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Deciding Where To Enter

Often as a startup or engineer within one, you will be asked to figure how to fix a broken system, rather than create a new system from scratch. While it is important to know how to map a business workflow, it is just as important to develop a sense of where you should intervene to have the greatest impact on your customers and positive effects downstream.

Yep, kinda like that. Not!

The entry point is always the same: a moment of struggle. As humans, we are very sensitive to bio-cost. We value experiences that help us conserve our energy and dislike ones that make is expend valuable energy needlessly. Struggle is a needless expenditure of energy.

Bio-cost is the energy, attention, and stress that people expend over time to achieve their goals—to get what they want” [Ashby 1956]

It's also really easy to find struggle, once you go looking for it. Simply ask your friend to open up their favorite social media app and use it like they usually would, but stop before actually posting. When doing this have her think their thoughts aloud as she's doing it, especially when they're feel frustrated with some feature of function. Give her a few minutes to do this and watch carefully as they struggle.

Pretty quickly you will see that there are many moments where the experience creates different levels of struggle even in apps we use every day, but we tend to ignore them and cope. Lifting this veil and actively looking for the feeling of struggle in yourself and your customers is the first step to decide where to intervene in an existing experience.

When you do, you may find that there's tons of struggle underneath. It just that we choose not to see because we are wired to cope rather than come up with solutions. It takes significantly more mental energy to keep a frustration alive and act on it than it does to ignore it and work around it.

That is not to say we do not register struggle. We feel it every single time but choose to ignore it. As engineers and startups, this is where you start thinking about change. Whether its a new or existing workflow, go through the process your customer would yourself and notice where you feel frustrated. Only then watch your customer go through the same experience. Patrick Collison, founder of Stripe advises you to "find unnoticed pain and build a business to solve it"( his interview is worth listening to in its entirety).

One way to give voice to this frustration is to complete this sentence when you come to a moment of struggle: Why Can't You ____________ ?! This is you asking the interface, "Why can't you _________ ?!".


On Facebook ( which I no longer use ) my why can't you's sounds like:

1. "Why can't you show only the people I really care about ?!"

2. "Why can't you connect me to new, authentic people who have something in common with me?!"

3. "Why can't you stop showing me posts which make me feel bad about myself?!"

4. "Why can't you show me posts that force me to consider the other person's point of view?!"

5. "Why can you show me and my close friends the same feed so we have something to talk about ?!"

6. "Why can't you help me renew my relationships with friends I care about on a regular basis?!"


The Why Can't You's cut to the heart of the matter and gives a voice to your customers' struggle. Notice that my struggles run the range from what I see to what I find missing. This is because my emotions are involved and they have their own intelligence. I have an unstated intention that is being frustrated and my emotions bring that to the surface.

The Why Can't You cuts to the heart of the matter and gives a voice to your customers' struggle

How do you decide which struggle to take on? Simple. Discuss within your group which struggle would create the biggest ripple downstream and make a positive difference to your customers lives? For instance, amongst all the things Facebook could do to "fix Facebook" the biggest ripple and the most benefit to society would be to make sure that filter bubbles do not exist. That you and I are seeing the same information so we have a common basis for having a conversation. If every newspaper had different news, we would never be able to have a meaningful conversation. That's item 5. I would even settle for just my close friends and family having the same feed so the people who matter to me are seeing the same feed.

A way to test the validity of your selection is to play out what would happen as a consequence of this intervention. This is a series of If We.. Then.. statements.


Here's how it works:

If We: show the same feed to friends and family

Then: the group will have something in common to talk about

Then: the group will be able to have discussions on what they like and dislike

Then: the group will be able to have constructive conversations amongst themselves

Then: the group will be able to form informed opinions based on dialogue

Then: the group will be less vulnerable to manipulation from the outside

Then: the group will show more solidarity when faced with inflammatory posts


Do you see the size of the ripple increasing as you move further downstream? The If We..Then.. makes the downstream ripples visible so you can process the implications of the change. You rely on your natural tendency to think in scenarios to come up with these. One "then" leads to the next in increasing circles of impact.

The If We..Then.. makes the downstream ripples visible so you can process the implications of the change.

Off all the places you could enter to fix Facebook, this, in my view, would be the most powerful since it has the largest effect on the most number of customers. That does not mean doing it is easy; filter bubbles are baked into its business model and they will need to do some serious soul-searching before they do this on what's more important: revenue or democracy.

But then any significant change is never easy. If it was, someone would have done it. At the very least, this approach will pull the wool back from over your eyes and allow you and your team to see clearly the consequences of what you choose to fix in a workflow. I cannot promise you it will not leave you dazed, but I can promise you it will leave you energized.

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