Inclusive Software

Data Science That Listens. See opportunities to broaden the variety of people you support with solutions. Measure their success at their goals. Indi Young’s empirical method.

Critical Thinking Requires Awareness

Indi Young
Inclusive Software
Published in
9 min readMar 14, 2025

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😆 So now that our use of AI has reduced our critical thinking skills🤔 (hopefully not true), maybe it’s time to explore what goes into critical thinking. Why? Because our orgs make expensive mistakes without it.

Here’s an example. I added a new foundation at the bottom of Maslow’s Hierarchy of Needs called “Caring for Others.” It means taking care of others first, before taking care of yourself. I want to see what you think.

Maslow’s old pyramid of needs, with a new layer at the bottom called “caring for others.” This means someone takes care of another before taking care of their own physiological needs. And lots of viewers might think “women” do this, so there’s a comment next to the lowest layer of the pyramid with three faces, one of which has a mustache, saying that if you thought “women,” then you will want to read the essay.
This pyramid is a good example of a thrilling simplification.

It’s a trap. I expect a bunch of people to think, “Oh, for women this would certainly be true. They take care of their kids before taking care of their own needs.” Except gender does not cause people to care for others. And kids are not the only ones being taken care of. Caring first for others appears in all kinds of genders.

In fact, I’ve never been a fan of this pyramid of human needs because it is so generalized and normative. Tons of us have a variety of different priorities.

Humans See Patterns & Make Decisions Fast

This essay is about our very-human tendency to make assumptions about people.

I want to help us change our first reaction from “this is a thrilling simplification” to “there are all kinds.” If we set aside the idea of “women” in reaction to the altered pyramid above, then we can step back and think critically about what we actually want to accomplish.

But let’s not make this about gender. Assumptions happen in all sorts of situations.

The Employ-Your-Kids Scheme

This next example shows someone making assumptions about others in conversation. It is just social conversation, but conversation is the root of how our teams collaborate. (Unless your org is hierarchical and does not encourage conversation. In this case your org’s culture may not allow for critical thinking.)

The setup: I was one of the first four people to arrive at a meetup. The other two people were design leaders in Silicon Valley. We stood in a little group to introduce ourselves.

The conversation flowed through little topics until one of them said, “There’s this service I just ran across that’s interesting. Your household is a business. And this service has a way for you to specify payments to your kids for services rendered. Age-appropriate services, like for a five-year-old it would be sweeping.”

I missed the next bit because I was sidetracked by the statement-of-fact at the start: “your household is a business.” (Yes, and five-year-olds sweeping.)

My emotional reaction was this: my household is the last place I want capitalism and “increasing my profit at any cost” to influence decisions. It’s where I want to emphasize supporting neighbors, celebrating, playing … wait. I’m not paying attention.

I quickly tuned back in. The person was saying, “The service will issue 1099’s to your kids and track payments over the whole year. And it only costs $20 a month. That’s hardly anything.”

Okay, hang on. 1099’s to your kids? Aren’t there child-labor laws that would prevent you from issuing 1099’s to kids? I was still distracted by doleful five-year-old doing their sweeping chore. By the way, 1099’s are the way we signal to the US Internal Revenue Service that someone earned income from us, and that this someone might need to pay taxes. 1099’s kick in when you pay someone $600 or more. I was thinking $600 a year must be higher than most households would be paying each kid (outside of giving their them an expensive gift each year). And the $20 a month subscription — that’s a significant cost to most people.

I was fixated on the numbers, so I asked, “This must be a service for the high-income household?”

There was a pause. They looked at me. I must be missing something, so they filled me in. “You put the money in a custodial ROTH IRA, which is a tax-free account.” I nodded. A ROTH is a US instrument for retirement savings where you don’t pay taxes on money you withdraw when you are retired. You pay taxes on what you contribute. They said, “So your payments to your kids go into this ROTH account.” Huh. “I’ve never heard of that for a kid,” I said. They must think I was really out of touch.

Instead, their energy picked back up. “Well, this service helps you do it, and you get to write off the payments as expenses for your household.” Their eyes gleamed. Now the fog was clearing in my mind. It’s a tax write-off. A loop-hole. The service this person was excited about helps high-income households avoid taxes.

In theme with this essay, I wanted the person talking to be aware of their assumptions:

  • Most people aren’t in a high-income household.
  • Not everyone has kids, or kids in an eligible age range.
  • Not everyone is comfortable using loop-holes to avoid taxes.

My face must have shown my emotional reaction, because they changed topics. Then an old friend of mine dropped by to say hello. The two Silicon Valley people ducked out of our conversation to go get drinks and find somebody more fun to chat with.

Later I looked around the internet to see what I could learn. The initial statement-of-fact, “your household is a business,” is typically used to encourage people to track expenses, avoid overspending, and save for future expenses and mishaps. When I searched on “help me with taxes by putting money in ROTH IRA for my kids,” indeed a host of investment firms like Fidelity & Schwab showed up, along with advisory sites like NerdWallet and Investopedia. Anyone of any income level in the US can do it, and it looks like kids can take the money out long before they retire. But the trick about tax-evasion via the 1099’s seems unique to this service that was mentioned. And, apparently the IRS “is well aware of this common scheme.”

Becoming Aware of Assumptions

Let’s presume the person in the example genuinely wanted to help people at the meetup by spreading the word, and was simply not aware of the scheme-i-ness of the $20/month service. If they had started the conversation with, “do you have kids,” or “are you open to using tax loop-holes,” then their intention of being helpful could be more successfully applied to people who say yes, and avoided for people who say no.

You can ask about assumptions like this in your team conversations at work. You can ask about assumptions with decision-makers as you explore ideas together. It is possible to develop a culture-wide habit of thinking “there is variety,” which then highlights assumptions you might have missed.

Awareness of assumptions, and asking about them, is the first step to critical thinking. What’s going on here? What do we want to accomplish? It’s a lot easier to see where you are going when you highlight and explore your assumptions.

Starting with awareness also allows your org to improve the value and outcome that people receive from your solutions. If people are able to accomplish what they are intent upon, that will bring value to your org. (But this concept is not in fashion with decision-makers.)

The Popularity of Throwing Darts at the Wall

Most of the orgs in tech measure themselves by internal metrics. How quickly can we do this? How much cost can we shave off? How can we lower turnover and bounce? We want better numbers in time for next quarter’s report. Naturally, making quick decisions comes with this culture. Move fast and break things. In this culture the goal is to “get ahead.” (It’s not popular to say, “Let’s provide support that is of value to people.”)

Human prowess at seeing patterns is tied up with our brains’ ability to make quick decisions based on the patterns. (However our ability to doubt or pick apart the patterns is also not popular these days.)

And we can’t change what’s popular.

Or can we?

Aside from Waiting for Disastrous Examples

We might get some (exponentially) disastrous examples pretty soon.

Many AI start-ups are based on assumptions about what people and orgs value. (Privacy? Security? Reliability? Deeper models rather than simulating appearances?) Too often it seems like their founder had an idea in the shower, “validated” it by talking “to” a couple of potential customers, and got millions in funding from investors who are clearly only playing a numbers game.

Investors throw so many darts at the wall that one will hit a bullseye some day. It doesn’t matter to investors which dart or which bullseye.

The numbers game doesn’t make sense to the rest of us, because we can’t fathom the oceans of money investors are working with. In our little bucket of millions, costs count.

In the meantime we can help our teams recognize the assumptions.

To do this, we add a third category of goals to what teams track. The added goals measure value-to-people. They measure people’s outcomes according to their thinking, emotions, and personal rules.

Trio of goal types, dependent on one another:

  1. Outcomes for the org (OKR’s and their KPI’s)
  2. Outcomes of what the solution produces (if it does what we expect and designed it to do; e.g. evaluative research, and tweaking via testing)
  3. (currently missing) Outcomes for people in terms of the larger thing they are trying to address or accomplish (value-to-people measurements)
Diagram showing towers like in a city skyline with sticky notes under some of them, representing an orgs capabilities in support of those towers. Sparklines appear below the towers, too, showing measurement per tower of how much the capability supports the intent of people’s focus in that tower.
Sparklines measure value for two different categories (thinking styles) of people.

Measuring Outcomes for People

Orgs have always wanted to understand how much customers “like” something or whether they will “recommend” it to others. But people’s outcomes are a level above. Outcomes are about how well people have been able to address the larger thing they were trying to address.

When we have this third type of measurement, our orgs gain magical abilities.

  1. Pivot Easily: When the AI start-up meets measurements in #1 & #2, currently it looks good in the investors’ portfolios. But if that start-up fails in #3, founders and investors can see it and pivot to something that will meet #3.
  2. Pivot Before Spending: When strategic research provides knowledge up front, and #3 is not met, a pivot can happen before our little bucket of millions are spent.
  3. Accelerate Time-to-Value: Knowing value-to-people up front helps an org “capture the market” earlier than it would have if it went through the whole process of launching a “dart thrown at wall” solution.

It also helps the org make something of lasting quality with valuable outcomes to people. (Which also isn’t fashionable right now — this is a secondary argument. But it might catch on when orgs see the value being reflected back on them, especially in comparison to disastrous outcomes.)

Your org will do better and last longer because of awareness of assumptions.

Thrilling Simplifications

Sam Ladner has been writing about “stylized facts,” which are thrilling simplifications that we use to catch the attention of people at our orgs. For example, “Less than half of women care first for another before taking care of themselves.” “About half of near-miss incidents don’t involve a car.” “3 out of 5 employees believe that working extra hours will shield them from being laid off.”

There’s a reason for catching people’s attention, and it’s not just to thrill them. It’s to highlight assumptions and explore what deeper variety exists. We catch attention, show what we learned about assumptions, and thereby help build the habit of thinking “there is variety.” This habit shifts culture toward thinking critically about what we actually want to accomplish.

Critical thinking about where we’re headed is really good for the org. Instead of just guessing with our little bucket of millions, we can see clearly how to capture the market with something of lasting quality. (And we can see when it’s healthy to do our work without investors and their reassuring oceans of money.)

Catch Attention — Show Assumptions — Shift to “There is Variety” — Invite Critical Thinking — Improve Outcomes in all 3 categories

It’s not about research; it’s about adding a measurement: value-to-people.

The new measurement is based on strategic research, but don’t tell anyone. No one but researchers want to know how the sausage is made. People just want the sausage. (Unless it’s breakfast sausage delivered via insulated pods from Google. 😆)

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Inclusive Software
Inclusive Software

Published in Inclusive Software

Data Science That Listens. See opportunities to broaden the variety of people you support with solutions. Measure their success at their goals. Indi Young’s empirical method.

Indi Young
Indi Young

Written by Indi Young

Qualitative data scientist, helping product teams clients find opportunities to support diversity. Books https://indiyoung.com/books/