We recently spoke with Connor Bradley, Growth Team Lead at Jobber to learn about how he approaches one-on-one meetings. Jobber is a platform that helps small home service businesses organize their entire operation.

Learn about how Connor gets his direct reports to open up, the books that helped shape his management style and more.

A little about Connor

• First-time manager 🥇
• Managing 3 onsite direct reports 👥
• Has one-on-ones biweekly for one hour ⏳

---

Why are you having one-on-one meetings? 

I have one-on-ones to get a better understanding of what direction my direct reports are looking to head in. I also use it as a time to learn if they’re blocked (and by what). To me, the purpose of one-on-ones it to ensure that my team and I are aligned on a shared vision of what they’re looking to accomplish and how that ties back to our team, and company goals and expectations.

How do you prepare for your one-on-ones? 

I block 30 minutes in my calendar ahead of each one-on-one to prep. I take this time to review previous one-on-one discussions and think about what my direct reports might want to discuss (if our agenda is empty). On top of that, I prepare myself in case that these topics do come up. 

For example, if a direct report has a conflict with another member of the team and they’ve added something related to that on our one-on-one agenda, I’ll prepare for that conversation. I do this by gathering my thoughts on the situation and preparing a few open-ended questions that will encourage them to work through the conflict. 

Do you use a meeting agenda?

Yes. Having an agenda is so important because it allows us both to come to every meeting prepared, which makes the conversation much more meaningful and productive. Having an agenda also allows us to prioritize the most important items and discuss them first. 

The expectation that I’ve set with my direct reports is that we are both expected to add items to our agenda before every meeting. However, the agenda format isn’t rigid. I like to keep the format relatively open to ensure that my direct report has the time they need to address anything they want to. After all, it’s their time with me.

What are your go-to one-on-one questions?

• What are you not working on that you do want to work on? 
• What are you working on that you don’t want to work on? 
• How do you feel about the priorities of the team? 
• What’s top of mind for you right now?
• What’s the best use of our time today?

I love asking these questions because they allow me to ensure that my direct reports are motivated and excited about the work they’re doing. I realize that is easier said than done but when asking the questions above, I’m also able to better understand my direct reports on a personal level and can sense their passion behind certain areas of work. This allows me the opportunity to attach that work to them when possible. If I can remove a barrier, provide a valuable new perspective, or increase their confidence, then I have the opportunity to make them more successful. 

What do you do to get your direct reports to open up?

In my experience, the best way to help them open up is to open up yourself. Too often managers feel the need to fill a predetermined role that puts them into a position of power. As a result, we’re afraid to admit fault and are unwilling to be vulnerable with our team. This is a missed opportunity. I fully admit my own mistakes and areas that I’m personally looking to grow with my direct reports. I let them know that I’m a new manager and some of this is new to me, my goal is to work alongside them and get feedback along the way. This allows them to be comfortable sharing their fears, mistakes, and challenges with me. We’re all figuring it out and it’s okay to be honest about that. 

What’s your biggest challenge when it comes to one-on-one meetings?

The biggest challenge is trying to not get tactical in our conversations. We love the work, so it’s no surprise that we love talking about it. However, that can very easily move towards a status update conversation, which we’re always aiming to avoid. My method to minimize this is to set expectations on the purpose of the meeting. If I have to do this every meeting, I will. That’s because one-on-ones are such an important time to build trust and that’s tough to do if this time is treated as a status update. 

What do you consider a successful one-on-one meeting?

When it comes to my one-on-ones, I have two goals. The first is to gain insight into my direct report’s perspective on what they feel is working (and not). From there, if we can decide on an action plan to improve, then that’s a win for me! 

The second goal is that I’m able to achieve one or all of the following: 

• Learn about and remove a barrier they’re facing.
• Provide them with a new and valuable perspective. This can be things like sharing a different way to tackle a project or advice on how to approach a teammate with feedback. 
• Increase their confidence. This can be as simple as letting them know that they did an awesome job with a specific project they completed since our last meeting. 

What’s the biggest mistake a manager can make in a one-on-one setting?

The biggest mistake a manager can make in a one-on-one meeting is saving your guidance or feedback for these meetings. Having scheduled one-on-ones isn’t a reason to put off effective strategies of everyday communication. It’s important to continuously provide feedback and guidance on a day-to-day basis and leverage your one-on-ones to reinforce that feedback and/or guidance. 

What advice would you give to a new manager who’s about to run their first one-on-one meeting?

As a new manager, these three books have really helped me with one-on-ones:

1. Radical Candor by Kim Scott
2. The Making of a Manager: What to do when everyone looks to you by Julie Zhou
3. No Hard Feelings: The Secret Power of Embracing Emotions at Work by Liz Fosslien & Mollie West Duffy

Outside of these books, my biggest piece of advice would be to not pretend like you have it all figured out. It’s okay. Establish real relationships with your direct reports and create a dialogue that allows them to feel comfortable bringing their fears, uncertainties, and doubts to the table.

At times when you might feel a little too overwhelmed, prioritize yourself and seek support from other leaders to avoid unloading on your direct reports in a way that negatively affects them. 

---

Want to learn about how other people managers run one-on-one meetings? Learn from:

• Sara McGuire, Content Marketing Lead at Venngage
• James Carr, Infrastructure Engineer Lead at Zapier
• Lorena Scott, Head of People Operations at Ritual

What you should do next

You made it to the end of this article! Here are some things you can do now:

1. Check out our YouTube channel for more tips on management skills and team building.
2. Learn more about Hypercontext and how it can help you run a high performing org.
3. If you found this article helpful, please share it with others on Linkedin or X (Twitter)