Good Work—Edition Nº 24

🎶 This Wheel’s On Fire by Bob Dylan

Overwork is nearly always just a synonym for ‘bad management and poor planning.’DHH*

We just hit a critical internal milestone for an upcoming big launch, and then sent our CEO on vacation. At Holloway, we value the time our team members spend outside of work, with family, pets, partners, parents, grandparents, on healthy activities (or a good night on the town), on hobbies—we believe in giving our brains a break.

Still, it’s not always easy to step away, even when doing so is a core value. I’m the canary in the coalmine at Holloway: the only member of the small 6-person team with kids, who are barely emerging from the very demanding stage. I’m most likely to first feel the pinch of long hours and unreasonable expectations. But kids aren’t the only thing that matters here. What I’m the first to notice, everyone else will suffer soon thereafter, giving up time they’d spend with loved ones or just out in the world, living life. For those relationships and breaks to be meaningful and restorative—for people to not be burned out as a project comes screeching across the finish line half on fire—your team needs to Get Things Done when everyone is at work. You need reliable project management.

Endless status meetings. Gantt charts. Tedium… Shudder.

“But that will just get in the way of moving fast!” some cry, especially at startups. Bullshit, I say. Forgoing even lightweight project management merely pushes the unintended consequences onto the people carrying the more uncertain and ever-shifting loads. Project management is the gutter cleaning and furnace filter changing of companies—ignoring it feels perfectly comfortable right up until the moment it is suddenly very unpleasant. We don’t want to ever stand on some stage, thanking the people who work here for spending huge chunks of time away from their families. (Okay, the standing on the big stage part would be awesome, just not the rest.)

Yes, project management is hard. I’m still no expert at it. If you’re brave enough to Google “project management best practices” the results may as well be narrated by David Attenborough witnessing an ongoing battle of warring acronym-laden animal tribes. There’s a million tools and countless methodologies. Agile, sprints, PMI, oh my. There is no holy grail or single way of managing projects, and every organization needs to figure out what works for them. Pick a tool (or two or three, if that makes sense for your team), a methodology, and Stick. With. It. Write as much down as you possibly can. When it’s not entirely working, figure out why, change that bit, and keep going.

This Week

Project Management

• One of the most-referenced books on project management is likely Getting Things Done. It’s a classic that many still swear by, but it’s still more about organizing and executing tasks and less about modern, agile, team-built products.
• If The Goal (and narrative business novels in general) rubbed you the wrong way, then Critical Chain probably will too. But author Dr. Eli Goldratt’s Theory of Constraints (here applied to project management for knowledge workers instead of the production line) has teeth. At Holloway, we call this “Doing the hard stuff first.”
• Yep, we’re sharing Deep Work again. Really, if you haven’t read it yet, please do. We promise it’s worth it.
• “Your job as a leader is to model how work can be a container for your team to do their best work.” This interview with Jerry Colonna (from Krista Tippett’s On Being podcast) on bringing your whole self to work is probably an open tab in everyone’s browser at Holloway right now.
• I can’t wait to dig into this new Basecamp book on how they plan and ship things.
• There’s a growing backlash against backlogs. It makes sense to this former cognitive scientist: backlogs are extra cognitive load you’re carrying around at all times, making it harder to see and focus on what’s right in front of you that really needs to get done.
• “Take good notes.” This might be the best project management advice out there. (Along with: “Don’t panic.”)
• This is a helluva list of project management tools. (At Holloway, we use a few, including Notion, Airtable, Todoist, Slack, and lots of GSuite parts.)

That’s Good Work for this week. Looking forward to what’s next.

Courtney and the Holloway Team