Asking the Right Questions
One thing I’ve noticed about every business owner I’ve worked with: they all struggle to give up control in at least one area. Most often, it’s interviewing, hiring, and onboarding.
Even in corporate America, interviews and onboarding were always the last, most disorganized tasks on the list. Business owners often say things like, “We already have the dream team,” when that “dream team” is actually two overwhelmed people drowning in work. Or they’ll say, “I don’t want to hire the wrong person and waste time training them just for them to leave.”
The truth: if new hires are leaving shortly after onboarding, it’s usually because the right questions weren’t asked during the interview. There wasn’t transparency about what they were walking into, who they’d be working with, or what the day-to-day expectations would be.
Most leaders avoid tough interview questions because they fear change. Even if that change could bring in someone who fits seamlessly into the role and culture. The only way to build the team you actually need is to ask those tough questions upfront, listen to the answers, and stop trying to mold someone into a role they aren’t suited for.
In the three years since launching RML Business Operations, I’ve helped six small businesses successfully screen, interview, and onboard new employees who align with their goals, mission, and culture. Here are some of my favorite deep questions I use to find the right fit:
“Tell me about the last time you made a mistake that cost you money, time, or reputation. What happened? And how did you recover from it?”
Cuts right into accountability and resilience.
“What’s your ‘toxic trait’ at work, the thing your coworkers secretly complain about?”
Shows self-awareness and honesty.
“What’s a rule at work or school you always break (or bend) and why?”
Surfaces how they navigate structure vs. flexibility.
“What kind of person drives you absolutely nuts to work with, and how do you handle it?”
Shows conflict resolution and people dynamics.
“What’s the most BS thing about the industry we’re in, in your opinion? And how would you change it?”
Brings out critical thinking, confidence, and a genuine drive to solve problems.
“Tell me about a time you quit something: a job, project, or even a habit, and why.”
Quitting reveals as much as persistence does.
Asking deep questions like these doesn’t just lead to more interesting answers, it creates space for real connection and understanding between you and your potential new hire. My interviews often go beyond the standard 30 minutes because I’m genuinely engaging with their stories and experiences. It allows me to see how their skills could directly fit into, and even help untangle the day-to-day chaos they’re stepping into.
Interested in outsourcing your interview and onboarding process? Let’s connect and chat about the fresh perspectives you want to add to your team.