Running Effective 1 1s

Running Effective 1:1s

Help the user run effective one-on-one meetings using frameworks from 7 product leaders.

How to Help

When the user asks for help with 1:1s:

1. Understand the relationship - Ask about their role, the report's tenure, and current dynamics 2. Identify the purpose - Determine if the 1:1 needs to focus on tactical work, career development, or emotional support 3. Suggest structure - Recommend appropriate formats based on the situation 4. Coach on coaching - Help them shift from advising to empowering their reports

Core Principles

Coach, don't advise

Rachel Lockett: "Great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems." Shift energy into curiosity when a report brings a hard problem. Avoid the urge to provide the answer immediately.

Dedicate time to deep career conversations

Kim Scott: "I would have three separate 45 minute conversations, so one about their past, one about their future, and one about their present to create a plan." Conduct a "Life Story" conversation to understand motivations, a "Future Dreams" conversation to identify long-term visions, and create a "Career Action Plan" to map current skill-building to those dreams.

Monitor recovery and joy

Hilary Gridley: "In my one on ones... I'm asking them, 'What do you do for joy? Are you doing something every single day that's bringing you joy in your life?' And if they say no, I'm like, 'That's a problem.'" Ask reports directly about what brings them joy outside of work. Treat a lack of daily joy as a performance risk that needs a plan.

Consider cutting standing 1:1s

Howie Liu: "I actually cut my one-on-one roster by default... Just having more standing one-on-ones actually precludes me from engaging in more timely topics." Consider a barbell approach: high-quality, less frequent relationship catch-ups (e.g., monthly walks) vs. urgent topical meetings scheduled as needed.

Use 1:1s for emotional processing after crises

Matt Mochary: "With each and every person on the stay team, you have a one-on-one with their manager for one hour and all the manager does is say, 'I'd like to know your thoughts and feelings,' and the person shares and then all the manager does is make them feel heard." Post-crisis 1:1s should focus entirely on active listening and emotional processing.

The 1:1 belongs to the report

The report should own the agenda. As manager, you're there to support their success, not to get status updates.

Questions to Help Users

• "When your report brings you a problem, do you tend to give the answer or ask questions?"
• "When was the last time you had a deep career development conversation (not a performance review)?"
• "How do you know if your report is recovering well outside of work?"
• "Does your report own the 1:1 agenda, or do you drive it?"
• "Are your 1:1s tactical or strategic? What's the right balance?"

Common Mistakes to Flag

• Status update theater - Using 1:1s for updates that could be async
• Always advising - Solving problems instead of coaching the report to solve them
• Skipping career conversations - Only discussing immediate work, never long-term development
• Ignoring wellbeing - Not noticing when a report is burning out
• Manager-driven agenda - The manager dictates topics instead of the report owning the time

Deep Dive

For all 10 insights from 7 guests, see references/guest-insights.md

Related Skills

• running-effective-meetings
• running-decision-processes
• post-mortems-retrospectives

Running Effective 1:1s - All Guest Insights

7 guests, 10 mentions

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Hilary Gridley

Hilary Gridley

"In my one on ones, and I'm checking in with people, I'm asking them, 'What do you do for joy? Are you doing something every single day that's bringing you joy in your life?' And if they say no, I'm like, 'That's a problem. What are we going to do about that? And do you even know what those things are?'"

Insight: 1:1s should be used to monitor an employee's 'recovery' and joy to ensure long-term high performance.

Tactical advice:

• Ask reports directly about what brings them joy outside of work.
• Treat a lack of daily joy as a performance risk that needs a plan.
• Help reports identify their 'behavioral activations'—small actions that reliably lift their mood.

Timestamp: 01:17:13

Howie Liu

Howie Liu

"I actually cut my one-on-one roster by default, and the idea is not that I don't want to spend time one-on-one with people, but rather that I found that the ... Just having more standing one-on-ones actually precludes me from engaging in more timely topics."

Insight: Move away from rigid weekly rituals toward high-quality, relationship-building catch-ups and urgency-driven topical meetings.

Tactical advice:

• Cut standing 1:1 rosters to free up time for timely, insight-driven topics
• Use a barbell approach: high-quality, less frequent relationship catch-ups (e.g., monthly coffee walks) vs. urgent topical meetings

Timestamp: 00:16:41

Kim Scott

Kim Scott

"I think one of the really important things that all managers can do for their direct reports to show that they care is to have real meaningful career conversations, where you talk about their life story... I would have three separate 45 minute conversations, so one about their past, one about their future, their dreams for the future... Then the third conversation is to sort of sit down with your director report and come up with a career action plan."

Insight: Managers should dedicate specific 1:1 time to deep career development conversations beyond tactical updates.

Tactical advice:

• Conduct a 'Life Story' conversation to understand what motivates the employee.
• Conduct a 'Future Dreams' conversation to identify 3-4 long-term career visions.
• Create a 'Career Action Plan' to map current skill-building to those future dreams.

Timestamp: 00:33:31

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"The question that I like to ask is, 'What could I do or stop doing that would make it easier to work with me?'... you want to think about who you're going to ask that question of, and if everybody can write down their question, who they're going to ask it of and then pop it into their calendar right now, this will be one of the most productive podcasts in all of podcast land."

Insight: Leaders must proactively solicit criticism to build trust and improve their own performance.

Tactical advice:

• Ask a specific 'go-to' question that invites criticism rather than a generic 'Do you have feedback?'.
• Embrace a 6-second silence after asking to force the other person to answer.
• Reward the feedback by fixing the problem or explaining why you disagree.

Timestamp: 00:37:35

Matt Mochary

Matt Mochary

"With each and every person on the stay team, you have a one-on-one with their manager for one hour and all the manager does is say, 'I'd like to know your thoughts and feelings,' and the person shares and then all the manager does is make them feel heard."

Insight: Post-crisis 1:1s should focus entirely on active listening and emotional processing to stabilize the remaining team.

Tactical advice:

• Dedicate a full hour to 1:1s following major organizational changes.
• Focus the agenda entirely on the report's thoughts and feelings rather than status updates.

Timestamp: 00:51:34

Petra Wille

Petra Wille

"Get yourself a list of great questions that you could ask in one on ones if you don't have the time to prepare. That will be one of my tips as well. There's several great coaching books out there. Some of questions are in my book as well. Yeah, just find some coaching questions, make your small compilation, and then really see what resonates with your team, and that often is a bit of a health check. So how are you doing? What would make you more successful in the role that you're currently having?"

Insight: Using a prepared list of coaching questions ensures 1:1s remain valuable even when the manager is busy.

Tactical advice:

• Maintain a go-to list of coaching questions for unprepared meetings
• Ask 'What would make you more successful in the role that you're currently having?'
• Use a list of emotions to help reports articulate their current state

Timestamp: 00:30:57

Rachel Lockett

Rachel Lockett

"Great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems. And coaching is a different way."

Insight: Shifting from an 'advisor' role to a 'coach' role prevents the leader from becoming a bottleneck and empowers the team.

Tactical advice:

• Shift energy into curiosity when a team member brings a hard problem.
• Avoid the urge to provide the answer immediately.

Timestamp: 00:09:24

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"The first skill is active listening... Level three listening is global listening. So, that's what I'm hearing beneath the words. I'm hearing what you're communicating, not just what you're saying. I see your body language. I notice your tone of voice."

Insight: Effective coaching requires 'Level 3' listening, which involves picking up on non-verbal cues and emotional subtext.

Tactical advice:

• Practice global listening by observing body language and tone.
• Reflect back the emotions you notice to make the person feel seen.

Timestamp: 01:13:31

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"Second skill, powerful questions... I use a GROW model. So, the GROW model just is four different categories of kinds of powerful questions. So, the G in grow is goal... The R in the GROW model is about your current reality... The O is about your options... And the W in the GROW model is the way forward."

Insight: The GROW model is a simple framework for guiding team members toward their own solutions during 1:1s.

Tactical advice:

• Ask 'Goal' questions: What does success look like?
• Ask 'Reality' questions: Where are you stuck?
• Ask 'Options' questions: What are the various paths you could take?
• Ask 'Way Forward' questions: What are you going to do next?

Timestamp: 01:18:37

Keith Yandell

Keith Yandell

"I say how I run one-on-ones in my 'how to work with Keith' document, and the last 10 minutes of my one-on-ones are career development conversations."

Insight: Dedicate a fixed portion of every 1:1 to career development to ensure long-term growth isn't sidelined by tactical updates.

Tactical advice:

• Reserve the final 10 minutes of every 1:1 for career coaching
• Use the T3 B3 framework (3 positives, 3 constructives) to ensure a balanced feedback loop

Timestamp: 24:33