Questions to Ask During 1-On-1 Meetings

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

“Winging it” in performance reviews or employee check-in meetings will get you nowhere. I learned this lesson the hard way. In the early stages of Executive Presence, I would hold open-ended, monthly check-ins with each team member, thinking I was being flexible and giving them space to bring up anything they wanted to discuss. I wanted their constructive feedback on the company as much I wanted to offer my own on their performance. But over time, I realized these 1:1 review sessions were not as productive as I thought. People didn’t always know how to use that time effectively. That’s when I worked with my executive coach, Victoria (Tory) Wobber, CPCC, and she gave me a simple but powerful piece of advice: “Give more structure to the conversation in advance.” Instead of a free-for-all, I started framing the discussion with clear, intentional questions - ones that gave my team a chance to reflect before our meeting. These are the questions I started using: 1️⃣ How are you doing outside of work? Anything new? 2️⃣ How are we supporting our clients? Any suggestions for improvement? 3️⃣ How are we functioning as a team? Any feedback or ideas? 4️⃣ Anything else you’d like to discuss? This approach shifted the dynamic. People were able to come to the table with thoughtful responses, and the conversation became more meaningful. I could use my time better, and my team members felt more prepared and empowered to engage. If you're looking for additional tips on making your performance reviews or other 1:1 meetings more meaningful, check out a recent Forbes article combining advice from 20 Forbes Business Council members (see if you can spot me 👋): https://lnkd.in/gyCnHQeX Structured, intentional questions turn scattered check-ins into powerful conversations. Give your team the time and direction to prepare, reflect, and engage deeply.

Do you respect one-on-ones with your team? These should be the most important meetings on your calendar but I often see them neglected and lacking strategic focus. Yesterday, I had the privilege of hearing Tyronne Stoudemire speak about leadership and diversity done right. While there were MANY powerful insights I’ll unpack in future posts, there was one moment that pushed me to finally write and publish this post… At one point, he shared three simple questions every leader should ask in their one-on-ones: ‘What are you most proud of?’ ‘What’s standing in your way?’ ‘How can I help?’ Too often, one-on-ones are the first meetings we’ll reschedule or treat like a quick checkbox exercise. But they should be the most protected time on our calendars. Think about it… these meetings are where real growth happens, where your team should feel seen and supported. When you consistently reschedule or rush through one-on-ones, you’re sending a clear message: ‘Your growth and challenges aren’t a priority.’ In 2025, make it one of your leadership goals to guard your one-on-ones fiercely. Show up fully present. Ask these questions. And watch what happens when your team knows their success is your priority. [For team members looking to make the most of your one-on-ones, the video below has some specific strategies to maximize these crucial time slots.] Video description: A woman with brown hair and red glasses in front of a brown woven screen.  For the first 3 seconds there's a yellow box above her head that says "Making the most of one-on-ones".