The most impressive question I've been asked was: "If I joined Bright Force Electrical, what would I need to do in the first 12 months to become someone you can fully trust on your biggest jobs?" It stood out because it wasn't about salary, perks, or hours. It was about responsibility and long-term value. In electrical contracting, trust is everything. We deal with live power, switchboards, and compliance obligations. One mistake can have serious consequences. That question showed the candidate was thinking about growth, accountability, and earning trust. We ended up hiring him, and today he runs complex jobs independently.
One question that impressed me was, "Based on our conversation, what are the honest odds of me getting this role?" Usually, candidates don't ask for this at all and often stick to questions like, "When am I going to hear back from you?" or "What are our next steps?". The latter questions are fine, but boldly asking for transparency on where the candidate stands in the hiring process signals that they are proactive, no-nonsense, and transparent. This shows that they value culture fit, clear communication, and their own time, which reflects how they would participate as a team member later on.
When a candidate asked me, "What is the largest difference between the present state of the company and your vision for it three years from now, and what are the main obstacles that prevent us from closing the gap quicker?" I was blown away. This question signaled from the very start that the potential employee was ready to enter into some type of strategic partnership rather than be evaluated in a traditional candidate manner. Most candidates spend almost all their time worrying about their fit in and perks from the company; this question demonstrated a level of co-ownership and ownership thinking on behalf of the candidate. It showed this candidate was not simply looking for a job but wanted to understand the roadblocks associated with the company's engine and how they could help navigate the road ahead. They exhibited a maturity as well as a level of business savvy that is very uncommon; they were more interested in the reality of the job than the shiny advertisement in the job description. A CEO must be willing to be vulnerable in order to be open and honest about the friction points in a business; when a candidate invites that level of vulnerability, they are essentially asking about how they will become the lever for growth. Our experience has shown that the candidates who have inquired about bottlenecks when scaling engineering teams are generally the candidates who make the largest measurable impact to the business, as they focus their attention on solving the right problems versus just executing task completion. At the senior or leadership level, hiring really comes down to finding people who can handle the truth about the difficulties associated with growing businesses. When a candidate inquires about the roadblocks the company faces during scaling, they are indicating that they have no fear of the friction that will occur as the company grows. Therefore, it creates an immediate level of trust and shows the candidate is searching for an alignment with the company's true direction long-term, and not just a short-term position.
The most impressive question a candidate asked me was about the company's revenue and profit goals over the last few years. A woman interviewing for a high-level position asked for our top-line and bottom-line financial numbers. That nearly flipped the script on who was interviewing whom. And, yes, she was hired.
The question that stopped me mid-interview came from a candidate for a role on my COO team. After we had gone through the standard back-and-forth, they looked at me and asked: "What question has not been asked that I should answer for you, that will give you confidence and conviction that I am the best candidate for this role?" I had to pause. That doesn't happen often. What made it so impressive wasn't boldness for its own sake. It was the layers behind the question. In one sentence, this candidate acknowledged that interviews are imperfect, that I might have unspoken concerns, and that they were willing to go wherever the conversation needed to go to close that gap. They flipped the dynamic entirely, from candidate answering to candidate leading, without a trace of arrogance. Most candidates spend the final minutes of an interview asking about culture or growth opportunities. Safe questions. Forgettable questions. This one did the opposite. It signaled self-awareness, preparation, and genuine confidence rooted in competence rather than performance. For anyone hiring at the leadership level, that distinction matters enormously. We are not looking for someone who can execute a script. We need people who can read a room, identify what's missing, and act on it. This candidate demonstrated all three in a single question. They got the offer. If you are preparing for an executive interview, stop rehearsing answers and start thinking about what the person across the table actually needs to feel certain about. Then give them a way to ask for it. That is the move most candidates never make.
I had one candidate who actually ask me to tell her about a time when an employee pointed out a mistake I'd made, how I reacted, and how I learned from the experience. It was frankly audacious, but also an important question for an employee to ask, since it gave her insight into how our relationship would operate. This was clearly someone who expected to be taken seriously and needed the freedom to push back and defend her position. She ended up being a great hire.
A candidate once asked, 'How do you apply your credit analyst background from the oil industry to assess homeowner risk in ways that typical real estate investors might miss?' That question genuinely impressed me because it showed they'd researched my unique path and understood how I blend corporate financial analysis with personalized solutions--it wasn't about the property alone, but about seeing the full human and financial picture behind each deal.
One candidate asked me, 'How do you apply the risk management frameworks you developed in the military to evaluating a real estate deal here, and could you walk me through a recent example?' That impressed me because it connected my core leadership experience directly to our business decisions--it showed they understood that disciplined, systematic assessment of both property risks and human factors is what protects our sellers and our reputation, not just chasing the next purchase.
The best question I've been asked was: "What's the one problem in your day-to-day operations that, if I solved it in my first 60 days, would free you up the most to serve sellers and tenants better?" It stood out because it wasn't about impressing me--it was about taking ownership and making an immediate impact, which matters when you're scaling fast like we did going from one property to 300+ doors.
Once, a candidate asked me, "How do you see Blues City Homebuyers evolving in the next five years, and what role do you envision this position playing in achieving that vision?" That question stood out because it showed they weren't just looking for a job; they were thinking strategically about our future and how they could contribute, aligning their ambitions with the company's growth trajectory.
A candidate once asked, 'Can you tell me about the most complex problem you had to solve for a client that had nothing to do with the house itself?' That question immediately told me they understood our mission isn't just about property; it's about being a problem-solver for people during a stressful time, whether that means arranging movers or handling other details so they don't have to worry.
The question that genuinely stopped me was: 'When a homeowner calls you frustrated and skeptical, what's the first thing you say to make them feel heard rather than sold to?' It impressed me because it got straight to the heart of what we actually do -- we're not just buying houses, we're helping people through some of the hardest moments of their lives. A candidate who walks in already thinking about the human connection before the contract tells me they get it in a way that's really hard to teach.
The question that really stood out to me was: 'You've evaluated tens of thousands of properties--what's the one red flag that makes you walk away from a deal immediately, and how do you communicate that to a homeowner without leaving them feeling hopeless?' I was impressed because it recognized the sheer volume of my experience while also drilling into the human side of delivering tough news; in this business, you have to protect your numbers but also respect that you're often speaking to someone in a vulnerable moment, and a candidate who understands both sides of that coin is someone I want on my team.
The question that genuinely caught me off guard was: 'With your background in ministry and construction, how do you decide when a homeowner needs a fair offer versus when they just need someone to sit with them and help them figure out what they actually need?' It stood out because it showed they understood that 25 years of swinging hammers and a decade pastoring people taught me the same lesson -- trust is built before any deal is discussed. A candidate who already sees that the conversation matters more than the contract is someone who fits exactly how we operate.
The question that stuck with me was: 'What does success look like for a homeowner you've helped six months after the closing?' It stopped me in my tracks because most candidates ask about sales numbers or growth targets -- this person wanted to know about the long-term human outcome. In our business, the transaction is just the beginning of someone's fresh start, and a candidate who thinks that way is already living our values before they've signed an offer letter.
A candidate asked, 'Can you walk me through a time when a deal had multiple layers of obstacles--like title issues, family disputes, or a difficult timeline--and what key step you took to untangle it all for a win-win solution?' It stood out because it showed they grasped that our real value isn't just the cash offer; it's our ability to navigate the messy, complex human problems behind distressed properties to deliver a simple, hassle-free closing for the seller.
The most impressive question I've gotten was: "Can you tell me about a time you advised a seller not to sell to you--and what you did to help them anyway?" It stood out because it cut straight to integrity and service, which is the real business in off-market real estate; if someone's thinking like that in an interview, I trust them to protect our reputation on the phone and in the living room.
A candidate once asked, 'How do you maintain integrity and transparency when dealing with a seller in a tight financial spot, and can you share an example?' What impressed me was that they recognized that our niche involves personal financial crises, not just numbers, and they wanted to understand how we uphold our ethical commitment in challenging situations, which mirrors my own focus on treating each note as a personal story, not just a transaction.
A candidate once asked, "Given your journey from college student buying your first home to developing a rental portfolio and then wholesaling, how do you see the 'financial freedom' principle evolving within Myers House Buyers, and how would my role contribute to that ongoing mission for our clients and ourselves?" That impressed me because it showed they didn't just see a company; they saw the evolving philosophy behind our success and were asking how they could actively participate in building that for others.
A candidate once asked me, 'What's one lesson from living through your own renovations with your wife that you still apply when helping sellers navigate stressful situations today?' That question stood out because it showed they understood our hands-on experience--washing dishes in the bathtub, living in disarray--shaped how we empathize with people going through the chaos of selling, and that we've lived the stress our clients feel before we ever ask them to trust us with their home.