Understanding Leadership Styles Through Interviews

Recently, I was asked by someone deciding between two jobs: "How do you know if a leader is a good leader to work for?" He shared that many leaders talk about "culture" and "feedback" but it's hard to discern reality from perception. My recommendation was to ask these 4 questions to your prospective boss: #1: "When have you had to sugar-coat the truth — or avoid telling the truth — to your team?" This reveals their integrity. If they laugh and say "all the time" too casually, they may habitually mislead employees. If they're hesitant to admit anything, that's a red flag too. Ideally, they'll admit in a nuanced way when they've chosen not to be transparent, and explain why. #2: "What do you think is your own greatest leadership blindspot?" This reveals self-awareness. Look for someone who's clearly reflected on this rather than struggling to answer directly. #3: "What does 'success' for the company look like to you?" Listen carefully. If they focus solely on "winning," "making money," and "dominating competition," the work environment will revolve around that. If they also mention building a healthy culture and supporting employee fulfillment, expect that to be reflected. #4: "What would an employee who's left the company say it's like to work for you?" This may feel tough to ask but is potentially most important. It shows how aware they are of past leadership behavior. Be wary of leaders who mention only positives. -- If you're concerned these questions might offend your prospective boss, that itself signals they might not be the leader you hope for. The best welcome tough questions and appreciate your desire to understand their leadership style.

Transactional interviews are a piece of cake. But transformational hires? That’s where founders and CEOs hit a wall. “I just need a sales leader who gets it.” - What a CEO told me in January 2024 He was juggling late nights and weekend marathons Caught in a whirlwind of meetings and fires to put out All while chasing ambitious growth goals He wanted someone to step in and take the reins. But he also wanted to save money by hiring on his own. Fast forward 7 months, he called me in a panic. ... They had missed yet another quarter by 67% ... The new hire hadn’t built a team ... Their forecast was a total disaster And that “get it” leader?.. Not delivering. When I reviewed their interview process, the issue was painfully clear. The interviews were transactional. Pure box-ticking: ✔️ How many people did you hire? ✔️ What were your targets? ✔️ What markets did you sell to? On paper, the hire checked all the boxes. In practice, they weren’t the leader the company needed. This isn’t a one-off story. In the last 6 months, I’ve consulted on 57 hiring processes, and this pattern repeats like clockwork. When interviews feel like a checklist, the real signals are missed: 🚥 How they think under pressure 🚥 Why they approach challenges the way they do 🚥 If their leadership style fits your company culture 🚥 How their competency aligns with your job to be done Excellence in hiring isn’t about filling a seat. It’s about finding someone who can carry the baton and run with it, especially when the hurdles pop up. This CEO needed more than a hire. They needed clarity. So we rebuilt their process, turning transactional interviews into strategic conversations. ... How did you approach building your last team? ... What unexpected challenges did you face, and how did you handle them? ... How would you apply that lesson here, and why? Within three months of hiring a new sales leader: ... Productivity was up by 38% ... They had onboarded 4 people blowing away their ramp expectations ... Their pipeline projected a 47% revenue increase for the next quarter The difference was night and day. If you’re ready to avoid costly hiring mistakes, here’s where to focus: 𝐃𝐞𝐩𝐭𝐡 > 𝐛𝐨𝐱𝐞𝐬: Resumes and referrals are starting points, not the full story 𝐂𝐨𝐧𝐯𝐞𝐫𝐬𝐚𝐭𝐢𝐨𝐧𝐬 > 𝐜𝐡𝐞𝐜𝐤𝐥𝐢𝐬𝐭𝐬: Dig deep - Assume nothing - Follow the signals 𝐏𝐫𝐨𝐜𝐞𝐬𝐬 > 𝐰𝐢𝐧𝐠𝐢𝐧𝐠 𝐢𝐭: A clear, consistent method trumps gut-instinct hiring Hiring the right leader can change everything. So, are you stuck in the transactional hiring trap? Or ready for clarity that transforms your business? Let’s talk, I've got my Windex bottle ready.

In an interview, I asked the hiring manager: “Can you tell me about the last person you promoted?" It’s a simple question that revealed a lot about their investment in your future. Once, after moving under a new boss, I noticed that none of their direct reports had been promoted in years. Meanwhile, their peers on other teams were celebrating regular advancements. When I raised the issue, the response was a chuckle and a vague, “Well, I guess I have higher standards.” But those so-called “standards” didn’t reflect any reality. A few months after I left that group, I began to see promotions going through: the ones I had pushed for. It was a reminder that leadership matters — and not every manager is truly invested in developing their team. It is your career and you need to manage it, but if you come across a boss who doesn’t promote people, you are fighting an uphill battle. No amount of managing up may help in this case. So before you join a team, consider asking your future colleagues, or even the manager directly: "Who was the last person you promoted?" If the answer is vague, or they can’t recall anyone, that’s a red flag. Don’t ask generic questions like "What’s the culture like?" — you’ll just get fluffy answers. Ask questions that get to the heart of the matter. How do you assess whether a leader is truly invested in growing people?