One Step Ahead: Mastering One-on-One Meetings

One Step Ahead: Mastering One-on-One Meetings 

One-on-one meetings are a vital part of any manager’s toolkit, offering a dedicated space for meaningful conversations with employees. But that is only true when these meetings are done right, and with nearly 70% of managers stating that they struggle to offer value during one-on-ones, that is far from a given. 

I believe it’s impossible to discuss one-on-one meetings without mentioning the quintessential guide, “High Output Management” by Andy Grove. I’ve revisited the chapter on meetings numerous times, and I’m constantly amazed by how relevant, straightforward, and practical it remains, even four decades after its initial publication.

Inspired by Andy Grove’s timeless management classic and my personal experience leading over 1,500 such meetings, I’ve gathered practical insights and tips on how to make the most of one-on-ones, with a look at both traditional methods and innovative AI-driven approaches.

So, let’s begin our meeting and review the main points, shall we? 

Q: Why are one-on-one meetings so important for managers?

A: I agree with Grove’s philosophy, which considers a meeting “Nothing less than the medium through which managerial work is performed.” When managed efficiently, these meetings form the backbone of communication and progress between managers and their team members.

Q: What’s Grove’s method for organizing one-on-one meetings?

A: After onboarding, a recurring one-on-one meeting is scheduled with the employee (I will address the meeting frequency later). During the initial meeting, I set up a shared Google Doc that serves as a “hold file,” described by Grove as a place “Where both the supervisor and subordinate accumulate important but not altogether urgent issues for discussion at the next meeting… both the supervisor and subordinate should have a copy of the outline, and both should take notes on it.” By pre-planning, we can make the meeting more focused and efficient, ensuring nothing is overlooked.

Q: What should be included in a one-on-one agenda?

A: I start by outlining my expectations for a 1-on-1 agenda. This includes discussing work-related topics, evaluating processes, addressing personal issues, focusing on the employee’s development, and talking about anything else that may be on the employee’s mind. 

One key point from High Output Management that I always stress is that one-on-ones should not be a place for urgent matters. Major frustrations or critical feedback should be communicated immediately, not saved for the scheduled meeting. This approach prevents issues from festering.

Q: How does the dynamic of one-on-one meetings change with employee seniority?

A: Grove points out that one-on-ones “Should be regarded as the subordinate’s meeting, with its agenda and tone set by them.” Junior employees often find it difficult to fill the agenda, so the manager typically leads those meetings. On the other hand, senior employees use the time more effectively, bringing up initiatives, identifying defects, or preparing for upcoming discussions. The meeting evolves to reflect the employee’s level of ownership and engagement.

Q: What role do one-on-ones play in personal development?

A: One-on-one meetings often serve as a natural setting to discuss personal development, although I’ve found that these discussions can sometimes lack direction, especially in tech companies where roles and expertise change rapidly. In my experience, personal development conversations are more effective when held with a director or group manager, as they tend to focus on broader team-building and vision-oriented aspects, making them more suited to those discussions.

Q: How do you handle difficult conversations during one-on-ones?

A: Grove warns that “The supervisor should be wary of the ‘zinger,’ which is a heart-to-heart issue brought up at an awkward time. More often than not, these come near the end of a meeting,” often as a way to avoid difficult follow-up questions. For example, employees might announce their resignation at the end of a one-on-one. Handling such moments requires careful planning: first, control the flow of information by determining who already knows; second, see if retention is an option; and third, ensure a smooth transition to minimize disruption.

Q: How can AI enhance one-on-one meetings today?

A: One of the more experimental ways I’ve enhanced one-on-ones is by integrating AI tools like ChatGPT. I’ve uploaded ‘hold files’ to an AI assistant and asked for suggestions on meeting agendas or feedback summaries. This allows for deeper insights and helps create personalized development plans. It’s an innovative step that brings efficiency and trend detection across meetings.

In summary, what makes one-on-ones valuable?

I’ve found that preparation, a clear agenda, and structured discussions elevate these sessions from basic check-ins to powerful growth opportunities. Whether through traditional methods or incorporating new technologies like AI, these meetings remain essential for driving both performance and personal development.