The first 1:1 with a new report

The first 1:1 with a new report isn't a 1:1 like the others, and treating it as one would be a missed opportunity. Every 1:1 after it will be about tracking the work, clearing blockers, adjusting priorities.

The first one is what makes all the others possible. The practical consequence is often surprising: you don't bring an agenda to this meeting, because the goal isn't to start tracking, but to learn how this person works. This page details how to approach it. It extends our complete guide to 1:1s.

Why the first 1:1 isn't a 1:1 like the others

At the first meeting, there's nothing to follow yet. No commitments made last time, no progress to review, no blocker in place. Trying to run the usual template there just fills empty air. The point is elsewhere: this is the moment to set the ground rules for the ones that follow. That's where mutual expectations, the way you each work, and the trust that will later make candid conversations possible get established.

This first exchange also sets a precedent. The way it's held, who speaks, what gets covered, how much time you give it, tells the report what this ritual will be for them: a space to be heard or a reporting session. Best to set the right tone from the start.

Don't bring a shopping list

A good manager's instinct is to come in prepared, with points to cover. For this first 1:1, that's exactly the instinct to resist. A loaded agenda turns the meeting into a handover of instructions, when it should be a chance to listen. Preparing for it isn't about gathering work topics, it's about working out what you want to understand about the person, and what you want them to understand about you.

A few concrete moves help.

• Set a longer slot than usual (an hour, typically), with no tight agenda, to let the conversation breathe.
• Tell the report ahead of time what kind of meeting this is, so they don't show up dreading a status check they have nothing to report on yet: letting them know this first 1:1 is about getting to know each other and setting the basics for the ones that follow is enough to set the right tone.

And resist the urge to fill the silences, which are more instructive here than anywhere else.

The questions of the first 1:1

The questions in this first conversation cover three areas: mutual expectations, how you each work, and the person's background. They're there to understand the person, not to assess what they already know how to do.

• On expectations: what would make you say, three months from now, that your arrival went well? What do you expect from me as a manager? What, in your previous roles, helped you or got in your way?
• On the way of working: how do you prefer to receive feedback? How do you work best, and what throws you off? When you're stuck, do you prefer to search on your own for a while or talk about it right away?
• On the background: what made you want to join us? What are you most proud of in what you've done before? What do you want to learn here?

For the questions of the following 1:1s, once the relationship is established, the 1:1 question list by intent takes over.

The basics of collaboration

The most useful moment of the first 1:1 is when you make explicit what others leave implicit. The practice is nothing new: it's known as the "working-with-me manual", or "user manual for yourself", a document that spells out a person's communication and collaboration preferences, along with the strengths they want to share. We've built a generator to help you, which we encourage you to use: playbook.serendly.com/

This conversation is about the "meta": the cadence and format of the 1:1s, their length, the prep expected ahead of time... and this is where the reliability principle should be set: you don't cancel a 1:1, at worst you reschedule it (see our article on 1:1 frequency).

It's also about what gets said and not repeated: making clear that the 1:1 is a space where you can speak candidly, and that what's said there won't feed a disguised evaluation, shapes how honest future updates will be. Finally, you settle how you'll communicate and what you each expect, autonomy on one side, support and availability on the other.

The next 11 1:1s (the first 90 days)

The first 1:1 marks the start of the new report's day-to-day. Over the first three months, the 1:1 becomes habitual, almost automatic, and grows into its full role at the pace of the report's onboarding.

Topics tied to contextualization (understanding the environment, clearing the fog, checking that the first weeks go well...) should give way to more operational questions, as the person finds their footing.

By the three-month mark, the 1:1 should have reached its standard format: tracking wins and priorities, spotting blockers, tying back to the team's OKRs, and so on. The evolution of these 1:1s is an excellent early indicator of the report's integration and engagement.

So it's the manager's job to make sure this evolution happens.

At Serendly, we help managers and teams keep the thread of these conversations from a report's first day, and tie them to the team's objectives as they grow more autonomous. To see how, discover our approach to 1:1s that contribute to company performance.