How to Run One-on-Ones That Actually Matter (Not Performance Theatre)

Three months into my first management role, I realised my one-on-ones were useless.

Every Tuesday at 2pm, I'd meet with each team member. We'd discuss project status (which I already knew from standup). They'd say "everything's fine" (it wasn't). I'd ask "anything I can help with?" (ritualistic, not genuine). Thirty minutes would pass. We'd both leave having exchanged information but created zero value.

I was running performance theatre, not one-on-ones.

The turning point came when a team member quit with two weeks' notice. In the exit interview, they mentioned burnout, unclear expectations, and feeling disconnected from team direction—all issues we could've addressed months earlier. "Why didn't you mention this in our one-on-ones?" I asked.

"You never actually asked," they said.

I had asked. Every week. But I'd asked in ways that invited safe, professional non-answers. I'd optimised for smooth conversations instead of useful ones.

Here's what I learned about running one-on-ones that actually matter.

What Makes Most One-on-Ones Useless?

The traditional one-on-one follows a predictable pattern:

Manager: "How are things going?" Report: "Good, making progress on the X project." Manager: "Great. Any blockers?" Report: "Nothing major." Manager: "Let me know if you need anything." Report: "Will do."

This exchange contains zero information that wasn't available elsewhere. Project status belongs in project tracking tools. Blockers should surface in daily standups. "Let me know if you need help" is passive abdication of management responsibility.

The conversation optimises for comfort, not truth. Both parties perform their roles—the competent report, the supportive manager—whilst avoiding anything uncomfortable.

Why this happens:

1. Unclear purpose. Neither party knows what the meeting is actually for beyond "it's on the calendar."
2. Power dynamics. Reports self-censor because career progression depends on the manager's perception.
3. No preparation. Both show up having done no reflection on what matters.
4. Status update default. Work discussions feel safer than personal/career conversations.
5. Fear of silence. Pauses feel awkward, so both rush to fill space with safe content.

The result: a standing meeting that everyone attends but nobody values.

The Actual Purpose of One-on-Ones

One-on-ones exist to surface information that wouldn't emerge elsewhere.

Not project status (that's for standup). Not tactical decisions (that's for Slack). Not feedback on specific work (that's immediate, not saved for scheduled meetings).

The unique purpose of one-on-ones:

• Career development conversations that require sustained focus
• Early-warning signals about morale, burnout, or team dynamics
• Misalignment detection between individual goals and team direction
• Relationship building that creates psychological safety for harder conversations
• Context setting about organisational changes, strategic direction, or priorities
• Feedback exchange (both directions) that's too nuanced for async communication

These conversations don't happen spontaneously in Slack. They require dedicated time and explicit invitation.

"The best one-on-ones I've had were when my manager asked questions I hadn't thought about yet. The worst were when we just recapped what I'd already documented elsewhere." — Senior Engineer, 8 years experience

The Framework: Four Rotating Themes

Instead of free-form "what should we talk about today?" meetings, I rotate through four themes:

| Week | Theme | Core Question | |------|-------|---------------| | Week 1 | Work & Priorities | What needs to change about how you're spending your time? | | Week 2 | Growth & Development | What skill gap is blocking your next goal? | | Week 3 | Team & Relationships | What's unsaid that needs to be said? | | Week 4 | Manager Feedback | What should I stop/start/continue doing? |

Each theme has specific questions (detailed below). The rotation ensures we cover all domains without letting any atrophy for months.

Why this works:

• Predictable structure lets reports prepare meaningful answers
• Rotation prevents staleness from asking identical questions weekly
• Balanced coverage ensures we don't fixate on only projects or only career
• Built-in manager feedback removes the "when should I bring this up?" barrier

The theme is announced at the end of each one-on-one: "Next week is growth week—think about what skills you want to develop next quarter."

Week 1: Work & Priorities (Not Status Updates)

This is not "what did you accomplish this week?" That's visible in your project tracker.

This is: "Are you working on the right things? Is anything preventing you from working effectively?"

Questions That Work:

1. "What percentage of your time went to your stated top priority this week?"

Most people discover it's under 30%. This creates productive tension: if the priority matters, why isn't time allocation reflecting that?

Follow-up: "What absorbed the other 70%? Was it valuable or just urgent?"

2. "What's one thing you did this week that you shouldn't have to do?"

Surfaces process problems, missing tools, or responsibilities that should be delegated/automated.

One report mentioned spending 6 hours weekly reformatting data from System A into System B. We automated it within a month. That's 24 hours/month returned.

3. "If you could delete one recurring meeting, which would it be and why?"

Meeting debt accumulates invisibly. This question gives permission to name what everyone tolerates.

4. "What decision are you waiting on that's blocking you?"

Identifies dependency chains and whether you are the blocker without realising it.

5. "What would you do differently if you had 20% more time?"

Reveals what's being sacrificed for urgency. Often: documentation, refactoring, learning, or strategic thinking.

What This Reveals:

• Misaligned priorities between manager expectations and actual work
• Process inefficiencies that waste time
• Hidden blockers not visible in project tracking
• Capacity issues before they become burnout

Example Exchange:

Me: "What percentage of your time this week went to the API redesign?" Report: "Maybe 20%?" Me: "That's your stated top priority. What took the other 80%?" Report: "Mostly support tickets and bug fixes." Me: "Are those more important than the redesign?" Report: "No, but they're urgent." Me: "What needs to change so urgent doesn't always override important?"

This led to creating a support rotation system so urgent work didn't always fall on the same person.

Week 2: Growth & Development

Career development is the thing managers most commonly neglect. It's never urgent, so it never happens unless explicitly scheduled.

Questions That Work:

1. "What skill do you want to have in 6 months that you don't have now?"

Forces specificity. "I want to be better at X" → "I want to be able to do Y specific thing I currently can't."

Follow-up: "What's one action this month that moves you toward that?"

2. "What work are you doing now that you want to stop doing in a year?"

Identifies what someone's trying to grow out of, not just into. Often reveals misalignment between current role and desired trajectory.

3. "Who in the organisation is doing work you'd like to do?"

Creates concrete role models and opportunities for mentorship or shadowing.

4. "What's something you're curious about but haven't had time to explore?"

Opens space for experimentation. Sometimes curiosity becomes next quarter's development focus.

5. "What's a project you saw on another team that you wish you'd worked on?"

Reveals interests that current work might not be serving.

What This Reveals:

• Skill gaps blocking next-level work
• Career trajectory misalignment before someone starts interviewing elsewhere
• Opportunities for stretch projects or role expansion
• Learning needs that justify conference attendance, courses, or books

Example Exchange:

Me: "What skill do you want in 6 months that you don't have now?" Report: "I want to be able to lead architecture discussions, not just participate." Me: "What's stopping you now?" Report: "I don't know how to evaluate trade-offs at system level. I can implement what's decided but not decide." Me: "What would help you develop that?" Report: "Maybe shadowing you in architecture reviews? And reading more about how other teams made similar decisions."

This became a concrete development plan: shadow 5 architecture discussions, write up analysis of trade-offs, then propose architecture for next mid-sized project.

Week 3: Team & Relationships

This is the "what's unsaid?" conversation. Team dynamics, interpersonal friction, morale issues—things people won't mention in group settings.

Questions That Work:

1. "What's a team dynamic that's working well right now?"

Start positive. This isn't only about problems.

Follow-up: "What's making that work? How do we preserve it?"

2. "What's a team dynamic that's not working?"

Opens space for observations about process, communication, or interpersonal issues.

Critical follow-up: "Have you mentioned this to the people involved?" (Often the answer is no.)

3. "Who on the team should you be working with more closely?"

Surfaces missed collaboration opportunities or siloed work.

4. "Is there something happening on the team that I might not be seeing?"

Managers have visibility gaps. Reports often see what you can't.

5. "What would someone new joining the team struggle with most?"

Reveals unwritten rules, missing documentation, or onboarding gaps. Also surfaces culture issues ("they'd struggle with our lack of clear ownership" = ownership is unclear).

What This Reveals:

• Interpersonal conflict before it escalates
• Team morale signals that group meetings hide
• Process problems that affect collaboration
• Manager blind spots about team dynamics

Example Exchange:

Me: "What's a team dynamic that's not working right now?" Report: "The code review process. PRs sit for days, then get rushed approval right before deadlines." Me: "Why do you think that's happening?" Report: "I think people don't feel they have time for thorough review. So they defer it until it's urgent." Me: "Have you mentioned this in retro?" Report: "No... I didn't want to sound like I was blaming anyone." Me: "But it's a process problem, not a people problem. Should we discuss it in next retro?"

This led to creating explicit "review time" in everyone's calendar and setting PR review SLAs.

Week 4: Manager Feedback (The Scary One)

This is the week most managers skip. Asking "how am I doing?" feels vulnerable. Hearing honest criticism is uncomfortable.

But if you don't create space for upward feedback, it accumulates as resentment.

Questions That Work:

1. "What's one thing I did this month that was helpful?"

Anchors with positive. Also tells you what's working so you can do more of it.

2. "What's one thing I should stop doing?"

Forces specificity. Not "you could improve generally" but "stop doing this specific thing."

3. "What decision did I make recently that you disagreed with?"

Disagreement is healthy when it's discussable. This question normalises it.

4. "What's something you need from me that you're not getting?"

Could be resources, air cover, decisions, context, or time. Often reveals unmet needs they've been working around.

5. "If you were managing me, what would you do differently?"

Invites perspective-taking. Sometimes surfaces blind spots you hadn't considered.

Creating Safety for Honest Answers:

The hardest part is getting honest answers instead of politically safe ones.

Tactics that help:

• Demonstrate non-defensiveness. If you justify or explain every critique, people stop giving them.
• Act on feedback. If someone mentions something and you do nothing, they won't mention things again.
• Share your own uncertainties. "I'm not sure I'm giving you enough context on strategy. Agree?" models vulnerability.
• Normalise disagreement. "I know you disagreed with my prioritisation call last week. Tell me why."

Example exchange:

Me: "What's one thing I should stop doing?" Report: "...honestly? You tend to 'yes, and' every idea in brainstorms. It makes it hard to tell what you actually think should be prioritised." Me: [Resisting the urge to defend myself] "That's fair. I'm trying to be supportive but it's probably confusing. What would be more helpful?" Report: "Maybe after brainstorming, summarise which 2-3 ideas you think are strongest and why?" Me: "I can do that. Thanks for flagging it."

Preparation: The 10-Minute Pre-Work That Changes Everything

The difference between useful and useless one-on-ones is often: did anyone prepare?

Manager Preparation (5 minutes):

1. Review last one-on-one notes. What was committed? Was it done?
2. Check this week's theme. Which questions will I ask?
3. Note anything from the week. Specific moments I want to discuss (positive or constructive).
4. Identify decisions I owe them. Am I blocking anything?

Report Preparation (5 minutes):

Send them the theme and specific questions 24 hours ahead:

"Tomorrow is Work & Priorities week. Think about:

1. What % of your time went to top priorities?
2. What work shouldn't you have to do?
3. What decision are you waiting on?"

This transforms the meeting from impromptu to prepared conversation.

The Meeting Structure: 30 Minutes That Matter

Minutes 0-5: Human connection

"How was your weekend?" or "What's on your mind today?" isn't wasted time—it's psychological safety investment.

Particularly important for remote teams where casual interaction doesn't happen organically.

Minutes 5-20: Theme questions

Ask 2-3 questions from this week's theme. Actually listen to answers instead of waiting for your turn to talk.

Use follow-up questions:

• "Tell me more about that"
• "What would good look like?"
• "What's one action that would help?"

Minutes 20-28: Open agenda items

"What else should we discuss?"

Reserve space for topics they brought or urgent issues that don't fit the theme.

Minutes 28-30: Actions & next theme

Critical: Document specific commitments.

"You'll send me the architecture proposal by Friday. I'll review and give feedback Monday. Next week is manager feedback week—think about what I should stop/start doing."

Documented commitments create accountability. Vague "let's keep an eye on that" creates nothing.

What to Document (And How)

I use a shared doc for each report:

# One-on-One: [Name]

## 2024-09-12 | Work & Priorities
**Time on top priority:** ~30% (goal was 60%)
**Blocked by:** Waiting on design review from Sarah
**Process improvement:** Automate data formatting between System A and B

**Actions:**
- [Manager] Ping Sarah about review timeline
- [Report] Document automation requirements by Friday

**Next theme:** Growth & Development

Why shared documentation matters:

1. Both parties have access (transparency)
2. Actions don't get forgotten (accountability)
3. Patterns become visible over time ("we've discussed this blocker three times")
4. Onboarding continuity if manager changes
5. Performance review evidence of growth and challenges

The five minutes documenting is often more valuable than the 30 minutes talking.

Red Flags: When One-on-Ones Reveal Serious Issues

Sometimes a one-on-one surfaces problems that require immediate action beyond next week's themes.

Warning signals:

• Repeated "everything's fine" with visible stress signals (likely they don't feel safe being honest)
• Declining engagement or energy (possible burnout or disengagement)
• Consistent misalignment between your priorities and their work (communication breakdown)
• Mentions of interpersonal conflict that's affecting work (needs mediation)
• Hints about external recruiting conversations (retention risk)

What to do:

• Name what you're observing. "You've said things are fine, but you seem stressed. Want to talk about it?"
• Create explicit safety. "This won't affect your performance review. I'm asking because I want to help."
• Escalate if needed. Some issues require HR, mediation, or organisational changes beyond your scope.
• Follow up quickly. If something serious surfaces, don't wait another week.

One report mentioned feeling overwhelmed by scope creep on their project. I heard it as venting and moved on. Two weeks later, they were crying in our one-on-one because they'd been working weekends trying to manage it all.

I should have stopped, asked "what would help right now?", and created immediate plan to reduce load. Instead I let it accumulate for two weeks.

Lesson: When someone signals distress, even subtly, address it immediately.

Adapting for Remote Teams

Remote one-on-ones have different dynamics than in-person.

What changes:

• Video fatigue is real. Offer "walk-and-talk" voice calls occasionally.
• Technical difficulties happen. Have backup channel (phone) if video fails.
• Casual conversation doesn't happen organically. Make explicit space for it—first five minutes matter more remotely.
• Non-verbal cues are harder to read. Ask explicitly: "You seem hesitant—is there something you're not saying?"
• Timezone challenges require flexibility. Rotate who takes the inconvenient time slot.

What improves:

• Documentation feels more natural (you're already on computer)
• Screen sharing for collaborative problem-solving (reviewing code, documents, or tools together)
• Chat backchannel for links and references during conversation

Common Mistakes I Made (And How to Avoid Them)

Mistake 1: Cancelling one-on-ones when "too busy"

Why it's bad: Signals that the relationship isn't a priority.

Fix: Protect the recurring meeting. If you must reschedule, do it proactively—don't make them ask.

Mistake 2: Letting them become only status updates

Why it's bad: Wastes the unique opportunity for deeper conversation.

Fix: Explicitly ban status updates. "I can read your updates async. Let's talk about what's not in the updates."

Mistake 3: Not documenting actions

Why it's bad: Commitments evaporate without accountability.

Fix: Shared doc updated during the meeting, not retrospectively.

Mistake 4: Dominating the conversation

Why it's bad: It's their meeting, not yours.

Fix: Track speaking ratio. If you're talking more than 30%, ask more questions.

Mistake 5: Avoiding difficult conversations

Why it's bad: Problems compound when undiscussed.

Fix: Name the discomfort. "This is awkward to bring up, but..." disarms defensiveness.

When to Adjust Frequency

Standard is weekly or biweekly, but one size doesn't fit all.

More frequent (weekly) when:

• New hire in first 90 days
• Performance improvement plan requiring close collaboration
• High-stress project needing regular check-ins
• Explicit request from report who values the touch point

Less frequent (biweekly or monthly) when:

• Senior individual contributor who's highly autonomous
• Strong trust and communication make weekly feel redundant
• Explicit request to reduce meeting load

The frequency itself should be negotiable: "How often feels right for you?"

Measuring Success: What Good Looks Like

You can't always measure one-on-one quality directly, but here are proxies:

Good signs:

• Report brings their own agenda items (they find it valuable)
• Difficult topics surface early (psychological safety exists)
• Career development progresses (growth conversations lead to action)
• Actions from previous meetings get completed (accountability works)
• Retention (people don't leave for preventable reasons)

Bad signs:

• Frequent cancellations or rescheduling (neither party prioritises it)
• Conversation is mostly small talk (no substantive content)
• Same problems mentioned month after month (no resolution)
• Surprise resignations (serious issues weren't surfacing)
• "Fine" is the default answer (honesty isn't happening)

The Question That Changed Everything

After two years of iterating on this framework, I added one question that's become the most valuable:

"What's true about work right now that you haven't said out loud yet?"

It's deliberately open-ended. It gives permission to name the unsaid thing—the frustration they've been managing around, the misalignment they've been tolerating, the idea they thought was too risky to mention.

One report answered: "I don't think my role exists in a year. The work I'm doing will probably be automated or consolidated into someone else's job."

We spent the next three months creating a transition plan into a new role. They're still with the company, doing work they find more meaningful.

If I hadn't asked, they'd have quietly started interviewing.

That's what one-on-ones are for. Not status updates. Not performance theatre. But creating space for truths that matter to be spoken and acted on.

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TL;DR: Running one-on-ones that actually matter

• Rotate four themes: Work & priorities, Growth & development, Team & relationships, Manager feedback
• Prepare in advance: Share questions 24 hours early so both parties can think
• Document actions: Shared doc with specific commitments and accountability
• Ban status updates: Reserve the time for conversations that can't happen elsewhere
• Ask hard questions: "What's true that you haven't said yet?" surfaces what matters
• Create safety for honesty: Non-defensiveness and action on feedback build trust

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