The Three Magic Questions To Ask Your Team
The fastest way to uncover what’s really happening on a team is to simply ask.
As a leader, you’re constantly looking to get information from your teams and managers. Whether it is diagnosing an issue, ramping up as a new leader, or simply doing a health check, it is invaluable to hear directly from people on the team. Over the years, I’ve found three questions that cut through the noise and surface insights almost immediately.
The Three Questions
1. What is working?
Start by reinforcing positives. This encourages people to reflect on what’s going well and sets a constructive tone. It can also put teams at ease since you are not jumping directly into the problems. It gives you insights on areas to build from or to simply leave alone.
Showing teams that you want to amplify their strengths can reinforce a culture of recognition. It can also help build a sense of pride across a team when they realize that there are some areas that are working well.
2. What is not working?
This opens the door for candid discussion about problems, blockers, or frustrations. Encourage individuals to be direct and honest. Give them space to vent but avoid any paths of direct blame. Get a full sense of what is not working before diving into why something is not working.
By regularly asking what is not working you can grow a culture that does not shy away from problems or sweep them under the rug. Training team members to be open about issues without casting blame gives the ability to directly attack problems and avoid attacking people. It helps stamp out politics and empowers the team to fix their own problems.
3. If you could wave a magic wand and change one thing, what would it be?
I love this question because it allows the individual to think boldly while also focusing on a single key priority. The follow up question of “why do we need a magic wand to fix this?” can also expose blockers.
Forcing the team to consider the bigger picture and dream big is healthy. It pulls leaders and teams out of their rabbit holes and their comfort zones. And if a team or individual is able to make the change they describe in their answer to this question, it is often transformational.
Where to Use Them
These questions are versatile and can be used in a variety of settings:
Skip-level meetings: I always found skip level meetings to be a luxury, but when I could do them, I would always use these questions. It is valuable to hear directly from team members two or three levels down in the org and contrast that with what your leadership is telling you.
Retrospectives: You can use this structure with some small tweaks to hear what worked, what didn't, and what you would change the next time. This can be a great starting topic to drive a meaningful retrospective.
1-on-1s: This can be used regularly to gauge status and determine priorities. Allow the individual to decide if they should be doubling down on their strengths, or fixing their problems. Use the magic wand as a way to push them to be bold.
Offsites: Doing this with a wider group where each individual does this without sharing with any of the others can open up a broad discussion not just on strategy and where the company and team are headed, but also communication and teamwork.
Spotting Misalignment
One of the most valuable outcomes of these questions is seeing where perspectives diverge. For example:
A manager might say “everything is working,” while their team lists a dozen blockers
Leadership may think the product roadmap is clear, but the team’s “magic wand” wish is for more direction
Executives may believe morale is strong, but front-line employees highlight burnout
I could come up with dozens of examples. These gaps are gold for leaders because they highlight where communication, trust, or alignment is breaking down. They are often the smoke before a fire.
Final Thoughts
Great leaders are comfortable asking difficult questions and show genuine curiosity with the answers. The three magic questions are simple enough to use in any setting, but powerful enough to uncover deep insights about alignment, morale, and focus. They will not solve every problem, but they are a quick tool that any leader can use to quickly gather critical insight into the health and status of any team.