Tips for Engaging 1-on-1 Meetings

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?

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.

Most 1:1s are just status updates in disguise. If that's what yours are, your team is telling you less than they should.   A 1:1 isn't a progress report. It's a conversation. And the quality of that conversation starts with the quality of your questions. Here are 12 I teach leaders: 1️⃣ Where do you think your skills are being underused? Underutilized people become disengaged people. Action: Find one way to close that gap before your next 1:1. 2️⃣ How do you want your career to look in the next year? Career conversations belong in all 1:1s. Action: Make a commitment to their development in the meeting. 3️⃣ What opportunity do you think you aren't being given enough access to? High performers who feel unseen start looking elsewhere. Action: If you can open that door, open it. If you cannot, say why honestly. 4️⃣ Where do you think the team's biggest blind spot is? The people closest to the work can see what leadership often cannot. Action: Take it seriously even when it's uncomfortable. 5️⃣ What does a bad day at work look like for you? Recurring bad days are a system's problem. Action: Look for patterns. Then address the root. 6️⃣ Is there a relationship on the team you find difficult to navigate? This opens doors people rarely open alone. Action: Listen before you problem-solve. 7️⃣ What's something you have changed your mind about in the last 6 months? Growth shows up in updated thinking. Action: A person who can change their mind is a person who can lead through change. 8️⃣ Where do you feel most confident in your role right now? Confidence tells you where to give them more runway. Action: Stretch it into a bigger opportunity. 9️⃣ What part of your role feels unclear or undefined? Ambiguity is a performance tax you're charging them. Action: Clarify it before the meeting ends. 🔟 What skill do you want to develop in the next 6 months? Growth should be intentional. Action: Build it into their work before you leave the room. 1️⃣1️⃣ What's one thing I do as your leader that makes your job harder? Most leaders never ask this. The ones who do earn trust that lasts. Action: Don't justify or defend. Just listen and then change. 1️⃣2️⃣ What's one goal you have that has nothing to do with work? People grow in all directions. The best leaders acknowledge that. Action: Ask how their work can support that goal. The quality of your questions is a reflection of the quality of your leadership. When you get curious about your people, not just their work, everything changes. So save this list and bring it into your next 1:1. Your team will feel the difference. Which of these do you find hardest to ask? Every day inside The Leadership Boardroom, I share free leadership coaching for VP and C-suite leaders. Thousands of leaders around the world are already inside. 👉 https://lnkd.in/g2WGzder ♻️ Repost this for leaders who need better 1:1 questions. And follow me, Cicely Simpson, for daily leadership insights.

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 🫡

How you run your meetings matter. 🤝 After spending years working directly with CMOs, CROs, and VPs, here's how I structure and run my 1-1 meetings as a 4X demand generation leader. I still use it with my demand gen consulting clients, and they love it. Why? ↳ It doesn't waste time & gets to what matters, fast ↳ Highlights what's been accomplished + what's next ↳ Focuses on action + consistent alignment on goals Here's what I do: I structure my 1-1 meetings around three major areas... 1️⃣ Notable Updates This is where I'm laser-focused on the metrics that matter for the team. I break down how we're pacing to our goals and targets -- especially around marketing generated pipeline and revenue. I also highlight if there are major funnel conversion rate inefficiencies happening that are impacting our lagging indicators since these are typically high-priority fixes that involve collaboration between the sales team. BONUS: I build custom dashboards with my clients and their ops team to ensure we're all using the right data to stay 100% aligned. In this section, I'm also sure to spotlight notable campaign successes or failures to keep us up to date on how new messaging, experiments, or audiences are performing. This helps us understand what's working (or not), so we can double down or pivot quickly. 2️⃣ Roadblocks This is where I dive into bulleted areas I need their help blocking and tackling. These items could relate to resource allocation needs, team communication breakdowns, or anything that is preventing me/the team from driving the most impact. Don't get caught up in the weeds too much here and keep it punchy, but provide as much transparency as needed so it's easier for your leadership to address. 3️⃣ Priorities This is where I lay out what's prioritized next (taking into account what we discussed in notable updates). The key here is getting feedback on these priorities. This part should be a conversation because things shift constantly and it's crucial to stay aligned to save you time and keep you/your team focused. This is also a great place to share WHY items are prioritized or should be deprioritized based on performance, workload, or new needs. We can't do it all, so be ruthless with your prioritization. I've found this meeting structure works great to keep my meetings focused, impactful, and transparent. And the best part -- it's not complicated 🙌🏻 I hope this helps you have more productive conversations with your direct managers, agency partners, or consultants. What are some things you'd add or do differently in your meetings?

Save this for your 1:1 meeting this week or next → 8 questions that dig deeper than “What are your goals for Q1?” (1) "What could we accomplish by end of Q1 that would feel like a satisfying win for you? Why is that? How can I be supporting you in that project?" (2) "What project / part of the work are your most looking forward to this quarter? Why? What can I do to help make sure that work stays energizing for you?" (3) "What do you think is making our team successful at the moment? Where can we both be greater contributing to that?" (4) "What feels like our greatest barrier to success this quarter / this year? What are things you and I can work on together to reduce that barrier, if anything?" (5) "What feels unclear, or do you anticipate feeling potentially frustrating? What can I give greater clarity on and/or remove blockers around?" (6) "What are areas in year that you’re looking to grow and stretch in, personally? How can I help you invest in those areas?" (7) "Does the energy you are giving to your role feel sustainable right now? How can I help support that sustainability?" (8) "What are ways in which we can improve our own working relationship? (Communication, workflow, processes, etc.)" -- Any 1:1 questions you would add to the list? #leadership #meetings

What If Your 1:1s Became the Best Meeting of the Week? One-on-ones might be the least effective meeting in corporate America today. How do I know? They’re also the most frequently canceled. That’s a shame — because when done well, one-on-ones can build trust, accelerate performance, and create space for meaningful coaching. Here’s a 4-question framework to make your 1:1s something your team actually looks forward to: 1️⃣ What are you most proud of since our last 1:1? Start on a high note. This question energizes the conversation and gives your employee space to celebrate wins. Acknowledge their accomplishments and connect them to the broader impact. If you’ve noticed other great work, highlight it here too. 2️⃣ If you could do anything over again, what would it be? Once trust and psychological safety are established, this opens the door to reflection and learning. In my experience — and repeatedly confirmed through 360 assessments — employees are often their own toughest critics. This question makes constructive feedback a routine part of the conversation, rather than something that only shows up in performance reviews (where it can feel like judgment). 3️⃣ What are you looking to accomplish between now and our next 1:1 — and what’s your approach? This is a classic FeedForward moment. Reinforce their confidence, offer strategic input, and ensure priorities are clear. 4️⃣ How can I help? You might get “crickets” the first few times. Stay consistent. Over time, you’ll get thoughtful, genuine answers that deepen your partnership. When you follow this simple framework, your employee leaves each 1:1: 🔹Energized by what they’ve accomplished 🔹Reflective about how they can improve 🔹Clear on their game plan going forward 🔹Supported by you as their leader Now that’s a meeting worth keeping on the calendar! #OneonOne #coaching #Leadership #LinkedInbyScottZ

Last year, a mentee confided in me about her struggles with 1-on-1s feeling awkward: She felt like a kid in the principal's office. 🤔 How could she make these interactions more natural and open? My mother was a university professor, and it gave me a unique perspective growing up. To me, teachers weren't authority figures, but rather just normal adults with whom I could connect and learn. I suggested my mentee undertake a similar shift in perspective: 👯 See Your Manager as a Person First: View them not as a superior but as an equal. This mindset change can transform the dynamic of your interactions. A 1-on-1 isn't just about solving problems, it's also about connecting and growing trust. 👋 Engage on a Personal Level: Express genuine interest in their life. Really observe if they're tired or energetic or happy or sad and ask them about it. Engage in conversations beyond work tasks. Managers, often in isolating positions, often appreciate this human connection. 🌏 Share Your World: Letting them glimpse into your personal life, within professional boundaries, humanises you. It's about being seen as a complete person, not just an employee. ❤️ Show Appreciation: This should go for everyone, but I've long said and maintained that we should all compliment each other more. You like praise from your manager, right? Then you should also give praise back! Notice and say something when they do a good job in a meeting, or when a resource they share is particularly helpful to you. This approach is especially effective in the tech industry. When you're seen as more than just a technical colleague, people are naturally more inclined to assist and less likely to judge. "Kindness is catching": when you show kindness and understanding and an interest in those around you, you will find that begins to reflect back onto you. Remember, effective communication is about engaging on the same level and creating mutual respect and trust. From this foundation, it is far easier to expand technical collaboration. The update? Last week she shared that the advice had worked, and that everything was feeling much smoother and more collaborative. She didn't feel like a kid in the principal's office any more. What do you think? What do you (either as manager or employee) like to do to ease the way in 1-on-1s? #techcommunity #techcareer #communicationskills

Rethink your 1:1s: Stop the time drain, start driving impact. I’ve sat through more 1:1s than I can count - across teams, geographies, and companies in transformation. And here’s the truth: Most of them are broken. They’ve become status updates. Laundry lists of topics. Career convos squeezed into 45 minutes every week. A calendar drain for leaders and employees alike. We need a new paradigm. The traditional model isn’t working. Weekly or bi-weekly check-ins often feel forced. Career discussions every week? Overkill - and it rarely moves the needle. Managers run the agenda instead of letting directs own it. 1:1s balloon into 60 minutes (or longer), chewing up time better spent on real work. Here’s the truth: 1:1s are not your meeting. They’re your team member’s time. A better model for 1:1s? 1. Flip the agenda: It’s not about your updates. It’s about theirs. Let them drive. If they have nothing urgent? Cancel. That’s a sign of empowerment, not disengagement. 2. Ditch the weekly career talk: Career growth doesn’t happen in 7-day sprints. Schedule quarterly check-ins dedicated to development and goals. Make them deep and meaningful, not rushed after project chatter. 3. Keep them tight (30 minutes max): Don’t let 1:1s become endless status meetings. Use other tools (dashboards, Slack, shared docs) for routine updates. 4. Add thematic conversations: Instead of cramming everything into one recurring slot, schedule focused discussions - a session on roadmap priorities, a creative brainstorm, or a culture pulse. 5. Empower, don’t babysit: Your job isn’t to approve every move. Encourage your team to decide, act, and inform, not wait for your permission. Three powerful questions for any 1:1: 1. What’s the most important thing on your mind right now? 2. Where do you need my support - or my air cover? 3. What’s slowing you (or the team) down that we can fix together? These questions shift the tone from “status” to strategy and support. Why this matters: Your team’s time is precious. Every meeting is a signal of what you value. Are you showing trust, autonomy, and clarity - or micromanagement and overload? Meetings - especially 1:1s - are culture moments. They reflect how aligned you really are. They can fuel momentum, or quietly drain it away. But here’s the most honest question: Who needs the 1:1 more - you or them? Is it your safety net because you lack other mechanisms for visibility, alignment, and progress tracking? Or is it truly serving to support their performance and therefore ultimately, their growth? If not, maybe it’s time to rethink what this time should accomplish.

I might get hate mail for this: Appearances and first impressions still matter—big time. Zoom calls and remote work culture erupted over the past decade, and somewhere along the way, we stopped caring about the 'little things'. Salespeople, missing the details = lighting cash on fire 🔥. 💰 Every call on your calendar costs your marketing team a few thousand dollars. Each meeting could be thousands in commission for you. That CMO you’re meeting with? Her 30 minutes is worth $500. When she brings her team, they spend $3k in salary just showing up. So, why do we show up like we don’t give a sh*t? Sweating the details can often be a waste of time, other times it's worth the effort. 💡 Here are 6 details you should never skip: 1) Do your research.  Asking where they live or what their company does—things you could Google in 5 seconds—doesn’t build rapport; it just makes you look unprepared. Instead, come in with a point of view on something you've already researched. 2) Use a good webcam & mic.  Who would you rather spend 30 minutes with in the screenshot below? You don’t need to break the bank—a solid cam/mic setup costs under $100. 3) Get your lighting right.  Clear the shadow from your face. Sit in front of good lighting. A $20 ring light can do wonders. 4) Dress like you care.  Would you rather be over-dressed or under-dressed when you're presenting to the C-suite of a $2billion dollar company? Toss the wrinkly T-shirt and baseball cap. Throw on a button-up or polo. Maybe even take a morning shower and comb your hair. 5) Send a follow-up the same day.  Buyers appreciate a quick recap they can share internally. Tools like WINN.AI, Gong, or Sybill can automate this, so you can get the email out in minutes instead of hours. 6) Send a pre-meeting brief.  An engaged audience = a better meeting. Prime their brains before the call. *Bonus tip: Send personalized messages to each stakeholder - this takes more effort, but it's worth it. A CMO has different interests/problems than a Sales Manager. Make it clear that you took the time to curate messages for each person. These details might seem trivial, but it's worth it if they make you even 1% more engaging. I get it—some of you will think I'm an old-fashioned grandpa. (Probably true.) Some will think, "it’s 2025, and this stuff doesn’t matter anymore." 🎲 But are you willing to gamble your company's hard-earned pipeline (and your own commission) on that? Deals are won or lost by tiny margins. Skimp a little here, skimp a little there, and watch your win rates suffer. (Legit, I had a rep almost lose a deal because he presented a deck using the customer's outdated logo <- the CMO was not smiling about it. We did damage control for 2 weeks.) ⚖️ My stance: obsess over the details. Alone, they might seem minor, but together, they will tip the scales and split success from failure. Would love to hear what details you swear by?