Bite off more than you can chew--and spit it out (a housekeeping tip from mom)
plan to fail
If you plan your quarter to take on a little more work than you expect you can accomplish, then you'll always have something worth doing--but it's more likely you'll drop some projects.
(This is how we practice quarterly project planning at work, not actually tips from my mom.)
Bite off more than you can chew ... #
Before the quarter begins, plan:
- Pick a bunch of projects and write up high-level proposals for them.
- Ask the engineering team to provide high-level estimates for how long it should take for each project.
- Pick a bunch of projects that should take just over a quarter's worth of time.
... look at the rest of your plate, ... #
Halfway through the quarter (before everyone starts to worry "will we fail at our stated goals?"):
- Look at how much progress the engineering team has made on each project, and how confident they feel at completing each project.
- Look at new project requests that have come in since the quarter began.
... and SPIT SOME OUT. #
Now is the time to "fail early" and cut losses, so you can
move your the goalposts clarify (or even change outright) what "success" means.
- Decide which projects to scale back, cancel, reschedule--or add in.
Maybe finish chewing? #
Towards the end of the quarter:
- If there's free time, decide which cancelled projects to revive. Because there's already inertia in the form of plans and work already done, they should be easier to pick up than scrambling to build whole new plans.
- If there's still free time, let workers pick their own projects. People usually have good ideas on what deserves time spent.
How to make this less painful #
Remind everyone that real-world project management is hard #
- Remind everyone constantly that estimation is hard--but planning, investigation, and retrospectives improve future estimates.
- Remind everyone constantly that life happens unexpectedly: people get sick/injured and need time to recuperate, people's dependents get sick and need a caretaker, people should take bereavement leave for attending wakes and funerals, etc.
- Remind everyone constantly that external events happen: shifts in the political scene, natural disasters, customer feedback, etc. (Sometimes you can predict the external events and set up some contingency plans.)
- Remind everyone that we work within complex sociotechnical systems, with many moving parts that need juggled.
- Remind everyone that "success" is what we agree to as an organization.
Build up knowledge #
Regularly host "blameless post-mortem" retrospectives regularly for incidents, projects, and the most recent work period. Write down situation, behavior, and impact. Share the notes with the class. Make retrospectives easy to host and record using templates, video recording, and a facilitator to run logistics and move along discussion.
- Regularly review project status: progress (how much is completed) and shipping confidence (how likely is this project to be completed). Make status updates easy to write and read using a spreadsheet mapping each project across each week, or a form and report in Jira or whatever.
External accountability #
Even when people are intrinsically motivated to do the work and manage their own systems to ensure projects get done in a timely manner, it's not a joke that "projects, like gas, expand in scope to fill the available space in the cacalendar." So, capitalist management exists to try and decide what's worth working on and ask the workers to follow through on that.
- Project leads ask team members weekly "how are your tasks coming along? progress, blockers?"
- Line managers ask project leads weekly "how are your projects coming along? progress, blockers you can't resolve yourself?"
- Middle managers ask line managers every other week "how are your team's projects coming along? progress & shipping confidence, on a scale of 1-10? do you need to rescope to accomplish this important thing?"
- Upper management ask middle management every month "how are OKRs coming along, on a scale of 1-10?"
- The board asks upper management
"where's my money""how is the company's bottom line coming along this quarter?"