Four Questions Every Leader Should Ask Themselves—And Why They Matter

Leadership can often feel like juggling on a tightrope. You’re constantly balancing the immediate needs of your business with long-term strategy, all while managing people, navigating external pressures, and trying to maintain your sanity. In a recent Economist article, four critical questions were posed to help leaders take stock of their team and processes. Each question touches on hiring, retention, culture, and automation—arguably the pillars of any successful organization. Let’s explore why these questions are not only essential but also potentially transformative.

Would I hire this person again?

This is probably the most loaded question on the list, but also one of the most insightful. It forces you to consider whether the people you’ve brought on board are still aligned with your vision, values, and the current needs of the business. We’ve all made hires in the past who were perfect at the time, but businesses evolve, and sometimes, so do the roles. Asking yourself if you’d make the same choice today helps you recognize if someone’s skills, attitude, and performance are still adding value.

But here's the trick: if the answer is no, don’t immediately think about letting that person go. Instead, ask what can be done to either re-skill, reposition, or re-inspire them. Maybe it's time to invest in development or rethink their responsibilities. And if it truly isn't working, parting ways might be the best for both parties. As someone who’s spent years advising and recruiting top talent, I can’t stress enough how important it is to regularly reevaluate your team.

How often am I hearing dissent?

The second question digs deep into the culture you’ve cultivated. A company without any dissent is either perfect (unlikely) or silent because of fear or complacency. If no one is pushing back, challenging ideas, or suggesting improvements, something’s wrong. Encouraging dissent might sound counterintuitive, but it’s essential for innovation, growth, and avoiding groupthink.

As a leader, you should seek out differing opinions, especially from your team. Honest feedback—especially when it stings a little—is a gift. It allows you to see blind spots, question assumptions, and ultimately make better decisions. In cleantech, where innovation and disruption are key, fostering an environment where people feel safe to speak up isn’t just nice to have; it’s mission-critical.

What should we automate?

Automation has become a buzzword, but here’s the reality: automating repetitive, time-consuming tasks frees up your team’s energy for more strategic work. Yet, many leaders hesitate, fearing that automation will dehumanize their company or reduce the need for people. In reality, it’s about giving your team more time to focus on creativity, problem-solving, and growth.

This question challenges leaders to look beyond the surface and find those tasks or processes that can be handled more efficiently by technology. The cleantech and e-mobility sectors, where Hyperion Executive Search focuses, are prime examples of industries where leveraging technology can streamline operations and drive innovation. Whether it’s automating customer follow-ups, data management, or certain HR functions, smart automation can be a game changer.

How many people are leaving my team?

Turnover is a reality in any business, but it’s also a warning sign. High turnover rates should prompt some serious reflection. Why are people leaving? Is it due to leadership, company culture, or perhaps unmet expectations? Often, the problem lies not just in hiring the wrong people but in failing to retain the right ones.

It’s crucial to not only ask this question but dig deep into the reasons behind each departure. Conduct exit interviews, look for patterns, and don’t be afraid to ask hard questions. Turnover, particularly of high-performers, is costly both in terms of money and morale. On the flip side, if your retention rates are high, take the time to recognize what’s working and replicate those practices across the company.

The Road Less Stupid

If there’s one resource I recommend to any leader grappling with these questions, it’s The Road Less Stupid by Keith Cunningham. The book emphasizes the importance of thinking time—a concept we often neglect amidst the hustle and bustle of leadership. Making time to ask yourself these tough questions, and giving yourself the space to reflect on them without distraction, is one of the best ways to avoid costly mistakes and cultivate long-term success.

In leadership, we’re often so focused on doing that we forget to think. Cunningham's book has had a profound impact on me, and I’d urge you to pick up a copy. You’ll thank me later.

Why These Questions Matter

To lead is a privilege, but it comes with enormous responsibility. These questions aren’t just about operations—they're about your most valuable asset: your people. Hiring, retaining, and nurturing talent, while balancing automation and culture, is a constant challenge, but it’s also where the most significant rewards come from. Get it right, and the impact on your team—and your business—will be profound.

So, when was the last time you sat down and asked yourself these questions? In the fast-paced world of cleantech, where innovation is relentless, it’s easy to get caught up in day-to-day firefighting. But making the time for self-reflection, for asking yourself the right questions, is how you stay ahead.

And if you ever want to talk about hiring, retention, or team culture, you know where to find me.

David