5 questions every manager should ask in their 1-on-1s (but almost never does)
Most 1-on-1s cover tasks and deadlines and miss the one thing that actually keeps people engaged. Here are 5 questions that change that.
MANAGER EFFECTIVENESS
Fernanda Brasileiro
7/9/20262 min read
Most 1-on-1s are status updates in disguise. Task check-ins, project reviews, deadline reminders. All useful and necessary, but they're missing one very important thing. It's the one thing that actually determines whether someone stays engaged, motivated, and happy in your team: the relationship.
Here are 5 questions that shift a 1-on-1 from transactional to developmental.
1. "What's one thing that would make your week easier?" This opens the door to real support instead of performative check-ins. It also tells you where friction lives before it becomes resentment.
2. "What are you learning right now, even if it's not work-related?" Curiosity about someone as a whole person builds trust faster than any performance conversation ever will. It also often reveals strengths you haven't tapped into yet.
3. "Where do you feel stuck, and what have you tried already?" This question does double duty. It surfaces real obstacles and shows you whether someone is problem-solving on their own or waiting to be rescued.
4. "What feedback do you have for me?" Most managers skip this one entirely. It requires a level of self-trust that many leaders haven't built yet, because it means sitting with an honest answer without getting defensive.
5. "What would make you excited to come to work tomorrow?" This question gets at motivation directly instead of guessing at it. The answers are almost always more specific and more useful than anything an engagement survey will tell you.
Most managers avoid these questions. Not because they don't care, but because asking them means holding space for answers they can't control. That takes self-trust. It takes knowing you can hear something uncomfortable and stay steady.
Why this matters: Patrick Lencioni's work on team dynamics identifies trust as the foundation everything else is built on. Not trust as a nice-to-have, but trust as the base layer that determines whether a team can have real conflict, commit to real decisions, hold each other accountable, and produce real results. Without trust, teams default to guardedness and politics. With trust, everything else becomes possible.
The manager-employee relationship works the same way, just at a smaller scale. Every 1-on-1 is either building that foundation or quietly eroding it. When a manager only asks about tasks and deadlines, the message an employee receives is that the relationship is transactional. When a manager asks a question that requires real trust to answer honestly and then receives that answer without judgment, something shifts. The employee learns this is a person they can be honest with.
That kind of trust doesn't get built through one great conversation. It gets built through a pattern of small moments where someone shows up, asks a real question, and responds to the answer with steadiness instead of defensiveness. Over time, that pattern becomes the foundation Lencioni describes. It's what allows an employee to bring you a problem before it becomes a crisis or admit a mistake before it compounds.
A 1-on-1 is one of the highest-leverage leadership tools you have. Use it accordingly.
This is the kind of practical work we do in the Intentional stage of Lead From Within. If you want to build this across your manager cohort, let's talk.
Fernanda Brasileiro
People Development Consultant & Strategist
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