First Ten 1:1s for Engineering Leaders

Every successful leader says that 1:1 is one of the essential things in their job. But for fresh managers, these sessions are tough.

I did hundreds of 1:1s in my career. Today I cannot imagine a better way of working with my teammates. But the early days were super hard.

Each session was stressful for me. I was afraid that I wouldn't have anything interesting to say. I worried about what my teammates thought of this meeting. Were these 30 - 60-minute sessions a well-invested time for them?
With all of these in mind, 1:1s felt awkward at the beginning.

And this is why I created a workbook, First Ten 1:1s for Engineering Leaders.

Practical material walks you through the first ten sessions with your teammates. It brings some ideas for subjects to discuss during the meeting, how to prepare, and how to ensure the continuity of the big picture.

Thanks to this workbook

• You will feel more confident as an engineering leader and ensure that these sessions are your and your teammates' most valuable time within a week.

• You will build your position in the organization as an influential leader thanks to achieving your goals and growing your teammates.

• You will become an inspiring leader for your teammates, help them perform better, get a promotion, and reach their potential.

• You will build professional and personal relationships with your teammates.

You should get it if

• You are a fresh engineering manager or technical leader

• You want to start having regular 1:1 sessions with your teammates

• As an individual contribution, you want to see what you can expect from your line manager

Preview

Table of contents

• Intro - 5

• General rules to read before every 1:1 - 6

• First Ten 1:1s - 7

• First 1:1 / Preparation and hello meeting - 7

• Second 1:1 / The feedback - 10

• Third 1:1 / Company's big picture - 12

• Fourth 1:1 / Expectations, competencies - 14

• Fifth 1:1 / Personal goals - 16

• Sixth 1:1 / Goals agreement - 18

• Seventh 1:1 / Regular check-in - 20

• Eighth 1:1 / Goals check-in - 22

• Ninth 1:1 / Teammate’s potential and delegation - 24

• Tenth 1:1 / The framework - 26

• Appendix - inspirations to be a better software engineering leader - 28

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The Workbook Preview

Intro

1:1 is an essential tool for managers. As a leader, you work on strategy, goals, the organization's culture, feedback, priorities, and many more. 

And 1:1 meetings are where you make these things real. 

• This is where you translate strategic things into day-to-day actions. 

• This is where you implement the company's culture. 

• This is where you support your teammates to reach their potential, grow and succeed as professionals. 

This document gives you an example plan for starting 1:1s with your teammates. It's very practical. It talks little about 1:1's theory, mentoring vs. coaching differences, etc. The path described here is to build a touchpoint with your teammate, grow your relationship, and outline the overall value of 1:1s.

The goal you will reach after completing the first ten 1:1s is confidence. I want you and your teammates to develop a shared willingness to continue these discussions and get as much value as possible from them. And I want you to be confident in picking things to discuss. I want you to see these meetings as an excellent opportunity to improve rather than seeking excuses for skipping them. 

General rules to read before every 1:1

• Always take a 📓notebook and 🖊️pen to take handwritten notes during the meeting rather than distracting yourself with a laptop open.

• Start with a once-a-week meeting. It can be more often when working with a low-experienced person (intern, junior, or new joiner). After a few sessions, you can switch to a bi-weekly meeting, but do not start with that cadence.

• Listen to your teammate actively. Silence is better than talking 90% of the time. Give them enough time to think and express their feelings/ideas/thoughts.

• A few first 1:1s should be at least 45 minutes long. Give yourself enough time to focus on the conversation, listen actively, and discuss each case thoughtfully. Over time, you will decide whether to extend the time to one hour or decrease it to 30 minutes. 

• A 1:1 is not a reporting meeting. It is a session to exchange feedback, support your teammate, listen to them, help them grow, improve their well-being, and help them be successful. 

• Don't skip 1:1s unless you are off this day. A 1:1 is the most important meeting within the week. In extreme cases, reschedule it as soon as possible.

First Ten 1:1s

First 1:1 / Preparation and hello meeting

Preparation

• Let your teammate know you will meet regularly for 1:1 sessions, ideally every week. Tell them that during the meeting, you will discuss challenges, their growth, the support they need from you, exchange feedback, etc.

• Schedule a regular meeting with your teammate in the company calendar. If you don’t have one, you can use Google Calendar. Book a room if it’s an in-office meeting. If it’s a remote one, guarantee full privacy.

• Create a private shared document for you and your teammate. 

  • The document should have an agenda, meeting notes, action points, a link to the teammate's goals, etc.

  • For inspiration, check the template document (Notion, Google Docs).

• Ask your teammates to prepare ideas for what they want to take from these meetings.

First 1:1 meeting

• Remember to take notes. Coming to the meeting with all the topics already written down is okay.

• The first meeting can feel awkward, and it's fine. You are just starting. A warm-up question always helps. Ask your teammate how they are doing and what's interesting in their life. Be natural with these questions.

• Discuss the 1:1 contract between you and your teammate.
  Here are a few examples:

  • Things discussed in the meeting stay between you and your teammate until clearly stated otherwise.

  • You don't skip meetings unless it's an extreme case.

  • You both come prepared. You add your points to the agenda. You review a meeting's plan beforehand. 

  • There are no distractions, no mobile phones, and no laptops (unless it's really needed).

• Explain and discuss the purpose of 1:1 sessions.
  Important things to cover:

  • This meeting entirely focuses on the teammate and how you can make them successful. You'll focus on making them competent and helping them reach their potential.

  • A 1:1 meeting is not a reporting session. Whenever you discuss tasks, metrics, or goals - it's about understanding the context behind them, their validity, and how you can help make them happen.

  • This meeting is a time to exchange honest feedback. You both will talk about bad and good things. You won't judge people but discuss situations and behaviors.

  • Your work and the value of these meetings will be assessed by teammate success. These can include accomplishing projects, gaining competencies, getting promoted, or building visibility.

• Ask your teammate about what they would like to get from this meeting. Write it down.

• Ask your teammate how things are going—on a project, in a team, or at work. Dig down and ask about things you can help them with. Narrow subjects down to exact action points. Write them down. Be clear with your teammate about when they can expect updates from you.

Homework

At the next 1:1 meeting, you will focus on exchanging feedback.

• Tell your teammate that starting from the next session, you will expect to discuss:

  • Three good things from a week (project, team, company, their work, their wellbeing, wins - don't set clear boundaries to keep this question open),

  • Three bad things from a week,

  • You will also share your good and bad points with them.

After the first 1:1

• Complete your notes in a shared document. Remind your teammate where these notes can be found. By that, start building the habit of using this document as the interface between you and them.

• Follow up on action points as soon as possible:

  • If you can accomplish them quickly, do it.

  • If you cannot make them happen, send a note to your teammate - this is how you build trust and present your accountability.

This was the preview of the workbook’s content. For more, I invite you to become a paid subscriber of Practical Engineering Management. You will get access to a full workbook and tens of other articles and materials for impactful software engineering leaders.