Plan first, then hire

Reflecting on my product management experience, I’ve realized that a PM’s attitude toward planning looks quite like the mastery curve. Young PMs oversubscribe the importance of planning because it’s a newfound super power, middle-school PMs tend to take planning easy and don’t give it the credence it deserves, and seasoned PMs treat planning with a well-reasoned religiosity.

Great PMs know that plans are useless, but planning is essential.

Most new PMs are overly prescriptive about planning. They’ve paid their dues, apologizing to customers while in the trenches of customer support or operations, and lamenting the engineers for never building fast enough.

Or conversely, they were engineers who complained in private Slack channels that their MBA didn’t know what was going on… or that their PM seemed to have the personality of a squirrel-chasing dog, altering the roadmap whenever they or their manager had a new brilliant idea.

When I was an intermediate level product manager, I misapplied the advice of Marty Cagan and was too lax with planning, under the false notion of empowering my engineering partners. After failing to start and end planning on-time for a few times, we’d developed an unhealthy pattern of flying autopilot.

The engineering team was out for a GCP conference? Sure, we’ll move planning to Monday. Running late from lunch? Sure we’ll start planning 10 minutes late. Our team’s best IC spent last sprint working on his own dev experience project? Sure looks like he got all his other stuff done. So productive!

Unsurprisingly, this led to missed KPIs, even when we’d expanded our team by hiring new engineers. We’d invested in writing JDs and interviewing, but our team was still losing our games, and the players were unhappy.

I only understood the value of planning when I analyzed how I was spending my money on food. After importing my bank statements into Google Sheets, I made a note on each line item that was an "unplanned" meal: a rushed lunch after working out, or takeout dinner after realizing I had run out of groceries.

Looking at the data, I learned that I was eating 6-10 meals per month at fast-casual places like Tabonette or grabbing takeout from the local Thai restaurant. On average this was ~$200 per month on "unplanned eating expenses".

It wasn’t that I was eating poorly (Tabonette is delicious), but as someone who enjoyed learning to cook and trying new restaurants, spending 33% of my meals on repeat takeout didn’t seem to align with my values.

Over time, I learned that this behavior mostly stemmed from unplanned social events. Last-minute meetings meant that I’d have to grab a quick lunch. Cooking dinner for friends after playing basketball meant utilizing the ingredients I had set aside for one week, and scaling up into one (delicious, but nonetheless one) meal.

To solve this, I spent the start of each week planning next week’s social events, using dinner and drinks with friends to fill up the majority of my calendar, and then filling in the remaining slots with home cooked recipes. While this took the course of several weeks to implement (and a few cheat meals slipped in between), overall I felt healthier and more creative.

On the cooking side, I was able to cook more salads and proteins with healthy fats like salmon and chicken as well as explore new 4 recipes, including a new favorite from Joshua McFadden’s Six Seasons cookbook (hint: beets). I’d also been able to eat with friends at 8 restaurants that I’d yet to experience like Mighties, Milu, and Nene’s Taqueria. Use the savings from cooking, I was able to spend at pricier restaurants with a more refined experience, including some with Michelin stars.

The most surprising benefits of planning came in the form of health and social improvements. Because I had been eating more consistently with less sodium and more protein, I was able to hit several PRs in squatting, deadlifting, and bench pressing. And because I had intentionally planned my experiences around new restaurants with friends, I’d actually expanded my social circle, creating memories around new experiences and ending up with more photos.

Reflecting on the years where I’d acted on autopilot, both personally and professionally, I now give planning the kudos she deserves. Just like how Stephen King writes about sitting at his desk in hopes of bumping into his muse every day, it’s about the ritual. Plans are useless, planning is essential.