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Regarding “missed” and “slipped” deadlines

I really like Basecamp’s concept of “Hill Charts”. The gist of it is that each project we work on has two distinct phases: a “figuring it out” phase and a “making it happen” phase:

To quote from their post about it:

First there’s an uphill phase where you figure out your approach. You have a basic idea about the task, but you haven’t figured out what the solution is going to look like or how to solve all the unknowns.

Eventually you reach a point where there aren’t any more unsolved problems. That’s like standing at the top of the hill. You can see clearly all the way down the other side. Then the downhill phase is just about execution.

“Figuring it out” is full of uncertainty, unknowns, and problem solving. “Making it happen” is all about certainty, confidence, and execution.

I bring this up because one of the issues with quarterly planning cycles and committing to due dates on that cadence is that teams are often asked to commit to dates during the “figuring it out” phase. There’s a lot of uncertainty and unknowns, so teams have to make best guesses. The problem with this is that these do not reflect what Cagan calls “high-integrity commitments”:

The key is to understand that the root cause of all this grief about commitments is when these commitments are made. They are made too early. They are made before we know if we can actually deliver on this obligation, and even more important, if what we deliver will actually solve the problem for the customer.

So what inevitably happens is that, for a lot of projects, the date that teams provided “slips”. I believe this language matters, and I think by framing it this way an org tells teams they did something wrong. But the irony is that in the majority of cases, if teams move a date after they reached the “top of the hill”, they are doing the right thing for the business. They are saying that they have now figured out all the unknowns and uncertainties, and they are ready to make a high-integrity commitment. Again, here is Cagan:

So the compromise is simple. The product team asks for a little time to do product discovery before commitments are made, and then after enough product discovery is done to consider the risks, we are willing to commit to dates and deliverables so our colleagues can effectively do their jobs as well.

I think it’s important to encourage behavior that does the right thing for customers and the business. The right thing would not be to try to cut corners to meet a date that was committed to during a “figuring things out” phase. I also don’t believe the right thing is to inherently communicate to teams that moving a date once they reach the top of the hill means they “missed” a commitment.

I think we should be very clear about the nature of commitments when we make them. What is our confidence in our dates? Are we still figuring things out? Or are we at the top of the hill and ready to make a high-integrity commitment? The health of any Product org can be improved if we say that it’s ok to communicate what we think we can accomplish early on in the quarter, and move to high-integrity commitments once teams reach the top of each project’s hill.

My 2024 in Music

I love reading end-of-year music wrap-ups from the personal blogs I follow (two highlights this year include the posts by Sarah K. Moir and Simon Collison), so I wanted to make an attempt at my own as well. I decided to wait until Dec 31 so I can have accurate data from my Last.fm profile, where all my listening stats go (I use Spotify and Roon for streaming, and I also send my physical media listening stats there).

So according to my listening stats, here are my favorite releases from 2024 (plus two standouts from earlier years that I discovered this year and became obsessed with). Links will take you to my side project site Listen To More with some more info about each album.

#1 – A LA SALA by Khruangbin

A return to super chill vibes from the Texas indie soul trio, this is #1 in listen count because it’s a beautiful album, but it’s also wonderful dinner / hangout music. So we put it on a lot over here.

#2 – Songs Of A Lost World by The Cure

Only #2 in listen count because it was released so late in the year… This is my personal Album of the Year. What a gift to get this absolute masterpiece so late in The Cure’s career. If Endsong is the last song they ever make, I will be happy. “Left alone with nothing at the end of every song”. Dang.

(more…)

A career ending mistake

This is lovely post by John Arundel (“Come for the schadenfreude, stay for the thought-provoking advice” indeed!). I especially like the section on how to become a good manager:

If you want to become a great manager, which I think is the only kind worth being, start practicing now. Learn people skills, communication, collaboration, psychology. Work on understanding the things that make different kinds of people tick. Manage yourself excellently. If you can’t organize yourself, how do you expect to be responsible for a team?

Code shufflin’

In Code shufflin’ Robin Rendle writes about why he, as a designer, still messes around with coding projects. I think this is why I continue to obsess over my side project as well—and proactively reach out to indie devs who use the Cloudflare platform to see if I can help.

I’d forgotten what it feels like not to ask permission for changes and instead make pull requests and break things. There’s a momentum to this sort of work that I crave deep down in my bones because it doesn’t rely on meetings or six months of quarterly planning or going up the chain of command. And what I love most about shuffling code around is that every day there’s progress, every day there’s a tiny degree of success you can point to.

How Murderbot Saved Martha Wells’ Life

I love the Murderbot books, and this interview with author Martha Wells is a delight:

Of all her characters, Wells has said, Murderbot is the one she’s put the most of herself into. It’s a surprising claim, until it’s not. It’s obvious that Wells feels a distance from other humans, even as she’s spent a life trying to relate to them, to understand them.

The cruelty of gentle parenting

This is a really interesting rebuttal of some modern parenting methods by Marilyn Simon:

The job of the parent is not to prevent any potential “trauma”, it is to love the child even when they are bad, and to punish them, and most importantly to forgive them. A child can’t understand the lightness of forgiveness without understanding first that one needs it.

How to Make Planning Better

Lots of great planning advice in this First Round article. There are two things related to Strategy that I especially like. First, this definition (Strategy is not a vague vision statement!):

Strategy is the sequencing of how you take a very long-term end goal and break that down into more digestible components. Done right, it gets you a really clear picture of what’s in your long-, mid-, and short-term plans, where you stack up in the market, and how you’ll win.”

And then, the importance of org design in executing that strategy well:

Org design is how you deliver on your plan. Instead of meticulously planning all of the ‘what,’ the right org design will give you the ability to hand a talented group of people a new goal, and have them continuously come up with the best way to achieve it.

The post also covers another topic I’ve been thinking about a lot, which is the cadence for planning, and how to make the quarterly (or however often you do it) planning cycle less painful/stressful. We’re in our annual planning cycle right now—once we’re done I will write a post that touches on these topics, and more.

What does a date actually mean?

James Stanier has a good argument for why deadline-driven development is so… difficult:

Given that non-technical people don’t understand why software is hard, dates become the stick that they beat you with when you don’t deliver on time. Don’t ask me why, it’s just human behavior. I’m sure you’ve done it when roadworks have taken longer than were specified on the sign, or if a delivery of a package was late. Dates mean something to people, so handle them with care. In fact, perhaps we could do something entirely different instead.

What’s the “something different”?

So, instead, you should take a forecasting approach that follows the uncertainty curve that we outlined above. You start wide, and you taper in. At the beginning of a given project, you might even just have the year that you’re aiming to ship. Then, as you progress, you can start to narrow it down to a quarter, then a month, and finally a specific date.

This is why I will always advocate for time horizon roadmaps.

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