The Continuous Flow of Weekly Planning

9 min readJan 7, 2018

Strategy and planning are the heart of great leadership and management.

Why? Because a goal without a plan is just a well intentioned wish or hope. You most likely won’t achieve your goal without a plan.

As a leader you need to enjoy and become great at planning.

When I was a line manager I loved weekly planning. I lived it. I was in a continuous flow of planning.

For me planning peaked each week on a Friday afternoon, when my team would agree our goals and plans for the coming week. I loved these meetings. To me they were a microcosm of everything it means to be a leader and a manager.

This blog post is an attempt to describe my weekly planning flow from back when I was a line manager, managing 8 engineers on our Ops team. Hopefully some folks find it useful or highlight ways in which I can be better.

===

Monday — before standup

Monday is always a special day. It starts a new week, a new cycle, a new sprint, a new everything. It’s a new opportunity to start afresh and put down a marker. I try to never waste the magic in the air on a Monday. I want to lead by example, to model the behaviors and attitude I expect from the people on my team.

To get myself into the right frame of mind, on the way to work I might listen to some upbeat music, listen to an inspiring speech from an Irish sporting legend, or even listen to Al Pacino’s famous “Any given Sunday” speech.

Next I re-read through my team’s goals for the week, making sure I know exactly what they are, why we’re taking them on, what success looks like, what the risks are, who should be doing what and which of them we’d like to demo or showcase to other at the end of the week. Why? Because achieving goals, knocking them out of the park, is what I’m here to do. Add as much value as quickly as possible. I do these things in a way that’s fun, creative and sustainable. That’s my job, that’s how I earn money and how I earn self respect and pride. Life is short, make the most of it.

I make sure our goals are properly recorded in our project management tool. Why? This tools serves many purposes, not least of which are (1) a way for teams to see what each other are working on and (2) a way for teams to be held publicly accountable for hitting their weekly goals.

Next I load up on all other secondary contexts I need to help me and my team plan and execute well this week and this day.

I read & review:

any new bugs or Github issues that were tagged for my team and updated since our last standup
any pages that fired for our team since our last standup
our key operational metrics dashboards looking for anything out of the ordinary
all the high level goals being taken on this week by other relevant/adjacent engineering teams

From these things I decide and note down anything that I might need to bring up with the team at standup.

Monday — at standup

Standup happens at 9.30. I like to be first to standup, to arrive with a smile on my face and set the tone … happy, positive, optimistic, organized, eager to get started. We go around the room, asking each person to quickly and succinctly remind the team what their goals for the week are and what they’re aiming to get done today.

Sometimes I’d ask someone else to paraphrase what the last person just said to make sure we all understand what each other is doing. Why? If we don’t understand we can’t help.

After sharing weekly goals and tasks we move on to “post-scrum”. It’s not actually scrum we’re practicing, but we still called this but post-scrum, old habits die hard.

Here we’d discuss any of those things I’d jotted down from my pre-standup review and anything else other folks needed to discuss. This post-scrum bit usually takes about 5 mins.

Monday — after standup, write and send your weekly status report

Each Monday after standup, I’d write and send out a weekly status email for my team to all of engineering.

This was a simple email with the following sections:

Highlights from last week, what were the top 3 things we accomplished and why you should care?
Goals Hit — Which of our goals for the did we hit, what was the value of doing so?
Goals Missed — Which of our goals for the week did we miss and why?
Goals for this coming week — What are we committing to achieve this week and why?

A lot of people complain about status reports. People say they don’t have the time to write them and complain that nobody reads them.

My 2 cents …

If you don’t have the clarity of understanding to be able to quickly write out those 4 headings in 30 mins or less then you have a bigger management problem that needs addressing.

Regardless of who reads these things (and senior people read them more often than you think) the public act of accountability keeps you honest and motivated to improve.

Tuesday -> Friday standups

The routine for standup for the rest of the week looks like this…

Pre-standup planning is pretty similar, before standup I follow the same checklist as was already listed for Monday.

At the standup we go around the room and say what we did yesterday and what we’re doing today and what we’re blocked on.

I’d also ask each person whether they’re on track to hit their weekly goal to explain/justify the answer. Any goals that are on track get green dots beside them, any goals that are not on track get red dots beside them. If a goal is off track for more than one day we ask can we help the person or re-scope the goal to something smaller/easier by still valuable. This re-scoping, helping and generally fighting to never let a goal go gently into that good night is what we call hustle. It’s magic. Always be creating hustle.

Tuesday — 1on1 with my boss

Tuesdays were when I had my 1:1 with my boss. I’d spend some part of this 1:1 to bring him up to speed with how the team is doing this week and get any input/context required for future planning. Manage up. It’s important. Be a team.

Wednesday — 1on1 day

I’d hold 1:1’s with my direct reports on Wednesdays. A part of each 1:1 would be used to talk about how things were going this week and what we thought should be done next week. Generally I’m asking more questions than I am giving out advice. I’m trying to use as much of a coaching style as possible to give as much autonomy for folks to create and drive their own plans. Why? Coaching + Autonomy = Growth+ Accountability.

Friday

The Friday afternoon team planning meeting is THE MOST IMPORTANT MEETING OF THE WEEK. It’s an expensive meeting for a start, it’s an hour long and everyone attends, so it’s a huge waste of time if everyone, myself included, doesn’t come prepared. It’s also really important because this is where goals and plans for the whole team get made for the coming week.

Friday — ~11am

Quick check-in with each person on the team over Slack…

“Hey, how are you set for planning later today? What goals are you bringing, is it still what we chatted about on Wednesday or has it changed? Lemme know if you need a quick F2F sync on anything that I can help with.”

Friday — 2pm -> 3pm — strategic thinking time

This is where my serious Friday pre-planning starts. For the rest of the day, for the next 3 hours, I’ll be “pre-planning” or “planning”. I had a check-list of things that I’d go through to get me ready to run our planning session at 4pm.

The things I’d go through were:

Re-read our team’s mission and values and ask myself if I’m happy with how we’re performing against them?
Review our quarterly roadmap and goals and assess how well we’re doing against our bigger commitments. Are we still working on the right things? Are we moving fast enough? Is our quality bar high enough?
Review our key metrics and operational dashboards, make sure to look back over a decent time horizon, zoom out and see if there are any trends to spot.
Think about my own performance. Am I helping? Am I innovating? Am I pushing outside of the comfort zone or am I coasting? Am I happy? Am I proud?
Think about the folks on the team. Who’s doing well and who needs to do better. Who’s stressed or tired and might need a break?
Am I proud of our team? Where do I rank our team amongst the other teams I know of at Intercom. What does it take to get/keep our team as the highest performing team at Intercom? Seriously, I want us to be THE BEST TEAM at Intercom. If that’s not what I’m shooting for and working hard for then I’m letting people down.

Friday — 3pm -> 4pm — pre-planning for next week

Put together the agenda for the impending team planning meeting that will happen at 4pm.

Make sure I’ve a good idea of the work / goals that folks will need to do next week and as much as possible have it jotted down already in my notepad. I want to spend as much time as possible with my head UP looking at people, being present, listening, asking questions, talking, leading and as little as possible taking notes.

Make sure I’ve jotted down any “hot topics” I want to bring up in the planning session.

Decide whether this is going to be a “sustaining success” planning meeting where I dole out recognition, highlight the things we’re doing well and generally try and keep the controlled high tempo of the team on track for another week … or whether this is going to be a “get back on track” planning meeting, where more of a retro is needed or where I try to reset the tone, expectations and ambitions of the team to be something better than what it currently us.

I practice everything that I want to say. I saw things out loud to see how they sound. Sometimes I’d role play it with a peer. Why? Role playing is for management what code review is for software development.

Friday — 4pm -> 5pm — planning for next week

The team all come in to our meeting room. Most people have a beer in their hand.

Start with accountability. We kick off the meeting by closing out on our goals for this week. Which goals were hit, which were missed. Which can be demo’d to our peers.

It’s always a yellow/red flag for me if there is nothing that we’d like to demo to peers. We’re probably not scoping things as well as we should.

After closing out the week, we’ll quickly skip through:

pager metrics
key/ops metrics
open issues
other hot topics

This will all be fast, because I’ve already gone through all this in the previous few hours and I draw attention to anything that’s important so that we can quickly and efficiently discuss it as a team.

Next I’ll run through our mission, values, roadmap and goals to remind people of the bigger picture context. I do this so often I can nearly sing it. We’ll talk about whether the goals are on track or behind. Why? We should see the coming week within right context of the bigger goals we’re shooting for.

Now, fully loaded with context we go around the room and share candidate goals for the coming week with each other for the coming week. I mostly have these all written down already from my questions earlier in the day. I make any minor adjustments as necessary. I’ll often ask person X for feedback on person Y’s goals. Why? Sometimes to make sure everyone understands what’s being discussed, sometimes it’s get real feedback and insight on how the goal/plan can be improved, and sometimes it’s just to make sure everyone gets a chance to contribute and have their opinions listened too.

From our list of goals for the next week, I’ll ask which or what are we going to demo next week. This will help put an even finer focus on what needs to get done next week.

Finally, I’ll read out the meeting minutes and sum up what we’re committing to as goals for the coming week. Why? It’s important that there are no misunderstandings and that we’re all clear on what we’ll be doing and trying to achieve next week. I’ll thank everyone and hope they have a great, relaxing weekend! Monday coming will again be a magical day and we’ll be ready to start afresh with our best foot forward 🚀

while true  reflect_and_think
  set_context
  create_focus
  drive_impact
  cultivate_growthend

If any of this sounds fun — I’m hiring, we’re hiring, drop me a note :-)