1:1 Meetings: How to make them matter

We observe that most founders implement 1:1s when their team hits 7-10 people. The daily conversations fade, alignment gets harder and suddenly you need "proper meetings" because that's what growing Startups do. But here's what we've learned from hundreds of founders: most 1:1s are theater, not strategy.

The difference between the two determines whether your team actually trusts you or just manages up to you.

Why 1:1s are worth taking seriously

Here's the uncomfortable truth: most meetings are optional. 1:1s aren't.

Done right, they're your highest-leverage tool for building trust and catching misalignment before it becomes a crisis.

Google's Project Oxygen research found that managers who run regular one-on-ones are rated significantly higher by their teams. But the research doesn’t capture the deeper truth. These meetings create psychological safety that makes everything else possible.

The problem is that most founders treat 1:1s like necessary evils. They squeeze them into overcrowded calendars without the mental energy to address what actually matters. They cancel them first when things get busy, then wonder why their team feels disconnected.

This isn't another meeting to squeeze into your calendar. It's the one that holds everything else together.

Two types of 1:1 Conversations

Before we go into detail about how to set up 1:1 meetings we want to distinguish between two types of meetings:

The Tactical 1:1

These are your short, work-focused check-ins. Think of quick problem-solving sprints: unblocking, prioritizing, clearing confusion. As your team grows, many of these become group sessions. They're important, but they're not what we're focusing on here.

The Relationship 1:1

These are the conversations that matter most. Higher altitude, slower pace, more personal. They build trust and alignment at the level that actually affects performance. Topics range from career growth, feedback, and the team dynamics everyone feels but avoids naming. As trust deepens, they open space for the personal context, shaping how someone shows up at work. Great leaders make it safe to bring the human stuff into the room.

The tactical stuff can also happen in Slack. The relationship stuff requires intentional space.

How Often and How Long?

The right frequency reflects the level of support someone needs, not your theoretical preferences.

Frequency:

Bi-Weekly for new hires, C-level executives, or anyone in a critical transition
Monthly works for most established team members

Duration: Always block 60 minutes, even if you typically finish faster. You need enough time to not feel rushed and space for proper follow-up. The conversation expands to fill the safety you create.

The most important rule: Never cancel, only reschedule.

1:1s are typically the first meetings sacrificed when calendars explode. If you don't protect this time, why should they take it seriously?

What matters most isn’t frequency. It’s consistency.

How to set them up?

Most 1:1s we see for the first time already fail in the setup.

Here's our suggestion to create the conditions for conversations that actually matter:

Before the Meeting:

Protect the sacred hour. Block the full time with the same reverence you'd give a crucial investor pitch. No Slack notifications bleeding through. No "quick 5-minute calls" that fracture your attention.
Review your last conversation notes. Not to create an agenda, but to remember where you left last time. Any things you committed to that should be brought up?

The most important preparation happens internally. The shift that matters most is psychological. You’re moving from the relentless urgency of “getting things done” to the slower, more complex work of seeing another person clearly. This is the same mental preparation you’d bring to pitching a major client or investor, with that focused, present-moment awareness where everything else fades to background noise.

The difference? Instead of performing, you're receiving. Instead of convincing, you're listening for what isn't being said.

And just before you walk into that room (or open that Zoom), ask yourself: What stories am I telling myself about this person? What assumptions am I carrying? What part of me is already solving their problems before I've truly heard them?

This is the foundational work that determines whether the next hour creates genuine connection or just burns time on both your calendars.

1. Define the setting

Begin every 1:1 series with a meta-conversation. Don't assume your peer understands what authentic dialogue looks like in a professional context. Most people have been conditioned to believe vulnerability and talking things out is career suicide.

Most high-performers have been rewarded for appearing effortlessly competent. They've learned to hide struggle, doubt, and confusion. But those hidden complexities are exactly where their deepest growth opportunities live.

Greg, I want to be clear about something. These conversations aren't performance reviews in disguise. I'm not here to evaluate how well you're managing up to me. What I can't get anywhere else is insight into how you're actually thinking about your work, your challenges, your growth.

Notice what you're doing here. You're offering explicit permission to be human in a professional space.

This is your time. You own the agenda. My job is to help you think through whatever's actually weighing on you. What are you wrestling with? What support do you need? What conversations are we avoiding that might matter?

You're not just delegating agenda-setting. You're modeling a different relationship to authority. Instead of positioning yourself as the person with answers, you're becoming a mentor.

Don't assume this lands the first time. Repeat this framing in your next few meetings. Your consistency with this message becomes the evidence they need to believe it's safe to bring their whole into the room.

2. Be present

Be on time. Close your laptop. Take notes by hand. These aren't small gestures. They're psychological signals that this interaction operates by different rules than the rest of the hectic business day-to-day.

Start the meeting with a check-in: "How do you enter this meeting?".

This question does subtle psychological work. It acknowledges that people don't show up neutral. They carry the residue of their last interaction, the weight of whatever crisis is simmering in their inbox, the emotional labor of managing up and down simultaneously.

By asking how they arrive, you're creating permission for them to be human before they have to be functional. And answer this question yourself. This will get you in synch.

3. Listen to understand, not to answer.

Most leaders treat hard conversations like emergencies. The moment someone shares a problem, our minds start racing, and we rush into solution mode. Even with good intentions, this often shuts down the very dialogue we need.

When someone brings you a problem, lead with curiosity, not fixes. Let silence do the work. Count to five before speaking. This is not a trick. It is a discipline. It puts the focus on the other person instead of your own urge to solve.

The best insights often come in the space between what is first said and your response. That awkward pause you want to fill is where trust grows.

There is another trap here. The urge to improve the solution. You might see a way to make it 5% better. But once you add your mark, it is no longer their solution. Commitment can drop fast. A 95% solution with full ownership will beat a “perfected” idea that no one feels is theirs. In a 1:1 relationship, your job is not to win the brainstorming. It is to leave the other person fully committed to the next step.

Powerful questions to get things going or dive deeper:

• If nothing changed in the next 3 months, what would worry you most?

• What’s draining your energy right now?

• Where do you feel the most tension in your role?

• What’s something you’ve been thinking about but haven’t said out loud yet?

• When did you last feel frustrated or unseen at work?

4. Be vulnerable

Vulnerability rarely starts as a two-way street. It has to be modeled, and as the person in power, that job falls on you.

You don’t have to overshare. But you do have to be real. Admit when you’ve been scared, unsure, or wrong. It’s not weakness. It’s leadership. The moment Lena owned her fear, she shifted the whole dynamic. Not because it solved the tension, but because it made space for something more honest to happen.

Vulnerability de-escalates ego and invites truth. You don’t get real commitment from your team by looking bulletproof. You earn it by being human.

5. Be radically candid

Radical candor [1] is caring personally and challenging directly at the same time. Most leaders tilt one way. They protect feelings and avoid the truth. Or they tell the truth in a way that harms the relationship.

It is not radical candor if you are blunt and call it honesty. It is not radical candor if you avoid the hard truth in the name of protecting trust. It is both care and clarity in one move.

Radical candor sounds like this. Warm. Clear. No soft landing. No hard hit. Both at once.

6. Find commitments

Honest conversations are great but without clear next steps, they fade. 

What turns good conflict into forward motion: shared clarity on what we do next.

This is where many 1:1s stop too early. The truth is shared. Tensions are named. Emotions are felt. But nothing changes unless both sides walk away with a new commitment.

Clarity + agreement = commitment. And it’s the moment trust turns into traction.

After the meeting

Follow-up matters more than most people think. It shows you’re not just listening, you’re following through.

Send a short recap within 24 hours. Keep it simple:

• Summarize any commitments or next steps

• Note emerging patterns or things to watch for

• Keep the tone warm and open

This isn’t about documenting everything. It’s about reinforcing trust through clarity and accountability.

On Hierarchy: Does Seniority Change the Setting?

Late stage founders often wonder: Should I run 1:1s differently with my C-level team versus individual contributors?

The short answer: kind of.

The long answer: it’s not about seniority. It’s about power, trust, and how real you’re willing to be.

The Peer Paradox
Your relationship with senior leaders comes with unique tension. They're building the company alongside you, making decisions that directly impact your success. And C-Level or VP hirings post Series A are also often significantly older. Yet they still report to you. 

This creates what we call the “peer paradox.” You need them to challenge you like equals while still reporting to you as their leader. And that can be confusing.

And yet we believe it’s still about building trustful relationships!

Make it more reciprocal. Ask for their perspective on your leadership, company direction, and blind spots you might have:

• “What’s one thing I’m currently doing that makes your job harder?”
• “Where do you think I’m too involved or not involved enough?”
• “If you were in my seat, what would you be worried about?”

Here's where most founders get stuck: they think being vulnerable with senior leaders will undermine their authority. The opposite is true. Your C-level team already knows you don't have all the answers. Pretending you do creates distance, not confidence.

The key is distinguishing between appropriate vulnerability and emotional dumping. Sharing that you're uncertain about a strategic decision invites collaboration. Sharing that you're having an existential crisis about whether you're cut out to be CEO... that's a conversation for your coach or therapist.

The deeper truth is that hierarchy in 1:1s is less about title and more about what each person needs to do their best work. Some senior leaders need more strategic sounding board time. Some individual contributors are naturally strategic thinkers who thrive on big-picture conversations.

Pay attention to the person in front of you, not just their position on the org chart.

The Internal Resistance You'll Face

Every founder we work with hits similar mental traps when it comes to 1:1s and building trustful relationships. Recognize them early:

"This feels touchy-feely and unproductive."
Your engineering brain wants metrics and deliverables. But relationships are the infrastructure that makes everything else possible. One difficult conversation avoided in a 1:1 becomes three emergency meetings later.

"I don't have time for this."
The most common misconception we hear founders say about 1:1s. Actually, you don't have time not to do this. Every misalignment that festers in your team will eventually explode in your calendar at the worst possible moment.

"They should just tell me if something's wrong."
Hierarchy creates blind spots. People need explicit permission and safe spaces to bring up hard topics. Your job is to create those spaces consistently. Fear of conflict is a direct result of lack of trust.

"I'm not good at the emotional stuff."
You don't need to be a therapist. You need to be genuinely curious about the people who are building your company with you. The skills develop with practice. And by the way, if you’ve ever heard yourself say that you are not good at the emotional stuff, this might be wonderful data for huge potential. [2]

As a summary for all the above statements, we love to bring up the idea of the book The 5 Dysfunctions of a Team, which clearly outlines how trust is the needed foundation to step up to exceptional results. When you never invest in the trust layer, you will have a hard time getting the results your company needs. And relationship-focused 1:1s are one controllable instrument to build trust in your relationships.

For the Skeptics: What Success Actually Looks Like

After 6 months of consistent 1:1s, you'll notice:

• People bring up problems while they're still small and solvable

• Your team feels more aligned without constant check-ins

• Difficult conversations happen in private, not in public meetings

• People feel genuinely supported in their growth, not just managed

• You catch misunderstandings before they become conflicts

Your Next Step

If you don't have regular 1:1s scheduled with each of your direct reports, block time this week to set them up. Start with the conversation about what these meetings are for.

If you do have them scheduled but they've become routine status updates, reset the frame in your next meeting: "I want to make sure these conversations are valuable for you. What would make our time together more useful?"

The question isn't whether you have time for meaningful 1:1s. The question is whether you can afford not to.

Your team is building your company alongside you. They deserve to feel truly seen in that work. And you deserve to actually know the people you're trusting with your vision.

Start there.

Notes

[1] Framework by Kim Scott

[2] Common new founder reaction: “NVIDIA doesn’t do 1:1s.” Our take: Jensen Huang at NVIDIA has around 60 direct reports and no standing 1:1s. But he runs a three trillion dollar company with leaders who have worked together for decades. The culture there is built on direct, in-the-moment communication. Most startups are not there yet. You are still building trust, alignment, and psychological safety. Skipping 1:1s at your stage is not bold. It leaves you blind to the issues that will cost you most.

*This story is inspired by real coaching work with founders. Details have been adapted and names anonymized to protect confidentiality. The examples are written for learning purposes and do not describe any one individual.