LeadershipFramework I Built

1:1 Upgrader

Most 1:1s are status updates. These questions turn them into development conversations.

What it is

The 1:1 Upgrader is a set of questions designed to transform your one-on-ones from status updates into genuine development conversations. Most managers use 1:1s to check in on tasks. The Upgrader shifts the focus to growth, blockers, and the things that aren’t being said.

💡Why it matters

Think about the last ten 1:1s you had. How many were just someone reading you their to-do list? Status updates belong in Slack or a project tool, not in the most valuable 30 minutes you have with another human. A great 1:1 should leave both people feeling clearer, more supported, and more challenged. If it doesn’t, you’re wasting the meeting.

🛠️How to use it

Replace your standard 1:1 questions with these. Instead of “What are you working on?” ask “What’s the one thing I could do to make your work easier this week?” Instead of “Any blockers?” ask “What are you avoiding?” Instead of “How’s it going?” ask “What’s not being said on the team right now?” The key is to ask questions that go beneath the surface. You’re not checking on tasks - you’re developing a person.

💬My experience with it

I ran hundreds of 1:1s at Startmate and the quality of those conversations directly correlated with how well the team performed. The moment I stopped asking about tasks and started asking about energy, avoidance, and unspoken tensions, everything changed. People started bringing me real problems instead of polished updates. That’s when the coaching actually happens.

🚀Try this today

In your next 1:1, try asking just one different question: “What are you avoiding right now?” Don’t fill the silence after you ask it. Let them sit with it. The answer that comes after five seconds of discomfort is always more honest than the first thing they were going to say.

Read the full article