Questions for Our First One on One

I believe that 1-1s with my direct reports are one of the most important things that I do as a manager and leader. At the top of that list is the “intro” 1-1, where I spend time connecting and learning about who they are, their likes, dislikes, motivations, aspirations, and favorite emojis 🙌!

In my time as a manager, no meeting has been more critical in building a strong foundation and I refer back to these answers often when providing feedback to people, looping back on growth opportunities, or finding helpful ways to support them! It is definitely an essential meeting to have with your people.

So…prioritize this discussion! But, how to run it?

How do I run this?

First, this is a conversation, not a checklist. These questions are meant to open up dialogue and not about speeding through to the finish line. For example, if you ask someone what motivates them and they talk about it, which leads to an example of a project that they are proud of…ask what made them proud…ask about the project!

The ultimate goal is to understand your teammate better! There are a lot of questions here and it might take 1 or 2 one-on-one sessions. That is FINE and I would encourage that! However, if you see that it takes 3 or more sessions or weeks to finish, then wrap it up, its important to be timely and focused!

And yes, definitely ask these questions in your own words…for example, I may not ask “what makes your grumpy” word for word, instead I may say “So, how do I know when you are in a bad mood?”, then talk about that and transition to “OK, so what are some things that may put you in a bad mood or make your grumpy”.

This list is heavily inspired by Lara Hogan, Camille Fournier, and my own experience. Also, here is a handy dandy template! Please let me know what works and doesn’t!

Lastly, it is never too late to have this conversation, even if you missed the “intro”, no worries. Carve out time and make it happen!

Let’s get it!

Intro 1-1 Questions:

General:

How are you doing?
If someone is new to the company/team/squad/etc.
- How’s the first week been?
- What are you most excited about?
- Any surprises since you have joined, good or bad, which I should know about?

These are good questions to ask when someone has just joined the team or company, a good starting point/ice-breaker-ish to help you get into the flow. Plus it helps you learn if there are any surprises, I once had someone mention they had not yet received their work laptop!

1-1s & Support:

What makes 1:1s the most valuable for you?
What do you need from your team?
What do you need from your peers? (outside the team)

These questions are invaluable. Particularly the first one. I typically ask a bunch of follow ups here.

Working with your manager:

What do you need from your manager?
Are there any manager behaviors that you know you hate?

I find these questions are very helpful to get answers to as it keeps me honest as a manager, holds me accountable. I want to be at my best so I can best support you! Please note in the second question, I know “hate” is a strong word, so sometimes I replace with this “don’t like” or something similar.

Career & Goals:

What motivates you? What are your motivations?
What are your goals for this year? And for the next 3 months?
Do you have any clear career goals that I should know about so I can help you achieve them?

There will definitely be follow ups here. Once in my first meeting, someone told me they wanted to be a staff engineer in the next 6 months while another said they wanted to be a manager one day. These questions help set the initial lighthouses to steer towards, helping me clarify and understand each person better. I find this is a solid foundation that sets up future career conversations.

The way you work:

When do you feel the most productive? (time of day)
Do you have a preference on when you would like to have 1-1 meetings?
How do I know when you are in the “zone”? (e.g. headphones on, slack messages on away”)

I try not to interrupt folks as best I can - especially when folks are in their “maker mode”. I also try to schedule 1-1 meetings at days/times that work best for my direct report.

Feedback & Recognition:

How do you like to be praised, in public or in private?
What is your preferred method of communication for serious feedback? Do you prefer to get such feedback in writing so you have time to digest it, or are you comfortable with less formal verbal feedback?

These set of questions are critical. It is better to know ahead of time before you are having a crucial conversation or providing praise. When it comes to praise I want to provide it in ways that people can enjoy it and not feel uncomfortable. Regarding feedback, I want to make sure we are having open dialogue and I provide feedback in a way that someone will be most able to hear it. This is of the utmost importance to me.

Grumpiness & Mood:

What makes you grumpy?
How will I know when you’re grumpy?
How can I help you when you’re grumpy?
Are there things that always put you in a bad mood that I should be aware of?

These are great questions, I have found that it unlocks so many things and helps me learn my teammate so much better.

Most Important:

What is your favorite way to treat yourself?
What’s the your current favorite tv show/album/artist/sports team/videogame/other?
What is your favorite emoji?

Take a moment to learn how folks treat themselves! I keep a list of different items and sometimes give things as gifts or just follow up to ask how their favorite book/tv show is going! With one direct report we still chat about our love for fantasy books even through we have not worked together in 4+ years! These questions are IMPORTANT! You never know when they will come in handy (I’m looking at you favorite emoji! 👀)