High Leverage One-on-Ones

Thinking back to my first job as a software engineer, I recall feeling uncertain about why my manager insisted on meeting with me every week. While it was helpful during my onboarding phase, once we settled into a routine, we struggled to make the most of our time together. Our weekly meetings started to become little more than routine status updates.

At first glance, providing status updates during these meetings might seem like a reasonable use of time. However, given that there are typically more effective ways to convey status updates, relying on this approach is, at best, a missed opportunity to use the time for more meaningful endeavors.¹ In fact, even spending the time building a stronger relationship with your manager would be a more valuable use of this time.²

What to do Instead

Take Ownership

First and foremost, if you're the report in the relationship, it's essential to view one-on-one meetings as a regular touchpoint that belongs to you. This mindset is crucial because taking ownership allows you to shape one-on-ones to fit your needs. While your manager will also benefit from these meetings, they should primarily belong to you.³

It's important to emphasize that a one-on-one meeting is designed for the person reporting to the other person. While it's mutually beneficial, your manager will get the most out of it when you lead the way. Otherwise, your manager will have to guess what's important to discuss. Generally speaking, your manager will know far less about what's relevant to you than you do. By taking ownership, you can turn one-on-ones into high-value touchpoints.

To capitalize on this mindset of ownership, set aside a few minutes before each meeting to consider how you'd like to spend the time. This way, you can ensure that the time is productive and aligns with your goals.

Use an Agenda

Organizing your one-on-one meetings with an agenda can be extremely helpful.⁴ To get the most out of this approach, write your agenda down. It can be as simple as a few high-level bullet points encapsulating the topics you want to discuss, or a more detailed set of notes. Regardless of the level of detail, writing it down will help you remember what you want to cover, as well as crystallize your thoughts and ideas. Investing just ten to fifteen minutes developing your agenda will go a long way.

For example, my routine for preparing for one-on-ones involves reviewing notes I've taken throughout the week in a document shared with my manager. I'll refine these into a bullet list of talking points that I'll use to drive the conversation. I usually order these items by priority, with the most important ones at the top of the list. Depending on the length of the meeting, we may not get through everything, so some carryover of less important items is expected.

If you find yourself building an ever-increasing backlog, it may be worth taking a closer look at your topics. Some may warrant their own meetings entirely, especially if they become thematic. One side effect of structuring your conversations with an agenda in this way, is spotting these kinds of themes. Once you do, you can decide how best to proceed.

What to Talk About

• Challenges: Especially as an individual contributor, it may not be clear what to do talk about, if not project progress. However, it's important to remember that work is rarely free of challenges. Take this opportunity to discuss any problems you've encountered, both big and small. This might include issues with your workload, colleagues, or projects. It might also cover cross-functional or larger organizational issues you're seeing.

• Solutions: Furthermore, when flagging issues, it's a great time to offer a suggested resolution. Perhaps the aging monolith is reaching capacity and can no longer bear the load of the current product needs. You might observe this and offer next steps which could range from investigating the problem in more depth with your team to a new architectural direction entirely. Offering potential solutions in this way is also strong growth signal to your manager, who can work with you to weave discussions like these into your growth narrative.

• Personal Development: One-on-ones are also a valuable opportunity to discuss your personal growth and career development. Share your goals and aspirations with your manager, and ask for feedback on how you can improve your skills and take on new challenges. This can also be a good time to discuss any training or development opportunities you may be interested in pursuing. Consider periodically revisiting goals and progress towards them with your manager.

• Insight from Your Manager: Remember, your manager has a unique perspective on the company and its operations and how your team and work fits into everything. You might use this time to ask for their insights into what's happening within the organization or in your department or team. This could include updates on company goals, upcoming changes, or any trends they may have observed. Ideally, you'll have a clear picture of how your work fits into the broader goals of the business and these insights can help strengthen that connection.

• Feedback and Coaching: One-on-ones are an ideal time to follow up on feedback with your manager. Consider discussing any action items, and explore any additional aspects that might benefit from a deeper dive. If you find that you need more guidance or support, you might consider asking for coaching from your manager. Remember that coaching is a collaborative process which requires active engagement from both parties, so be prepared to work together.

Bear in mind that these meetings are meant to be tailored to your needs. Focus on the topics that matter most to you and don't be afraid to ask for what you need to succeed. With practice, you'll develop a feel for how to shape these meetings to maximize their value.

A Better One-on-One

During that first job I had mixed feelings about one-on-ones. Since we used them almost exclusively for status updates, they felt superfluous.⁵ However, I decided to turn my hesitation into an experiment: What would happen if we used one-on-ones differently?

I started focusing on my personal growth, using our meetings to ask my manager to coach me in areas where I could contribute the most to the business and grow my own abilities. From that job to the next, I doubled down on this approach, using one-on-ones not just to prioritize my individual impact but also as a means to collaborate with my manager on larger organizational change. I began to see these meetings as exceptionally valuable because they gave me access to parts of the organization that were otherwise out of reach and meant I could effect even larger change.

By far the biggest contributor to whether one-on-ones are effective or not is empowering ownership of the time to the person who's meeting with their supervisor. If you're a manager meeting with your reports, coach them to use this time for themselves. If you're meeting with your manager, take charge and show up with a structure to guide the conversation.

To make the most of one-on-ones, it's crucial to have a clear agenda that goes beyond just status updates. Topics to consider include discussing problems and offering solutions, discussing your own growth, gaining insights from your manager, and leveraging feedback and coaching. Tailor the conversation to your specific circumstances and prioritize what's most important for your growth and impact.

By taking ownership of one-on-one meetings and using them as a forum for growth and collaboration, you can transform them from a routine check-in to a valuable opportunity to advance your career and make a meaningful impact on your organization.

Footnotes

1. As Cristina points out, there are many forums for updates – notably, these forums are asynchronous and make it easier to share more broadly. Consider that one-on-ones are typically synchronous and private, making dissemination of updates more challenging. ↩

2. Please don't be tempted to forego the meeting altogether; it's imperative to meet regularly, even when it feels like there's nothing to talk about. ↩

3. Whenever one-on-one time becomes overburdened with too many things, especially those that aren't being driven by you, set up separate meetings to address those topics instead. ↩

4. In fact this is true of virtually all meetings: always use an agenda if you can! ↩

5. And used in that way, they were! ↩