New Hires: The Most Important Decisions You’ll Make
Every small business owner has a story about the one hire they wish they could do over. Turns out the person had the skills, but not the values. Sure, they looked good on paper, but they were a poor fit for the culture. In small teams, there’s no place to hide that.
It’s been my experience that when we’ve made a bad hire, it wasn’t the person’s ability to do the job or their technical skills, that were the misfit. Our managers were good at discriminating between those who could do the job and those who couldn’t. Hiring mistakes almost always came down to a bad cultural fit.
The stakes are high. In a 1,000-person firm, a bad hire might go unnoticed for months and never create a blip on the income statement. In a 10-person team, everyone feels it by Friday. One values mismatch can breed tension, erode trust, and slow everything down. It’s disruptive, and it’s a missed chance to bring in someone who could have moved the culture forward.
That means that the small business owner must personally review every hire; not to second-guess skills, but to protect and shape the firm’s culture.
Culture Is the Ultimate Competitive Advantage
I’ve written previously about the importance of culture in a small business. Think of culture as how people behave when no one is watching. It’s a mix of unwritten rules, shared values, and everyday behaviours that guide decisions and shape how work gets done. It shows up in how your team handles customer complaints, shares credit, communicates across departments, and even how they show up on Monday morning.
Get it right, and you have a team that runs smoothly, treats customers well, and sticks around. Get it wrong, and you spend your time cleaning up messes. Culture affects everything: customer experience, collaboration, productivity, morale, and brand reputation.
And here’s the thing: culture isn’t what you say. Culture is what you tolerate, reward, and do. You can have all the values posters in the world, but they mean nothing if behaviour and decisions don’t align.
Great companies like Trader Joe’s, Shopify, and Firespring are recognized for their distinctive cultures. That didn’t happen by accident. It happened because someone at the top made culture their job.
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Hiring for Values
I can say with complete confidence that no one was ever hired in a company I owned or ran that I didn’t personally interview. My role was to be the final cultural gatekeeper. I had a veto. This was to ensure that they were not just a technical fit, which would have been predetermined by their potential manager, but also a cultural fit.
Not once did I ever use my veto. I suppose that’s a testament to how well our management embodied our values every day.
Your hiring process should also aim to do that. Early in the process, you should transcend any technical examination and assess the candidate on their character, integrity, and motivation.
Look at how they treated the receptionist. Did they display a collaborative or autonomous decision-making style? Did they ask thoughtful questions or just sell themselves? Did they display some humility to go along with their ego?
Ask Value-Centric Questions
Try asking some value-testing questions like:
- “Tell me about a time you made a decision that wasn’t popular but felt right to you.”
- “How do you handle situations where your manager is wrong?”
- “What kind of work environment brings out your best?”
Listen for their personal values, not polished answers. Try to uncover a bit of their personality and character.
Topping the process off with a final interview with the owner sends a clear message: culture matters here. It keeps change intentional and evolutionary, and gives the owner a chance to gently steer the culture in a deliberate direction.
“But I Don’t Have Time to Interview Everyone”
You might think you don’t have time to interview every hire. But the truth is, you don’t have time not to. A single bad hire, especially in a customer-facing or leadership role, can cost thousands in lost productivity, morale, and customer trust.
The cultural fit conversation doesn’t need to take an hour. Even 15 minutes of focused questions can reveal a lot. Let others handle the technical screening, but never outsource the final call. That’s your job.
Bring Your Personality To The Process
From 1999 to 2006, Jeff Bezos famously made a point of asking every Amazon candidate a deceptively simple question about mindset:
“On a scale from 1 to 10, how much do you attribute your success to luck?”
The goal wasn’t humility or ego; it was insight into mindset. Those who recognize a blend of personal effort and external opportunity tend to stay grounded, motivated, and resilient, all key traits for thriving in high-pressure, innovative environments like Amazon.
For years, I asked every final-round candidate one of a handful of questions. Never about their resume, but about who they were.
One I borrowed from my brother applied only to sales people. I would casually ask them what salary that they had asked for (as if I didn’t already know!), and then regardless of what their number was I would look at them stonefaced and ask, “what on earth makes you think you’re worth that kind of money?”
I was intentionally being a bit confrontational to see how they’d react when a customer challenged them. It’s particularly powerful when they’re asking for a reasonable salary, but better to find out now that you’re hiring a salesperson who doesn’t like to be challenged.
Another favourite was to ask them what their last (or current) manager would say about them.
The Owner is the Culture Architect
Culture is built one hire at a time. It doesn’t take many people to change the tone of a small company, for better or worse. That’s why the owner must stay close to hiring. You set the tone. You decide who gets in. And that final interview? It’s your last line of defense.
Check out this related post on the importance of company culture.
