---
title: Undercover Founder
teaser: 'Drift can happen between business goals and boots on the ground. When that
  happens, problems arise.

  '
tags: user experience,user research,product design
author: Eric Bailey
published_on: 2021-01-05
---

Let me first say that [Undercover Boss][undercover-boss] hurts people. It is an
exploitative mess that rubs our collective nose in many socioeconomic
inequalities, and should have never been given airtime. Websites and apps,
however, aren’t people. They are built by people, which is an important thing
we’ll get to in a bit.

If you’re not familiar, Undercover Boss is a TV show where the owner of a
company goes out and spends time with their employees, <i>The Prince and the
Pauper</i>-style. The boss then learns about how the business is run, resumes
their mantle, and then doles out rewards and, uh, working condition
improvements. Lessons are learned, talking head shots are recorded, and
everything wraps up in a tidy 30 minutes.

One of the points the show makes—the sole point I think is redeemable—is that
drift can happen between business goals and boots on the ground. When that
happens, problems arise. You might see where I’m going here.

Generally speaking, [the web is a mess][web-mess]. Apps are starting to get that
way, as well. For example, here’s a website that’s checking all the business
need boxes, but is what we in the user experience industry would call “a
godforsaken trainwreck.”

![A mobile website completely obscured by overlapping banner ads, auto-playing video, sponsored content, and miscellaneous widgets.](https://images.thoughtbot.com/blog-vellum-image-uploads/tAgcXh9bSUqlKfmrophA_a-godforsaken-trainwreck.png)

## Going undercover

If you’re in charge of a digital product, here’s a challenge: go undercover. No,
I am not saying you should pretend to be a new developer, designer, product
manager, copywriter, etc.

What I am saying is that you should look at the state of your product with fresh
eyes. Forget things  like your OKRs, your ROI, NPS, burn rate, and your growth
curve. You need to turn off your business objectives
[Terminator-vision][terminator].

Look at your product. I mean, *look at it*. Resist the urge to break it apart
into its component pieces and consider the experience as a holistic whole
instead.

## The map is not the territory

Put yourself in the mindset of [who you imagine your target customer
is][personas]. Ideally, try to do this outside of your working hours. Get a
snack, throw something crappy on Netflix, and do some multitasking. Try to
have a verbal or text conversation with a family member or friend.
Maybe [get a little tipsy][drunk], as well!

The idea here is to [shake your connection to your product][shake-connection],
and instead try to achieve the mindset and flow state of a normal, busy person
who has multiple competing concerns demanding their attention.

Now, try and do the main thing that makes your product money. Do you need to
create an account to get there? Do that. Do you need to add payment information?
Do that too.

Take notes about what gets in your way—you don’t even need to know the official
name of it, just a quick description or sketch is sufficient. My personal
favorite here is the survey prompt that fires before you conduct the action
you’re supposed to give feedback on. Does something take forever to load? Write
that down as well.

All of these notes represent [friction][friction] that keep your product from
delivering on its core value.

## Lies, damn lies, and statistics

How did we wind up here? There’s usually a main culprit.

A lot of companies double-down on [quantitative metric][quant] gathering tools,
as they’re easier to generate. While quantitative information *is* valuable
information to collect, understand that collecting it at the expense of ignoring
qualitative experiences means you avoid uncovering the big-picture things
blocking success.

If you’re not convinced, know that [quantitative metrics in a vacuum][vacuum]
can also run into a few large problems. Don’t take my word for it, either.
Here’s a great article from one of the world’s preeminent experts on user
research:

<figure
  role="figure"
  aria-label="Risks of Quantitative Studies, Nielsen Norman Group">
  <blockquote>
    <p>
      Number fetishism leads usability studies astray by focusing on
      statistical analyses that are often false, biased, misleading, or overly
      narrow. Better to emphasize insights and qualitative research.
    </p>
  </blockquote>
  <figcaption>
    <p>
    <a href="https://www.nngroup.com/articles/risks-of-quantitative-studies/">
      <cite>Risks of Quantitative Studies, Nielsen Norman Group</cite>
    </a>
    </p>
  </figcaption>
</figure>

Jakob Neilsen does a far better job explaining the potential pitfalls than I
ever will—it’s well worth a read.

## Don’t get mad, get curious

Remember when I said that websites are built by people? Don’t take out your
frustration on them. Sit with your emotions for a bit. Understand that the
friction you’ve identified is a manifestation of your direction, and this is
usually the best attempt to translate the abstract into the actual given the
resources made available to them.

Make no mistake: this sobering moment presents an opportunity to refine your
user experience. This is a gift.

## Don’t jump to conclusions

Resist the urge to upend everything and start again. Redesigns are a tricky,
delicate thing. You need to balance rolling out improvements with not alienating
the people who already use and rely on your product—I’ve seen more than one
large, popular website fail because of this.

You’ll want to [start with the problem][start-problem] when detangling things.
The idea behind this is to shake out underlying concerns and motivational
factors. This will help treat more of the cause, and less of the symptoms.

I’m also not so arrogant as to suggest a visual refresh will fix everything.
Oftentimes these surface-level issues are the manifestation of a tough business
decision, and is [the least-worst call][least-worst] someone can make in a bad
situation. Changing a 3 pixel border radius to 5 simply won’t address the
problems that need to be dealt with.

Another common pitfall is treating your product like a series of snapshots, and
not a living, breathing ecosystem. Those least-worst call implementations I just
described are often released in a vacuum, and then never revisited. Taking a
broad, cross-silo look at the situation may identify shared pain points amongst
these disparate solutions, which creates [opportunities to solve once for
many][lateral-thinking].

## The micro is the macro

While it is good to fight analysis paralysis and break things down into the
smallest possible actionable tasks, you also don’t want to forget the bigger
picture. Employing a variety of [qualitative research methods][qual] can help
check to see if you’re on the right track.

And what is that bigger picture? It’s the people who use your product. Freeing
yourself of a tail-wagging-the-dog mentality opens you up to listen, really
listen to what they have to say about the experience. It might be shocking at
first, and it might hurt, but you’ll probably learn a whole lot.

## Be the change

Armed with knowing what your problems are, the structural and experiential
changes that can help address them, and the metrics that can verify it, you are
well-positioned to empower your employees to go about making positive change.

Know that this might take time, and there might be missteps. That’s okay!
Fostering a culture where experimentation is encouraged actively pushes against
a culture of doubling down on optimizing the wrong things.

You also don’t have to go it alone. thoughtbot has years of experience helping
companies of all sizes create successful projects. If this sounds like something
you’d like help with, [get in contact today][hire-us]!

[undercover-boss]: https://en.m.wikipedia.org/wiki/Undercover_Boss_(American_TV_series)
[web-mess]: https://youtu.be/OFRjZtYs3wY
[terminator]: https://youtu.be/zzcdPA6qYAU
[personas]: https://thoughtbot.com/blog/using-personas-in-the-product-design-sprint
[drunk]: https://austinknight.com/writing/ux-insights-from-a-drunk-guy
[shake-connection]: https://thoughtbot.com/blog/the-world-does-not-revolve-around-your-product
[friction]: https://measuringu.com/cost-task-failure/
[quant]: https://www.nngroup.com/articles/quant-research-practice/
[vacuum]: https://www.uxmatters.com/mt/archives/2021/01/potential-dangers-of-becoming-data-driven.php
[start-problem]: https://thoughtbot.com/blog/start-with-the-problem
[least-worst]: https://themargins.substack.com/p/taboola-outbrain-and-the-chum-supply
[lateral-thinking]: https://blog.makingsense.com/2018/01/something-to-try-this-2018-lateral-thinking/
[qual]: https://measuringu.com/qual-methods/
[hire-us]: https://thoughtbot.com/hire-us
