In the good old corporate world, it’s a well-known fact that, as you make your way through your career path and rise through the ranks as a leader, the amount of effort spent on giving and receiving feedback you receive decreases exponentially. It takes a backseat to the long list of other essential things.
Now, sure, it is a manager’s job to solicit feedback from their team. But, when you think about it, part of the fault also lies with the team members. Whether it be discomfort in giving honest feedback to a higher-up or even asking questions that could potentially strike the wrong nerve, something or the other is always missing.
It’s okay, though—it’s only natural for a direct report to hesitate a little when giving feedback to their manager—someone who’s been in the industry for far longer. What’s not okay, however, is not making any changes and continuing to be dishonest about things.
To that, I say, it’s time we make some changes, no?
If you’re a direct report and are confused or struggling to find the right questions to ask your manager for your next one-on-one, no worries, we’ve got you covered. Here’s a list of 38 upward questions you can ask your manager during your 1:1 meetings.
What should upward questions look like?
When initiating a 1:1 with your manager, it is essential to remember that you’re about to engage in a two-way conversation that involves the exchange of information and feedback.
To that end, you need to make an effort to ask the right set of questions to learn more about the larger picture—what do you think about your manager’s style of management, what can they improve upon to make work further streamlined for you, what do you expect more and less of from them, what they have in store for you—along with the most important of all, letting them know if you are or aren’t happy with the feedback that’s been delivered to you.
Keeping that in mind, we can see that upward-facing questions usually revolve around the specific competencies of a manager. Let’s go over each competency and see what questions you can pose to your manager during your 1:1 check-ins.
Questions about career development
- If you wanted me to improve upon one skill between this meeting and the next, which one would that be?
- Are there any new skills that you think I need to learn?
- Can we discuss my current career trajectory?
- How can I progress further within the company? What steps do you recommend?
- How can I support others in our team?
- Where do you see me by the end of this year?
- Who do you go to for advice and guidance?
Questions about goals and strategies
- What can I do to achieve my key results or help our team achieve our key results?
- What roles are you thinking of hiring for our team?
- Are there any significant changes down the road in the next six months?
- How are we collectively progressing on our goals?
- In which sphere can I take more ownership over?
- Why were we unable to achieve [a goal]? Should we do a retrospective review?
- Is there anything that worries you about our team?
Questions about communication
- How would you rate the quality of my work so far?
- Do you think I understand the task briefs correctly?
- What’s the best time to get feedback from you?
- Do you find it easy or difficult to share things with the rest of the team and me?
- Do you think there is anything that any of us in the team often miss informing you about?
- Do you think we’re currently working with an ideal meeting cadence? Do you think that we need to reduce the meeting load?
Questions about culture
- I noticed that you were working on the weekend. Should I expect this to trickle down to the rest of the team?
- I’ve seen some team members book meetings on our scheduled no-meeting days. Will you be correcting this?
- Have you been facing burnout? What do you do about it?
- After a plan goes awry, how do you regain yourself?
- Do you feel that your work and your team align with the organization’s values?
- What is the one value of our culture you hold in the highest regard?
- Do you wish to change any aspect of our company’s culture?
Questions about leadership
- How often should we do conduct our hold 1:1 meetings?
- If there is one thing you’d change about your leadership style, what would it be?
- I think our [task] process is unnecessarily lengthy. I have some suggestions. Would you be willing to listen?
- How are you coping with the recent changes in priorities and goals?
- I am not entirely happy about the ratings that were given to me. Can you please justify them for me?
- Will you be mentoring those of us who will soon take up managerial roles for the first time in our careers?
- Are you content with the way the team is currently functioning?
Questions about how the manager is doing
- How is managing our team going for you?
- How’s your workload looking this quarter? How do you feel about it?
- How’s your work/life balance going?
- What is your favorite/least favorite part of being a manager and why?
Tiptoeing your way through upward feedback
Now, it’s no surprise that upward-facing questions and upward feedback, in general, can feel like a minefield for an individual.
Knowing about both the benefits and the drawbacks of asking pointed questions to your manager is essential to foster a healthy, positive, and meaningful relationship with them. That said, let’s look at each of them in depth.
Benefits of asking questions with your managers
- You gain insights on how the organization works
- It helps foster a positive relationship with your manager
- It gives you a direction to work in and helps bring out the leader in you.
Drawbacks of asking questions to your manager
- There may be lack of information on your part, and you may end up asking questions without context
- The answers may not be honest, for reasons ranging from confidentiality to lack of willingness to divulge extra details, despite you and your manager’s best efforts.
- Your manager may not be open or receptive to the questions.
3 tips for asking upward-facing questions
Asking your manager questions during a 1:1 check-in can be a tricky thing to do—almost like walking on a tightrope, to be honest. You may potentially damage your relationship with your manager with one wrong move. So, you want to ask questions that matter while being mindful of your boundaries.
However, that’s no reason for you to simply not ask them any questions. As long as you keep the following tips in mind, there’s no way your questions will ever miss the mark.
1. Limit your questions to your own opinions and knowledge
Understand the fact that a manager has to oversee things far beyond the scope of your role and more often than not, your team’s work as well. As such, it is impossible for you to have all the puzzle pieces here. So, limit your questions to only gaining knowledge on certain matters and sharing your opinions without explicit suggestions.
2. Be specific with your questions
Asking vague questions would breed ambiguity between you and your manager. So, make sure that there is legitimate intent behind asking each question that the manager also understands well.
3. Keep it honest and real
The most important piece of advice—if there’s something on your mind that you wish to ask your manager, ask it. As long as it lies within the scope of your role and your relationship with the manager, avoid sandwiching your opinions between fluff and praise and dare to ask the hard questions with your manager.
And that’s pretty much it. Despite how difficult it may seem to ask the right questions to your managers, know that doing so is helping you and your manager. With these questions, they’ll be given an appropriate space to reflect on their responsibilities and actions and use the insights gained to fill in their blind spots and polish their leadership skills further.
