Knowing What to Ask (and When) in One-on-One Meetings

Ask your manager the right questions at the right time during your one-to-ones and you can transform them into the most valuable meetings you have all month.

Read on for our pick of simple questions you can use to get on the same page as your boss, make sure you're doing your best work, and get on the right track to grow your career. 

How to ask for a one-on-one meeting with your manager

Regular one-on-ones are your ticket to career success.And any manager worth their salt knows one-on-one meetings are their secret weapon and will make sure you’ve got a regular facetime set in stone on the calendar.

But maybe you’ve got a new manager who hasn’t got around to setting up a regular meeting time yet. Or things got busy and your one-to-one meetings got dropped and haven’t been picked back up again.

Whatever the reason you don’t have regular meetings in the diary with your boss, here’s a simple email script you can use to set them up:

Hey,

I’d love the chance to meet with you regularly to make sure we’re on the same page about how I should be spending my time (and to find ways I could be making your job easier for you).

Could we set up a regular half-hour check-in every few weeks? 

Happy to meet at a time that suits you, so let me know when would best work for you.

Thanks

What manager wouldn’t want to receive an email like that? That simple script should get you a regular one-to-one in the calendar in no time.

What do you discuss in a 1-on-1 with your manager?

You’ve got a regular one-to-one meeting with your boss on the calendar.

But what do you talk about?

Well, this face-to-face time with your boss is the perfect opportunity to:

• Make sure you’re spending your time on the right things. If you and your manager aren’t on the same page about what you should be prioritizing you could both have some serious headaches to deal with down the line.
• Find out what you could be doing better. Feedback from your boss on what areas you could do with improving in – as well as what your greatest strengths are – can do wonders for your career development.
• Plan your career growth. A good manager can help you develop the skills and gather the experience you need to take the next step in your career.
• Discover better ways of working together. Get to grips with the way your boss likes to do things and you’ll quickly become an indispensable member of their team. 

You might not want to cover all of these bases in every one-to-one. But regularly touching on these four areas will help you manage your relationship with your manager as effectively as possible.

What are good questions to ask managers?

You're wasting a huge opportunity if you don’t use your facetime with your manager to make sure you’re both on the same page – and that you’re doing what you need to be doing to land a pay rise or a promotion.

Ask these constructive questions during your one-to-ones to make sure you’re on track to fulfill your career ambitions: 

Priorities to focus on 

The most important part of any one-to-one is making sure you’re not spending your time barking up the wrong tree. Fail to ask the questions that would have got you on the right track and you could seriously set your career aspirations back – or even risk being out of the job.

Make sure you’re walking away from every one-to-one knowing exactly what you should be spending your time on by asking questions like:

1. What should be my priority right now?
2. Is there anything I shouldn’t be spending time on right now?
3. Here’s what’s on my to-do list. Should I add or remove anything?
4. What do you want to be done before our next one-to-one?

Career growth and personal development 

Having your manager in your corner will open all kinds of doors for you to grow your skills, take on more responsibility, and climb the corporate ladder.

Ask these questions in your one-to-ones to show your manager you’re ready to take on opportunities when they show up:

1. Where do you see my role evolving in the next year?
2. Are there any extra responsibilities I can take on right now?
3. If I could improve one skill before our next one-to-one, which would you choose?
4. What skills do you think our team is lacking?

Communication  

Some bosses like to receive regular updates on what you’ve been up to while others aren’t interested in the day-to-day as long as deadlines are getting hit. Some would prefer you ask for sign-off on your ideas, others that you just let them know how they went. Some prefer to speak over the phone, others over email.

Ask these questions during your one-to-ones to get to grips with how your manager like to communicate:

1. How do you like to receive updates about my work?
2. What parts of my work do you want to be kept up to date on? And how often?
3. When’s the best time to get feedback on my work performance?

Feedback 

The people who tend to go the furthest in their careers are the ones who are most open to receiving feedback.

Your manager has been around the block a fair few times more than you. They’ve more than likely been there, seen it, and got the T-shirt when it comes to any problem you’re facing. 

Ask them these questions during your one-to-one meetings and you’re bound to get better at what you do as fast as possible:

1. What do you wish I did less of? More of?
2. What are my biggest weaknesses? My greatest strengths?
3. Where do you think I should be focusing more of my attention?
4. What do you wish I took more ownership over?

When should I ask my questions in a one-on-one?

Here’s the flow of a good one-to-one.

A status update

You should always start a one-to-one by getting your manager up to speed on everything you’ve been working on, what’s next on your to-do list, and any blockers holding you back from being able to get your work done.

To make sure this part of your one-on-ones are successful, keep a running list of everything you need to update your manager on in a one-to-one template. Then you can simply pull this up and run through it with your boss in your next meeting.

Ask how you can help

A simple way to become invaluable to your manager is to take a moment to ask them how you can help make their lives easier.

This isn’t complicated, but it’s rarely done. The easier you can make your boss's life, the more responsibility they’re likely to give you. And the more responsibility you have, the more likely you are to land a pay rise or promotion. 

You’ll seriously set yourself apart from most of your colleagues by taking a moment in your one-to-ones to ask your manager questions like:

• Is there anything I can help you with?
• What are your priorities at the moment?
• If you could have one thing handled for you, what would it be?

Ask your questions

Last but not least, it’s time to ask any questions you have for your manager. You probably don’t want to touch on every base in every one-to-one. But regularly asking about your career growth, how you can communicate better, and whether you can be doing things better will help you grow your career as quickly as possible.

The final word

Finishing up your one-to-ones with the questions we've listed out here is a simple but incredibly effective way of pouring rocket fuel on your career growth. 

Stick to these tips – as well as preparing properly for your one-to-ones and keeping the one-to-one do’s and don’ts front of mind – will help you make sure you’re always having effective one-to-one meetings with your boss.

‍