AI-Powered 1:1s

If you manage people, you know the debate around one-on-ones. Some leaders swear by them and never miss a week. Others think they are a time sink that does not scale. The truth is it depends. The right approach changes based on the employee, their role, and their stage.

But one thing is not up for debate: if you are going to spend that time, it has to be valuable. Too often it is not. Managers show up scrambling for topics. Employees come half-prepared. The first half of the meeting is spent on updates that should have been an email. Only occasionally does it touch on something meaningful.

Why Existing Tools Fail Managers

Here is part of the problem: the tools meant to “help” you run one-on-ones are not actually built for managers. They are built for HR. They track processes, enforce consistency, and generate records, but they do not fit into your workflow. Logging into a separate app, filling out forms, and remembering to use it does not help you walk into a 1:1 prepared. That is why most teams default back to a blank Google Doc or nothing at all.

What Managers Actually Need

You do not need another system to manage. You need support in the flow of work. That means:

• Walking into every 1:1 already prepared
• Making sure your employee feels heard and has space to bring up what matters
• Spending less time on updates and more time on real issues
• Building a living record automatically so when performance reviews roll around, you have six months of conversations, themes, blockers, and progress already in one place, no scrambling to remember what happened

That is what turns 1:1s from a checkbox exercise into one of the most powerful tools you have as a manager.

A Better Way: AI-Powered, Native, Automatic

That is why we built One-on-Ones powered by Windy. Instead of another tool you have to remember to use, it lives where you already work, Slack and your calendar.

Here is how it works:

• Automatic detection: Windy spots 1:1s on your calendar. No setup required.
• Perfect memory: Drop thoughts to Windy in Slack whenever they come up. Windy holds onto them until your next 1:1.
• Employee input: The day before, Windy asks your direct report what they want to cover.
• Work context: Goals, blockers, projects, and feedback are pulled in automatically so you are starting from substance, not catch-up.

Smarter Conversations, Lighter Time Investment

Windy builds the full agenda in advance, what you want to discuss, what your employee wants to discuss, plus recent activity and context. You can scan it in minutes and walk in prepared. After the meeting, action items are captured automatically.

That flexibility makes recurring 1:1s sustainable. A slot can be thirty minutes, or it can shrink to twenty, ten, or even be skipped if there is nothing pressing. You keep the rhythm without wasting the time.

Organizational Intelligence

And because everything lives in Windmill, you build that long-term record automatically. Leaders also get visibility into how 1:1s are happening across the org without forcing rigid process.

The Result

Managers walk in prepared. Employees feel heard. Leaders gain visibility. One-on-ones stop being another calendar obligation and start becoming a tool for growth. With Windy, it is like having a chief of staff dedicated to your team relationships, always ready, always plugged in.

Interested in learning more? Get started today.