In any organization undergoing a digital transformation, stakeholders often hold the answers—but not always in the way designers expect. At first glance, teams might assume that non-technical stakeholders require a separate stream of workshops, isolated from conversations about UI/UX, design systems, or day-to-day usability. But the truth is, a well-crafted workshop, guided by the right prompts and structure, can yield critical information across multiple layers of a redesign—brand, mission, visual systems, and functional requirements—without burdening participants with technical jargon or design theory.
We recently completed a series of stakeholder workshops with a client that gave us exactly the insights we needed—without having to run separate sessions. The client teams weren’t very technical or familiar with web terminology, but that didn’t get in the way. They still provided everything we needed to move the digital transformation forward. We’re sharing how we ran those workshops at ArtVersion, because this approach helps design teams work more efficiently and makes the process smoother and less overwhelming for clients.
One Workshop, Many Outcomes
It’s tempting to compartmentalize workshops: one for branding, another for UX, a separate session for content, and another for back-end needs. But this often leads to repetition, disconnects in the bigger picture, and fatigue among participants, especially when working with large teams. Instead, we bring together small groups of up to 12 people from across the organization—executives, marketers, IT, and administrative staff—into a single workshop. This gives us a more complete view of how the organization operates, communicates, and plans to evolve.
Rather than diving into technical details, we focused on thoughtful prompts and natural conversations. This allowed us to uncover everything from brand direction to functional needs—without overwhelming the participants or diluting the workshop’s momentum.
Setting the Stage: Mission Before Modules
To begin, it’s essential to ground the workshop in purpose. This isn’t just about “getting a new website”—it’s about evolving how the organization shows up in the world, internally and externally. We framed the session around the firm’s brand mission and future positioning. This wasn’t a brand exercise in the traditional sense—it was an alignment session.
We asked:
- What does the firm stand for today, and what does it aspire to be in five years?
- What has changed about your audience, and how have your services adapted?
- What do people say when they describe your firm—and what should they say?
These questions unlocked brand tone, voice, and even new content direction. More importantly, they created momentum and inclusion. Suddenly, stakeholders weren’t being “interviewed”—they were shaping the future.
Using Plain Language to Uncover Deep Design Needs
Design teams often ask about workflows, pathways, and interactions. But to a non-designer, these terms can feel abstract or confusing. Instead, we reframed:
- “What do people come to your site to do?” → “What’s the first thing people ask when they call you?”
- “What are your primary calls to action?” → “What do you wish people would do more often on your site?”
- “Where are the pain points in your current user flows?” → “What frustrates you most about how the current site works?”
By using the language of everyday experience, we collected invaluable data about user intent, friction points, and functionality gaps. We learned about internal frustrations with uploading documents, confusion from prospective clients trying to find the right department, and inefficiencies in routing contacts—all without referencing UX heuristics or wireframes.
Mapping Stories to Functions
One of the most effective techniques we used was story mapping. Instead of asking for features or wishlist items, we asked stakeholders to describe:
- A day in their role, and how the website intersects with their work
- A recent interaction with a client or user that stood out
- A time when something didn’t work as expected on the site
These real-world anecdotes often carry embedded UI/UX requirements. For example:
“I had to walk a client through how to find a information on the phone—it wasn’t intuitive.”
That single moment reveals three things:
- The current site architecture lacks findability.
- The firm relies on digital assets to streamline operations.
- The redesign must prioritize quick-access elements like a resource hub or search-enhanced resources.
These types of stories helped us build use-case driven requirements without needing to draw up technical specs in the room.
Surfacing Brand Through Visual Language
During the second half of the workshop, we transitioned into visual brand alignment. But again, we avoided asking questions like “What’s your preferred aesthetic?” Instead, we posed:
- “What visuals currently feel outdated?”
- “What does ‘trustworthy’ look like to your audience?”
- “What more sophisticated look and feel means to you?”
These metaphorical questions helped surface adjectives, emotional tones, and style references we could use to shape the brand refresh. Some teams wanted to appear more “approachable but authoritative.” Others emphasized “legacy with modern accessibility.” These insights became the foundation for color palette evolution, typography selection, and even how we structured visual hierarchy in the interface.
Building a Content Strategy Without a Separate Session
Content strategy is another area that’s often isolated into its own process. But during our unified stakeholder workshop, we naturally extracted content needs by asking questions that weren’t overtly “editorial” in nature:
- “What questions are you tired of answering?”
- “What’s the one thing you wish your audience better understood?”
- “What content gets the most clicks?”
From this, we learned which FAQ answers should be embedded in core pages, which pillars should be elevated in navigation, and what types of multimedia might resonate more than static content. We also uncovered outdated language and jargon that no longer reflected the firm’s values.
Translating Stakeholder Insight Into UI/UX Direction
By the end of the workshop, our design team had a full picture of:
- Brand voice and tone – From how stakeholders talked about the company and its clients
- Visual design direction – Through metaphors and outdated references
- Core user journeys – From real-life stories and usage scenarios
- Usability needs – Through frustrations and missed opportunities
- Navigation priorities – From common client questions and internal shortcuts
- Functional requirements – Through “wish list” comments framed in conversation
And all of this came from one well-structured workshop with non-technical staff. We didn’t use post-its during the workshops as most of the things were done remotely. We didn’t diagram user flows live with them. We just facilitated open dialogue, transcribed everything, and synthesized it later into experience architecture, user pathways, and wireframe plans.
Lessons for Design Teams
Too often, we assume that design thinking must be explained before it can be applied. But the inverse is often more powerful: let people express their needs, and reverse-engineer those expressions into your design process. Here’s what other design teams can take away:
1. Combine, Don’t Separate
Don’t plan for 4 different workshops if one can be orchestrated thoughtfully. A single, mixed-discipline session gives you alignment faster—and prevents departmental tunnel vision.
2. Ask Questions That Translate
If a stakeholder doesn’t understand your prompt, that’s not their fault. Rethink the language. Design is about empathy—so lead with familiar phrasing that unlocks insight without alienating contributors.
3. Make It Conversational
The more natural the session feels, the more real the responses. Avoid overly rigid structures or presentation decks. Treat it like a roundtable, and people will offer more nuanced input.
4. Listen Between the Lines
A stakeholder saying, “That part of the site feels clunky,” may be hinting at poor mobile responsiveness, a broken interaction pattern, or poor load time. Train yourself to decode surface-level feedback.
5. Capture First, Sort Later
Don’t aim to categorize feedback in real time. Let the conversation unfold, capture everything, and synthesize afterward. You’ll find patterns you didn’t expect.
Final Thoughts: Designing With, Not For
At the heart of any digital transformation is the idea that users and stakeholders aren’t separate. Everyone is a user—of systems, tools, workflows, and experiences. When we run workshops that feel more like collaborative conversations than investigative audits, we bring these voices into the process in a meaningful way.
For design teams navigating complex redesigns or brand evolutions, this approach offers an efficient, empathetic, and insightful alternative to segmented workshops. It also builds early-stage trust—essential when those same stakeholders will later be reviewing the first visual concepts, prototypes, or testable interfaces.
Ultimately, digital transformation isn’t just technical. It’s cultural. And the best way to reflect culture is to listen carefully, ask wisely, and design from the inside out.