First-Time Management: 1-on-1s Assembled with AI

Introduction

Starting in July 2026, I became a manager. I had never managed direct reports before, and the only team leader experience I had was about ten years ago for roughly a year. Despite that background, I found myself responsible for three members, each with a different job function. I am a Growth Lead, but my direct reports are an engineer, a designer, and a project manager.

At Classmethod, we hold 1on1s on a regular basis. I have had various managers facilitate them over the years, and the approaches have truly varied from person to person — there is no fixed template.

When it came time to run 1on1s myself, I started by deciding what kind of time I wanted these sessions to be. This post is a record of how I designed that structure, using AI (Claude) as a sounding board.

What a 1on1 Actually Is

Starting with the general definition: a 1on1 is a regular one-on-one dialogue between a manager and a direct report. The purpose is not progress tracking but rather supporting the direct report's growth, building trust, and catching concerns and issues early.

In Classmethod's internal materials, 1on1s are positioned as follows:

• A minimum frequency of once per month is recommended
• A space for understanding the member's situation, handling consultations, and giving feedback

The lower bound on frequency (at least monthly) is set, but everything beyond that is left to each manager's discretion. I hold sessions either weekly or biweekly depending on each member's situation.

Deciding What Kind of Space to Create

Since there is no fixed template, I first decided on a fundamental question: what do I want this time to be, at its core?

I decided I wanted 1on1s to be a space where the member is the main character. I wanted it to be a time when members could express their honest thoughts without anxiety, make decisions for themselves, and come away more positively focused on their work.

• Because the member is the main character → try not to let it become a status-report session
• So they can decide for themselves → let the member choose the topic to discuss, as a default
• So they can speak honestly without anxiety → prioritize trust and establishing ground rules for the space first (especially in the beginning)

To be candid: when I started, I would rate the trust I had built with my members at around 50% by my own assessment. So for the first session, I decided to go all-in on "building a foundation where they feel safe to talk," rather than on growth support.

Built with AI: Three Sounding-Board Scenes

I used AI (Claude) as a sounding board to translate the above approach into concrete practice. Here are three exchanges from those conversations.

① How to engage with members who have different specialties

Concern: Can I really be helpful when our expertise differs?
My team consists of members with different job functions, and honestly, each of them knows the details of their own domain far better than I do. When someone comes to me in a 1on1 with a question in that area, I feel a little anxious about whether I can genuinely be of help.

AI's suggestions

• What makes members anxious is not that their manager lacks specialized knowledge — it's being on the receiving end of someone pretending to know things they don't. So it works better to honestly tell them that you trust them to make the expert calls in their domain. That said, you should still maintain a genuine curiosity about and interest in what they do.
• A manager's role is not to step in as a substitute for expertise, but to create an environment where members can do their best work, ensure they are recognized fairly, and remove obstacles. That contribution is equally available regardless of job-function differences.

How I applied it
In the first session, I told each member: "For the deep expertise in your domain, I want to trust and defer to you — you know it best. In return, I'll contribute on the evaluation, coordination, and quality-of-work-life side." I helped them understand that when I don't know something, my job is to ask with genuine interest rather than pretend, and to connect them with the right person if specialist support is needed.

② How to use 30 minutes well

Concern: What should we talk about in 30 minutes?
As I prepared, the list of things I wanted to cover kept growing — clarifying my role, understanding what they dislike, background I should know, career aspirations, and more. Should conversations like "where do you want to be in the future?" or "what's weighing on you most right now?" be saved for a separate goal-setting meeting?

AI's suggestions
Exactly right — you can't fit everything in. It helps to sort topics into three layers:

• Things to establish in the first session (foundation and ground rules)
• Things to handle in goal-setting meetings (heavy conversations about goals and career)
• Things to cycle through in each regular 1on1 (ongoing day-to-day support)

How I applied it
I separated what I would cover in the first session from what I would cover going forward. By limiting the first session to understanding the member and agreeing on rules and flow, and explicitly deciding that "the heavy conversations happen elsewhere," I was able to focus on building the foundation.

③ What makes for a meaningful conversation

Concern: How do I draw out what they want to talk about?
I learned in a training session that it's good practice to let the member choose the topic. But if you just say "talk about whatever you like," that's hard to do when you're not used to it. So I thought I'd prepare a few options each time and let them choose from those. Given the nature of 1on1s, what kinds of options would work well?

AI's suggestions

• Options are just a prompt to get things flowing — make sure they don't override what the member actually wants to talk about. The order should be: first ask if there's something they want to discuss → if not, choose from the options.
• Make "how things are going lately" and "anything you're struggling with" your regulars, and rotate the rest. Too many choices can actually make it harder to choose.

How I applied it
I start each session by checking whether there's something they want to talk about today. If not, I have them choose from a prepared list. Currently I have seven topics ready, and when they have nothing specific in mind, they choose from the following:

• A recent vague unease (not necessarily a problem — just something that's been sitting awkwardly. But problems are welcome too)
• Something that went well recently, or something that felt like a win
• Something they worked hard on recently that isn't showing up as visible results
• Something they've been wanting to try or take on recently
• Just need to vent
• Want to think out loud and get some clarity
• Just want to chat — talk about something not work-related

What I Actually Covered in the First Session

Based on the design above, the first session roughly followed this order:

1. Declaring what this time is for: a 1on1 isn't a progress report — it's time for you. You'll be doing most of the talking.
2. My role: I'm here to support you on evaluation, coordination, and making work a good experience.
3. Confidentiality design: in principle, what's discussed here stays with me / HR matters and harassment-related topics are exceptions / anything else is your call.
4. Self-disclosure and getting to know them: management styles I found difficult when I was on the receiving end (e.g., being micromanaged made it harder to move), and what management styles work poorly or well for them.
5. Operational agreements: frequency, the default that they choose the topic, and that heavier conversations happen in goal-setting meetings.

I adjusted my wording and the proposed frequency based on each member's background and career stage. For newer members, I leaned toward "we'll work through things together"; for more experienced members, I leaned toward "I'll trust you to lead." On frequency, some members meet weekly and others biweekly — I let them decide.

My Weaknesses and What I Watch Out For

There was a training session from HR before I started doing 1on1s, and it helped me become aware of my own weak spots. I'm reasonably good at affirming and asking questions, but I struggle to stay quiet until someone finishes speaking — I tend to want to summarize in my own words, identify the issue, and jump to solutions. I also worried that having a dedicated conversation slot would tempt me to use it to pass along announcements, especially since I'm not working directly on the same projects as all of my members.

So I try to keep the following in mind:

• Avoid making it a communications slot as much as possible: there are times when it happens unavoidably, but I don't do it unless there's a real reason.
• Let them do most of the talking: I hold back the urge to summarize, listen first, and ask them to put things in their own words. Honestly, I'm still not great at this — it's a work in progress.
• Check whether they want to solve it or just be heard: for some people, being handed a solution right away is itself a burden, so I ask first. There was actually a moment when I was listening and thinking "they probably want me to help fix this," but when I asked, the answer was "please don't do anything yet — I just needed someone to hear it."
• Let them make the call whenever possible: I add a short phrase like "this is something you get to decide for yourself."

What I've Found: The Most Commonly Chosen Topics

Since switching to a model where they choose the topic, the option chosen most frequently so far is "something I worked hard on that isn't showing up as visible results." Of course, there are also sessions where someone says "I want to talk through how I'm approaching a project" or "I want to dig into my goals."

This feels modest, but I think it matters. Effort that doesn't show up as visible output won't get acknowledged unless someone says something — because it's simply not visible from the outside. When I ask about it, I sometimes hear things like "I was testing a tool I wanted other members to use too," and in cases like that I share it in the team Slack channel. A personal initiative surfaced in a 1on1 can ripple out to the whole team.

Closing Thoughts

It's only been about two months, so I'm not confident yet about how well things are going — but I have been getting positive feedback from my members. I'm still feeling my way as a new manager, and I'd like to write another post if I find more things worth sharing.