Setting Up Regular One-on-One Check-ins

Through my Engineering Success Podcast at DevDynamics and working closely with engineering leaders, I’ve had the chance to speak with 200+ Tech leaders and CTOs from growth-stage startups. The way they approach 1:1s is nothing like the “textbook” method, and it’s brilliant. Here’s what I learned about their approach: 1️⃣ The “Look Back, Look Ahead” Format Instead of getting into daily updates, they dedicate time to two specific areas: Look Back: Recap the past month’s challenges, progress, and any learning moments. Look Ahead: Discuss upcoming milestones, skill growth, and their engineer’s long-term goals. 2️⃣ Less Status Updates, More “Personal Growth Talk” They avoid project check-ins here, that’s for team meetings. 1:1s are about the engineer’s growth path. What tools will get them closer to the next level? What’s slowing them down? The focus shifts from “What did you do?” to “Where are you headed?” 3️⃣ Scheduled “Unstructured” Time One of the best hacks? They allocate 10 minutes at the end of each 1:1 for any topic their engineer wants to discuss, work or otherwise. This time often reveals insights that structured agendas miss. 4️⃣ Customized to Personality Type Introverts prefer reflecting on paper, while extroverts benefit from free-flow discussions. They’ve even adjusted frequency based on personality, some engineers have monthly check-ins, others bi-weekly. 5️⃣ Follow-Up Through Actions Set follow-ups in the calendar. If a challenge was discussed, they’ll check in again in two weeks, turning words into measurable steps. Every 1:1 becomes a little system in itself, and it’s working for some of the besting performing teams. Have you tried any of these approaches? P.S. Do check the latest episode of the engineering success podcast with Pranabjyoti Bordoloi from Junglee Games. P.S. 2 - Unrelated photo - someone said photos work better on Linkedin

At Stone Road, one practice I introduced immediately when I joined the team was implementing weekly 1:1 check-in calls. I firmly believe in the power of structured communication, regardless of team size – even in our tiny, two-person team, these calls have proven invaluable. They provide dedicated time each week to discuss ongoing projects and strategize for the week ahead, ensuring alignment and accelerating goal achievement. Our approach to these 1:1 meetings involves using a Google Sheet that we fill out before the meeting and alternate who leads each week. This allows both of us to openly share perspectives, ideas, and talking points, ensuring a collaborative and productive discussion. During these check-ins, we cover several key topics: 1. Last Meeting Follow-Up: We review highlights from our previous check-in to assess progress and identify outstanding tasks. 2. New Discussion Topics: We identify and discuss new topics for the week which are then followed up on in our next meeting, ensuring continuity and forward momentum. 3. Wins of the Week: Recognizing and celebrating both small and significant victories is essential, especially in our dynamic industry. Even in the most challenging weeks, we can identify at least 10 bullet points of wins we’ve had that week. 4. Action Items: We outline specific tasks to be completed before the next check-in, ensuring accountability and progress. 5. Weekly Deals: We assess our inventory and strategize on which SKUs to push and tailor our weekly deals around those specific SKUs. Do you conduct weekly 1:1 meetings with your team? I’d love to hear about the topics you find valuable to cover. Share your insights below! 👇

The Most Underrated Leadership Habit? A 20-Minute Conversation. OXYTOCIN #1 Think about the last time you felt truly seen by someone at work. Not for what you did—but for who you are. That moment, whether in an elevator, a feedback session, or a spontaneous check-in, likely triggered oxytocin—the brain chemical that makes us feel emotionally safe, connected, and trusted. 🧠 Oxytocin isn’t just about hugs or human warmth. In leadership, it’s a chemical pathway to empathy, collaboration, and trust. And one of the fastest ways to stimulate it? ➡️ Regular, intentional, one-on-one conversations. 🔬 The Science Oxytocin is released during emotionally attuned, face-to-face interactions (Zak, 2005). Even brief moments of vulnerability and connection lower cortisol (stress) and increase bonding (Kosfeld et al., 2005). According to Boyatzis (2009), leaders who coach with compassion—rather than correction—activate oxytocin circuits that enhance learning, resilience, and loyalty. Positive Organizational Interventions (POIs) such as: ✅ Empathic Communication ✅ Compassionate Leadership ✅ Strengths-Based Feedback …are effective precisely because they optimize the relational environment where oxytocin thrives. 📌 What to Do Structure monthly (or biweekly) one-on-one check-ins that go beyond project status. Ask questions like: “What’s been energizing you lately?” “What’s something you’d love to learn this quarter?” “Where do you feel most supported—and where could you use more?” “What do you wish we talked about more often?” Then: listen. With presence. No multitasking. No fixing. You’re not managing—they already know how to work. You’re showing that you care enough to see the human behind the role. 🕰️ When to Do It After a stressful period or change During onboarding and role transitions When performance slips or disengagement appears Or—ideally—before any of that happens One-on-ones don’t need to be long. They need to be real. 📊 KPIs to Track Psychological safety scores Retention of high-potential talent Employee Net Promoter Score (eNPS) Participation in development conversations Burnout or stress reporting trends 🚧 Common Objection “I don’t have time for regular check-ins.” 🔄 Reframe it: You don’t have time not to. A 20-minute conversation today can prevent: ❌ A disengaged employee ❌ A sudden resignation ❌ A conflict that festers in silence And if you truly can’t fit it in—delegate. Empower team leads to carry the torch of connection. 🧭 Bottom Line You don’t need an offsite to build trust. You just need 20 minutes and your full attention. Because oxytocin is the chemistry of being present with another human being. In a distracted, data-driven world, presence is a gift. And your team knows when they’ve received it. #oxytocin #empathicleadership #positiveorganizationalinterventions #trustatwork #employeeengagement #coachingculture #leadershippresence #psychologicalsafety #highqualityconnections #teamculture

Most leaders mishandle their 1:1s. They treat them as casual check-ins… or cancel them the moment the calendar gets tight. But here’s something I don’t hear often enough: your team wants a PREDICTABLE manager. Not rigid. Not distant. Just steady. A consistent 1:1 agenda removes anxiety and builds trust. HBR recently published a great piece on this, and I agree with most of it — but I want to share the framework I use with my directs every week. Same structure. Same rhythm. No surprises. 1) Start with 5 minutes of real life. Family, hobbies, what they’re excited about outside of work. This isn’t small talk. It’s a weekly signal that I care about them as humans, not just operators. 2) Workload check (1–10). 10 = “I’m overloaded. Help me reprioritize.” 9 = “Don’t add anything new.” 7–8 = Normal SaaS busy. 6 or below = Underutilized. The number matters, but trends matter more. 3) Morale check (1–10). 10 = Thriving. 7–9 = Healthy. 6 or below = Something’s off. I lean in. 4) What do you need from me? Where am I blocking you? 5) How’s your team? Highs and lows. 6) Top 3 priorities. Are we aligned? Are they working on the right things? 7) Open agenda. This is the non-intuitive part: I save all my “important but not urgent” ideas for this space rather than interrupting people all week. My directs do the same. It protects their focus and creates cleaner conversations. How we run it: • A single rolling Google Doc with our full 1:1 history • I take notes live • If a topic needs more time, we schedule separately • And I try hard not to cancel — nothing erodes trust faster than a constantly shifting 1:1 One more thing: this is not where we do deep performance discussions. Those happen in functional meetings and our weekly marketing team meeting. The 1:1 is for alignment, support, clarity, and connection. This system isn’t perfect, but it’s intentional. And more importantly: it’s consistent. Employees don’t need a manager who shows up everywhere. They need one who shows up reliably. https://lnkd.in/gaR3FMME

Are we done talking about 1:1s? I don’t think so. When I start a new role, the first ritual I establish is a recurring 30-minute 1:1 with each of my direct reports. At first, when they’re not used to it, some show signs of skepticism or even discomfort. But give it a few weeks — and if I miss one or two (yes, guilty as charged 😄), they start asking for them. There’s plenty written about why structured, regular, well-planned 1:1s matter. I won’t add to the pile — just Google it or ask ChatGPT :-) Instead, I want to share what’s worked for me — and what hasn’t — so you can build your routine. First: 1:1s are not for reporting, micromanaging, or correcting performance. If you use them that way, you’ll fall to the dark side. Your reports will dread them, and they’ll turn into dull, mechanical rituals — like bad standups. Instead, 1:1s should be a protected space to build trust, alignment, and real connection. They should center on the report — even if, sometimes, the conversation drifts toward your challenges. Keep them regular and structured. Even if you talk to your reports informally every day, 1:1s give you a moment to step back and think together — with intention. But don’t make them too formal either. That’s a fast track to 1:1 fatigue. Change the setting. Grab coffee. Go for a walk. Just one non-negotiable: track your conversations in a shared doc — Notion, Loop, whatever works. It keeps the thread going and is a lifesaver when performance reviews come around. Timing matters too. Mondays? Too heavy. Fridays? Everyone’s half gone. I’ve found Tuesdays and Thursdays work best — but experiment. Your context may vary. I used to stack 1:1s back-to-back for efficiency. Turns out, two in a row is my limit. More than that and you lose focus. Add buffer time between meetings — they often run over. (Especially when, like me, you tend to talk a lot 😄). Afternoons are also a sweet spot — after your team has tackled their most focused work. As for structure, here’s a simple template I use: Formal (15 min) - Individual: How are you? How was your week/weekend? - Delivery: Wins, blockers, incidents? - Technology: Any ADRs, experiments, tech insights? - People: How’s the team? Any interpersonal challenges? Informal (can be written) - Feedback for me: What should I improve? - Feedback from me: What’s going well? What could be better? - Career & growth: What’s next for you? - Wrap-up & actions. And sometimes… we just grab a coffee or pastry after, if we’re not rushing into the next meeting. Last thing: sometimes these chats get personal. That’s OK. Don’t be rigid. Be human. Be supportive. But know your limits — and keep sensitive matters in the right setting. You're not a therapist. That’s my 1:1 fifty cents. What about you — how do you run yours?

We don’t need more meetings. We need better ones. Here’s a 30-minute 1:1 agenda that helps me stay connected, aligned, and supportive as a leader—without overwhelming the calendar. 🔹 Quick Personal Check-in (0:00–2:00) • Ask how they’re doing personally 🔹 Wins Since Last Meeting (2:00–5:00) • Let them share recent wins or progress made 🔹 Roadblocks & Challenges (5:00–10:00) • Identify the obstacles, focus on solutions, or support needed 🔹 Priorities and Goals (10:00–15:00) • Align on their current projects and what matters most this week 🔹 Feedback (Give + Ask) (15:00–20:00) • Offer specific feedback and ask for feedback to support them better 🔹 Growth & Development (20:00–25:00) • Briefly discuss skill growth, learning goals, or long-term aspirations 🔹 Action Items and Close (25:00–30:00) • Review takeaways, set next steps, confirm alignment before ending Consistency over complexity. Listening over lecturing. Growth over status updates. How are you making your 1:1s more impactful? #Leadership #PeopleDevelopment #OneOnOneMeetings #TeamSuccess #GrowthMindset

If your one-on-ones are primarily status updates, you're missing a massive opportunity to build trust, develop talent, and drive real results. After working with countless leadership teams across industries, I've found that the most effective managers approach 1:1s with a fundamentally different mindset... They see these meetings as investments in people, not project tracking sessions. Great 1:1s focus on these three elements: 1. Support: Create space for authentic conversations about challenges, both professional and personal. When people feel safe discussing real obstacles, you can actually help remove them. Questions to try: "What's currently making your job harder than it needs to be?" "Where could you use more support from me?" 2. Growth: Use 1:1s to understand aspirations and build development paths. People who see a future with your team invest more deeply in the present. Questions to explore: "What skills would you like to develop in the next six months?" "What parts of your role energize you most?" 3. Alignment: Help team members connect their daily work to larger purpose and meaning. People work harder when they understand the "why" behind tasks. Questions that create alignment: "How clear is the connection between your work and our team's priorities?" "What part of our mission resonates most with you personally?" By focusing less on immediate work outputs and more on the human doing the work, you'll actually see better performance, retention, and results. Check out my newsletter for more insights here: https://lnkd.in/ei_uQjju #executiverecruiter #eliterecruiter #jobmarket2025 #profoliosai #resume #jobstrategy #leadershipdevelopment #teammanagement

📈 Make your one-on-ones better. 👊🏻 "Individual contributors with weekly meetings reported feeling 20% less anxious, dreading them 17% less, and feeling 12% more successful at their jobs, on average, compared with those who met with their managers less often" So, we should schedule more one-on-ones, right? Not so fast. My colleague, David Frost, is a huge advocate of them in his coaching practice, but we shouldn't lose sight of what they're for: to set the tone, connect the dots, and push. ⏱️ 𝗦𝗵𝗼𝗿𝘁𝗲𝗿, 𝗺𝗼𝗿𝗲 𝗳𝗿𝗲𝗾𝘂𝗲𝗻𝘁 𝗺𝗲𝗲𝘁𝗶𝗻𝗴𝘀. Don't spread 1:1s like peanut butter. Adjust the cadence based on the individual. Some need weekly check-ins; others monthly nudges. Keep them short (15–20 mins), focused, and consistent. - Low touch / low task: less frequent - Low touch / high task: more coaching - High touch / high task: more support - High touch / low task: less structure, more space 🎯 𝗔𝗻𝗰𝗵𝗼𝗿 𝗶𝗻 𝗢𝗞𝗥𝘀. Use OKRs to focus the conversation. Every 1:1 is a chance to ask: - What are we driving toward? - Is this work aligned with the outcome? - Are we on track or off? This is how you 𝘀𝗲𝘁 𝘁𝗵𝗲 𝘁𝗼𝗻𝗲, 𝗰𝗼𝗻𝗻𝗲𝗰𝘁 𝘁𝗵𝗲 𝗱𝗼𝘁𝘀, and 𝗽𝘂𝘀𝗵. 📝 𝗠𝗮𝗶𝗻𝘁𝗮𝗶𝗻 𝗮 𝗿𝘂𝗻𝗻𝗶𝗻𝗴 𝗮𝗴𝗲𝗻𝗱𝗮 𝗮𝗻𝗱 𝗱𝗼𝗰. Use a shared document (Google Docs, Notion) and a standard agenda to track priorities, wins, roadblocks, and context between meetings. Keep it simple and visible. Make preparation easy and collaboration continuous. 🧭 𝗖𝗼𝗻𝗻𝗲𝗰𝘁 𝘁𝗵𝗲 𝗱𝗼𝘁𝘀 𝘄𝗶𝘁𝗵 𝗰𝗼𝗻𝘁𝗲𝘅𝘁. People want to know how their work fits into the bigger picture. That’s your job: 𝗰𝗼𝗻𝗻𝗲𝗰𝘁 𝘁𝗵𝗲 𝗱𝗼𝘁𝘀. Use 1:1s to share what’s happening across the team, how priorities are shifting, and what it all means for them. 🚀 𝗙𝗼𝗰𝘂𝘀 𝗼𝗻 𝗼𝘂𝘁𝗰𝗼𝗺𝗲𝘀, 𝗻𝗼𝘁 𝗽𝗿𝗼𝗰𝗲𝘀𝘀. Skip the status play-by-play. Instead, define the outcomes and give people space to own the 𝘏𝘖𝘞. It’s a subtle but powerful way to 𝗽𝘂𝘀𝗵 without micromanaging. When needed, unblock. When possible, coach. Prioritize traction over checklists. 🧪 𝗨𝘀𝗲 𝗳𝗲𝗲𝗱𝗯𝗮𝗰𝗸 𝘁𝗼 𝗿𝗮𝗶𝘀𝗲 𝘁𝗵𝗲 𝗯𝗮𝗿. Create a feedback loop. Feedback is easier if it happens all the time and is framed as a choice, not a s*** sandwich. Make it a two-way street. Use 1:1s to reinforce fundamentals and stretch performance. Don’t save it for review cycles—normalize it. Read the full article which sparked these thoughts here: https://lnkd.in/ex9GSMxr