The Power of 1:1 Meetings (A Manager’s Perspective)

ITHAKA Tech Staff
ITHAKA Tech
Published in
4 min readFeb 9, 2023

By Crystal Housewright

Regular 1:1s are like oil changes; if you skip them, plan to get stranded on the side of the highway at the worst possible time. –Marc Hedlund

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In early 2022, I joined ITHAKA as an Associate Director of Software Engineering. I am not new to engineering or managing people, but I have never started a job as a remote employee. I wondered how I could cultivate connections with my team in a remote work environment. An idea came as I was reflecting on one of ITHAKA’s organizational values:

“We are systematic and use evidence in our pursuit of continuous improvement.”

Continuous improvement is the goal of Agile development. Why not apply this proven method to my new role? I could start with my Minimum Viable Product (MVP), seek feedback, and adapt my approach to iteratively improve my value and impact.

So what is the MVP in a manager’s toolbox? We all know that an MVP doesn’t need to be perfect, but it should give you a lot of good information about where to go next. To me, a manager’s MVP is the 1:1 meeting they have with each of their direct reports. 1:1s make space for managers to give each of their direct reports time and personal attention. In turn, 1:1s provide valuable insights from direct reports to their manager. So this is where I began when I joined ITHAKA. I deployed my MVP to learn what my team needs. From the information elicited in my 1:1s, I could adapt to meet them.

As managers, how do we ensure our 1:1s to live up to this opportunity?

Source: XKCD

Before the 1:1 meeting

Enable each person on your team to own their 1:1s:

  • Ask each person for their 1:1 preferences (e.g., frequency, duration, time of day).
  • Schedule recurring calendar events based on each person’s preferences. Respect the “maker’s schedule” so that you do not interrupt their flow. Reschedule the 1:1 if needed, but do not cancel unless there is a very good reason — regularly canceling 1:1s quickly erodes trust.
  • Use a shared document or 1:1 template to collaborate asynchronously ahead of the discussion. Prepare thoughtful, open-ended prompts for discussion. As a manager, you set the 1:1 structure; as a direct report, you supply the 1:1 content.

During the 1:1 meeting

Start the conversation by letting the other person talk about anything they want. This can go a few ways. They may have a list ready. If so, then you can rank and timebox discussion items. Another scenario is that they don’t know what to talk about, which is bound to happen from time to time. Don’t fret! Some of my most interesting 1:1s started with the phrase, “I have nothing to talk about.” If you find yourself in this situation, then ask great, open-ended questions.

Typically, I follow a version of the Simple Leadership Conversation:

  • How are you doing?
  • What’s in your way, and how can I help remove that obstacle?
  • What else can I do for you, or what else do you want me to know?

For every question you pose in a 1:1 as a manager, ensure you are asking for their benefit, not yours. For example, if they are talking about something that went well, then ask them why it went well. What skills did they leverage to get that win? This creates time and space to reflect. This moves into skills-based coaching. These pillars of success can then be shared or applied elsewhere in the future.

If nothing else, just be fully present in your 1:1s. The goal is to make a positive impact on the other person’s life. This means it’s their time, not our time for a status update. Use this time intentionally to talk about goals, feedback, and longer-term topics. As a manager, if you are successful in your 1:1s, you can help shape the way people feel about work.

After the 1:1 meeting

Thank direct reports for their time after each meeting. Make notes about the discussion and the next steps. Follow through on any concerns that need to be addressed and be clear about your expectations. Complete any tasks that arise during the conversation. You’ve spent valuable time making an investment in your working relationship. Do not lose that precious progress afterwards!

After a couple of 1:1s, ask for feedback on the structure of the meetings. Continue to ask periodically and make adjustments.

tl;dr

A manager’s priority is to ensure the success of their team and the individual success of each team member. 1:1s are just one tool in your manager’s toolbox to help achieve this goal. Don’t put too much pressure on any single 1:1 because relationships take effort and time. Earning trust and building rapport comes after many interactions and self-discovery. Each 1:1 is an opportunity to iterate on your relationship.

Do you love teamwork, problem solving, and trivia breaks? You’d love it here! Check out ITHAKA’s career opportunities.

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ITHAKA Tech Staff
ITHAKA Tech

Insights from the ITHAKA engineering team and beyond.