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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.

The Cure Deliver the Power-Doom Epic We’ve Been Waiting For

Great Rolling Stone review of a perfect late-career album by The Cure:

‘Songs of a Lost World’ is the triumphant power-doom epic it needed to be, fully the Cure’s best since ‘Disintegration’, as Smith reaches into the depths of his cobwebbed heart, going deep into adult loss and grief. It’s an album that begins with the line ‘This is the end of every song I sing,’ and closes with ‘Left alone with nothing at the end of every song.’ In between, he gets dark.

I’ve also slowly been making my way through the live-stream of the album release show. They definitely look the 60+ that they are, but man, they still sound incredible.

A Deadly Gravitational Pull in PLG B2B: Individual-Centric Experiences

Elena Verna on the importance of focusing on team experiences in B2B products:

The key to any successful B2B Product-Led Growth (PLG) strategy lies in connecting end-user adoption to enterprise-level deals. But because B2B PLG often looks like, smells like, and acts like consumer product, it pulls product and marketing teams into a deadly gravitation pull of crafting consumer-like experiences focused solely on the individual value. While acquiring individual users is a natural first step, failing to consider the dire need to connect that individual to a team and a company level value WILL sabotage your future growth.

Garden State was a good movie

I read about Zach Braff and His All-Star Benefit Concert for the 20th Anniversary of ‘Garden State’, and it reminded me how much I loved the movie despite all the hate it gets.

“Back in this era, the Virgin Megastore was around the corner from a movie theater in [New York City’s] Union Square,” Braff recalls in a phone interview. “And so many people were going directly from the movie theater to the Virgin Megastore to buy the soundtrack that Virgin had to put a sign in the CD slot that said, ‘We are out of the Garden State soundtrack. Please stop asking.’ The thing just caught fire.”

The Shins’ frontman, James Mercer, credits the soundtrack with transforming his career. “We have a lot of young people in our audience still, and I think it’s probably because of Garden State,” he tells Rolling Stone.

I always think of Spoon’s song Outlier as the hate example that cuts the deepest:

And I remember when you walked out of Garden State
‘Cause you had taste, you had taste
You had no time to waste

Rude.

47 (no, not that one)

I turned 47 this week. There was also an election. It was also the 8th anniversary of my dad’s passing. I know this is a Product blog, but allow me to take a moment to just say, dang, y’all. What a week. What a decade. I don’t have words for the era we are about to enter in the US. So, as always, I turn to music. Some people eat their feelings, I listen to mine.

First, I made a post-election feels mixtape on Spotify. I am deliberate about calling it a mixtape and not a playlist. There’s no specific genre, it’s all vibes. And if you do decide to give it a go, don’t shuffle. There’s an arc here.

Second, as I often do, I used my birthday to do a listen-through of as many Genesis albums as I can fit in (if you know me and my unnatural obsession with Phil Collins, this won’t surprise you). The song Undertow has always been one of my favorites, but this week it hit especially hard:

Stand up to the blow that fate has struck upon you
Make the most of all you still have coming to you
Lay down on the ground and let the tears run from you
Crying to the grass and trees and heaven finally on your knees

Let me live again, let life come find me wanting
Spring must strike again against the shield of winter
Let me feel once more the arms of love surround me
Telling me the danger’s past, I need not fear the icy blast again

We are heading into—sorry for using the word everyone is using but I don’t think there’s a better one—unprecedented times. Brené Brown says we should focus on “micro-dosing hope”. I like that. I don’t know where we’re heading, but I have to believe that Spring must strike again. And that when it does, we’ll need not fear the icy blast again.

Stay strong, friends. ❤️

“The kids are too soft”

This is another amazing AHP essay, this time about the critiques of Gen Z employees:

I’ve long argued that the critique of younger generations is a sublimated critique of a generation’s own parenting and child-rearing practices: no one wants to admit that the decisions they made (or tacitly endorsed) are responsible for the type of worker they find objectionable. But that sort of introspection requires, well, work.

It’s well worth reading the whole thing, but I also wanted to highlight the recommendations for what we (Gen X, etc.) can do about this:

So how do we break this cycle? If, upon encountering or even considering the attitude, ambition, or “work ethic” of a younger generation, your impulse begins to drift towards they don’t work like we do, my hope is we consider the following:

  • How have we, as a society — and how have I, as a leader — helped foster the conditions that encourage someone to work a certain way, with certain habits, or attitudes, or ambitions?
  • How much of my reaction is to the fact that someone is not working exactly the way I did at that point in my life — even though my circumstances were almost certainly wildly different?
  • How has our society — or our industry — tacitly agreed on an understanding of excellence that has little room for different ways of navigating the world, of making space to care for others, or collectivism just generally?
  • What if working differently is also an attempt to keep people in the industry for longer — and make the industry as a whole more sustainable?
  • What can I learn from the way they’re approaching work?

Thoughts and takeaways from the Lenny and Friends Summit

I spent the day at Lenny’s Summit with over 1,000 other product people. The line-up of talks was fantastic, but you never know how it’s really going to go. I am happy to say that the hit rate of good talks was quite a bit higher than some other conferences I’ve been to. I tried to write detailed notes, and below are my summaries and takeaways from 4 of the talks that I enjoyed the most.

There were also a couple of interviews that were really great—Lenny interviewing Shreyas Doshi, and Sarah Guo interviewing Mike Krieger and Kevin Weil (pretty cool to see two major competitors play nice on stage together)—but those were a little harder to summarize so I gave up on note-taking and just listened.

Product Management is Dead (or Will Be Soon) by Claire Vo (LaunchDarkly)

I’ll start with this one since the title is obviously pretty controversial. I expected to disagree with a lot of it, but it was actually really measured and interesting. Claire focused on the rapid transformation of product management due to AI, and outlined the need for product leaders and teams to adapt to these changes. She highlighted the evolving nature of product roles, driven by automation, and offered insights on how to prepare for an AI-powered future.

Key Insights:

  • AI Will Transform Product, Design, and Engineering.
  • AI is advancing faster than anticipated, reducing the need for traditional product management tasks and roles.
  • The key challenge is to not be caught off guard by these changes.

(more…)

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