PM’ing the Holidays
Ship the joy (just not on Friday)
The holidays are basically like shipping on a Friday: you could potentially sneak a win in before the weekend, juice your metrics and emerge a hero, or it could be an unmitigated disaster that only reveals itself in the dead of night, leading to untold headaches the next week.
In an effort to help you be a hero, here’s a guide to PM’ing the holidays.
👋 Hey, I’m Alex. I write Shipping on Fridays to explore the craft of how great products get built and what we can learn from the people behind them. I publish 1–2x a month, and every post is meant to be fun, useful, and a little unexpected; from design sprints to sailing races to holiday chaos. If you’re into learning, product or design, this is for you.
Know your Holidate
Who are you “holidaying” for? Are your in-laws coming to town? Are you going away with the kids? Is it you and your partner? Just you?
Competing segments? Prioritize, like any rational PM. Your holiday KPI? Holiday Cheer, a roll-up metric of happiness and the viral spread of jolliness.
Above, I mapped Holiday Cheer vs my confidence that I could actually boost the metric for each group. I thought about the trade-offs. For instance, focusing on my kids would result in medium cheer: they’re thrilled, but it drains the rest of us. I also rated them low confidence because they are so fickle - one forgotten candy cane and the day could go off the rails. 😕
On the other end of the spectrum, focusing on friends only and ignoring your family won’t generate too much holiday cheer (imagine the repercussions from your partner?!), but I’m highly confident I can do it really well.
The sweet spot for me is my wife (green dot above). Increasing her holiday cheer makes her a better person for my kids, parents, her parents and friends - everyone! It’s not a guaranteed win, but the upside is massive - which is why I’ve prioritized her.
Identify your Grinch
So now that we know our holidate, we must holiday them (ie increase their Holiday Cheer). How, you might ask? Is it donning a Santa Outfit? Pulling a cheesy stunt a la Love Actually?
No! Of course not - we’re jumping straight to solutions. First rule of PM’ing the holidays? Start with customer problems. What issues does our segment face over the holidays? Who’s the Grinch stealing our holidate’s Holiday Cheer?
For my chosen segment - my wife - there’s dozens of potential issues, but her Grinch is all the little stressors that stack into one sleep-stealing monster. Kid gifts, kid’s school parties, cards for teachers, mailing holiday cards, planning meals, etc. Taking these off her plate is a gift that will reduce her stress, allowing her to have more fun (a key driver of our metric “Holiday Cheer”).
Increase Holiday Cheer
From here, you know what to do. Once you’ve got your Grinch now it’s all about identifying solutions to defeat that Grinch. What will these be? More candy canes? Ensuring the latkes are served warm and with apple sauce? Maybe.
Here’s how I approached my Grinch. I went to the old PM standby: Effort vs Impact, err Holiday Cheer. On one end of the spectrum I could attempt to automate away all these small holiday stresses, which might increase my wife’s holiday cheer, but it’s not even clear I could reasonably automate everything. I settled on just silently taking on some of these tasks each day. I reasoned that disappearing the tasks without fanfare would surprise, delight and lead to larger increases in our North Star metric - Holiday Cheer.
Defeat your own Grinch
Now that you’ve got the framework, go out identify your own Grinch and ship some Holiday Cheer (just not on a Friday).





I love the practicality and humor infused. Always willing to pivot, but the realization in removing stressors from the Grinch, ultimately makes Whoville a happier place - whether at home or in the office. Share the joy!