Transformative Discovery: Integrating Coaching Principles for Project Success

The Human-Centered Approach to Discovery

At the core of effective discovery work lies the importance of coaching when gathering requirements. Over time, I’ve realized that meaningful insights rarely emerge from rigid templates or formal interviews; instead, they arise through genuine conversations where people feel supported enough to pause, think deeply, and express what they need.

Often, an initial request such as “We need a dashboard,” or “Can you shorten this workflow?” uncovers more fundamental issues like decision-making, team alignment, confidence, or communication barriers. By approaching discovery with a coaching mindset, we can reveal these underlying concerns rather than just addressing superficial symptoms. If you’ve ever experienced a discovery session that seemed more like coaching than interviewing, you’ll recognize the value of intentionally cultivating this dynamic.

Reflecting on my recent years of interviews, I’ve noticed a shift, they increasingly resemble coaching sessions. Initially, I thought I was merely “collecting requirements,” but over time, it became clear I was guiding people in clarifying their actual needs. Rather than just recording their requests, I was facilitating their thinking.

In early design meetings, users typically begin with basic asks: “We want a dashboard,” “Can you make this workflow shorter,” “Can we have a button that does X?” These are useful starting points, but they seldom tell the whole story. When I consciously adopt a coaching approach, slowing down, listening attentively, and posing thoughtful questions, the dialogue changes dramatically. At that moment, our focus shifts beyond the user interface into deeper topics: friction, decision-making processes, confidence, accountability, ambiguity, and the human elements hidden beneath feature requests.

Many professionals who have spent decades in their roles rarely get the chance to reflect on the patterns shaping their daily work. So, when I ask something as straightforward as, “What’s the hardest part about planning next season?” the answer often reveals gaps and bottlenecks behind the scenes, rather than issues with the software itself. These stories simply don’t surface during standard meetings.

Uncovering Deeper Insights through Curiosity and Coaching

Curiosity allows us to explore areas untouched by process charts and requirement documents. Prioritizing the individual over the process exposes context that’s invisible on paper, like emotional burden, workplace politics, quiet worries, workarounds, and shared tribal knowledge. Coaching fosters an environment where all these factors come to light, transforming them into valuable material for design decisions.

I used to think the better I got at systems, the less I’d need to do this. But it turned out the opposite is true. The better the system, the more human the conversations become. Coaching is almost like a bridge, helping people cross from “I think I need this feature” to “Here’s what I’m actually trying to solve.”

Active Listening and Guided Curiosity

Active listening forms the core of my approach, ensuring I deeply understand not just participants’ words but the meaning behind them. I reflect statements back — such as, “So it sounds like the challenge isn’t entering the data, it’s aligning on which data to trust, right?” — to confirm genuine understanding. This often transforms technical discussions into conversations about alignment, ownership, or governance.

A key tool is the “Five Whys” technique, which I use as a guide for curiosity rather than a rigid checklist. If someone requests better notifications, I’ll probe: “Why is that important?” and follow with questions like, “Why is it hard to notice things right now?” or, “What happens when you miss something?” By the fourth or fifth ‘why,’ the conversation surfaces underlying factors such as workload, confidence, or fear of missing out, revealing emotional and operational triggers beneath the initial request.

In workplaces, these deeper issues often connect to organizational culture. For example, a request for faster workflows sometimes indicates a real need for predictability or reduced chaos, rooted in communication or authority structures rather than the system itself. Recognizing these patterns enables more effective design decisions by addressing root causes instead of just symptoms.

Intentional silence is another valuable technique. After asking a question, I resist filling the pause, giving participants space to think and speak freely. This silence often prompts unfiltered insights, especially when someone is on the verge of articulating something new. Allowing this space helps participants trust and own their insights, leading to more meaningful outcomes.

Future-Focused Exploration and Empowering Language

I also employ future-anchoring questions like, “Imagine it’s six months after launch — what does success look like for you?” or, “If the system made your job easier in one specific way, what would that be?” These help participants shift from immediate concerns to aspirational thinking, revealing priorities such as autonomy or coordination that guide design principles.

Tone and language are critical for psychological safety. I aim to make discovery feel inviting, often assuring participants, “There’s no wrong answer here,” or encouraging them to think out loud. When people use absolutes — “We always have to redo this,” “No one ever gives us the right information” — it signals where they feel stuck. I gently challenge these constraints by asking, “What might need to change for that to be different?” This opens possibilities and helps distinguish between real and internalized limitations. Coaching-based discovery is key to uncovering and addressing these constraints for lasting change.

Reflections and Takeaways

Coaching Tools as Foundational Practice

Initially, I viewed coaching tools as separate from implementation work, and more of an optional soft skill than a crucial element. Over time, my outlook changed: I saw these tools as fundamental to successful outcomes. I noticed that the best results happened when participants truly took ownership of the insights we discovered together. That sense of ownership was strongest when the understanding came from them, even with my guidance. Insights gained this way tend to last longer and have a greater impact.

My approach to discovery has evolved significantly over time. Initially, I viewed discovery as a process focused on extracting insights from users. More recently, it has transitioned into facilitating users’ own self-discovery, enabling them to articulate intuitions and knowledge that may have previously been unexpressed. This progression from a transactional checklist to a collaborative and transformative meaning-making practice has had a substantial impact on my design methodology.

Efficiency through Early Alignment and Clarity

Contrary to prevailing assumptions, coaching-based discovery does not impede project timelines. Although it demands greater initial investment of time, the resulting enhanced alignment and mutual understanding often expedite progress. Early engagement in substantive discussions enables teams to minimize rework, clarify decision-making processes, and avoid misinterpretations, which can ultimately result in projects being completed ahead of schedule due to unified objectives.

Efficiency is driven by clarity. When users feel acknowledged and their perspectives are incorporated, their level of engagement and willingness to collaborate increases. The trust established during these interactions persists throughout testing, feedback, and rollout stages, mitigating many subsequent problems that typically occur when user requirements are not considered from the outset.

Strong Implementation Questions Are Strong Coaching Questions

At their core, effective implementation questions are essentially strong coaching questions. These are fuelled by curiosity, maintain a non-judgmental tone, and aim to empower others. Instead of guiding someone toward a set answer, such questions encourage individuals to uncover their own insights about the work.

Regardless of the type of discovery — be it design, implementation, or workflow — insight comes from those directly involved. Coaching goes beyond mere technique; it represents a mindset based on the belief that people already hold valuable wisdom. The coach’s job is to help draw out this knowledge, using thoughtful questions.

A key moment in coaching-based discovery happens when someone has a sudden realization, saying things like, “I’ve never thought about it that way,” or “Now I understand why this keeps happening.” These moments are where improvements in design and implementation begin.

Such realizations act as anchors throughout a project. When team members shift their understanding, these breakthroughs can be revisited during times of complexity or tough decisions, providing direction as a “north star” to keep teams aligned.

Coaching is not just a resource, it should be demonstrated in everyday interactions. As teams experience its benefits, they often adopt coaching practices with each other, leading to genuine transformation that extends past individual projects and influences wider workplace culture.

Ultimately, the real value of this work lies not just in the solutions themselves, but in the conversations that reshape how people engage with their work.

Designing with Empathy: A Universal Practice for Meaningful Collaboration

In an era marked by the rapid advancement of artificial intelligence, it is reassuring to recognize that the human capacity for empathy remains unique and irreplaceable.

Introduction

On a recent project I worked on I found that I was not very clear on the subject matter and the complexity of the problems that were presented. I did not know any of the business stakeholders well, and while I had previously worked with some of the project team members, I had not yet developed a meaningful working relationship with them. I needed to get up to speed quickly so that I could start thinking about how to run discovery sessions, and how to frame the problem and ask the right questions in my stakeholder interviews.

To arrive at that stage I needed to get to know the stakeholders, understand what was important to them and what motivated them to embark on this project. To accomplish this, I spent time both privately and in group discussions with the stakeholders. The one-on-one interviews I initially conducted with the stakeholders and the group discovery workshops were helpful in allowing them get to know me as a person first, before being the individual filling the role of the designer on the project.

I was able to gain the stakeholders’ trust by showing that my role was first and foremost focused on understanding their needs and goals, and that I was immersing myself in their experiences. This was essential for the stakeholders because they were trusting me to lead the design on a project that impacted their day-to-day work, and it was also essential for me to help establish a strong foundation and build trust as I embarked on this project.

When I reflect on how I was able to arrive at that stage of trust and partnership with the stakeholders, I realize that it was the fact that I understood and related to how they felt about their work, and that I tried to put myself in their shoes by rephrasing and reconfirming my understanding of their problems. I was successful in letting the stakeholders know that that they were not alone in the challenges they were facing, and that I was there to understand the problems they were trying to solve by really imagining myself as part of their team. I wanted to show that I could relate to them so that together we could start a journey to gain a better perspective and create a great solution.

This example is only one of many I can reflect on throughout my career as a designer, where I realized the fundamental role empathy plays in providing reassurance to myself and others I worked with, that we all shared a mutual care and understanding of our experiences and goals.

In this post, I explore the need for designers to consistently practice empathy throughout all aspects of their role. For designers, empathy extends beyond end users, encompassing every individual involved in the design process, including stakeholders and colleagues. I refer to this as Universal Empathy, wherein a designer is expected to genuinely understand and relate to everyone within their professional sphere to effectively create products that are usable, impactful, and successful.

Why Empathy Matters In Design

In psychology, empathy is defined as the capacity to comprehend and share the feelings of another individual. This extends beyond courteous or considerate behavior, involving the ability to perceive situations from another person’s perspective, understand their emotions, and respond appropriately in alignment with their perspective. Such an understanding allows individuals to convey genuine support, assuring others that their experiences are acknowledged and their needs are recognized.

Tim Brown identifies empathy as a fundamental element in design thinking, particularly when addressing complex problems [1]. As a human-centered methodology, design thinking requires a comprehensive understanding of users’ needs, business requirements, and relevant organizational and technological considerations to achieve successful product development.

Kouprie and Visser [2] provide an in-depth examination of the role of empathy in design by presenting a four-phase model. They describe how designers should adopt a dynamic, multi-stage approach to empathy that includes the following phases:

  • Discovery: In this phase, designers remain inquisitive, actively observing, learning, and asking questions about users.
  • Immersion: This phase involves designers engaging directly in the user experience through interviews, observation sessions, and shadowing activities.
  • Connection: At this stage, designers identify with users and establish a genuine understanding of their feelings regarding their experiences.
  • Detachment: Finally, designers apply their insights objectively, ensuring that design decisions are informed by the observations gathered during earlier stages.

The work by Kouprie and Visser further underscores the designer’s essential role in acting as a catalyst for the phases of empathy. This helps foster the creation of effective solutions that serve both end user and organizational goals.

Universal Empathy

I would like to emphasize how the designer’s universal approach to empathy is essential to their success, the success of their team, and ultimately the success of the products they design. This approach is essential throughout the product design lifecycle, beginning with the design thinking phase and through to the development and implementation phase. Designers play a pivotal role, not only in guiding design discovery and generating research-driven concepts, but also in fostering team cohesion and promoting a collaborative culture rooted in empathy. The designer accomplishes this by bridging the gap between the user needs, stakeholder needs and the project team needs by fostering a comprehensive understanding of the goals of everyone involved in the project.

The designer cultivates universal empathy by:

  • Listening to, understanding and connecting with user needs, connecting with their experiences and knowing when to disconnect in order to be able to make objective design decisions.
  • Building trust with stakeholders and connecting with their needs and establishing a strong foundation to collaborate on building a product that meets the needs of both the business and the end users.
  • Facilitating their team’s understanding of technical design aspects by readily addressing questions, remaining attentive to the team’s needs, and helping when required.
  • Fostering an overall inclusive environment that recognizes and values feedback from everyone in their sphere, promotes successful collaboration and addresses the diverse requirements and viewpoints involved in the design process.

Conclusion

I have consistently found that demonstrating empathy toward those around me has contributed significantly to my success in my work and my career. By cultivating this approach, I learned to listen, understand, acknowledge and fully immerse myself in the experiences and feedback from users, business stakeholders, and my colleagues alike.

I have also been able to help to foster a culture in which individuals support one another and feel comfortable seeking assistance when needed. In my experience, such an environment always promoted greater job satisfaction, personal growth and stronger professional relationships that extended beyond individual tasks and contributed towards shared goals.

In an era marked by the rapid advancement of artificial intelligence, it is reassuring to recognize that the human capacity for empathy remains unique and irreplaceable.

References

[1] Brown, T. (2009). Change by Design: How Design Thinking Creates New Alternatives for Business and Society. Harvard Business Press.

[2] Kouprie, M., & Visser, F. S. (2009). A framework for empathy in design: Stepping into and out of the user’s life. Journal of Engineering Design, 20(5), 437–448.