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Draw it until it works

Here’s a quick thought about ramping up on something new as a product manager.

If I don’t understand how something works in an organization, I do two things. I ask questions, and I draw boxes and arrows based on the answers. People sometimes make fun of me for this, but hear me when I say that nothing gets people aligned like a systems diagram they can disagree with.

B2C, B2B, Platform, Internal… the industry/product type doesn’t matter. Draw the flow of information through your product, get people to disagree, adjust until they agree. That’s the moment when you become a PM that can actually be helpful to the team and the business. You cannot improve the system until you understand it.

Make better documents

This has been shared around quite a bit over the past couple of weeks, but Anil Dash has written another[1] modern classic in Make better documents. Excellent advice all around, including:

Similar to the importance of sequencing and order, you almost always want to start by clearly and simply stating your conclusion, or declaring your request or question. Very often, people feel a lot of anxiety about the need to preface their big dramatic point with lots of build-up. But you almost never want to be building dramatic tension in a professional context; this isn’t a thriller where you’re trying to surprise them with twists and turns.

And:

Similarly, you’ll want to constrain your requests to your audience to be something they can react to constructively. “Do we want to invest at the higher cost of Option A to move faster, or go with the lower cost of Option B to be more cautious?” That’s an answerable question! And it’s perfectly fine if it leads to a conversation where a third option is explored — but you never would have gotten there with a prompt that says, “What do we want to do next?”

You’re Not Managing Enough

This is a good reminder about micro-management from Judd Antin. He says that maybe You’re Not Managing Enough (a big climbing analogy runs through the whole post):

As managers, we can be so afraid of micro-management that we risk moving into passive territory. We’re made to believe our main job is putting people in position to grow, and then going hands off to give them the space to do it. But that’s like encouraging a climber to take on a harder route, cheering them as they start while you check out TikTok instead of holding fast to the rope. To do their best, that climber needs an active belay from start to finish. It’s easy to try again when the rope caught you and you only fell a few feet. These are the most educational failures — it’s those big ones that you want to avoid.

There’s some practical advice in the post on the best ways to be more active and helpful in the right ways by providing clarity and making solid plans with your team.

Have Concerns And Commit

I like this alternative approach to the old “disagree and commit” adage. That idea always struck me as a little passive aggressive (“sure, I’ll do this stupid thing you want me to do…”), whereas this seems like a more active, helpful approach:

It’s much healthier to “have concerns and commit.” Some decisions you can agree with, some you can disagree with, but most you should either just “have concerns about” or “be supportive of”. […] If you’re not sure of the answer but have concerns, you want to make sure that your feedback is deeply considered. You can tell your team that feedback was heard but ultimately the people with the most context made the call, which is how it should be.

It’s important to note that this type of culture is only possible if leaders agree to provide a lot of context on decisions (which not everyone wants to do):

As much as you have to be humble in your approach to engaging with decisions, healthy companies and leaders should provide you with enough information to be able to understand decisions in enough detail to have confidence in supporting the decision.

Why do we do things that are bad for us? The ancient philosophers had an answer

I found this essay on why we do things that are bad for us really interesting. First, I learned the word “akrasia”, which means “the state of mind in which someone acts against their better judgment through weakness of will.” Second, this is not exactly a new thing. From Romans 7:18–19:

For I have the desire to do what is good, but I cannot carry it out. For I do not do the good I want to do, but the evil I do not want to do—this I keep on doing.

Anyway, I thought this was helpful advice:

To achieve your goals, it can be more effective to put into place a defined plan that doesn’t let you reconsider. The psychologist Peter Gollwitzer called this an implementation intention: come up with a specific if/then statement that helps you achieve your goal. If it’s Tuesday, then I will go to yoga class; if I buy spinach, then I will make this smoothie for breakfast the next morning.

The great rewiring: is social media really behind an epidemic of teenage mental illness?

This is a solid essay (and book review) on social media and teen mental health that includes much-needed academic research receipts. In short:

Two things can be independently true about social media. First, that there is no evidence that using these platforms is rewiring children’s brains or driving an epidemic of mental illness. Second, that considerable reforms to these platforms are required, given how much time young people spend on them.

This point is especially important:

Most data are correlative. When associations over time are found, they suggest not that social-media use predicts or causes depression, but that young people who already have mental-health problems use such platforms more often or in different ways from their healthy peers.

Books and newsletters that shape my thinking

I recently did a first draft of my manager README and I end it with some books and newsletters that have shaped my thinking, and continue to do so. I thought it might be useful to a broader audience so I’m sharing it here as well. These are the books I keep right next to my desk, and the newsletters I open every time they arrive in my inbox.

Books that have shaped my thinking

A few newsletters I really like

I am skipping some obvious ones (like Lenny and Platformer) that everyone already subscribes to.

The media dies a little less

For anyone else following along on “The Death of Media”… There are plenty of dire stories about layoffs and newsrooms shutting down, so I like finding stories of innovation (or small steps) in the space that appear to be working. I think 404 Media is doing great work, and their latest addition of a full-text RSS feed for paid subscribers makes me very happy:

Creating this feed was logistically quite complicated. We are thankful to Maxime Valette of FeedPress, who helped us make the feed, and to Ryan Singel of Outpost, who helped us sync the paid feeds with our Ghost member list. We’re also thankful to our paid subscribers, who have made it possible for us to pay for the development work needed to offer this and have also been very patient with us as we’ve worked behind the scenes to develop this feature.

In other actually good news on the media, The Atlantic is (finally) profitable! Mostly because they went hard on subscriptions.

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