TL;DR
Effective one-on-one meetings between a manager or leader and their direct report (you) normally address the practical and personal needs of the employee, seek to benefit their performance, growth, and well-being, as contribute to the success of their team and the larger organization. However, since managers typically run one-to-ones, your needs can be overlooked. It’s up to you, their employee, to ask the right questions to receive the feedback and attention you need. This is one area where your experience in ministry and resulting soft-skills can give you a clear edge. We’ve compiled 31 questions based on research and personal experience that can transform perfunctory one-to-one conversations into a wealth of usable insight. Why 31? It’s a good number for Baskin Robbins so we’re using it here.
When Jonathan started his new role, he learned he would have regular one-on-one meetings (1:1s) with his manager, Jessica. He saw it as a prime opportunity to become more aligned with his company’s goals, better focus his time and energies. He was looking forward to receiving support and mentorship from his boss. Those hopes quickly faded. In their initial meeting, Jessica focused on project metrics and timelines, then assigned Jonathan three new tasks. The weekly meetings continued this pattern; Jonathan began to feel micro-managed and saw little, if any, support for his future career path at the company.
Sadly, this story echoes many that appear in industry-wide research on 1:1s between managers and direct reports, personal experience, and anecdotal stories from friends.
Let’s establish a baseline. Good 1:1 meetings provide needed feedback for workers, including course corrections, updates regarding strategy, tactics, and timelines, instruction and training in unfamiliar skills, coaching, and practical advice. They can be a valuable resource for growth and success. They give employees a sense that they are valued, seen, and supported. In the best cases, 1:1s can increase team alignment and collaboration while leading to greater job satisfaction for everyone.
However, the benefits only materialize when both the boss and employee actively engage in each conversation. In fast-paced, high-stress environments, 1:1s can easily become an annoying routine, eating up productive time without providing a measurable benefit for either party.
Many of your future managers and bosses were promoted into their roles after finding success at your current job or a similar one. With the new title came responsibility to guide, equip, and lead a team. All too often, companies provide little or no training on how to provide that support. As a result, managers often stick to the numbers, processes they know, and whatever is generating the most stress that week. If their previous manager didn’t support them, micro-managed the team, or simply didn’t communicate, chances are high they will repeat that pattern with you.
Here’s where your experience in ministry can give you an unfair advantage. Ministry, in general, runs on the rails of relationships, not metrics. You probably learned how to listen well, pick up on nonverbal cues, hear what’s being said and notice what’s not being said. The questions below can give you a framework to apply those skills at work, proactively helping your manager to provide the support you need while offering your support in return. Who knows, you may even develop a healthy personal relationship with them one 1:1 at a time.
If you are in Jonathan’s position and your boss’s approach to weekly or monthly 1:1s leaves you feeling unsupported and unseen, you have an opportunity to shift the conversation. Asking timely and thoughtful questions can begin to steer each consecutive discussion toward your needs without devaluing your boss’s goals or disrupting their agenda. You’ll find a list of 31 starter questions below. Use them as they’re listed, or build on each for more focused insight.
Questions to Consider
Based on published research as well as data we collected from employees on important topics to broach in a 1:1, we have listed 31 productive questions in seven general categories to help you get more value from your meetings. Add your own questions or adapt these to fit your role. Then reword them to fit your own voice and personality.
Asking for Guidance and Input
These questions can help you get more insight or clarity from your manager on challenging tasks or projects and provide ways to request additional resources, input, or support.
- I am having some challenges and struggles with Project Q. Can you provide any insight to help me think about how I can navigate and address Q’s obstacles successfully?
- Do you have any ideas or suggestions about how I could get more support with Project Q? (Additional team members, time, funding, exposure, feedback, testing, etc.)
- What did you think of my idea regarding Project Q? Do you have any suggestions about how I might improve it? Or, is there a different approach or idea I should consider?
Clarifying Your Priorities against Their Expectations
Check in regularly to make sure you are on track with their expectations and applying your time and effort appropriately. Confirm that you and your manager are working to achieve the same results. Ask for any clarification you need on which tasks or projects need your greatest attention from their perspective and if any should be deprioritized.
- Given the things I’m responsible for, which tasks or projects should I be prioritizing now, and can you help me understand how those fit in the bigger picture here?
- As you review my workload, do you believe I am focusing on the right projects or tasks?
- Am I on track for hitting my goals and meeting your expectations from your perspective?
- Are there any areas where I need to refocus or re-prioritize my time?
- Is there any context I might need about the projects I am working on? For example, how does Project Q impact our company’s strategy and future goals?
Creating Alignment with the Organization’s Strategy
Ask questions to clarify how your role relates to the broader strategic goals of the organization and how it aligns with what leadership is thinking about the future. Some organizations may create separation or silos between teams or divisions. If that’s the case they can let you know.
- What is going on in other parts of the organization, or further up the org-chart, that would be helpful for me to know as I work on my tasks or projects?
- I’d like to understand the big picture more clearly. How does the work I’m doing or the assignment you just gave me fit into the overall goals and strategy?
- Is there anything that the management team is working on or considering that you think I should know about or its potential to impact on my role?
- Are there any new changes to our company’s strategic priorities that you believe I should know about?
Asking About Growth Opportunities and Career Advancement
Arrive at the meeting prepared to discuss your thoughts about your short- and long-term professional goals. Ask your manager what steps you could take towards achieving them.
- I would value your insight. What could I do to better prepare for future opportunities or to pursue my interest in _____________?
- As you look at where our organization is heading, do you have any thoughts about how I could improve or develop to best align with that future?
- What strengths have you identified in me and how might they be put to use in the future?
- From your perspective, what should I be considering as my next career move?
- Why do you recommend that position?
- How can I apply my skillsets to their best use in supporting the team and this organization?
- What can we do to make sure that I am performing to my fullest potential?
Requesting Feedback on Your Performance
Ask your manager their thoughts on how you are doing performance-wise. Be careful to not make every meeting into an unofficial performance evaluation. Instead, use these questions to check in periodically using the insight to recalibrate your efforts if your manager isn’t providing feedback proactively.
- Am I meeting your expectations and those of the company? I would value your perspective on my work performance and ways I might continue to improve.
- What feedback would you be willing to share about how I’m doing with A or B project?
- Do you feel I have any blind spots or areas I’m overlooking when it comes to A or B?
- As you consider what I do here, what should I start, stop, minimize, or continue doing?
Begin Building a Personal Relationship
Your One-to-One is an invaluable place to build and develop your relationship with your boss or manager. Dedicate some time at the beginning or end of your meeting to connect personally. Use your best judgment to calibrate your questions. Start slow and build your rapport over time.
- How has your day (or week) been going?
- How are things going for you? We normally discuss my role, could I ask if you’re getting the support you need in yours?
- What is something outside of work that you’re looking forward to?
- Is there anything you would like to know about me? Use a good measure of discretion and wisdom with this question. If your manager asks about a subject you don’t feel comfortable discussing, simply say “I’m not sure I’m comfortable talking about that at the moment, let’s save that conversation for another time..” Then follow that with “However, here’s something I’m personally excited about...” or “Given what you’ve shared with me in our meetings, I think you might be interested to know…”
Offering Your Support
Use your 1:1 meetings to explore ways in which you can support your manager in reaching their goals and making them more successful. Managers and bosses, like everyone else, need reassurance, they value support, and can always use assistance in reaching their goals. The best relationships are never one-sided but reciprocal. This does not mean your conversations should be transactional; instead, offer to lend them a hand. Approaching 1:1s with a perspective to serve as much as receive will also raise the potential for receiving what you need to succeed with each new meeting.
- What are your priorities over the upcoming days, weeks, or quarters?
- What could I do to support you in those goals?
- Where are specific areas in which I could help to make your role more effective?
- Is there anything about our team or projects that are causing stress that I can help with?
Use the Questions in Your Next Meeting
For each 1:1, pick one or at most two categories as your focus. You won’t have time to address them all in every meeting and limiting feedback to only a few areas will prevent the possible overwhelm of trying to change too much at once.
Use your calendar to schedule your questions and rotate through the list, starting over again after covering all topics. Set aside some time to plan your questions for the next several meetings. If an unscheduled subject needs more attention in the next meeting, pick the most relevant questions from that list to maximize your 1:1 time and bump the other questions to the next 1:1.
Choose different questions each time you cover a topic to create variety and avoid predictable patterns. If you cover a question asked at a previous meeting, rephrase it, ask it from a new perspective, or flip it upside down. If the question came from a positive angle, ask if from the negative— “What tasks should I be focusing on most this week?” could become “Which tasks should I move to the bottom of the list this week?” This allows you to sample multiple questions over time and adjust your approach with each new 1:1.
Be prepared to dig deeper into your manager’s responses to important questions. Simply asking “why?” or “can you say more about that?” can unlock valuable insight. Stick to open-ended questions when following up. Questions like “What are your personal thoughts about…” can take the conversation much further than simple yes or no options.
Use “mirroring” in your conversation to prompt more insight with answers you’d like to understand better. FBI negotiators use mirroring as a disarmingly simple way to keep people talking. All you do is repeat the last three or four words your boss said, word-for-word back to them. According to Chris Voss in the book Never Split the Difference, it’s so simple, most people discount its value. But his personal experience in the field proves it’s the closest thing to a Jedi Mind Trick you can find. In fact, a recent study followed a group of servers in a New York restaurant. The servers, by simply repeating each customer’s last three or four words back to them, saw their tips increase an astounding 90% over a comparison group who lavished their customers with praise.
By asking consistent, focused, and insightful questions in your regular 1:1 meetings, you can walk away with new insights into your organization’s future, strategies and values, and gain a better understanding of the big picture behind your daily routine. You will also begin to distinguish yourself from peers who don’t ask questions or show interest in understanding the growth and success of your organization.
Establishing a pattern of practical and engaging 1:1 meetings can be a game changer in your career and day-to-day experience at work. Consider each meeting as a chance to strengthen your relationship with your manager, stand out in the workplace, and build a healthy engagement with your team. It can be a catalyst for your mental health at work and keep your career from feeling like just another job.
