Hiring isn’t about gimmicks or clever gotchas — it’s about clarity.
If you’re like me, you've learned the hard way that resumes can only tell you so much. What really matters?
How someone thinks, solves problems, communicates under pressure, and whether their values align with yours. That’s why I lean hard on a handful of strategic, effective interview questions to help me hire not just for the job, but for trust, ownership, and impact.
In this video, I walk through the five questions that have helped me hire some of the most trustworthy, proactive, and self-led people I’ve ever worked with.
These aren’t trick questions — they’re human questions. And the answers? They show me how someone will actually operate once they’re inside the business.
Whether you're hiring an executive assistant, a fractional CMO, or your next ops lead, you need to understand more than what’s on paper. Because once someone’s inside, their habits become part of your culture.
That’s why every question I ask is designed to uncover self-awareness, initiative, and alignment.
Here’s a quick preview of the questions I dive into:
- What do they do when everything feels like a priority?
- Have they ever solved a problem before their boss even noticed it?
- What kind of leadership actually helps them do their best work?
- How do they respond when no one’s giving direction, but the pressure is still on?
- What value will they speak up for, even when it’s uncomfortable?
The stories people share in response to these tell me everything: how they think, what they care about, how they manage chaos, and whether they’ll be the kind of person who moves things forward or waits to be told what to do.
And I get it. Hiring takes time. But backtracking and cleaning up behind the wrong hire? That costs more.
So if you're ready to stop babysitting and start building a team that lightens your load — not adds to it — this video is a must-watch to learn how to …
- Ask questions that show how people think under pressure, not just what they know
- Look for real examples that demonstrate ownership and initiative
- Pay attention to how candidates align with your leadership style
- Gauge their comfort with ambiguity and lack of direction
- Use values-based questions to detect potential culture fit or clash
As a bonus, don’t miss the link to my Delegate to Elevate Guide in the description. It’s the roadmap I use to figure out what to offload, who to trust with it, and how to protect my time without losing visibility.
If you’re tired of hiring on potential and crossing your fingers, it’s time to get serious about the questions you ask. These five give you a front-row seat to how someone truly operates — before they ever step inside your business.
Watch the video, steal the questions, and start hiring for trust, not just talent.