Transformative 1:1 Meetings

Your next 1-on-1 is either building trust or breaking it. Most managers treat them like status updates. Most employees see them as obligations. After years of leading teams through growth and crisis, I've learned the truth: The best 1-on-1s aren't meetings. They're investments in human potential. When done right, these 30 minutes can transform: • Disengaged employees into champions • Surface problems become solutions • Good performers into great leaders Here's how to make every 1-on-1 count: For Managers: 1/ Start human, not tactical "What's on your mind?" beats "What's your update?" every time. Let them drive the agenda first. 2/ Listen like your success depends on it Because it does. Their challenges are your early warning system. Their wins are your team's momentum. 3/ Ask the question that matters "What support do you need?" Then actually provide it. Trust compounds when promises are kept. For Employees: 1/ Come with intention This is your time. Own it. Bring your real challenges, not just safe updates. 2/ Share what's actually blocking you Your manager can't fix what they can't see. But come with potential solutions too. It shows you're thinking, not just venting. 3/ Talk about tomorrow, not just today Where do you want to grow? What skills are you building? Make your development their priority. Great 1-on-1s don't just review work. They build relationships. They surface insights. They prevent fires instead of fighting them. The game-changer most miss: End every 1-on-1 with absolute clarity: 📌 What are the next steps? 📌 Who owns what? 📌 When will we check progress? Vague endings create frustrated teams. Your people don't need another meeting. They need a moment where someone truly sees them, hears them, and helps them win. Give them that, and watch what happens. What's one thing that transformed your 1-on-1s? ♻️ Repost if this changes how you approach 1-on-1s Follow Desiree Gruber for more insights on storytelling, leadership, and brand building.

After 15 years of managing teams, here's the framework I use to turn awkward 1:1s into sessions my team actually looks forward to: 1) Start on a high “What was your biggest win this month?” This isn't just feel-good fluff. When team members know I'll ask this question, they spend the entire month working toward wins we can celebrate together. If someone can’t name a win, that’s data. Now I know where to support. 2) Move to challenges “What’s been your biggest challenge lately?” or “What’s keeping you up at night?” Let them bring up the tough stuff first. You shift from a “me vs. you” vibe to a “we’ll solve it together” mindset. 3) Open the door “Tell me about you. How’s everything going?” This invites what doesn’t fit neatly on a status report: schedule needs, personal context, unspoken worries. Bonus questions I keep in my back pocket: • "How do you feel the team is doing?" • "Which team members do you wish you had more connection with?" • "What are your goals for this month?" • "How can I support you in growing toward those goals?" I conclude the call with a meta-question most managers skip: “What do you wish I asked you more often?” I learn whether they want more help on productivity, learning, career path, or just time to think together. These questions aren't scripts. They're starting points for real conversations. What's your go-to question for connecting with your team?

If your one-on-ones are mostly project updates, you're leaving one of your best leadership tools on the table. I've sat in a lot of one-on-ones over the years. Some felt like checking boxes. Others changed the trajectory of someone's career. The difference wasn't the agenda. It was the conversation. Project updates can happen in an email. A one-on-one is one of the few opportunities you have to understand the person behind the work. One thing I've noticed is that the best one-on-ones answer three questions. 🔵 What's going well? Not because people need praise every week. Because when you understand what's working, you can create more of it. 🔵 What's getting in your way? This is where I've seen good leaders make the biggest impact. Sometimes the obstacle is a process. Sometimes it's a lack of clarity. Sometimes it's another department. Sometimes it's us. One of my favorite questions is: "What's one thing making your job harder than it needs to be?" If you hear the same answer from multiple people, you've probably found a systems problem, not a people problem. 🔵 What's next for your growth? Growth doesn't always mean a promotion. It might be leading a meeting. Taking ownership of a project. Having a difficult conversation. Trying something they've never done before. I've found that people usually rise to the expectations of leaders who believe in them. The best one-on-ones aren't memorable because you covered every agenda item. They're memorable because someone walked away feeling heard, supported, and more confident than when they walked in. Leadership isn't built in the big speeches. It's built in conversations like these. One conversation at a time. #leadership #leadershipdevelopment #management #healthcareleadership #culture

If your 1:1s with your manager feel like status updates, you’re wasting your best opportunity for growth. A great 1:1 isn’t a recap. It’s a strategy session. A career checkpoint. A space to align, get support, and surface what actually matters. Here’s how to level up your 1:1s: 1. Come with a short, clear agenda. Highlight progress, blockers, and one area where you want input. Don’t wait for them to steer, lead the conversation. 2. Share impact, not just activity. Instead of “I fixed X bug,” say, “I unblocked the launch by resolving X issue, which let Y team ship on time.” 3. Surface patterns, not just problems. Instead of, “This sprint feels chaotic,” try: “I’ve noticed we’ve missed 3 sprint goals in a row, can we talk about scope planning?” 4. Make space for growth. Ask: • “What would it take to be seen as staff-level here?” • “Where should I focus if I want to expand my scope this quarter?” 5. Keep a running doc. Track what you discussed, what you committed to, and feedback you received. It’ll be gold when review season comes around. Because your manager can’t support a goal you haven’t shared. And they can’t advocate for progress they haven’t seen. Use your 1:1s wisely, and they’ll stop being routine. They’ll start accelerating your career. Help me share this post and let’s help other advance in their careers.

Ok, raise your hand if you've ever been the "fuzzy meeting person." 🙋♀️ 🙋♀️ 🙋♀️ I’d schedule sessions with no clear agenda, no defined outcome, basically, “let's chat and figure it out.” I’d leave half-exhausted, half-confused, thinking: "Did anything just get decided? Who’s doing what? Could this have been an email?" Probably everyone else thought that too. Waste of time. It took me a while, but I realized: the problem wasn’t the team. It was me. My meetings lacked clarity + intent. So I decided to get scientific about it. I started analyzing my meeting transcriptions with CoPilot. I wanted to see: - How much time I spent talking vs listening - How often I stated an explicit decision - Where confusion or rambling crept in The results were… eye-opening. I wasn’t just scheduling fuzzy meetings, I was enabling them. Here’s the system I built to fix it: Step 1. Define the single purpose (SO IMPORTANT) Every meeting needs a north star: “By the end, what should people know, decide, or do?” Step 2. Structure the agenda around outcomes List topics → assign a single desired outcome + time limit. Step 3. Prep key points, lead with decisions Skip long-winded context. Deliver the decision first, context second. Step 4. Track your talk ratio Use AI to see if you’re dominating or clarifying. Adjust accordingly. Step 5. End with explicit next steps Who does what, by when. No assumptions. Step 6. Follow up in writing 1–2 bullets summarizing decisions + assigned owners (you can do this with AI). Send within 24 hours. I also send transcripts if necessary. The transformation? Meetings went from draining and fuzzy → purposeful, productive, and trust-building. My coworkers leave knowing exactly what to do, and I finally stopped wondering why work wasn’t getting done. People like me more (hopefully?). Also, generally reduced my meeting frequency by 20ish%. Effectiveness frees us time, who knew. Moral: meetings are time, money, and trust. If people feel like you schedule fuzzy meetings, they'll be less committed. Use those steps to focus more on your clarity and intent. How do you make meetings more effective?

⛔️ “Sure, let’s discuss [reprioritizing your workload, your career development, how your performance is tracking midyear] in your 1:1.” Fast, easy, efficient. 🙌 “Let’s set up some dedicated time.” A few years ago, leaders in our team were having meaningful career conversations as a part of everyday management. Promotions happening, feedback exchanged real time, not saved for twice a year. Career was a normal part of 1:1 agendas, which felt in some ways evolved and baked in for a fast moving company. We cared so much, we were discussing weekly! But imagine our surprise when employee scores were rating us lower in career development. 🤔 Where was the disconnect? When we were talking career (skills, feedback, coaching) in the normal course of conversation and at the dedicated company mid year and annuals, it was getting lost in the couch cushions of busy schedules. Big rock topics get their own meetings with their own titles and notes/agendas. Even though no one wants another meeting. So we shifted to: -setting up repeating quarterly Career chat invites that allowed everyone to clear headspace for the convos -keeping dedicated notes about topics -starting running logs to track resume bullets and wins as mutual fodder for review seasons every 6 months -continuing real time feedback and thoughts in 1:1s, but threaded back to the quarterly chat Similarly, Dan Brodnitz used to set up meetings called Moving Day, which were solely for reprioritizing work when things got overwhelming. If Moving Day was on your calendar, that’s your leader taking your workload seriously and adjusting competing priorities for a busy and senior team. If the team is feeling disconnected from overall company goals during a busy season, a half hour on How Our Work Impacts Customers (bonus points if you have customer anecdotes) does wonders shining light and opening dialogue. Name it and claim it.

A 1-1 meeting with your manager isn't a status update. It's your best career development tool (if you use it right). This week, I was preparing for an upcoming 1-1 with my manager, and I realized how much my approach has changed over the years. When I was just out of college, I showed up (kind of nervously) to recurring 1-1 meetings and waited for my manager to ask me questions. Now, I realize that it's also on me to prepare and utilize these meetings. This starts with realizing that (in a healthy work environment) your manager *wants* you to succeed in your role and grow. Taking it a step further, you can use these meetings to get *strategic* about your career growth. Your manager is not responsible for your career growth; they are there to support you in it. You need to roadmap and drive your own career. And if you create the right setup, your manager can tell you the areas you're missing... and help you fill them in. ~~~~~~~~ Here's a framework to prepare for your next 1-1 with your manager: 》Catch up. Don't crack open your agenda items immediately. The first 10% of the meeting should be catching up on a personal level. Let your manager know what's been going on for you, and ask them the same. If you don't do this, you may be perceived as cold. (I see differing opinions on this on LinkedIn, this is mine). 》Set the context. Your manager might be coming right out of a meeting on a completely different topic into this one. Help them help you. If you have 20 minutes of time, you should state, "I wanted to cover X, Y, and Z today if that sounds good." 》Provide a recap of the last X weeks and a few key accomplishments that you're proud of. Tell them what was hard about reaching the objectives and your individual actions/contributions. 》Let them know what's difficult right now/where you are stuck. If you are facing any issues, you need to be able to communicate them professionally. For my early-career friends, remember to choose your words & tone carefully. You should be objective, solution-focused, and optimistic. 》Recap the actions / follow-ups from the above discussions. It might be training that your manager recommended, a new approach to try, or a mentor they suggested you reach out to on a specific topic. At the next 1-1, you should proactively bring up the previous meeting's follow-ups and what you did about them. Most early-career folks miss this part, waiting for the manager to ask. ~~~~~~~~ Every manager is different in their approach and style. Over time, you will learn what works for them, and they'll learn what works for you. You will also build trust over time to allow deeper, more vulnerable conversations. But it's on you to start down that path. Calendar Q4 is upon us. This is a great time to reflect on the past year, what worked, what didn't work, and next steps. How are you going to be more intentional for your next manager 1-1? #fieldnotes #managermeetings

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

Most managers waste their 1-on-1s. This is how I make sure I don’t: Early in my career,  I didn’t understand the power of a great 1-on-1. As a founder, I make sure my 1-on-1s drive growth, trust, and retention. As a Manager: Here’s what I do differently. ▶️ I plan ahead. My team knows the agenda before we meet.  No surprises, no wasted time. ▶️ I start with a human check-in. No one wants to jump straight into work talk.  A few minutes of real conversation builds trust. ▶️ I always give structured feedback.  I use “Start, Stop, Continue”: Start: What new actions could help them grow? Stop: What habits might be slowing them down? Continue: What are they excelling at? Reinforce their strengths. ▶️ I set meaningful goals with them, not for them. Using “The 3Ps” framework: Project: What’s the next big deliverable? Progress: How are their skills evolving? Path: Where do they want to go in their career? ▶️ I never cancel. If something comes up, I reschedule.  It’s a signal that their time matters. ▶️ I listen more than I talk.  My job is to unblock—not dominate the conversation. ▶️ I offer genuine support. Saying, “Let me know if you need anything” is lazy.  Instead, I make specific offers to help. As an Employee,  Here’s what I did to make my 1-on-1s count: ✅ I came prepared.  I treated these meetings as a chance to drive my own growth, not just report updates. ✅ I gave my managers feedback using “The H.O.W.” framework: Highlight: What’s working?  Start with the positives. Observe: What challenges are holding me back?  Be honest. Wish: What support do I need?  Be specific. ✅ I took ownership of my career. I didn’t wait for my manager to ask about my goals—I brought them up myself. ✅ I defined my own growth using the “G.R.I.T." framework: Goal: What’s my long-term career objective? Reality: Where am I right now? What gaps exist? Initiative: What skills, projects, or mentorship will get me there? Timeline: When do I want to reach each milestone? Invest in these conversations. You’ll see the ROI in trust, collaboration, and retention. What’s your 1-on-1 strategy? - - - - - ♻️ Share and repost if you found this useful. Follow me, Nader Alnajjar, for more 🫡

1:1s can be the most important meetings you have. Or they can be a total waste of time. Your choice. A lot of 1:1s never get past surface-level. But these conversations are when crucial developments can happen for team members. And it's one of the few times where both of you are fully focused on how to achieve personal and professional success. So whenever I'm in a one-on-one, these are the questions I'll ask: 1️⃣ How do you think things are going? ↳ Opens with self-reflection instead of your evaluation. 2️⃣ Is there anything creating stress that I should know about? ↳ Surfaces issues before they become performance problems. 3️⃣ Where do you feel like you're adding the most value right now? ↳ Shows where they feel confident and where they might need support. 4️⃣ What's something you're proud of that we haven't talked about yet? ↳ Creates space to recognize wins that might have gotten lost. 5️⃣ What would need to be true for this to feel like a "dream job"? ↳ Uncovers gaps between current reality and future fulfillment. 6️⃣ What are you interested in learning or taking on next? ↳ Signals that development happens continuously, not just in annual reviews. 7️⃣ What's getting in the way of your best work? ↳ Identifies blockers you can help remove. 8️⃣ Am I supporting you in the right way? ↳ Invites honest feedback about your leadership. 9️⃣ What's one thing you want to make progress on? ↳ Focuses the conversation on what matters most to them right now. 🔟 How can I help you going forward? ↳ Closes the conversation while letting them know you're there for support. Great 1:1s aren't measured by how many boxes you tick on paper. They're a chance to help your team achieve success based on what's important to them. When you ask questions that create space for deeper conversations, you build trust that lasts long after the meeting itself. Which of these would change your next 1:1? For more posts on leadership, follow Clif Mathews. ---- 📨 Every week, 23,000+ execs learn how to define their own success via socials and in my newsletter, Second Summit Brief. Sign up here so you don't miss out: bit.ly/SecondSummitBrief 🔁 Repost to help another leader run better 1:1s.