My System for Managing 1:1's and How AI Makes It Better

A detailed guide on how I leverage Notion and AI to make my feedback better

Following my previous post — A Manager’s Checklist for Long-Term Success, I’ve received numerous questions about my approach to 1:1 meetings, particularly regarding how I use Notion to manage these crucial interactions. In response, I’d like to share a detailed look at my system for organizing and conducting effective 1:1s with team members and how I leverage Notion and AI to make them better and more effective.

The Importance of Weekly 1:1s

Before diving into the specifics of my system, it’s crucial to emphasize the importance of conducting weekly 1:1s with all direct reports. These regular check-ins form the backbone of effective team management, fostering open communication, addressing concerns promptly, and supporting ongoing professional development. I truly consider it a manager’s superpower. I’ve discussed this topic in depth in this podcast, where I elaborate on the numerous benefits of maintaining a consistent 1:1 schedule.

Always Have an Agenda

I always make sure every 1:1 has a well-structured agenda. Throughout the week, I add agenda items to the calendar invite and encourage my team members to do the same. I’ve found this practice serves several crucial purposes:

1. It helps me ensure we cover the topics we intend to discuss, preventing us from drifting into less important subjects that might consume valuable time.
2. By filling in topics throughout the week, I avoid recency bias and ensure we address all necessary points, not just those that come to mind right before the meeting.
3. Seeing the agenda topics upfront allows both of us to prepare, reducing surprises during the 1:1 itself and leading to more productive conversations.

A typical agenda in my calendar invite might look like this:

By the time of the actual 1:1, the agenda will have several topics raised by both me and my team members. I find this collaborative approach to agenda-setting ensures that our meeting addresses concerns from both perspectives, maximizing its value for everyone involved.

Track Everything in Notion

I use Notion, a versatile digital workspace, as the backbone for all my management systems. For each team member, I maintain a dedicated page that serves as a comprehensive record of our interactions and their progress.

Each page includes the following categories:

• Personal information (i.e. their address and the name of their pet)
• General 1:1 questions to ask (useful in times when there are not enough topics to discuss or when I want to address topics we often don’t discuss)
• Action items (items I’m waiting on to get a response or things I’m responsible for providing an answer for. This way I keep the team accountable and make sure everyone, including me, delivers on our promises)
• “Next” section for upcoming topics — this is where I add topics for discussion throughout the week.
• Current meeting agenda — the “Next” section title is being replaced with the current date of the 1:1.
• Historical meeting notes from previous 1:1 meetings.

Interestingly, I have duplicate agendas — one in the calendar invite and another in Notion. The calendar agenda usually contains brief titles of the topics I want to discuss, while the Notion agenda includes additional information like details, dates, feedback, and examples. For instance, a calendar entry might simply state “Meeting With Moshe and David,” but in Notion, I’ll have several feedback points I’d like to touch on that occurred during that meeting. This dual system allows me to keep the calendar invite concise while still having all the necessary details at my fingertips during the 1:1.

Here’s how it looks:

General 1:1 questions are “Synced Blocks” — synced accross all notes

This structure maintains continuity between meetings and ensures important topics aren’t overlooked. Notion’s flexibility allows me to easily link related information, create templates, and quickly search historical data. For example, the general 1:1 questions are “Synced Blocks,” meaning that this text block is synced across every page it’s being used on. So, if I update a question, it’s automatically updated on every other Notion page. The same goes for team goals, for example.

Here’s an overview of my entire 1:1 system in Notion:

I keep everything in Notion, my notes with direct reports, skip 1:1s, key projects, and my personal planning notebook.

This setup helps me stay organized and always prepared for 1:1s, feedback sessions, meetings, performance reviews, and other crucial conversations.

The Achievement and Feedback Table

To maintain a comprehensive record of team performance, I leverage Notion’s powerful database feature. I’ve created a table that serves as a centralized repository for achievements and areas needing improvement across the entire team:

This table, which is essentially a Notion database, includes the following key elements:

• Specific feedback or achievements
• Team member name
• Date of the entry
• Type of feedback (Improve or Preserve)
• Tags (e.g., Trust, Project management, Communication)

I’ve made it a habit to update this table regularly throughout the week, ensuring that I capture important observations and feedback in real time. This approach is crucial for two reasons:

1. It allows me to collect concrete examples of achievements. These serve as powerful motivators during 1:1s and provide solid evidence for positive performance reviews.
2. It helps me track areas that need improvement, complete with specific instances. This makes it easier to provide constructive feedback and develop targeted improvement plans.

By having all this information in a centralized, easily accessible place, I can review and analyze it whenever needed. Before conducting a performance review, for instance, I can quickly pull up all relevant entries for that team member, giving me a comprehensive view of their performance over time. This ensures that my feedback and evaluations are based on a holistic understanding of the individual’s contributions and growth areas, rather than just recent events or vague impressions.

Besides a table view, you can also visualize the data as a chart

Adding AI for Enhancing the Feedback Quality and Accuracy

ChatGPT voice and Notion’s built-in AI capabilities provide an additional layer of analysis to my 1:1 process, significantly elevating the quality and effectiveness of these meetings. Having all the information in a structured database makes this process easier and more accurate. Here are some ways I leverage AI:

• Extracting relevant feedback points: Before check-ins or quarterly reviews, I use the built-in Notion AI to generate summaries and recommendations based on the accumulated notes and feedback.

• Generating tailored discussion prompts: AI can analyze past interactions and current goals to suggest relevant topics or questions for upcoming 1:1s, ensuring that conversations remain fresh and aligned with each team member’s development path.
• Simulating difficult conversations: I use ChatGPT voice abilities to practice challenging discussions by simulating both sides of the conversation. This allows me to prepare for unexpected questions and refine my approach, ensuring more productive and less stressful interactions.

• Role-playing scenarios: By playing both roles in a simulated conversation, I can gain new perspectives on potential issues and improve my communication strategies. This is particularly useful for addressing sensitive topics or delivering constructive criticism.

Prompt example:

I’m an engineering manager, and you’re my mentor helping me grow as a leader and prepare for critical conversations. I need to have a difficult discussion with one of my team members, Puptiz, about why he won’t be getting the promotion he requested. Please ask me the right questions to get the full context, suggest key points I should keep in mind during the discussion, and help me craft a strategy for delivering the message clearly and respectfully. Afterward, let’s role-play the conversation so I can prepare for potential reactions, handle unexpected questions, and ensure that my feedback is understood and accepted.

Benefits

Implementing this structured 1:1 system, enhanced by AI, offers several key advantages:

1. Improved recall and pattern recognition: While detailed note-taking ensures that specific instances are not forgotten, AI can identify trends and patterns across multiple interactions that might be missed by human analysis alone.
2. Data-driven, personalized feedback: AI-powered analysis allows for more tailored and actionable feedback, based not just on recent events but on long-term performance trends.
3. Comprehensive preparation: Managers can enter every 1:1 and important conversation with a clear understanding of the team member’s recent performance, ongoing challenges, and potential areas for growth, all synthesized by AI.
4. Tracking growth with predictive insights: The system allows for easy visualization of a team member’s progress over time, with AI potentially offering predictive insights into future performance or skill development needs.
5. Time efficiency: AI can quickly process and summarize large amounts of data, allowing managers to focus more on the human aspects of their role rather than administrative tasks.

Final Thoughts

A structured, AI-enhanced approach to 1:1 management can significantly improve team interactions and performance. This system offers data-driven insights that adapt to your team’s needs, representing the future of management where AI enhances human skills.

I encourage you to adapt these ideas to your style. The goal isn’t to automate human interaction but to make it more meaningful. By handling administrative tasks, AI frees you to focus on what truly matters — building relationships, fostering growth, and leading your team to success.

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