You Don't Need More Answers. You Need Better Questions.

I made a hiring decision last year that I second-guessed for the entire 3-months this person was with us. Right person, wrong seat, or wrong person, right seat, I genuinely couldn’t tell. I did what I usually do when I’m stuck: I called a mentor, ran it past my gut, slept on it, called another mentor.

Then I tried something different. I opened a chat window and typed one instruction: don’t give me an answer. Interview me. Ask me one question at a time until we both understand what I actually think.

Twenty minutes later I had my answer. Not because the AI was smarter than me. Because it asked me the seven questions I’d been too close to the decision to ask myself. What was I actually afraid of. What would I tell a founder in my exact situation. What did I already know but hadn’t said out loud.

I didn’t hand the decision to a machine. I finally heard myself think.

The Leader's Real Job Hasn't Changed

Gary Keller once told a young Geoff Woods something that’s stuck with me since I first read it in Woods’ book, The AI-Driven Leader: the best part of your job is that it’s your job, and the moment you hand pieces of your thinking away, you no longer have that job. Woods writes about AI not as a replacement for a leader’s judgment, but as what he calls a Thought Partner, something that interviews you, challenges your assumptions, and hands the decision back to you sharper than it found you.

That distinction matters more than almost anything else in this series. Every newsletter so far has drawn the same line: AI can prepare the moment, but a human has to own it. Leadership is where that line matters most, because leadership is where the moments are heaviest. Who to hire. Who to let go. Which acquisition offer to take. Whether to expand into another state or finally slow down.

Most leaders don’t struggle with these decisions because they lack information. They struggle because they’re too close to see their own blind spots, and too busy to sit still long enough to find them.

Putting AI in the Right Seat

Here’s the shift Woods’ work crystallized for me: stop asking AI for the answer. Ask it to interview you.

Instead of “what should I do about this hire,” try something closer to: act as my thought partner, interview me one question at a time about this decision, and don’t give me your recommendation until you’ve asked me at least seven questions. Instead of presenting your strategic plan and asking if it’s good, ask AI to challenge it the way a skeptical board member would, poking holes until you either strengthen the plan or find its weak seam.

Notice what’s happening in both of those. You’re still in the driver’s seat. AI isn’t deciding for you, it’s doing what a great executive coach does: asking the question you didn’t know you needed asked, then reflecting your own answers back to you as a clearer plan, a sharper strategy, a decision you can actually stand behind.

That’s the whole difference between AI replacing your leadership and AI amplifying it. One hands you an answer. The other hands you back your own clarity.

Where This Meets LMA

If you run on EOS (Entrepreneurial Operating System®), you know LMA: Lead, Manage, and hold Accountable. Leadership is vision, the thinking work of where the business is going and why. Management is execution, the doing work of how it gets done day to day. Accountability is what shows up when both are working, a natural byproduct of clear vision and clear follow-through.

AI has a real seat at each of those, and a real limit at each of them too.

In Leadership, AI can interview you into a sharper vision, the way I found my answer on that team member. It cannot want the vision for you. In Management, AI can help you turn a strategic plan into bite-sized milestones, check whether your calendar actually reflects your priorities, catch the operational gaps you’re too busy to see. It cannot walk the floor and notice that someone’s energy has changed. In Accountability, AI can help you prepare for a hard conversation, role-playing the pushback you’re likely to get so you walk in ready. It cannot have that conversation for you, and it cannot sit in the discomfort of a direct report’s disappointment while you hold the line anyway.

Woods puts it plainly: AI won’t replace you. Leaders who know how to use it will replace the ones who don’t. I’d add the other half of that sentence, the half that matters most in home care and I’m adding strong emphasis on this one: Home Care leaders who use AI to think more clearly will out-lead the ones drowning in decisions they never had the space to actually make.

The One Decision That Makes the Next Thousand Easier

Here’s where I think this goes deeper than any productivity hack. Every decision you interview yourself through gets easier when you already know your own Guiding Truths (I write more about Guiding Truths in my book, EntreThrive) the handful of non-negotiable beliefs that define how you lead and what you will not compromise, no matter how good the opportunity looks on paper.

I’ve written before about EntreClarity, self-awareness as a decision compass. Most founders never sit down and actually articulate their Guiding Truths. They feel them, vaguely, in the moment a decision feels wrong. But a feeling isn’t a filter. A named, written Guiding Truth is.

This is exactly where AI earns its keep as a thought partner, not by telling you what your values are, but by interviewing you until you can finally say them out loud, clearly enough to write down, clearly enough to apply the next time a decision shows up that would have taken you two weeks to sit with. One well-defined Guiding Truth, discovered through the right questions, can guide a thousand decisions after it. One of my favorite books, “Essentialism,” by Greg McKeown, talks about this in detail. Those who learn to become clear on what truly is “Essential” to them, they avoid the painful indecisions of many choices going forward.

The Leader Worth Following

The founders I trust most aren’t the ones with the fastest answers. They’re the ones who’ve done the work to know exactly what they believe, so when a hard decision shows up, they’re not starting from zero. They’re checking it against something true.

AI didn’t make my decision to let the wrong person go last year. It made me finally listen to what I already knew. That’s amplification. That’s what leadership, done well, looks like in the age of AI, and it’s the same principle that’s carried every room in this series: the tool clears the noise, the human still leads.

We built a free tool to help you do exactly what I described above, uncover your own Guiding Truths through a guided AI interview, not a generic assessment. Try it here: https://rivhc.com/guiding-truths/

P.S. It took me twenty minutes and seven questions to make a decision I’d been circling for weeks. AI is a fantastic Thought Partner.