a leader can ask

Hey - it’s Tom.

Welcome to this week’s Freedom Friday edition of Ctrl+Shift, where we unpack one core psychological challenge of leadership, and leave you with a single (sometimes uncomfortable) question to ponder.

Est. time to read: 2 minutes.

As a founder, your default setting is to be the ultimate problem-solver. A new project lands on your desk - a marketing campaign, a website update, a customer onboarding process - and you immediately start thinking about the steps to complete it yourself.

This edition explores a profound mindset shift that will unlock your time, accelerate your business, and force you to become a true leader.

A note from Tom: 'I’m terrible for this. It’s the eternal tinkerer in me I think. I once spent 40 hours learning basic video editing to create a welcome video for new customers. The video was shit. I later paid a freelancer who did it in 4 hours, and it was brilliant. I didn't save money; I wasted 36 hours of my life I could have spent on strategy. And I went slightly (more) bonkers in the process.

This painful lesson is at the heart of Who Not How, a concept by legendary entrepreneur coach Dan Sullivan. His work is built on a single, powerful premise: successful people don't ask "How can I do this?" They immediately ask, "Who can do this for me?"

This isn't just about delegating tasks you dislike. It’s a proactive strategy for everything outside your core genius. The immediate objection for most founders is cost. "I can't afford to hire a 'Who' for everything." But this misunderstands the math. The real cost isn't the freelancer's invoice; it's the thousands of dollars in value you failed to create while you were busy playing video editor.

Asking "Who?" forces a profound shift in your role. You stop being the chief "doer" and become the chief "architect." Your job is no longer to solve every problem, but to find, direct, and align the incredible "Whos" who can solve problems better, faster, and cheaper (when you factor in your own time) than you ever could.

For you to ponder:

If finding the perfect 'Who' for any task was free and instantaneous, what would you immediately stop doing?

Want to read more? This edition was inspired by learnings and insights from Who Not How by Dan Sullivan and Dr. Benjamin Hardy.

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That’s it for this edition, see you next Tactical Tuesday!

Cheers,

Tom

PS If you got value from this edition, feel free to Buy Me a Coffee!