Maximizing the Impact of One-on-One Meetings

I remember the dread well. Meeting with my former boss, let’s call him Peter, who liked to meet late on Friday afternoons. The timing itself was a signal, a subtle but clear message about the priority—or lack thereof—placed on these sessions. And too often, they were hastily canceled or postponed. But when they did happen, they were less about my personal growth or departmental achievements and more a barrage of questions, a testament to Pete’s intellect rather than an evaluation of my diligence.

I was leading a lean HR team, which meant we were stretched very thin to the point of feeling brittle. By the time Friday afternoon rolled around, I was depleted and frayed at the edges. Peter had a habit of peppering me with questions, exploring every angle and hypothesis, leaving me feeling more like I was on trial than being guided and supported. It was a cerebral exercise for him, an attempt to dive into the minutiae of decisions I had long agonized over and finalized with due diligence.

In those meetings, rather than feeling a sense of teamwork or guidance, I often felt undermined. Each question seemed to carry a subtext that perhaps I hadn’t considered all variables, that maybe I wasn’t as thorough as I thought. It was as if trust was a secondary concern to the display of his own analytical prowess. Decisions would hang in limbo, not because of their quality, but because Peter always had another question or avenue to explore. He loved the sound of his own voice, the thrill of the intellectual chase, but missed the fundamental point of leadership: building trust and empowering your team.

Reflecting on these experiences now, I realize that the art of one-on-one meetings is subtle yet powerful. It’s not about the questions asked but the connections made, not about the answers sought but the confidence built. It’s about understanding that such meetings can make or break the delicate relationship between a leader and their direct report. When strategically planned and executed, these sessions not only drive organizational growth but also play a critical role in cultivating individual career paths. However, too often, these meetings are not utilized effectively, leading to wasted time and energy. Below are best practices to transform one-on-one meetings from a dreaded calendar event to a cornerstone of effective communication and leadership.

Peter was not a bad guy; I actually liked him personally, but don’t be a Peter.

Set a Clear Agenda

Setting a clear agenda prior to a one-on-one is essential. This step ensures that both participants are well-prepared and aware of the meeting’s goals, enabling efficient prioritization and use of time. Either the leader or direct report may initiate the agenda, ideally sharing it 24 hours in advance to allow for thorough preparation and specific discussion points.

Cultivate a Safe Space for Open Dialogue

A successful one-on-one meeting fosters an environment for open, honest dialogue. Leaders should cultivate a judgment-free space, encouraging direct reports to voice their thoughts and concerns freely. Starting meetings with personal check-ins and showing sincere interest in their overall well-being can help break down barriers and build trust. Asking questions like, “How are you feeling this week?” or “Is there anything outside of work that’s impacting your performance?”

The Art of Listening

Active listening, characterized by full attention and empathy, is fundamental to effective one-on-ones. This practice not only helps in understanding the team member’s perspective but also in uncovering underlying issues and opportunities for growth.

Provide Constructive Feedback

Feedback is the cornerstone of personal and professional growth. However, the delivery of feedback can make or break its effectiveness. Asking if they are in a place to receive feedback, being specific (with a clear example), and avoiding the “sandwich” (positive, constructive, positive) approach can help maintain trust. Focus on behavior, not the personality of the individual, and be clear what behavior you want to see by focusing on the positive approach (not just what you don’t want to see).

Set and Review Actionable Goals

Meetings should conclude with the formulation of SMART (Specific, Measurable, Achievable, Relevant, Time-bound) goals. Collaboratively setting these goals fosters a sense of ownership in your direct report and lays out a clear path for future progress and assessments.

Consistent Follow-Up

The value of a one-on-one extends beyond the meeting itself. Regular follow-ups demonstrate a leader’s commitment to their team members’ ongoing progress and well-being. Such follow-ups should be supportive and not veer into micromanagement.

Sample questions to help set an agenda for a 1:1 Meeting

• What 3 things do you want to celebrate (accomplishments, successes, breakthroughs, proud moments)?
• What did you want to accomplish and didn’t?
• What challenges, if any, did you encounter since our last 1:1?
• What do you want to focus on during our 1:1?
• What do you want to be held accountable for?
• How can I help or better support you?

To harness the full potential of one-on-one meetings, leaders must transcend the traditional view of these interactions as mere check-ins. By integrating the outlined strategies—clear agendas, open dialogues, active listening, thoughtful feedback, goal setting, and regular follow-ups—these sessions become instrumental in aligning individual career aspirations with organizational goals. When approached thoughtfully, one-on-ones can be a transformative tool, fostering a climate of growth, satisfaction, and shared success within the workplace. If you need help showing up as the impactful leader you want to be, I’m here for you.