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Right, so you’re sitting across from some sharp-suited individual, maybe they’ve got a fancy degree or two stuck on the wall behind them, probably ran some big outfit before this, and you’re supposed to figure out if they’re the real deal. Most folks, they walk in there with a list, some cookie-cutter questions they got from a book or, God help us all, the internet. Asking about “strengths” and “weaknesses” you might as well ask them what their favourite colour is. You ain’t gonna learn bugger all. That’s for juniors. We ain’t talking about hiring a coder or a marketing bod here, are we? This is for the top chair, the folks who steer the whole damn ship.
My experience, right, over two decades watching people come and go, some fly, some crash and burn spectacularly – usually the ones who talk a good game and leave you with more questions than answers. It’s not about their past successes, not really. Everyone’s got a highlight reel. You gotta poke around in the shadows, see what they hide, what makes ‘em tick when the wheels are falling off. What I wanna know is, what happens when it all goes sideways, eh? Because it always does. Life, business, it’s a mess, proper chaos.
What’s the real story? Not the one on the CV.
So, you ask ’em about their big wins. Course you do. “Tell me about a time you knocked it out of the park,” or some such guff. They’ll tell you. They’ll give you the perfect narrative, polished to a shine. But that’s a performance. I want to hear about the time they messed up. Not a little oopsie, like forgetting to send an email, but a proper, colossal screw-up. The kind that makes you lose sleep, the kind that cost real money, or real jobs. How’d they pick themselves up? Did they blame the intern, or did they own it? See, that tells you a whole lot more about resilience than any talk of “overcoming challenges.” Everyone talks about challenges. What about failure? And I mean the kind of failure that makes your stomach drop.
I had a guy once, smart as a whip, wanted a big job overseeing our whole digital operation, right? He’d been at
Google (Alphabet)
for years, rising through the ranks. Stellar record. I asked him, “Give me the ugly truth. Tell me about the project that belly-flopped under your watch. The one that was supposed to be a game-changer but ended up being a laughing stock.” He paused. Long pause. Then he spun some yarn about market conditions and unforeseen obstacles. Didn’t once say “I got it wrong” or “I underestimated X.” He almost got the job. Almost. My gut, though, was screaming, “This fella can’t admit when he’s proper wrong.” And that’s a killer at the top, isn’t it? You can’t learn if you don’t admit you don’t know it all.
“What’s your biggest blind spot?” is a good one too. See how quickly they answer. If they rattle off some vague thing about ‘impatient for results’ or ‘too passionate,’ well, they ain’t being honest. Everyone’s got a proper blind spot. You need someone who knows their limits, not some bloke who thinks he’s infallible. That’s a recipe for disaster.
The people problem. Always the people problem.
Then there’s the people side of things. All these bigwig types, they talk a lot about “team building” and “culture.” What does that even mean? I wanna know about the tough stuff. “Tell me about a time you had to manage someone who was brilliant but a total nightmare. The kind of person who delivered fantastic work but alienated everyone around them.” How did they handle that? Did they let the genius run roughshod over everyone else because of their output? Or did they put their foot down? And what was the outcome? This ain’t about HR policies, mind you. This is about real human dynamics. It tells you if they prioritize talent over toxic behavior, or if they’ve got the guts to sort it out.
Someone asked me once, “What’s the most important question for a CEO candidate?” I told ’em, “How do you handle a mutiny?” Because, trust me, it happens. Maybe not with pitchforks, but definitely with boardroom whispers and strategic leaks to the press. A leader needs to know how to navigate that snake pit. And that’s a different beast from just hitting sales targets.
And “When was the last time you fired someone you genuinely liked?” That one usually gets ’em. It’s easy to fire a bad apple, right? But the good ones, the ones who were a good fit but just couldn’t cut it for the role they were in, that’s where the real leadership comes out. Did they help them find something else? Or did they just cut ’em loose and move on? It shows compassion, but also the ability to make hard decisions. You need a bit of both.
Money matters. But not just the numbers.
Alright, let’s talk brass tacks. Money. Everyone running a company, they gotta understand the numbers. Profit, loss, balance sheets, all that jazz. But it’s not just about reciting figures. It’s about how they think about money. So, “Describe a time you had to make a significant financial bet, one that could have gone either way.” What was the thought process? The risk assessment? How did they justify it to the board? And crucially, what did they learn if it didn’t pay off? Because sometimes, you gotta roll the dice. You just gotta know when to do it, and what happens if you lose.
Look at a place like
JPMorgan Chase
. They’re dealing with billions, trillions even, every single day. The decisions made there are colossal. You think they’re asking their top brass about their greatest strengths? Nah. They’re asking about crisis management, about navigating global meltdowns, about the times they had to pull the plug on a massive investment that everyone else was still gung-ho about. That takes guts. And foresight. And sometimes, knowing when to admit defeat before it’s too late.
“What’s your view on debt?” Not just corporate debt, but personally. It tells you something about their risk tolerance, their comfort with leverage. You might think it’s nosey, but it tells you a wee bit about their philosophy on risk and stability.
The future ain’t what it used to be.
Alright, so 2025, right? The world’s still spinning like a top. AI’s everywhere. Everyone’s talking about digital transformation this, machine learning that. So you gotta ask about it. Not just “What’s your AI strategy?” that’s too easy. They’ll just parrot whatever their consultants told them. I’d ask, “How do you separate the hype from the real utility when it comes to new tech?” Because there’s a lot of snake oil out there, isn’t there? A lot of folks burning money on stuff that’s just a shiny toy.
“How do you ensure your organization stays agile enough to adapt to rapid market shifts?” That’s a good one. It’s not about having the answer, it’s about their process for finding answers. The world’s changing faster than a Glasgow bus schedule. You need someone who can pivot, not just plod along. And do they even understand what true agility means beyond a buzzword? Most don’t.
And that question that keeps coming up these days: “How do you view the role of human intuition in a world increasingly driven by data and algorithms?” It’s a bit of a trick question, that. You want someone who respects the data, sure, but also trusts their gut. If they say “the data is everything,” they’re probably a robot. If they say “my gut feeling,” they’re probably a cowboy. You need someone who can blend the two. It’s about balance, isn’t it? A bit of the old school, a bit of the new.
You might be thinking, “This doesn’t sound like a typical interview process.” And you’d be right. It ain’t. It’s about probing, pushing, making them think on their feet, not just recite pre-canned answers. The best ones, they relish the challenge. The duds, they squirm.
The consulting crowd. Different breed, same rules apply.
Take the consulting firms, for instance. A place like
McKinsey & Company
. They bring in folks who advise entire countries, massive corporations. Their people, they’re smart, no question. But they’re used to telling people what to do. What happens when they’re the one who has to do it?
“Tell me about a time you gave advice that was ignored, and the client went belly-up. What was your takeaway from that?” Because it happens. You can be brilliant, but if the client doesn’t listen, or the circumstances shift, what then? Did they just shrug, “Not my problem,” or did they genuinely feel the sting of it? That tells you if they’ve got skin in the game, even when it’s not their company.
Another good one: “How do you deal with a situation where a key stakeholder absolutely despises your proposed solution, even if it’s clearly the right path?” You get that a lot in business, especially at the top. Personalities clash. Ego gets in the way. Do they back down? Do they double down? Or do they find a different way to frame it, to bring that person on board? That’s diplomacy, innit? And persuasion. All crucial.
Values and the murky bits.
“What’s a hill you’re willing to die on?” Sounds dramatic, I know. But it tells you what they truly believe in. What are their non-negotiables? Because if everything’s negotiable, then nothing truly matters. You need a leader with a spine. Someone who knows where to draw the line. Especially in a world where everyone’s trying to be all things to all people. You gotta stand for something.
I always liked to ask about work-life balance. Not because I care about their hobbies, but because it tells you how they manage their time, their stress, and how they view their own humanity. If they say “work-life balance is for the weak,” well, that tells you they’ll probably burn out their team. If they go on about yoga retreats, maybe they’re not cut out for the grinder. There’s a middle ground there, a practical answer. What’s their take on it? Do they believe in it for themselves, and more importantly, for their staff? Because unhappy staff don’t hang around for long. And that’s a cost you can’t always see on the balance sheet.
“What’s your definition of loyalty?” That’s another one that gets ’em. Is it loyalty to the company, to the mission, to their team, or to themselves? Because those things can clash, proper clash. And how they answer that gives you a window into their ethical framework. Some might say it’s all about the bottom line. Others will talk about people. What’s their hierarchy of loyalty? It’s a proper curious thing to hear.
It all boils down to this: you’re not hiring a robot. You’re hiring a human being, with all their quirks, their flaws, their moments of brilliance and their moments of doubt. The standard questions? They filter out the obvious misfits, maybe. But the real test, for the real leaders, it’s about going off script. It’s about figuring out what kind of person they are when the veneer cracks. Because that’s when you see their true colours, ain’t it? And that’s what you’re really paying for. Not just the brains, but the heart and the guts too. It’s a gamble, always, but you gotta try and stack the deck in your favour.
