The Four Must-Have Weekly Meetings for Engineering Managers πŸ—“οΈ

A Guide to Effective Team Management Through Weekly Rituals

The Four Must-Have Weekly Meetings for Engineering Managers πŸ—“οΈ

Issue No. 32

This is a project by Jeremy Brown. I'm a journeyman sharing insights on leading product & engineering teams, building products, and exploring technology.
I will also share occasional updates on my overall project as I build this newsletter and "The Retrospective" (a live show and podcast) in the open.

Just as our habits are crucial to our personal success, so are the meetings and rituals of a team.

πŸ’¬ In this issue, I cover the four key meetings I believe every engineering manager needs to master in order for them and their team to be successful:

  • The Four Must-Have Weekly Meetings for Engineering Managers πŸ—“οΈ
    • A Word On Planning Work With Projects And Milestones πŸ“
    • 1. Weekly Team Kick-off / Planning πŸ“…
    • 2. Daily Sync (aka Daily Standup) πŸ”‚
    • 3. One-to-ones πŸ‘₯
    • 4. Weekly Review πŸ”πŸ“§
    • πŸ’‘ Some Quick Tips
  • πŸ”¦ Highlight of the Week

The Four Must-Have Weekly Meetings for Engineering Managers πŸ—“οΈ

Keeping a team aligned and productive can be a daunting task.

I believe the secret to success lies in the simplicity of consistent, well-structured meetings and a weekly cadence or rhythm.

These meetings are not just about checking off boxes; they are about creating a rhythm that keeps everyone on the same page, fosters open communication, and drives continuous progress.

In this article, I'll explore four essential meetings that every engineering manager should incorporate into their weekly routine to ensure they and their team stay focused, motivated, and on track.

Side note: I'm actively trying not to mention tools here, as my focus is on the rituals themselves.

A Word On Planning Work With Projects And Milestones πŸ“

The way I like to look at the work of a team is as a series of "projects" sliced up into small "milestones". I prefer projects to be a timebox with a maximum of 6 weeks (and if it's bigger, create more projects) that are then composed of milestones that are smaller timeboxes of one or two weeks.

In my article on timeboxing, I wrote:

When coaching teams in delivery, I use timeboxes to set specific periods for completing the work. These periods can range from a day to multiple weeks. The goal is to use the shortest possible timeframe for our timebox.

I coach teams to set a timebox for any significant initiative (or project) they are working on. Suppose an initiative will take more than six weeks; in that case, we should chunk it up into multiple smaller initiatives.

Once we have our overall initiative (or project) timebox, we should then chop that up into a series of thin slices of value (or milestones). Each value slice is a week or two, three in extreme cases.

Applying the principles of timebox here means that if, as we get towards the end of a timebox, we realise we might be going over (backlogs always grow as we do the work due to what we learn and the unexpected) we can descope some work to be still able to release something that helps us reach our target outcome for the timebox. Then we re-evaluate, incorporate those learnings and have another go (if we decide to do another timebox).

I will write a more comprehensive article about this in the future, but I wanted to mention this here for context, as I will refer to projects and milestones later in this article.

Side note: I chose the words "project" and "milestone" here as they are more accessible to a wider audience. I personally prefer different terms such as "product initiative" and "product increment".

My guidance for teams is that they have a clear end date for the timebox for our current milestone and a good view of the timebox for the next milestone. The Engineering Manager should have a good idea of their upcoming milestones, but I don't ask them (and the team) to commit to hard and fast dates for those.

Suppose a team can limit their project size to a maximum of six weeks to try to ship an outcome and predictably deliver their small milestones. In that case, they usually have a good handle on their work and tend to be very predictable.

1. Weekly Team Kick-off / Planning πŸ“…

Why?: The Monday Weekly Kick-off is essential for setting the tone and direction for the week. It ensures everyone is aligned, priorities are clear, and no tasks are slipping through the cracks.

Who?: The whole team, including the Product Manager, UI/UX, etc. (Ideally, everyone working directly on the team's initiatives).

When?: Monday Morning with specific breakout sessions as needed as a follow-up.

Target Outcome: The team has aligned on what the team's goals for the week are, each team member knows what they need to do and they have committed to what they will do.

The weekly review is a dedicated meeting every week, usually an hour or two, where the team organises and focuses together for the week ahead. This time is not for working on tasks but for stepping back and connecting with the team's goals, priorities and work

As the manager of most team members, you must set priorities rather than micro-manage in this meeting and find ways to enable the team to self-organise. Your role is a facilitator, not a dictator.

On Monday mornings, plan the upcoming work week together as a team. Capture this plan and send it to the team to ensure everyone sees it and has access to it daily.

I believe that demos are a cornerstone habit of teams - decide beforehand what your team will demonstrate at the end of the week. If you don't plan for it and put it on your to-do list, it won't happen, or it will feel like a mad scramble at the end of the week to record and share a demo video.

There is no best format for creating a weekly plan. It's crucial to embrace flexibility. The style or format of your plan should match the challenges of the specific week ahead.

I prefer to have a single Kanban board for the team that shows all the work in the team, from tasks for engineers to tasks for the product manager, designer, and, yes, even the engineering manager. Make all your work visible.

I like to then find a way to highlight all the tasks that are crucial to achieving the team's goal of the week - frankly, the simplest way to do that is to move anything that is not part of the team's goal for the week off the board and have everyone focus only on what is important.

Don't forget to sense-check what is on the board and what the team can usually complete in a normal week. If you have team members on holiday, plan for a reduced capacity. If your team is regularly interrupted by requests or urgent bugs, plan for that, too.

Whatever you do, don't over-optimise and play Tetris - focus on flow by doing fewer things. Come up with a sensible WIP limit - a good starting point is WIP limit <= team size and then adjust over time.

Have each person sketch their goals for the week. Ideally, they should have a daily plan. Note that they shouldn't simply list things they want to get done each day, but instead, they should match their work to the time that actually seems available on those days.

A big part of the weekly planning process is working backwards from the team's calendar and availability to effectively fill in the available time.

The point is that the team should always decide beforehand what they will do with their week. What matters is that team members are in charge of the team's schedule.

2. Daily Sync (aka Daily Standup) πŸ”‚

Why?: The Daily Sync is crucial for maintaining alignment, addressing blockers, and fostering team cohesion. It ensures that everyone is on the same page and can quickly adapt to any changes or challenges that arise.

Who?: The whole team, including the Product Manager, UI/UX, etc. (Ideally, everyone working directly on the team's initiatives).

When?: Daily

Target Outcome: Team members connect with each other on a human level throughout the week. Any issues and blockers have been raised and addressed.

Most folks in the industry understand this ritual well, so I won't spend much time explaining this meeting here.

Micromanagers often abuse it - watch out for that!

Folks often miss out on the fact that these in-person or online meetings provide a valuable opportunity for socializing and team bonding. The focus of these standups should be on social interaction within the team as well as discussing issues.

Daily Sync's format can be in-person or asynchronous on chat. The team should choose the format that works best for them.

I recommend meeting once or twice a week, even if you conduct the standup asynchronously on chat.

A good rhythm is a Monday kick-off with the whole team, followed by catch-up meetings on Wednesday and Friday. A daily asynchronous update by a certain time, followed by a short team standup, can work really well.

Whichever approach you take on the format, I believe it is super important for everyone to look at the team's plan for the week and compare that to the reality of where the work is.

I personally like to screen share the team board I mentioned earlier in the team's daily sync, and I expect Engineering Managers to double-check it daily to catch if anything is going off track. For example, spot items getting stuck for longer than originally planned.

If the team is going to miss their plan for the week, they should know about it as early as possible. Don't wait until Friday to find out!

Maintaining the balance between social interactions and raising and addressing issues ensures that the team stays connected, informed, and motivated throughout the week.

3. One-to-ones πŸ‘₯

Why?: One-to-one meetings are essential for building strong relationships between managers and their direct reports. They are dedicated to personalized feedback, career development discussions, and addressing concerns or blockers.

This meeting is not for status updates or discussing the team members' work, so you can update Jira!

Who?: The manager and their direct report.

When?: During the week. It's advisable to batch these meetings to manage your time effectively.

Target Outcome: Team members feel cared for and supported by their manager. They understand what is expected of them and receive encouragement and feedback to grow and progress in their career.

You should meet with each direct report for at least one hour every two weeks. However, for some individuals, more frequent meetings may be necessary.

A good starting point is 30 minutes once a week for each team member. I personally prefer shorter meetings more frequently over longer meetings less often. The feedback loop becomes too long.

Based on the needs of the individual, you can adjust the frequencyβ€”either reducing it to every two weeks for an hour or increasing it to two 30-minute sessions per week or even more if additional support is needed (note: this is not about micromanagement).

Use the Task Relevance Maturity framework to determine the appropriate frequency of these meetings. Discuss the framework with your direct report and establish where they currently stand. This will help you schedule the one-to-ones appropriately, ensuring each team member receives the support they need to succeed.

If you see issues in how people turn up and interact in the rituals like the weekly planning or daily sync, then you should use this meeting to address them (unless they did something really out of order, in which case you should talk to them privately straight away).

Don't forget to take notes and share them during or after with your team members.

There is SO much more to get into here that I'll probably write a post dedicated to one-on-ones at some point!

4. Weekly Review πŸ”πŸ“§

Why?: The Weekly Review is an opportunity to step back and reflect on the past week and then update your stakeholders on how the team is progressing.

Who?: The engineering manager should lead this, but it is highly recommended that the product manager and tech lead be included. The Engineering Manager is responsible for this ritual overall.

When?: Friday, preferably in the afternoon.

Target Outcome: The team understands if they achieved their goals, and their work is clearly visualised for stakeholders. Any issues identified are being addressed.

The weekly review is composed of two parts. Updating and reflecting on the week and then communicating that to stakeholders.

Part 1: Reflect on the team's work and Update Your Work Management tool

  • Review the week just past - It helps that you already defined what a successful week would look like in terms of specific outcomes at the start of the week.
  • Review the weeks ahead, and think about the upcoming week - so you can raise these in the team's weekly planning meeting.
  • Revisit the team's goals and priorities.
  • Check any key metrics the team might be tracking.
  • Revisit the team's projects and their milestones and the team's backlog
  • Update project plans and supporting materials like risk trackers.
    • This should be straightforward because your team should update whatever tool you use for tracking work daily, and you should adjust plans during the week.
    • Never wait until the end of the week to update projects and their milestones.
  • Start to think about what your top three outcomes for the week ahead could be ahead of the weekly planning meeting.

Part 2: Share a written update with your stakeholders and raise any issues that come up during your review

  • Never wait until the end of the week to signal that a project is off track, has issues, or needs help.
  • Send a project update via email or chat, or post it in whatever tool you use for tracking your work.
    • The main point here is that you share a written update with your team's stakeholders in a short and clear format that is easy for a busy executive to understand.
  • For each project or initiative
    • Include a short update (if needed).
    • Signal its status clearly:
      • On track
      • At risk: No external help is required, but explain the issue and how you address it.
      • Off track: External help needed; explain what help you need and from whom.
    • Give the date for when the current milestone will be completed and the tentative timeline for future milestones.
    • Share a screenshot or short video demo of the current progress - no matter how technical! (Do you plan for this and talk about this in the weekly team kick-off? right?)
  • Share something positive from the team. Incorporating a celebration into your weekly update ensures consistent recognition, enhancing team cohesion and performance.
    • Celebrating small wins and recognizing team achievements is crucial for maintaining morale and motivation.
    • These celebrations remind the team that progress is being made and help build a positive culture where everyone feels valued.
    • Highlighting small wins creates a sense of accomplishment and momentum, fostering camaraderie and showing that you, as a manager, appreciate your team's hard work
    • It enables more senior folks and your stakeholders to recognise your team publicly for their wins.
    • As a manager, you should be one step ahead of your team - look for opportunities ahead of time and plan for them in the weekly kick-off.

πŸ’‘ Some Quick Tips

  • Put these meetings in the Calendar Ensure that you have recurring meetings that block your team's calendar for all of these rituals and treat them as sacrosanct. This helps maintain consistency and ensures that these important meetings are not overlooked.
  • Schedule gaps between your one-on-ones: You need time to write up your notes and send them, and you need time for yourself to context switch before your next meeting. Don't do too many meetings back to back without a break.
  • Go into every meeting with an agenda and a plan: Especially for the weekly kick-off, daily sync and, most importantly, your one-on-ones. Try to share these in advance with folks.
  • Keep Your Work Management Tool updated daily: Ensure your team updates whatever tool you use to track work daily. This makes it easier to adjust plans during the week and keeps everyone informed. Don't try to do it all on Friday. Don't have just one person responsible for updating it - it belongs to the team, and the folks doing the work are responsible for keeping their part updated.
  • Status Should be short and clear: don't ramble on, don't bury the lede, and get to the point.
  • Communicate Bad News Early: Never surprise people with bad news. The earlier you share it, the better. This allows the team to address issues promptly and find solutions.
  • Explain Your Needs: When sharing bad news, explain whether you need help. If you don't need help, clarify what you are doing to address the issue. This transparency builds trust and ensures that everyone is aware of the situation.
  • Embrace Flexibility: There is no best format for creating a weekly plan. Embrace flexibility and adapt the style or format of your plan to match the challenges of the specific week ahead.
  • Document Action Items and Follow-ups: It is important to document action items and follow-ups from each meeting (ideally as tasks in your work management system). This ensures accountability and tracks progress. Clearly assign responsibilities and deadlines for each action item and review them in subsequent meetings to ensure they are being addressed. This practice keeps everyone on the same page and helps identify any potential roadblocks early on.
  • Focus on Social Interaction: It is not all about work. We spend more time with our teammates than with friends and family. In your daily standups, focus on social interaction within the team and discussing issues. This helps in building a cohesive and motivated team.
  • Make these meetings inclusive: You must allow all voices in the team to be heard. Ensure remote team members or those in other time zones, including contractors, are included if they work with/for your team. I have found that the Lean Coffee format can be powerful in team meetings like the weekly check-in.
  • Don't fake small wins and celebrations: Everyone sees through them, so don't undermine your credibility and your team. If you see others doing it, don't join in, even if you think it is helping someone get ahead in their career. The people that matter (your team) see through it and won't respect you.
  • Continuous Improvement: I won't write about it much here, but I believe the retrospective is THE most important ritual in the life of a team. Constantly iterate on the format of your meetings and reports to improve their quality and reduce the effort it takes to stay on top of things.

Using these rituals and following these tips ensures that your team stays aligned, informed, and prepared for the week ahead.

πŸ”¦ Highlight of the Week

John Cutler has great advice on "How to Troubleshoot Status Updates and Syncs".

"Everyone seems swamped, so our updates feel more like venting sessions than strategic check-ins."When people are busy and overwhelmed, they don't have time to prepare for these updates, and it can seem like they're sort of phoning it in at the last minute. This situation is difficult because these types of updates aren't useful. People are typically sympathetic to the idea that everyone is overwhelmed. So, when you have a situation where everyone is overwhelmed, and the updates aren't actionable or useful, no one is in a position to call it out.Try This: Spend the first 10 minutes of the meeting writing your updates. Call out that people are too busy to make their updates useful.
"The updates are all over the place. We need a clearer thread to tie them together.""Why are we still using this format? It doesn't reflect our current goals or challenges."It's helpful to return to similar themes, goals, metrics, or anything that adds a consistent thread to these updates. If you're giving updates at a very tactical level but not linking them to the overarching goals, it can be not very helpful for people, and they lose interest. Similarly, if you dogmatically return to the same format repeatedly, and that format doesn't fit the current shape of work or mission, it can turn people off.Try This:Experiment with a new format each quarter. Rotate the meeting design owner.Keep what works.Always try to revisit certain goals and "pillars."