The End-of-Year 1:1: A Ritual Worth Doing Well

As 2025 winds down, many of us, whether in companies, nonprofits, or schools, are filling our calendars with end-of-year one-on-ones. And for a lot of people, this season brings way more dread than clarity.

Recipients often show up braced, nervous, or already running scenarios in their heads about promotions, raises, role shifts, or concerns about maintaining their jobs. Managers show up overwhelmed and rushed. The result is usually a surface-level check-in where no real learning happens, or worse, a conversation that creates more repair work than alignment.

We can create something much better here.

If you want your one-on-ones to be more effective and less stressful for everyone involved, the simplest move is this:

Do much, much less.

A great 1:1 doesn’t require a script, a form, or a checklist. It requires a real conversation about the thing that matters most to them, and your willingness to offer your full attention while they talk about it.

Start With One Essential Question

Begin your 1:1 by asking:

“What’s the most important thing you want to talk about today?”

As simple as it is, this question changes everything. It puts their world, not yours, at the center, reduces anxiety because they aren’t guessing your agenda, creates a chance to hear something genuinely useful, and helps make the conversation real.

And if you disagree with their topic? It doesn’t matter. If it matters to them, it matters to you. This time is about them and their needs and concerns.

Often, real leadership and powerful relationships involve entering someone else’s world, not dragging them into yours.

The thing they’re nervous to bring up is almost always the thing that deserves the most attention.

Set the Stage Ahead of Time

Send a short email like this:

“In our upcoming 1:1, we’ll focus entirely on whatever you feel most deserves our attention. If there’s something that feels hard to raise, that’s probably the thing we need to talk about most. If I have feedback for you, I’ll schedule a separate conversation so this space stays focused on what matters to you.”

This lowers anxiety, creates clarity, and separates development from evaluation. If you do need to give feedback later, consider using the SBII model, simple, direct, and human.

Presence Is the Real Work

Being fully with someone, prepared to be nowhere else, is rare. In today’s attention-splintered world, it almost feels rebellious.

When done well, presence is one of the most powerful acts of leadership. As a listener, it feels incredible when someone gives you their full attention. It signals something people rarely hear: I care about you, your challenges, and your growth.

How to Actually Listen

These are the mechanics of presence:

• Close the laptop.

• Silence your phone.

• Make eye contact.

• Use your whole body. 

Then ask simple, open-ended questions, rooted in The Coaching Habit and Fierce Conversations:

• What’s on your mind? 

• “Tell me more.”

• “What else?”

• “What’s the real challenge here for you?”

• “Of everything we’ve talked about, what feels most important?”

• “If this were resolved, what difference would it make?”

• “Who or what else is being impacted?”

• “What’s at stake for you?”

• “What are you doing, maybe unintentionally, to keep the situation exactly as it is?”

• “What’s the next step you can take?”

• “What could get in your way?”

• “What’s your ideal outcome?”

These questions help people get honest about their reality. Your job is to listen far more than you talk and let silence and open-ended questions do the work. 

The Real Purpose of a 1:1

At its core, a 1:1 is a chance to gain clarity together.

Workplaces drift. Truth gets blurry. People assume different things about the same situation. Everyone holds a piece of what’s really going on, no one holds the whole thing.

A strong one-on-one creates a space where you can put those pieces on the table and look at the picture together.

This is how better culture emerges, better strategy forms, how teams execute from a place of alignment, and how trust grows so you can get to the results you’re going for.

Close With Clarity

You don’t need a formal summary. Try something simple:

• “Here’s what I’m hearing…what do I have correct, and what did I miss?”

And one of my favorite prompts from MBS:

“What was most helpful to you?”

It reinforces learning and keeps the focus on their experience.

Fresh Starts Matter

Wharton Professor Katy Milkman’s research on “fresh starts” is useful here. Certain moments give us psychological permission to make a change:

• End of the year

• Beginning of a new quarter

• A holiday break or birthday

• Even a Monday

A December 1:1 can spark a behavior shift, a new agreement, a healthier pattern, or a clearer sense of direction. It’s a wonderful time to reset, realign, and recommit. 

If you can do this once a month with the key people on your team, your projects, and your life, the cumulative impact is enormous.

Try This This Week

• Schedule one meaningful 1:1.

• Ask the essential question: “What’s on your mind?"

• Offer your full presence.

• Listen like it’s your only job.

• Let the conversation go where it needs to go.

• Save feedback for another time (and use SBII when you give it).

Notice what shifts when clarity meets presence.

And remember Susan Scott’s reminder: The conversation is the relationship. One conversation at a time, you’re either building, weakening, or reinforcing your relationships.

Make this one count.

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This post was informed by, and I highly recommend reading, Fierce Conversations by Susan Scott and The Coaching Habit by Michael Bungay Stanier (MBS).