Engineering Manager 101 — A step by step tutorial on how to run effective one-on-ones

One-on-ones are one of the things that I enjoy the most at work. They are a great way to create a personal relationship with my staff, and they also allow me to provide a safe and private space to discuss whatever is needed. I will tell you all you need to start doing one-on-ones with your direct reports in this post.

Explain the rationale and expectations

Firstly, talk to your staff members and tell them that you want to start doing one-on-ones with them. Tell them that one-on-ones is a space for them to talk about anything they want and for both of you to build a stronger relationship. Set up the expectation of them bringing talking points to the one-on-ones, and expect them to share the talking points in advance so you can prepare. This means you have to agree on the medium you will use to manage your one-on-ones. If your company uses a product like Lattice, use their one-on-one tool. If not, you can use Google Docs or any collaborative writing product.

Set up a recurring weekly meeting

For each of your staff members, you will want to have a 30 minutes spot every week. Request what is the best time for them, and set a recurring weekly calendar event. I prefer doing my one-on-ones on Thursday and Friday because it’s a great opportunity to reflect on the week together.

Make sure you don’t cancel or reschedule your one-on-ones. This should be considered a sacred time, and by consistently canceling or rescheduling, you signal that you have more important things than building a relationship with them.

Prepare for your one-on-one.

One day before your one-on-one, review the talking points that your teammate might have added and add any talking points that you would like to discuss too. Also, take a look at the notes and action items from your previous one-on-one, and make sure to add a talking point if you have to follow up.

I invite you not to bring talking points that ask your direct report about a status update on their work. In my opinion, there are other mediums and ways to understand how things are progressing, and one-on-ones should be a time to figure out what’s going through their mind, how you can serve them better, and how you can build a stronger relationship.

Start your one-on-one

Start your one-on-one with an opener question or praise on anything your teammate has done since the last one-on-one. For opener questions, prevent asking questions like ‘How are you doing?’ or ‘How are things?’. Most likely, you will get a basic ‘I am good,’ which doesn’t give you any signal on what’s exactly going on in their mind. I like asking personal questions such as ‘What are your plans for the weekend?’. Without getting too deep into their personal life, asking personal questions will help you create a stronger personal relationship and show that you care about them outside of work.

Discuss the talking points

Ask your teammate which talking point they want to start with. Practice active listening and take notes that summarize the discussion. There are many types of talking points, but I want to focus on the one where your direct report is explaining a problem they are facing. For example: “I have been struggling with making progress on that user story. I can’t figure out how to make the SQL query performant”. For this type of question, don’t jump into solving their problem. Ask questions. A lot of questions.

At the beginning of my career as an engineering manager (and still sometimes nowadays), I jumped into trying to solve the problem for them. In the example above, I would ask them to share the SQL query, optimizing it myself. That’s not proper coaching, and you are not serving your teammate well. When a direct report brings a problem statement, ask questions to help them figure out the solution themselves.

A framework that I’ve been using a lot is the SOON funnel. Ask your direct report what success (S) looks like, what are the options (O) they have considered to achieve that success, what are the obstacles (O) that are getting on their way, and what are the next (N) steps. You might have to help your teammate to navigate each of the steps in the funnel, and that’s fine. The goal here is to get into a position where they have at least one next step to progress that problem.

What to do if there are no talking points?

If you get to a one-on-one with no talking points, suggest your teammate if they prefer to have their time back. If they want to chat, use this opportunity to get more information to serve them better. Below you will find some examples of the type of questions that I like asking:

1. What would you ask me if I had a magic wand and could do anything for you?
2. What’s a recent situation you wish you handled differently? What can you learn from it?
3. What is one thing I am not doing as a manager that I should be doing? What should I stop doing?
4. What is the worst thing about your job? What is the best thing?
5. Who are you grateful for at work? Have you given them praise?

Agree on action items

At the end of the one-on-one, quickly review the notes, and agree on any action items you or your teammate should do. Ensure the timeline to complete that action item is agreed to. After you have agreed on the action items, if you have time, do a summary of what you have discussed on this one-on-one, and thank them for their time.

Digest one-on-one notes

At the end of the week (I personally do this at 5 pm every Friday), go back to all the notes on your one-on-ones and review them. Think about what you discussed with your people, first individually: are there any things that keep repeating one-on-one after one-on-one? What type of things could you be doing to serve this person better? And then across your staff: are there any topics that have come up in all your one-on-ones? Is there an opportunity to propose a change that will help the whole team?

Congratulations, you have finished your first week of one-on-ones. Running effective one-on-ones takes a long time, and sometimes they will be uncomfortable. There will be uncomfortable silences, and you will get asked questions that you don’t know the answer to, folks won’t bring any talking points, etc… But once you start getting the gist of it, it is one of the best tools we have as managers, so use them wisely.