5 ways to conduct a One on One

The goal of a one-on-one is connections, not status updates. This guide provides ideas for questions, topics, and activities to help you connect and understand your team member.

You don’t need to be a ‘people person’ or an extrovert to do this. You just need to provide space for someone to talk. And then, you need to listen. “You need to listen,” is common advice. But what if someone just isn’t much of a “talker” and doesn’t want to discuss anything ever? Use this guide.

A few practical tips

It’s not an interview

Try not to make these sound like an interview or test. They should have back-and-forth conversations. Your team members should be able to ask you questions as much as you ask them. This is not just an opportunity for you to get information. The ultimate goal is for them to benefit because they receive

• dedicated time to self-reflect

• direct and timely feedback

• A better understanding of you, their manager
  

Take notes

Keep shared notes of your one one-on-ones. They will help you and your direct report during performance review time. During one one-on-ones, it will also help you reflect back to the person what you are hearing and ensure you understand.

Be Present.

This is easier to do in person. Remote, it can be very tempting to check Slack and get distracted when people are talking. I got called out for this myself once. It was embarrassing and a good reminder - people can tell. One-on-ones are only effective if you are listening. Focus. Be present.

One on One Classic

Here are a few topics to regularly revisit at any time of the year. Some are natural to ask when changes or big events happen. Others are just classic check-in questions.

I share this document with everyone on my teams, and periodically reshare it. A lot of people have no idea what to do with a one-on-one.

The Prompts

What are these?

1-1s are for you! Whatever you want to talk about. If you want it to be a status update, it can be, but there are better places for that (like stand up).

1-1s are a good opportunity to check in with yourself and how you are doing, check in with your progress, discuss your career, get feedback, provide feedback, ask for help, and discuss your weekend.

Not every 1-1 needs to be the same; it is up to you and what you need.

Cadence

Pick a cadence that works for you. An hour weekly? A half hour? Every two weeks?

Questions

In case you don’t have ideas of what you want to discuss, these are questions that might come up. Use these as a guide. Anything is valid!

General check-in questions:

1. How is everything going today? Tell me about this last week?

2. What’s on your mind this week?

3. Last time we spoke you said X was a challenge for you, how is that going?

4. What are your plans and priorities this week?

Alignment questions

How are you feeling about the direction of the team, org or company

1. Do you have any questions about the recent change involving X? (e.g., an announcement from CEO, merger, teams).

2. How confident do you feel with where the company/org/team is going?

3. How aligned do you feel with where the company/org/team is going?

Progress questions

1. What has energized you in your role [over a period of time]?

2. What has challenged you [over a period of time]?

3. What has gone well/not so well for you [over a period of time]?

4. What’s one thing (or a few) you learned this week?

5. Do you feel confident in how you/your team are progressing?

6. How are you/your team progressing towards established goals?
   

Team Interaction questions

1. How is everything going with the people you work with/on your team?

2. Any interactions you’d like to discuss?

3. What feedback do you have for me?

Career questions

1. Where do you see yourself in 1 year?

2. Where do you see yourself in 5 years?

There's a lot more you can ask here. I will dedicated a blog to this one.

What’s Next Questions

1. What are you committing to between now and the next time we meet?

2. What can I help you with between now and the next time we meet?

3. Is there anything we didn’t cover that you’d like to discuss next time?

Getting to Know You: Life Story

Try these questions when onboarding to a new team and getting to know new team members. 

A life story one one-on-one is a concept I borrowed from my interviewing experience at Shopify. It’s an exercise in connection and sharing beyond your resume. I find the best way to do this is to demonstrate by example. People often respond with a similar level of vulnerability as you share.

The Prompt

I'd like get to know you better. Let's share our life stories to understand how we got here.

What to share

Share the normal, name, location, years in industry, and a bit of your career history. But also answer questions about your interests, why you made certain decisions, what were big changes for you, and who are you as a person?

Yearly Reflection

These questions are great to revisit at least once a year. I recommend them when onboarding to a new team and getting to know the existing team. These can be harder for people new to the industry or new to a company to answer. If this is the first time doing the reflection, I recommend pairing this with the life story.

The prompts

Refresh

1. What aspects of your current work would be most important for a manager to understand

2. Who are the key stakeholders or partners you interact with regularly?

3. What aspects of our codebase or architecture are most challenging

4. What’s working well on the team? What is not? What would you change?

Reflect

1. What part of your recent feedback resonated most strongly with you

2. What skills would you like to develop in the next 6-12 months

3. How do you see your role evolving in the future? What are your career aspirations

4. What type of projects energize you the most

5. What support or resources would help you achieve your development goals

6. What obstacles do you foresee in your development path

7. What strengths do you feel are underutilized in your current role

8. How do you prefer to receive feedback and coaching?

Mini Retro

If someone has recently completed a meaningful project, suggest a mini retro to reflect on the project together. It’s a good opportunity to naturally provide feedback. It’s also a good way to encourage someone to pause and learn from their recent experience.

Try to let your direct report speak first. Ask questions, be curious. Let them know this is an exercise intended to help them learn from experience. This is not meant to be scary.

If you are a more gifted conversationalist than I am or prefer a less structured approach, you can naturally work some of these questions into a one-on-one conversation.

The prompts

What went well?

1. What aspects of this project are you most proud of

2. What skills did you leverage effectively

3. When did you feel most energized or in flow

What was challenging?

1. What obstacles did you encounter? How did you handle them?

2. What would you approach differently if you could do it again

3. Where did you feel stuck or uncertain?

Growth and learning

1. What’s one thing you learned about yourself as a developer/professional?

2. What technical or soft skills did you develop or want to develop?

3. How has your thinking around <topic relevant to the project> evolved?

Stack Rank the Company Leveling Guidelines

If your company has documented levels and guidelines of what to expect at those levels or a codified set of principles like Amazon’s famous Leadership Principles, this exercise can spark interesting conversations. It is a great way to have a conversation about how you and your team member interpret the guidelines and help clarify your expectations. It is also a good opportunity to understand how your team member self-reflects. 

This is also an effective preparation exercise ahead of performance reviews.

The Prompt

Exercise Prep

1. Start with a blank page

2. Copy and paste the leveling guidelines or principles. They can be in a completely arbitrary order

How to stack rank

1. Start with the first one in the list, it is automatically ranked “one” because it’s the first one we picked

2. Pick the second one in the list and rank how you think you are at this skill relative to the first.

3. As you go, discuss how you arrive at each ranking. Consider recent experiences and relevant examples.

4. Do this for each item in the list until the list is fully ranked

5. At this point, step back and see if the list makes sense. Move a few around if they don't seem right.

6. Draw a line between the items on the list that Strength areas and the items that are Growth areas. You may draw another line for items that are “won’t fix.”

A framework for thinking about Strength and Growth Areas

Not all growth areas or skill gaps are equal. Remember, people tend to be spiky.