indigo insights

The art of retrospective sessions

How Jung’s shadow work helps tackle complex digital projects

By Fran Ramirez, Senior UX Designer

A boat floating in a whimsical blue and purple body of water.

In the slow grind of digital product development, the work gets tough. There are missteps, miscommunications, and technical failures—both big and small. Yet, within this rough terrain lie all the growth opportunities. The only way to face challenges, learn, and improve is through clarity and truth. The best tool for this? An honest retrospective session at the end of each project phase.

Retrospective sessions are about more than just the work. They're about the people behind the work—the raw, unspoken emotions and unacknowledged frustrations. Complex digital projects often stretch teams to their limits. Clients, developers, designers, and product managers all speak different languages, yet they must walk the same tightrope, balancing vision with implementation. This is where retrospective sessions get a little uncomfortable; people often hesitate to speak their minds, fearing they might damage internal relationships. However, retrospectives should be a safe a space for reflection, honesty, and, above all, growth.

The method I suggest for these reflections is inspired by Carl Jung’s principle of shadow work— the idea that we must face what’s hidden, uncomfortable, or repressed within us to fully understand ourselves and improve. The same applies to teams: only by confronting our collective shadows—the frustrations, missteps, and miscommunications—can we become better, stronger, and more aligned. So, here’s how to conduct a retrospective using this approach:

1. The icebreaker: easing into the storm

A meaningful conversation starts with trust. The retrospective begins with each participant introducing themselves and answering a simple icebreaker question. It should be something light-hearted: What’s your favorite ice cream flavor and why? Or if this project were a film, what would it’s title be? This is not the time for heavy discussions but rather a way to get people talking and feel comfortable.

The key here is safety. If everyone feels safe, the real work can begin. You don’t dive into the storm without first checking the weather.

2. Objectivity first: what actually happened

Next comes the objective review—pure facts, no emotion. The moderator sets the tone ensuring that we lead with respect. Each team member shares what they did during the project focusing solely on the facts:

What tasks were completed?
What were the milestones?
What processes were followed or broken?

This stage is not about assigning blame but rather painting an accurate picture of the project’s events. Without this foundation, insights are built on shifting sand. Objective reflection grounds the team in reality and allows them to see what went right, what went wrong, and, most importantly, how to improve. It also fosters empathy by helping teams understand each other’s roles and challenges.

3. The shadow revealed: feelings and frustrations

This is where the real work begins. Retrospectives are not just about evaluating the project— they’re about evaluating the team. What did people feel throughout the process? What moments stood out? How did they feel working on this? Were they proud, frustrated, or indifferent?

Each participant is given time to reflect on their overall feelings about the project before writing them down. This isn’t a time for glossing over emotions or sweeping things under the rug. The shadows come out here. Which is why it’s crucial responses are both private and anonymous. No one else sees them… yet.

Strategy for honesty: The moderator plays a crucial role in creating an environment of trust. Start with empathy, encourage participants express themselves openly, reminding them this isn’t about blame, but about improving, as a team. The guiding principle here—“We’re all here to help each other grow and enjoy our work together.” If something made someone uncomfortable, it’s not a critique of the individual but an opportunity to improve the system that allowed that discomfort to exist. This shift in perspective helps turn criticism into constructive insight.

And the I becomes the responsible “We”.

4. Picking the shadows: prioritizing frustrations

Next, the team reviews the shadow notes and votes on the most relevant — the ones that impacted the project the most. This is a process of prioritization.

At this stage, people may either shy away from difficult conversations or become aggressive or overly critical. The moderator must uphold our golden rule: RESPECT. Hard truths must be spoken, but they must be framed as opportunities for collective growth.

Vague statements like "The communication breakdowns were frustrating" are not enough. Instead encourage specifics:

"The client didn’t receive the mockups on time"
"We missed the sprint deadline because we underestimated the scope for the feature"

Strategy for constructive feedback: The moderator can reframe critiques to separate people from problems. Instead of “You didn’t deliver,” phrase it as “The timeline didn’t align with our expectations.” Avoid language that could be perceived as a personal attack— this evokes defensiveness. Our goal is to keep the discussion productive.

Once frustrations are acknowledged, don’t dwell on them. Instead, move to the next stage, solution generation.

The collective transformation

This method turns shared frustrations into clarity and action. It’s a process of shadow work— where unspoken truths come to light, and in the heat of that process, transformation occurs. The team shifts from being individuals to a cohesive unit with a shared purpose: improving, learning, and growing.

When teams conduct retrospectives with honesty and structure, they build a culture of openness. They uncover their hidden frustrations (shadows) and use them to fuel creativity and growth. The result? Better projects, better collaboration, and ultimately, stronger, more resilient, more empathetic teams—ready for whatever challenge comes next.