We’ve all been there. It’s Wednesday afternoon, your calendar alerts you to a one-on-one with a team member in 30 minutes, and you think, “Do we really need this meeting today? Everything seems fine, and I’ve got that deadline looming…”
Before your finger hits that “cancel” button, let me share why rethinking—rather than removing—these meetings might be your best move.
Why That Cancellation Temptation Is So Real
Last month, I was chatting with Miguel, a tech lead who confessed, “I used to cancel one-on-ones constantly. They felt like casual coffee chats that weren’t moving the needle.” His perspective changed when a valuable team member resigned, citing in their exit interview that they “never felt their development was a priority.” That stings, right? But it’s also surprisingly common.
One-on-ones often fall victim to the “urgent over important” trap. When deadlines loom, these meetings can seem like the perfect calendar item to sacrifice. But what if, instead of canceling, we transformed them?
Flip the Script: From Status Update to Career Catalyst
Career Development: Plant Seeds for Growth
Rather than opening with “How’s that project going?” try “Where do you see yourself growing in the next six months?” Sarah, a product manager I worked with, started each one-on-one by reviewing one skill her report wanted to develop. When her designer mentioned wanting to improve presentation skills, they used subsequent one-on-ones to prep for an upcoming design review, practice the presentation, and later debrief how it went. That designer now leads the company’s client presentations.
Meaningful Feedback: Beyond the “Good Job”
“You’re doing great” feels nice but offers little guidance. Specific feedback moves the needle.
A finance director named James shared how he transformed his feedback approach: “Instead of general praise, I started noting specific behaviors. ‘The way you simplified that complex data in yesterday’s presentation really helped the executive team make a decision quickly. That skill for distilling information is something I’d love to see you continue developing.'”
His team member later told him it was the first time she understood exactly what her strengths were and how they impacted the business.
Strategic Context: Connect the Dots
Ever had a team member ask, “Why are we doing this again?” That’s often a sign they’re missing the bigger picture. Carlos, an engineering manager, realized his one-on-ones were perfect for sharing context his team rarely got. “I started each meeting with a ‘zoom out’ moment—sharing something from leadership meetings or industry trends that connected to their work. The lightbulb moments were incredible. One engineer completely reimagined his approach to a feature once he understood how it fit into the company’s new market strategy.”
Problem-Solving: Coach, Don’t Solve
When Rachel, a sales director, found herself giving solutions in every one-on-one, she tried something different. “When my rep mentioned struggling with a difficult client, instead of jumping to ‘here’s what I’d do,’ I asked, ‘What approaches have you considered? What do you think would happen if you tried X?’ The result? Her team started bringing her more thoughtful, half-baked solutions rather than undefined problems. And they began solving more issues independently.
Build Relationship Through Understanding
A CTO I know learned that his quietest developer did her best thinking while walking. Their one-on-ones now happen during strolls around the office campus, and she shares insights she’d never voiced in conference rooms.
These personal insights—whether discovering someone processes ideas best visually, needs time to reflect before responding, or has a passion project that could benefit the company—rarely emerge in team settings or project updates.
Making It Work: Practical Next Steps
- Come with an intention, not just an agenda: “Today I want to understand what’s energizing you most about your work right now” sets a different tone than checking boxes.
- Ask questions that can’t be answered in status reports: “What part of this project keeps you up at night?” or “Where do you feel we’re missing an opportunity here?”
- Listen differently: When Mark, a retail manager, realized he was mentally preparing his next question instead of truly listening, he started taking minimal notes to force himself to stay present. His team noticed immediately, with one person commenting, “This is the first time I feel like you’re really hearing me.”
- Create continuity: End by capturing a key insight or commitment: “So it sounds like you’re going to try that new approach with the client, and next time we’ll discuss how it went.”
When You Really Are Squeezed for Time
Let’s be realistic—sometimes your day implodes. When that happens:
- Consider a 15-minute check-in versus a full cancellation
- Be honest: “I’ve got a situation I need to handle, but I still want to connect. Can we focus just on your most pressing item today?”
- Reschedule promptly, ideally within the same week
A VP I worked with keeps a “one-on-one emergency kit”—three powerful questions she can ask even when time is tight: “What’s your biggest win this week? What’s your biggest challenge right now? How can I help?”
The Payoff Is Worth It
When David, a new manager, committed to transforming (not canceling) his one-on-ones, he was skeptical about the impact. Six months later, his team’s engagement scores had risen by 23%, and two team members specifically mentioned their one-on-ones as a reason they turned down offers from competitors.
The most effective leaders I know view one-on-ones not as meetings to endure but as their most powerful tool for developing people, solving problems before they escalate, and building the trust that drives high performance.
So next time that calendar reminder pops up and you’re tempted to cancel, remember it’s not just another meeting—it’s your best opportunity to be the leader your team needs you to be.
