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The One Question Every Leader Should Ask in a People-First Workplace

A recent conversation I had on a podcast reminded me of a simple but powerful question all leaders should ask of the people around them, especially during stressful times: How’s your family?

When the pressure is on — like when you and your team are working during a global pandemic, an historic recession, or some other crisis — it’s easy to focus on the business at the expense of the people who make the business successful.

Sales reports, manufacturing processes, and on-going client challenges all matter, but a question like “How’s your family?” helps personalize relationships. It increases your empathy for the other person’s problems and builds trust, because people seldom give their trust unless they know you care about them.

In my experience, leaders and teams both get better when the leader takes the time to proactively have conversations that begin with non-work questions. Later you might ask something like, “Is there anything I can do or the management team can do to help make life and work go more smoothly?” That’s when you’ll likely hear how things are going in the accounting department, with an IT project, or with a fickle client. But if you only ask those questions, you are only getting part of their story. And the part you miss out on might be what matters most.

John Ramstead, a former fighter pilot and the president of Alpha Principle, illustrated this nicely during our discussion with a story about an executive he was coaching for a defense contractor. The company had more than 85,000 employees and the executive bragged to John about one woman who came in every day during the COVID crisis and did amazing work.

“That’s awesome,” John said. “How is she doing personally?”

The executive didn’t have a clue. But he realized in that moment that he needed to call her and ask.

The next day he called John to recap his conversation with the employee.

“That was a two-hour conversation,” he told John. “I had no idea. Her husband is compromised. He can’t leave the house. She’s trying to hold down her job and she’s got kids and a sick mom and she is literally at her breaking point. But she would never show that at work. And if I hadn’t asked that question, I would probably have lost one of the best people on my team.”

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Some leaders have personalities that make people-focused conversations natural and easy. Others care about people but aren’t as inclined to chit-chat about non-work matters. I began my career as an accountant and I’ve always leaned toward the transactional when it comes to business conversations. This is particularly true when the pressure is on. I want to analyze the numbers, solve the problems and address the issue.

When I realized that approach was affecting my leadership, however, I knew I needed to become more intentional about having informal, life-focused visits with people — not to fake it to make them think I cared about their lives but to demonstrate how much I cared about their lives.

Leadership is about influencing others to do great things, and the more we know about the people we lead, the better equipped we are to bring out the best in them. Going beyond the obvious business-related questions might take you out of your comfort zone, but it will take your team places it otherwise might never go.


  1. Salt

    I am mindful of you taking the time to spend lunch with your employees and that being one of the best things you did as a leader. Asking the question, “how are you” and some other derivatives like “How is your family doing?” can be one of the best things we do – however if we ask that general question, let’s be sure to mean it. People hear that question a lot, and it’s rarely asked with much genuine interest or sincerity. The typical response is “fine”. When we ask, let’s be sure to take the time to find out the REAL answer. Exploring with genuine interest and concern will help us create the family atmosphere that keeps people around.

    Reply to Salt

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