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How to Effectively Run a One on One: A Complete Guide to Better Meetings

One on one meetings are the most powerful tool you have as a manager. Yet most people run them poorly or skip them entirely. This guide shows you exactly how to run effective one on ones that build trustsolve problemsand help your team members grow.

A good one on one isn’t just a status update. It’s a dedicated space where your team member drives the agendashares what’s really on their mindand gets the support they need to succeed. When done rightthese meetings reduce turnovercatch problems earlyand create stronger working relationships.

What Makes a One on One Meeting Effective

An effective one on one has three core elements:

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Regular scheduling. Meet weekly or biweeklysame day and time. Canceling sends the message that this person isn’t a priority.

Employee-driven agenda. Your team member should bring topicsnot you. You’re there to listenask questionsand help them think through challenges.

Focus on the personnot just tasks. Talk about career goalsroadblocksteam dynamicsand how they’re feeling about their work. Project updates belong in other meetings.

Most managers flip this formula. They cancel when busyfill the time with status checksand dominate the conversation. This turns one on ones into a chore instead of a valuable conversation.

Setting Up Your One on One Structure

Choose the Right Frequency and Length

Start with weekly 30-minute meetings. This gives enough time for meaningful conversation without overwhelming your calendar. If you manage many peopleyou can move to biweekly meetings after you’ve built a strong foundation.

For new team membersmeet weekly for at least the first three months. They need more support as they ramp up.

For remote teamsweekly check-ins become even more important since you lose the casual hallway conversations that happen in an office.

Pick a Consistent Time and Place

Block the same time slot each week. Tuesday through Thursday mornings often work well because Monday is catching up and Friday people are wrapping up.

For in-person meetingschoose a quiet space where you won’t be interrupted. A small conference room works better than your officewhich can feel intimidating.

For remote meetingsboth people should use video. You catch tone and body language that audio calls miss.

Create a Shared Document

Set up a shared Google Doc or Notion page for each person you manage. This becomes your ongoing agenda and record of past discussions.

The document should include:

  • Running agenda (employee adds topics during the week)
  • Action items from previous meetings
  • Notes from each session
  • Long-term goals and progress

This shared space makes the meeting collaborative from the start. Your team member can add items throughout the week instead of trying to remember everything five minutes before the meeting.

How to Effectively Run a One on One

Preparing for the Meeting

What Your Team Member Should Do

Send them this simple framework one week before your first one on one:

“Add 2-3 topics to our shared doc before each meeting. Good topics include: challenges you’re facingideas you want to discussfeedback you needcareer questionsor anything affecting your work. This is your timeso bring what matters to you.”

They might need a few meetings to get comfortable owning the agenda. That’s normal.

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What You Should Do

Review the shared document 15 minutes before the meeting. Look at:

  • Topics they’ve added
  • Action items from last time (did you follow through?)
  • Patterns over the past few meetings
  • Any context from team updates or projects

Don’t plan a counter-agenda. Your job is to show up ready to listen and help with whatever they bring.

Running the Meeting: A Step-by-Step Framework

Start With a Human Check-In

Begin with a simple question: “How are you doing?”

Then pause. Actually wait for a real answer.

Most people will say “fine” at first. That’s okay. Over timeas trust buildsyou’ll get more honest responses like “honestlypretty stressed” or “really goodI solved that problem we discussed.”

This opening creates space for emotions and context before diving into work topics.

Let Them Lead the Agenda

Ask: “What’s most important to talk about today?”

Work through their list. Take notes in the shared document so both of you can see what’s captured.

If they haven’t added anything to the agenda beforehanddon’t punish them. Use these prompts:

  • “What’s gone well this week?”
  • “What’s been frustrating or blocking you?”
  • “Is there anything you need from me?”
  • “How are you feeling about [current project]?”

Listen More Than You Talk

Your ratio should be 70% listening30% talking.

This is hard for managers who love solving problems. You want to jump in with answers. Resist that urge.

Insteadask questions:

  • “Tell me more about that.”
  • “What have you already tried?”
  • “What would success look like?”
  • “How can I help?”

Questions help them think through the problem themselveswhich builds their problem-solving skills. You also learn much more about what’s really happening.

Research from Harvard Business School shows that managers who ask more questions during one on ones have more engaged teams and better retention (https://hbr.org/2018/05/the-surprising-power-of-questions).

Dig Into Recurring Themes

If someone mentions stress about deadlines three meetings in a rowthat’s a pattern worth exploring.

“I’ve noticed you’ve brought up deadline pressure in our last few conversations. Let’s talk about what’s driving that and what might need to change.”

Patterns reveal systemic issues that need fixingnot just one-off problems.

Discuss Career Development

Every third or fourth meetingdedicate time to career growth:

  • “Where do you want your career to go?”
  • “What skills do you want to develop?”
  • “What kind of work energizes you?”
  • “What would you like to do less of?”

Then connect their goals to real opportunities. If they want to improve public speakingcan they present at the next team meeting? If they want to learn a new technologycan you adjust their project assignments?

Growth conversations show you care about them as peoplenot just as resources for your team’s work.

End With Clear Action Items

Spend the last five minutes reviewing:

  • What you committed to do
  • What they committed to do
  • When you’ll check back on key topics

Write these directly in the shared document.

Following through on your commitments is how you build trust. If you say you’ll talk to another team about resourcesactually do it before the next meeting.

Common Mistakes and How to Fix Them

Mistake: Turning It Into a Status Update

What it looks like: “How’s project X going? What about project Y? When will Z be done?”

Why it’s wrong: You have other meetings for status updates. Standupsproject check-insand email all work for this. Using one on one time for status wastes the opportunity for deeper conversation.

The fix: If you need status informationget it elsewhere. Use the one on one to discuss how they’re approaching the workwhat support they needand how they’re developing through these projects.

Mistake: Only Meeting When There’s a Problem

What it looks like: Skipping meetings when things are calmonly scheduling when there’s an issue to address.

Why it’s wrong: This trains your team to hide problems. They associate one on ones with bad news and criticism. You also miss chances to celebrate wins and build relationship during good times.

The fix: Protect this time no matter what. During calm periodsfocus on growthlearningand future opportunities. The regular rhythm matters more than having a crisis to discuss.

Mistake: Doing All the Talking

What it looks like: You fill the silence with your thoughtsadviceand observations about their work.

Why it’s wrong: They leave without sharing what’s on their mind. You miss early warning signs about problems. They don’t develop their own problem-solving abilities because you’re always supplying answers.

The fix: Count to five after asking a question. Let silence hang. Most people will fill it if you just wait. When you do speakask another question before giving advice.

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Mistake: Canceling When You’re Busy

What it looks like: “I have to push our one on oneI have a conflict” becomes a pattern.

Why it’s wrong: It signals that this person isn’t a priority. Trust erodes. They stop preparing because they assume you’ll cancel. Issues that could have been caught early grow into bigger problems.

The fix: Treat one on ones as sacred. You wouldn’t cancel a meeting with your CEO because something else came up. Show your team members the same respect. If you absolutely must rescheduledo it immediately with a specific new time.

Mistake: Avoiding Difficult Topics

What it looks like: You sense tension or know there’s a performance issuebut you stick to comfortable subjects.

Why it’s wrong: Problems don’t disappear because you ignore them. They grow. Your team member knows you’re avoiding somethingwhich damages trust.

The fix: Name the awkward thing directly. “I want to talk about something that might be uncomfortable.” Then be honest and specific. Give them a chance to share their perspective. These momentswhile hardare where real progress happens.

Advanced Techniques for Experienced Managers

The Career Ladder Discussion

Once or twice a yearhave a dedicated session about leveling up.

Bring a copy of your company’s career ladder or competency matrix. Review it together:

  • “Here’s where you are now.”
  • “Here’s what the next level requires.”
  • “Let’s make a plan to close those gaps.”

This takes career development from vague (“I want to grow”) to concrete (“I need to demonstrate technical leadership and mentor two junior team members”).

The Stay Interview

Every six monthsrun a stay interview:

  • “What would make you leave?”
  • “What keeps you here?”
  • “What could we change to make this the best job you’ve ever had?”

These questions reveal retention risks before someone starts job hunting. You can often fix issues if you know about them early.

The Energy Audit

Ask them to categorize their work:

  • What energizes them (gets them into flow)
  • What drains them (feels like pushing a boulder uphill)
  • What’s neutral

Then work together to shift the ratio. Can you give them more of the energizing work? Can you automate or delegate the draining tasks?

People perform better and stay longer when their work aligns with their strengths and interests.

Handling Different Scenarios

When Someone Says “Nothing to Talk About”

First time: That’s okay. Use it as coaching time. Ask about a recent project and help them reflect on what went well and what they’d do differently.

Repeated pattern: This is usually a trust issue. They don’t feel safe bringing real topics.

Try: “I notice we often don’t have much on our agenda. I want these meetings to be valuable for you. What would make them more useful? Is there anything that would make it easier to share what’s really going on?”

When You Need to Give Critical Feedback

Don’t ambush them. If you have tough feedbacktell them at the start:

“I want to spend today’s time discussing something I’ve observed. I care about your successwhich is why I want to talk about this directly.”

Then:

  1. Describe the specific behavior you observed
  2. Explain the impact it had
  3. Ask for their perspective
  4. Discuss how to move forward together

Example: “In the last three team meetingsyou’ve interrupted others while they were presenting their ideas. This makes people hesitant to speak upwhich means we’re missing valuable input. What’s your take on this? Let’s figure out how to make sure everyone’s voice is heard.”

When Someone Is Consistently Disengaged

Disengagement shows up as short answerslack of preparationchecking phoneor seeming distracted.

Don’t ignore it. Address it directly:

“I’ve noticed you seem less engaged in our one on ones lately. That makes me think either these meetings aren’t valuable for youor something else is going on. Help me understand.”

The answer might surprise you. Maybe they’re burned out. Maybe they’re dealing with something personal. Maybe they don’t see the point of these meetings. Whatever it isyou can’t fix it without understanding it.

When You Manage Someone Remote

Remote one on ones need extra intention.

Always use video. You need to see facial expressions and body language.

Start with more personal connection since you’re not bumping into each other at the coffee machine. Ask about their weekendtheir familytheir setup at home.

Be more explicit about everything. In personyou pick up on subtle cues. Remotelyyou need to ask directly: “How are you really doing? Being remoteI might miss signals that something’s off.”

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Consider occasional in-person meetings if possible. Even one face-to-face meeting per quarter strengthens the relationship.

Sample One on One Formats

The Standard Weekly Check-In

TimeActivity
0-5 minPersonal check-in: How are you doing?
5-20 minTheir agenda items (2-3 topics)
20-25 minYour questions or observations
25-30 minAction items and follow-up

The Monthly Career Focus

TimeActivity
0-10 minRecent wins and challenges
10-25 minCareer development deep dive
25-30 minNext steps for growth

The Quarterly Big Picture

TimeActivity
0-5 minCheck-in
5-20 minReview last quarter: winsstruggleslessons
20-40 minLook ahead: goalsconcernsopportunities
40-45 minUpdate development plan

Rotate between these formats to keep meetings fresh and cover different levels of conversation.

Measuring Success

How do you know if your one on ones are working?

Signs They’re Effective

  • Your team member adds topics to the agenda without prompting
  • They bring up problems early instead of when they’re critical
  • You learn things you wouldn’t have known otherwise
  • They ask for feedback and coaching
  • Conflicts are resolved before they escalate
  • People rarely leave your team voluntarily
  • Exit interviews reveal that one on ones were valued

Signs They Need Improvement

  • Meetings feel like pulling teeth
  • You’re doing most of the talking
  • Topics are always surface-level (weatherweekend planstask status)
  • Problems surprise you because no one mentioned them
  • People seem relieved when you cancel
  • Your team has higher turnover than similar teams

The best measure is simple: Ask. Every few monthsdirectly ask your team members: “Are these meetings valuable for you? What would make them better?”

Tools and Resources

Documentation Tools

  • Google Docs: Simplecollaborativesearchable. Best for most teams.
  • Notion: Great if your company already uses it. Templates make structure easy.
  • Fellow: Purpose-built for one on ones with agenda templates and action item tracking.
  • 15Five: Combines one on ones with weekly check-ins and OKR tracking.

Pick whatever your team member will actually use. The fancy tool that sits empty is worse than a basic Google Doc that gets filled out.

Question Banks

Keep a list of good questions for when conversation stalls:

About their work:

  • What’s the most interesting problem you’re working on?
  • Where are you blocked?
  • What would you do if you had complete authority over this project?

About the team:

  • How’s your workload compared to others?
  • Who on the team do you want to work with more?
  • Are there any team dynamics that bother you?

About you as their manager:

  • What should I start doing?
  • What should I stop doing?
  • How can I better support you?

About growth:

  • What do you want to get better at?
  • What are you learning right now?
  • Where do you see yourself in two years?

Further Reading

For deeper understanding of management practices and one on one conversationsThe Manager’s Path by Camille Fournier offers excellent guidance on engineering leadership (https://www.oreilly.com/library/view/the-managers-path/9781491973882/).

Conclusion

Running effective one on ones comes down to consistencygenuine listeningand making it about themnot you.

Show up every week at the same time. Let them drive the conversation. Ask more questions than you answer. Follow through on what you commit to do. Focus on the person and their growthnot just the tasks and projects.

These meetings are an investment. They take time. They require preparation. They force you to have difficult conversations you might prefer to avoid.

But this investment pays massive returns. You catch problems early. You build trust that carries your team through hard times. You develop your people’s skills and judgment. You create a place where people want to work.

Start this week. Block recurring time with each person you manage. Create a shared document. Send them the agenda framework. Then show up and listen.

Your team will notice the difference within a month.

Frequently Asked Questions

What if my team member never adds anything to the agenda?

Keep asking good questions to fill the time and show them what valuable topics look like. After a few meetingsexplain directly: “I want these meetings to focus on what matters most to you. Try adding 1-2 topics before our next meetingeven if they feel small. What’s challenging you? What do you want feedback on?” If this continues for more than a monthit signals a deeper trust or engagement issue worth exploring.

How do I balance one on ones when I manage 10+ people?

With a larger teammove to biweekly 30-minute meetings instead of weekly. Prioritize weekly meetings for new hires (first 3 months)anyone struggling with performanceand anyone going through major life or work transitions. Use brief daily or weekly standups to handle status updates so one on ones stay focused on development and deeper issues.

Should I take notes during the meeting?

Yesbut do it in the shared document where they can see what you’re writing. This keeps it collaborative rather than feeling like you’re documenting evidence. Note key discussion points and action items. Avoid capturing every detailwhich makes people self-conscious. If something is too sensitive to write downjust listen fully in the moment.

What if I don’t have answers to their questions or problems?

That’s completely fine and actually healthy. Say: “I don’t knowbut let me find out” or “Let’s think through this together.” Your job isn’t to have all answers. It’s to help them work through challengesconnect them with people who can helpand remove obstacles. Admitting you don’t know something builds trust more than faking expertise.

How do I handle one on ones with someone who performs poorly?

Keep the regular meeting schedule but adjust the content. Be direct about performance gaps using specific examples. Create a clear improvement plan with measurable goals and regular check-ins. Balance tough feedback with support. Ask what they need from you to improve. Document these conversations in case formal action becomes necessary. Poor performance usually doesn’t improve without consistenthonest dialogue.

MK Usmaan