Tips for Successful One-on-One Meetings with Supervisor

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11 min read

Tips for Successful One-on-One Meetings with Supervisor

Disclaimer

  1. I started seriously considering 1:1 opportunities after reading this article by vgod, and many of the feasible methods mentioned in this article are derived from it, with some modifications based on my actual situation.

  2. My supervisor and the organizational culture I am in have greatly influenced my implementation of the content mentioned in this article. Therefore, if I were to switch to another company, I might not adopt this approach.

TLDR

  1. We should proactively plan what to discuss during one-on-one meetings.

  2. Share the document with the supervisor

  3. Don't report work progress

Intro

In software companies, we often need to have one-on-one meetings with our supervisors. Before I understood the purpose of one-on-one meetings, I always thought there was no need to prepare in advance and that it was just a casual chat with the supervisor, similar to being called into the teacher's office for a check-in during childhood. It wasn't until I read vgod's 《軟體工程師的修煉與成長 (5) — 1:1該談什麼才能讓職涯起飛?》 that I suddenly realized I had been wasting time in one-on-one meetings all along. Therefore, in this article, I will share my practical views on one-on-one meetings and how I conduct them.

What is 1:1

However, before delving further, I'd like to discuss the importance of one-on-one meetings for both managers and subordinates. I have previously served as a manager and have exchanged ideas on this topic with other managers. Now that I have returned to the role of a developer, I can share some experiences from both perspectives.

For supervisors, 1:1 helps them understand...

I've usually experienced unprepared 1:1s that unfold like this:

Manager: "Hi, Z, how have you been lately?"
Me: "Not bad, I've been working on the xxx project."

Manager: "Have you encountered any difficulties recently?"
...
Manager: "Are there any areas you'd like to learn more about?"
...
Manager: "Is there anything I can help you with?"
...

However, when I became a manager, my concerns in 1:1s without a clear purpose can be summarized into the following three points:

  1. Ensuring subordinates have no intention of leaving;

  2. Understanding the work situation and mood of subordinates;

  3. Grasping if any crises need to be known in advance.

I believe that the above conversation doesn't help much in driving progress, as these conversations can also take place in other situations. Moreover, in the 1:1s I've participated in, over 90% of the time, I have nothing particularly unsatisfactory to share.

For employees, 1:1s should be...

I think 1:1s have the following purposes for employees:

  • Confirm my manager's expectations and requirements for me

  • Understand my manager's evaluation of my recent performance

  • Seek development opportunities

  • Discuss issues that are difficult to resolve within my area of responsibility or matters that may require the involvement of higher-level management

Confirm my manager's expectations and requirements for me

I believe that understanding my supervisor's expectations is crucial, as it pertains to what they expect me to achieve in my current role across various aspects. For instance, if I am a junior-level engineer, my supervisor's expectations might include:

  • In development, they expect me to write clean code and participate in code reviews with senior engineers.

  • In project execution, they expect me to create actionable tasks, such as clearly defined Key Results (if our company uses the OKR system), and share progress and potential obstacles with the team during daily meetings.

It is essential to recognize that when supervisors evaluate subordinates, they typically consider whether all aspects meet expectations, rather than focusing solely on one aspect of performance.

So, if today there are two junior-level engineers:

  • Engineer A has excellent coding skills, is familiar with various design patterns, and can even help review large system architectures, but their project planning is a mess, they cannot break down subtasks, and no one knows what they are doing during daily meetings.

  • Engineer B, on the other hand, meets both expectations, can consistently write decent code, and shares progress during daily meetings, allowing the team to provide suggestions.

If I were the supervisor, I might think that B's performance is better than A's, or I might shift my expectations for A, trying to find a role that can leverage their strengths and compensate for their weaknesses. However, we cannot control the supervisor's thoughts, so during 1:1 meetings, I would try to understand their expectations for me in various aspects and further ask how my current performance is evaluated under these expectations.

Understand my manager's evaluation of my recent performance

In order to comprehend my supervisor's expectations as mentioned earlier, I would like to inquire about their assessment of my performance in these areas. Although we should be capable of determining whether we have met expectations in our daily work, the reality is that expectations for each level may not be precisely defined. For instance, writing good code is a vague statement. Moreover, there might be a discrepancy between self-assessment and others' evaluations, with the most common reason being impostor syndrome, which often makes us feel as though we can never achieve our goals. For example, your code might already be satisfactory and meet the supervisor's expectations, but we frequently believe that our coding skills still have room for improvement.

During 1:1 meetings, in addition to evaluating my current performance, I would attempt to ask my supervisor which aspects I have already met the standards for the next level and which ones still have gaps. Simultaneously, I would inquire about the specific aspects of these gaps, such as asking my supervisor, "Is it because I didn't do xxx in a certain project that you think I haven't reached this part yet?"

Requesting a next-level evaluation during 1:1 meetings not only informs the supervisor of my desire for promotion, but also, by discussing past performance, we are essentially discussing how I should approach similar opportunities in the future. If possible, the supervisor could also be on the lookout to help arrange related opportunities for me.

Seek development opportunities

Achieving specific goals often requires particular opportunities. For instance, if you aspire to be promoted to a senior-level position, you might need a chance to showcase your ability to lead cross-team projects. Likewise, if you aim to become a manager-level employee, you need a mentoring opportunity to demonstrate your capacity to manage a team. The exact requirements may differ based on the company and context, but what's consistent is that these opportunities might not always be readily available; there may not always be new team members to mentor or a constant demand for cross-team projects. Therefore, during 1:1 meetings, we should discuss with our supervisor whether any relevant opportunities are foreseeable in the near future and if it's possible for us to take on these opportunities.

Such conversations can help us determine our direction in career development and convey our desire for personal growth and promotion to our supervisor. Simultaneously, it also informs the supervisor of our dedication to work and our eagerness to assume more responsibilities.

By communicating with our supervisor, we can ascertain whether our current position offers corresponding opportunities or if there are other possibilities to explore. Furthermore, we can seek advice or guidance from our supervisor to better prepare for and embrace future opportunities.

Discuss issues that are difficult to resolve within my area of responsibility or matters that may require the involvement of higher-level management

Occasionally, issues arise at work that are challenging to resolve within our area of responsibility, particularly those that may necessitate involving higher-level management. These matters can be addressed during one-on-one meetings. For me, such discussions transpire less frequently during one-on-ones, but they prove to be quite valuable when needed.

These issues typically arise in cross-team collaborations or are influenced by top-down organizational decisions. By discussing them with our supervisor during one-on-one meetings, we can jointly explore solutions or escalate them to higher management levels. However, if we can discuss these matters with our supervisor during regular working hours, I believe there is no need to wait for a one-on-one meeting to tackle them.


Action Items

After writing so much, if this entire article could be condensed into one sentence, what I want to say is:

We should proactively plan what to discuss during one-on-one meetings.

Next, I will share some practical things I do when planning one-on-one meetings.

Share the document with the supervisor

I always have a private document that I share only with my supervisor. This document contains a summary of what we discussed during each one-on-one meeting (organized at the end of the 1:1), as well as what I plan to discuss in the next 1:1. I believe this document offers several benefits:

  1. It's difficult to recall everything that happened during the 1:1, so having a place to record events as they occur is important.

  2. The supervisor can review the document's content before the meeting and consider these topics, allowing for higher-quality discussions.

  3. Keeping a record of each 1:1 helps avoid repeating discussions and allows us to clearly understand our progress on each issue.

A day before the 1:1, remind the supervisor to take a look at the document

Before the upcoming meeting, I will remind the supervisor that the document has been updated and briefly outline the topics I wish to discuss. The reasons for doing this are that the supervisor may not always be able to check for document updates, and sometimes 1:1 meetings serve different purposes. For instance, a regular 1:1 and a 1:1 following a performance review should not be treated the same way. As a result, clarifying the purpose of the 1:1 before the meeting can be extremely beneficial.

In the beginning, spend some time making small talk

This part is inspired by vgod's article, which suggests spending about five minutes on small talk at the beginning of a 1:1 to help build trust between both parties. I think this depends on how well I know my supervisor; if we have been working together for a long time, I might choose to skip this part.

Questions I might ask

I've noticed that in every 1:1 meeting, I almost always ask the following questions:

  • In the xxx project, if you were me, would you have taken a different approach? What would you have done?

  • In the past period, what is something you think I did well/not well enough/shouldn't have spent time on?

  • In the team, what are some aspects you think I can learn from a certain member?

I believe these questions are very helpful for my personal growth. Since managers are usually promoted from strong developers (at least in my case :P), asking "In the xxx project, if you were me, would you have taken a different approach? What would you have done?" is essentially helping me review the decisions I made during that time. In the second question, "In the past period, what is something you think I did well/not well enough/shouldn't have spent time on?" I pay special attention to the part about what I shouldn't have done, because everyone's time and energy are limited. If there's something that I "shouldn't have spent time on," I need to think carefully about the reason for doing it. The last question, "In the team, what are some aspects you think I can learn from a certain member?" is because, from a manager's perspective, they can see what the entire team is doing from a higher angle and appreciate a certain behavior of a member. This essentially provides a more concrete answer to the manager's expectations for me in a certain aspect.

Things to avoid during 1:1

Here are my very subjective thoughts on things that I believe should be avoided as much as possible during 1:1s:

Don't report work progress

Work progress can be updated during daily meetings or task management tools (e.g. Jira/ClickUp), so using 1:1s to report progress is a waste. This is a mistake I made initially.

Avoid excessive small talk

Building trust with supervisors or colleagues is important, but spending the entire 1:1 on small talk is a wasted opportunity.

Don't gossip about others

Since 1:1s are private, some people may see it as an opportunity to gossip or criticize others' work performance. However, this is a dangerous behavior that can damage your relationships with colleagues and label you as a complainer.

If you encounter work difficulties, it's better to address the issue rather than the person. For example, mention that a project is stuck or express concerns about resource and time allocation. Honestly, I'm not sure about the best approach for this.

Don't lie

Trust is valuable, so I hope not to lie at work. If faced with a question I can't answer, I think the best approach is to say, "I may or may not know the answer, but either way, I don't think I should answer this question." However, as a supervisor or subordinate, I haven't encountered a situation where I couldn't answer a question.

Reflection

Lastly, I have the following two reflections on 1:1 meetings:

Is this approach too aggressive?

I currently think it's fine, mainly because I don't do everything mentioned above in every 1:1 meeting. Usually, 1:1 meetings may have different themes, so interspersing the ideas mentioned above among various topics doesn't seem too aggressive to me. Additionally, I often confirm this with my supervisor during 1:1 meetings. Also, as I mentioned at the beginning, I believe the organization I am in encourages such behavior and culture, so I can confidently proceed this way.

Why isn't the supervisor responsible for 1:1 meetings?

As a supervisor, I might help my subordinates share some of the responsibility for planning 1:1 meetings. However, as mentioned earlier, the concerns of a supervisor may be different from those of a subordinate. At the same time, I believe we should try to control what we can.

Conclusion

I believe that as subordinates, we should take the initiative to manage what is discussed in 1:1 meetings and share the practices that I find helpful for me. I think proactively managing 1:1 meetings provides me with a good opportunity to share my thoughts on personal development and career goals with my supervisor, ensuring that the time spent in 1:1 meetings is used effectively and communication with superiors is smooth, making it more valuable.

Acknowledge

  1. the article from vgod

  2. ChatGPT, the conclusion and many paragraphs within the article were polished and completed with the help of ChatGPT.

  3. Photo by krakenimages on Unsplash