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Picture credits: Dash

I originally published this on my personal site.

“Should I learn how to code?”

Before starting my first PM role, I read as much as I could about the skills it takes to be a successful PM. “Should PMs learn how to code?” was the one question that kept coming up. So many product managers agonize over whether they should learn how to code.

However, I wonder why PMs don’t agonize over learning design as much as they do about development. …

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I’ve always thrived on having structure. When I was a breakdancer in high school, I set a practice schedule. I’ve practiced a 9–5 workday since I was a college student. Today, I do weekly, monthly, and annual reviews.

“Isn’t all this restricting, Tim? Are you ever spontaneous?”

I’ll admit. My way of structuring my life isn’t normal. I think my craving for structure came from realizing as a kid that I didn’t achieve my goals if I didn’t have structure.

However, I believe it’s human nature to thrive in structure. In this essay, I’m going to share some thoughts on how there’s no such thing as a structureless person, how structure is paradoxically freeing, how structures should develop organically, and how negative emotions that come from structure are an opportunity to reflect. …

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“Fishermen” by Ang Kiukok, 1992

I originally published this on my personal site, here.

The phrase “bias towards action” is popular in knowledge work. It means do something before overanalyzing what you should do.

I’m not sure who officially coined the phrase, but Google and Amazon made it popular. From Amazon’s values:

Bias for Action: Speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.

A bias for action is useful. Especially in organizations that have a tendency to plan and are resistant to trying new things. …

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I originally published this on

In remote work, we communicate primarily through writing. We send messages in Slack. We document projects in Notion. We send meeting invites with a written description of the purpose. We’re writing all the time.

Many organizations are working from home at the moment. Thus, writing is even more important.

Here’s why.

Writing saves time.

Take this contrived example: You have a distributed team. Most of them live in SF, but one member lives in London and another lives in Manila. Both the London and Manila teammate couldn’t make a Very Important Meeting because of time zone conflicts. No one wrote up a summary of decisions made in the Very Important Meeting, so the London teammate reaches out to the Organizer to schedule a Meeting After the Meeting to catch up them and the Manila teammate up on the Very Important Meeting. …

What separates bad collaboration tools from good ones

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In our time of social distancing and working from home, workplace collaboration software has become clutch.

For instance: Zoom’s worldwide downloads has skyrocketed from 90,000 in January 2020 to 343,000 in March.

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Similarly, Slack’s number of simultaneously connected users grew 20% between March 17–25. That’s 12.5 million simultaneously connected users in total.

The shift to organizations working from home has put tremendous demand on collaboration software to help these organizations continue to get their work done.

But even before the coronavirus outbreak, workplace collaboration remained a popular category. Gartner, a leading research and advisory company, estimates that the collaboration software market is expected to be $4.8 billion by 2023. Both Slack and Zoom IPO’d in April of 2019, paving the way for cloud-based collaboration tools to make it big. This is a confirmation of current workplace trends: more remote work, more distributed teams, and the need for organizations to remain adaptive in today’s rapidly changing environment. …

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I originallly published this on

My role as Product Strategist at Sanctuary Computer is a bit more nuanced than the traditional “PM” role: I help define the strategy of the products we design and develop for our clients. It’s a pretty unique role, largely because we offer product strategy as its own offering, which is rare for small studios to do (usually product strategy is part of a larger product design offering).

Since I started this role in August 2019, I’ve subconsciously been wrapping my head around my own point of view on what product strategy is. …

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“Outcomes over outputs” is an axiom in tech. Yet most companies are still output-focused.

Last month, I wrote an essay that tried to understand why so few companies work in an outcome-focused way. I came up with three reasons:

  1. Maximizing outputs are rooted in larger systemic forces.
  2. Meaningful change starts with experiencing the cost of not changing.
  3. We bias towards action at the expense of making sense of our context.

I asked others for reasons they’ve seen, and folks’ responses got me to think more bit more about it. …

Good product & org design assumes that people do the right thing.

Salt and pepper shakers shaped like hourglasses
Salt and pepper shakers shaped like hourglasses
Let me just pour salt and pepper one grain at a time. (Source)

In 1960, social psychologist Douglas McGregor developed Theory X & Theory Y—an idea that revolutionized the way we think about management.

The idea is that a manager’s beliefs about how people are motivated affect how they manage.

Theory X managers assume the following:

1. Work is inherently distasteful to most people, and they will attempt to avoid work whenever possible.

2. Most people are not ambitious, have little desire for responsibility, and prefer to be directed.

3. Most people have little aptitude for creativity in solving organizational problems.

4. Motivation occurs only at the physiological and security levels of Maslow’s Needs Hierarchy. …

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Image credits to Anton Repponen.

While “teaching” and “coaching” are often used interchangeably, it’s helpful to think of the two as different.

Teaching a person/team when they have prior experience with the thing you’re teaching them can backfire. They may be less receptive to new ideas you introduce since you weren’t aware of their knowledge level. They may even trust you less.

On the flip side, coaching a person/team before they have any knowledge or experience on the thing you’re coaching on can also backfire. “You’re leaving me with more questions than answers. Just tell us what to do!” …

Why many companies still maximize output.

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The tech industry holds “outcomes over outputs” as an axiom.

Outputs are what we build. They’re the features we ship, the user stories or epics we produce, the bugs we fix, and the code we put into production.

Outcomes are the differences we make as a result of our output. They’re the user problems we solve, the possibilities we discover, and the behavior we change.

The reasons for focusing on outcomes instead of outputs are clear:

  • We’ll save time. We don’t spend time working on features that don’t produce the result we want.
  • We’ll stay customer/user-focused. Customers don’t want features, they want their needs met. …


Tim Casasola

Product & organization design. Product strategy at Sanctuary Computer. Writing now at

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