Situation

Covenant Eyes has been helping people quit porn for over 25 years. The service relays activity from a person’s device to someone they’ve chosen to hold them accountable.

Historically, this all happened via emailed reports which were passive and static.

When we launched Victory — a reimagined version of our flagship accountability service — as a mobile app in 2021, in-app communication became possible. It was a more active, bi-directional channel which brought both opportunity and complexity.

“Check-ins” began as a modest upgrade of our traditional email-based reporting. As we realized the true potential, however, we set our sights on something bigger: a deep, self-reflective experience, helping people connect in a more effective, relational way.

Image showing we progressed from data-heavy to more informational email reports, with check-ins marking a brand new chapter in how we deliver key accountability information.

Email reports had gone through many iterations over the past 15 years, and check-ins marked a brand new chapter.

Problem

Everyone was excited by the idea of check-ins, but as scope expanded it became clear the problem was no longer feature design — it was conceptual alignment.

The team was operating in a state of “presumed agreement.”

Jeff Patton on how we go from presumed to actual agreement

Courtesy of Jeff Patton & Associates (https://jpattonassociates.com/glad-we-all-agree-2/)

Team

My role was to support the design lead by diagnosing and resolving conceptual misalignment across stakeholders.

TK

Tim

Product Designer (lead)

BB

Ben

Product Designer

AS

Aaron

UX Researcher

CM

Collin

Product Manager

SB

Sam

Director, Recovery Ed

JO

Justin

Marketing Manager

RB

Robert

Member Care Manager

NM

Nicole

VP Product

JP

John

Product Strategist

Constraints

  • Stakeholders expected concrete artifacts, while the real risk lived at the conceptual level. Tim and I deliberately paired his concrete artifacts with my abstract modeling to maintain momentum without locking in faulty assumptions.
  • The workshop was designed for in-person collaboration, with Tim facilitating. I needed to be an active participant but was not able to attend in person. We were able to overcome this, and it turned out better than anyone expected.
  • We had timeline pressure: just 3 weeks to plan and prepare, including running a series of pre-workshop stakeholder interviews.

Objective

We needed to surface and resolve stakeholder misalignment before screens or detailed specs committed us to a direction that might lock in faulty assumptions or create product debt.

Diagnosis

The team was operating under the presumption that everyone agreed. This apparent consensus masked quite a bit of misalignment and subtly stood in the way of progress.

Key fault lines included:

  • Who the experience is primarily for (hero vs. ally)
  • What information a check-in should contain
  • Degree and timing of hero control
  • Whether check-ins would be more transactional or relational

Without resolving these issues (and others) at an early stage, the downstream UI work would become a battleground where deeper disagreements re-emerged.

Approach

1. Pre-workshop interviews

I conducted six interviews with individual leaders who’d been invited to the workshop.

Diagram showing how we designed the workshop to lead from presumed agreement to actual agreement

These interviews were a foundational step toward alignment

Using lightweight prompts, I focused on surfacing these issues:

  • Individual definitions of check-ins
  • Assumptions about structure, cadence, and ownership
  • Where confidence existed, and where it didn’t

While there was generally strong agreement on desired outcomes, there was weak alignment on the information structure and mechanics that would allow us to achieve those outcomes.

2. Agenda designed to foster productive conflict

Heatmap of topics that warranted deeper debate

Interviews suggested a number of areas where disagreement was likely, but only some of those topics would be productive at this stage.

Rather than presenting solutions, Tim and I decided to frame key areas of misalignment that were worth arguing about.

The goal wasn’t consensus, it was reaching a shared understanding of tradeoffs.

3. Conceptual modeling in real time

During the first day of the onsite, I took detailed notes and created simple visual models in real time, in order to make abstract disagreements tangible and keep the discussion anchored in the right level of detail.

This allowed stakeholders to disagree productively without defaulting to screens.

Diagram showing how ally involvement will vary depending on the hero's current situation and goals

People need different things, but there's a structure to those differences.

Diagram showing how progress and motivation interact

People want progress, but it matters how we help them measure it

Key Decisions

Align on concepts before screens

We deliberately paused screen-level exploration to resolve foundational questions about what a check-in is, how it relates to reporting, and why it should exist in the system at all.

This moved beyond the organization’s default expectations for UX — and initially outside Tim’s comfort zone — but it prevented downstream decision churn and rework.

Surface individual perspectives before group dynamics flattened them

Productive disagreement is inevitable in the early stages of a project. The risk is letting it surface too late, in the wrong form.

I met with each stakeholder to prevent that from happening.

Notes from a stakeholder interview

I used a 'mad libs' format to gather peoples' answers to simple - but critical - questions

Here were my discoveries:

  • Stakeholders had a lot of thoughts about how check-ins could benefit customers, so I encouraged Aaron (our researcher) to bring a strong “customer outcomes” angle, based in research, to keep these aspirations grounded.
  • Few had a clear idea of what information a check-in should contain. They described its characteristics but not what the information would actually be. I recommended Tim get into this on day 2.
  • We have two basic types of users: heroes and allies. Stakeholders were not aligned on who we were designing for. I suggested that Tim could raise this topic and help the group find common ground.
  • Some stakeholders (including the VP of Product) had strong opinions about the structure and mechanics of check-ins, while others barely mentioned it. We would need to understand the deeper “why” behind their ideas.

Together, these insights shaped both the workshop agenda and the order in which decisions needed to be made.

Facilitate in person

Being in the room allowed for disagreement to emerge and be channeled in a productive direction. Tim’s in-person facilitation was critical to maintaining momentum once difficult topics surfaced.

How the meeting room was set up for virtual and in-person attendance

As a virtual attendee, I could show my work on the monitor or the projector

Participants were also able to do hands-on activities like sketching. This leveled the playing field and helped each person play a more active role in decisions.

Outcome

Explicit agreement

The team moved from assumed alignment to explicit agreement on the fundamentals, including:

  • Check-ins as a container for reporting
  • Relationship-building as a primary goal (vs. something we presume will happen)
  • Clear boundaries around information sharing, with an emphasis on user privacy and agency
We determined to shift the balance from just the behavior toward the relationship

The balance between behavior and relationship is at the heart of our service, and we agreed to shift that balance toward the relationship

Working definition

We arrived at a working definition of “check-in” which became a stable reference point for design, product, and leadership decisions.

Check-in (noun)

An opportunity for a hero to reflect on:

  • What they want for themselves
  • What they’ve committed to do
  • The progress they’ve made (or not)
  • What they can learn from their experience

…In the presence of another whose intent is to help the hero achieve what they’ve committed to, where:

  • The ally’s agenda is secondary and contingent on the hero’s
  • Their engagement contributes to greater motivational autonomy for the hero
  • They engage in a way that’s healthy and optimized for the long-term relationship

Successful launch

This foundation materially improved our ability to move forward, enabling:

  • Faster, more confident downstream design
  • Streamlined (not perfect!) decision-making
  • Stronger buy-in across Product, UX, Marketing, and executive leadership

The feature launched in January 2025. While challenges remained (as they always do) we avoided larger failures by addressing the right problems at the right level.

Reflection

Most “design disagreement” is not about UI.

It’s usually about peoples’ unexamined differences in one of these areas:

  1. System model: we disagree on how the system should work and why
  2. Mental model: we disagree about who we’re designing for and what they want, need, and expect
  3. Conceptual model: we disagree about how to reconcile #1 and #2

UI will amplify those differences, however, it’s not the root cause.

My role is to identify where disagreement actually lives and help teams resolve it consciously before it becomes product debt.