Eight Questions to Ask in Your Next One-on-One to Get Better Feedback

As an engineering leader at HubSpot, I run a team of incredibly talented engineers who embrace engineering values like Move Quickly and Iterate as well as Complacency Equals Failure. It’s a high-energy atmosphere fed by agility, quick-thinking, and action. In spite of this, or perhaps because of it, I know just how important it is to step back and take stock, to reflect on your work, your team, and yourself.

Otherwise, amidst all of those fast daily decisions, how will you know that you’re on the right path? Or how you could do better?

All of this brings me to the subject of feedback.

One study from OfficeVibe found that 65% of employees want more feedback. It also found that only 58% of managers feel like they’re giving enough.

Are you getting enough feedback? 

One of my favorite leadership books is Radical Candor, by Kim Scott. Kim developed an approach to feedback based on the balance of caring personally with challenging directly. The cornerstone of the success of Radical Candor is being comfortable giving and getting effective feedback. In an interview Kim emphasized “People just don't give feedback because it's hard and it's scary.” 

How can you make feedback less hard and scary for your manager?

If you’re going to truly grow in your role you need to get into the (very healthy) habit of asking for feedback. It may feel like you’re exposing your vulnerabilities, but what you’re really doing is arming yourself with knowledge all while inviting your manager to be comfortable challenging you empathetically. Allowing your one-on-ones with your manager to devolve into project status updates week after week is cheating you out of some potentially career-defining conversations. 

So, although tips and tricks for managers on how to give effective feedback are always important ⁠— employees, this one’s for you.

Here are eight questions to ask (and one not to) during your next one-on-one that will lead to more feedback, and help you grow better. Before we dig in, though, let’s start with what you shouldn’t ask:

The Feedback Inhibitor: Do you have any feedback for me?

This may feel like the natural question to ask if you’re looking for more of a growth conversation with your boss. But it’s surface-level at best. It pretty much begs the response “Not that I can think of” or “None at the moment.” It’s not far off from asking “How are you?” and hearing the response “Fine.” If you want to have a real conversation, you need to ask real open ended questions that invite deeper thought.

What’s a real question look like, you ask? Read on.

1. Where have I had the most impact this month from your perspective? 

This one’s a good starting point. It’s a safe question that allows you to build self-awareness ⁠— a positive edit of the classic “Do you have any feedback for me” that’s deeper and more constructive. That said, ask for honesty here. If you aren’t having real impact, find out what needs to change. A good corollary question is “On a scale from 1 to 10, what was my impact this month?” A 1-to-10-style question only begs a one-word answer but always leads to an interesting follow-up conversation around why.

2. What do you think it would look like for me to be twice as good at what I do, or for this project to go twice as well?

I love this question because it opens up areas for growth that you may not have known were there. Maybe you completed a project and thought you did an amazing job, but didn’t hear that positive feedback from your boss. This is a bold way to tease out of them, “How could that have gone even better?” Be specific here, and ask for details about communication, execution, results, timing, architecture, how you worked with others, etc.

3. What would a mediocre [insert your role here] do each day? What would a great one do?

This is called the Inversion Technique. We often ask about what “great” looks like. But it’s also important to make sure that you’re not tripping into “mediocre.” Having more clarity about what suboptimal looks like can help you to avoid it (and build on it into greatness).

4. If you were away for a month, what do you fear would get dropped, stall, or fail?

This is a question that I frequently ask tech leads and engineering leads about their team members, and about themselves. The conversation naturally flows into, “How could someone else take on those responsibilities so they wouldn’t stall?” How your own manager answers this question will reveal to you gaps in your own knowledge, relationships, context, and abilities. Most of all, it’ll give you an idea of the level of trust between you and your manager. A response to this question will show you what you need to work on to become a better co-pilot on the team.

5. Where do you see me get stuck most often?

This one’s all about identifying your own blind spots. Do you often get mired in helping other people and neglect your own work? Do you over-research? Get too caught up in perfection? Have a tendency to not ask for help? We all have something, and this is an efficient way of zeroing in and excising the habits that are holding you back.

6. What would I need to learn or improve to take on a project like X? How would you know I was ready?

A lot of your inspiration is going to come from your manager or someone further along in their career than you here. Think about a complex project that they recently tackled ⁠— was there a reason they didn’t give it to anyone else on the team to lead instead? Ask your manager, “If I want to run a project like that next time around, what are some skills I need to grow?” The discussion that results is going to shine a light on some gaps in your expertise, yes, but it’s also going to show you what great looks like ⁠— and get you that much closer to it yourself.

7. You’re exceptional at X. How did you get so good at this?

This is an awesome question for a manager or an admired peer. The initial answer likely won’t be a surprise: “A lot of hard work.” But the details of what they say will allow you to dig in the same way they did: read the same books, study the same techniques, learn how they approached a problem from square one, not just how they solved it. 

8. What’s your biggest challenge? 

One-on-one time with your manager isn’t just about finding out how you can do better in your role. It’s about looking ahead, and seeing what it means to grow at the next level. Ask this question to get a sneak peak at the exciting challenges you’re going to face down the road. And listen to your manager’s answer with empathy ⁠— understanding what they go through in their own role will bring you closer as a team and give you insight into what their priorities are and another clue to more impact.

I’m not numbering this last one, because it’s a given: 

How do we make sure everyone on our team feels included?

This may seem like something a manager should be discussing with your team as a whole, and if they are, great. But you should be bringing it up as well, whether or not your manager makes it a part of your team’s regular conversations. Inclusivity should be on everyone’s minds — it doesn’t just come from the top. There are a number of actions that anyone can take to both build diverse teams and foster inclusion and belonging, and thinking about how you can implement some of them on your own team is a good conversation-starter with your manager.

There it is ⁠— a feedback starter pack for great growth conversations with your manager. A reminder here: you shouldn’t plan to ask all of these questions in a single one-on-one. Prep your leader with one or two in advance so they have time to think about their responses. Sprinkle these conversations throughout the year, act on the feedback you receive, and watch yourself grow stronger where you are, and grow closer to where you want to be.

So what are you waiting for? All you have to do is ask.