One-on-Ones

When I was in the military, I often wished for a feedback loop with my superiors. I wanted to understand whether I was doing well, share my preparation efforts (like reading Clausewitz), and express my desire to contribute meaningfully. However, the opportunity never came. In retrospect, I might have needed to push more on my side, but I didn’t want to overstep or reach beyond my rank. I wanted to earn recognition through hard work. All of this could have been avoided with inclusion of one-on-ones.

I first encountered the concept of one-on-ones in Small Unit Leadership: A Common Sense Approach, an 80s military leadership manual. The idea made perfect sense to me. We’re dealing with living, breathing people, not cogs in a machine. Understanding this helps prevent burnout and ensures you’re getting the best out of your team.

What Are One-on-Ones?

Are one-on-ones just sitting in a room and chatting? Not quite. The best one-on-ones have clear goals and structure. For example, the first one-on-one sets the tone for the relationship, and subsequent meetings should happen regularly. I prefer monthly meetings, but the frequency can vary depending on the team and individual needs. The key is consistency and meaningful information exchange.

One-on-ones are about creating space for meaningful dialogue, whether virtually or in person. Every great relationship starts with a conversation.

Building Connections and First Impressions

One-on-ones are an opportunity to understand the people you work with on a personal level. While group communication is essential, nothing replaces individual connections. Ask questions like:

• Why did you choose to work here? (Reassure them this isn’t a job interview—“a paycheck” is a valid answer!)

• What does success look like for you?

• What are your hobbies?

• Who inspires you?

• How do you prefer to communicate?

It’s important to create an atmosphere of trust where people feel safe sharing their thoughts. You may not get direct answers to these questions initially, but the goal is to build rapport and show you genuinely care about them as individuals.

First impressions are critical. A positive initial one-on-one can shape your reputation and establish trust. Conversely, a poor first impression can take a long time to recover from. I’ve seen both junior and senior team members light up when they realize their leader genuinely cares about them. It’s a powerful motivator.

Key outcomes of effective one-on-one meetings: Trust, emotional insight, and job satisfaction are the building blocks of a strong team. Regular check-ins bring these benefits to life.

One-on-Ones in a Remote Era

In today’s remote work environment, don’t relegate one-on-ones to text. The best option is face-to-face, and the next best is a video call. These formats allow for richer communication and foster connection.

Ongoing Check-Ins

One-on-ones shouldn’t be isolated events. They’re like mini-retrospectives for issues that might not surface in team meetings. Use these check-ins to ask:

• How do you feel about your work tasks?

• How do you feel in the company overall?

• On a scale of 1 to 10, how satisfied are you with your current situation?

The goal isn’t to collect information for HR but to create an atmosphere of care and support. Team members should know their job security isn’t tied to their answers. This encourages honesty and fosters a culture of trust.

Surprising Outcomes and Leadership

One-on-ones often reveal surprising insights, from feelings of inadequacy to newfound ambitions. Addressing these proactively can transform a team. For instance:

• Help someone struggling with anxiety by providing clear plans and support.

• Encourage a team member’s ambition, even if it means they might outgrow their current role. Helping your team succeed—even beyond your team—is a hallmark of great leadership.

A well-timed one-on-one can reignite motivation, just like a phoenix rising from the ashes. Leadership is about transformation.

Great leaders like Caesar, Teddy Roosevelt, and Richard Branson understood the importance of caring for their people. Their people-centric leadership laid the foundation for modern practices like these. When people feel valued, they’ll go to great lengths for you.

Conclusion

One-on-ones are a simple yet powerful tool for leaders. They’re not just about work—they’re about understanding and empowering people. By investing time in your team, you’ll not only build stronger connections but also unlock their full potential. Start small, stay consistent, and watch your team thrive.