From Struggle to Progress: A Team's OKR Story in Empowering User Communication
Have you ever launched a product, or a new feature, only to see a stark division among your users? Some are ecstatic, shouting praises from the rooftops, while others churn away, frustrated and perhaps even angry. In the world of digital products, especially those dealing with life-changing decisions, this polarization can feel like an unavoidable reality.
On a product where I once worked, dedicated to helping people find new homes by swapping apartments, this truth was lived every day. For its users, the outcome was undeniably binary: either you succeeded in finding a swap, or you didn't. When success happened, users were overjoyed, often leaving top-tier feedback. But for those who tried, perhaps for months or even years, without finding that perfect match, the experience could be soul-crushing. Their frustration often translated into the lowest possible scores, reflecting a sense of failure not just in their apartment search, but sometimes even in their perceived effort or the service itself.
It was easy to dismiss this as "just the nature of the beast." After all, finding a new home is a complex, high-stakes endeavor, influenced by countless external factors. But the team I was part of couldn't shake the feeling that the experience of trying didn't have to be so unforgiving. While we couldn't magically create more apartments or instantly align every user's expectations and needs perfectly, we believed we could empower its users to navigate the process with greater clarity, understanding, and ultimately, a more positive sense of agency, regardless of the final swap outcome. Timing, for instance, was a significant, uncontrollable factor; a user might search for three months without a suitable match appearing, only for the perfect swap to become available immediately in a different three-month period.
Our hypothesis was simple: if we could make every user a "great swapper" – equipping them with the knowledge and tools to effectively participate and become truly proficient – we could temper some of that extreme negative sentiment. They might still face challenges, but they'd understand why, and feel more in control of their journey. The question, then, became: How do we turn every user into an effective participant in a deeply human, often challenging process?
Uncovering the "Meaning": Beyond the Obvious Problem
To truly understand how to make every user a "great swapper," we knew we couldn't just guess. We had to dig deeper than surface-level complaints. Our approach was rooted in understanding the "job" its users were trying to get done, and more importantly, the "struggles" they encountered along the way. We wanted to move beyond simply building features and truly address the underlying human experience.
Me, our designer, and our data scientist embarked on a focused research initiative. We conducted in-depth interviews and meticulously analyzed usage data from two distinct groups: our product’s most successful swappers and those who, despite trying, either didn't succeed or consistently gave low satisfaction scores. What emerged wasn't a single "aha!" moment, but a clear, undeniable pattern: effective communication between our users was a cornerstone of success.
It wasn't just about finding a match; it was about the ability to clearly express needs, to understand others' offers, and to engage in clear and respectful conversation. The struggles were palpable: messages going unanswered, apartment listings that failed to convey crucial information, and new users feeling lost about how to best represent themselves or what to expect. This deep understanding of the user's journey and their specific communication struggles became the "meaning" that would guide our entire effort.
Note: This clarity wasn't confined to the small research team. We fostered an open, communicative culture where insights were shared as they emerged.
Crafting the OKR: Meaning Before Metric, Measure Before Method
With a clear understanding of the user's struggle and the "meaning" we aimed to create, we turned to a structured goal-setting framework. For us, OKRs provided what we needed to articulate our ambition and measure our progress.
What are OKRs? (Objectives and Key Results)
OKRs, or Objectives and Key Results, is a popular framework for setting and achieving ambitious goals. At their core, they provide a clear "language" for what you want to accomplish and how you'll measure progress.
Objectives (O): These define what you want to achieve. They are qualitative, inspirational, and time-bound. Think of them as the destination – where you're heading.
Key Results (KR): These define how you'll measure progress towards your Objective. They are quantitative, specific, and measurable outcomes. Think of them as the signals that tell you if you're on the right track to reach your destination.
OKRs power lies in their ability to align teams, provide focus, and ensure that effort is directed towards tangible, measurable outcomes. They're not just about checking boxes; they're about driving meaningful change.
Our Objective was designed to be aspirational yet grounded in the user's experience of progress: Empower every user to engage in effective and respectful dialogue, boosting their journey to a new home.
This Objective wasn't just about building features; it was about enabling a fundamental change in user behavior and capability. It spoke to the progress users wanted to make and the core struggles they faced around communication.
To measure if we were truly "empowering" users, we defined three Key Results representing the changes in user behavior that would indicate if we were successfully reducing struggle and helping them achieve their goals. We focused on metrics that would either "increase" a desired positive outcome or "minimize" a negative one.
Here were the team's Key Results for that period:
Increase the percentage of initial reach-out and show of interest messages receiving a response within 3 days from X% to Y%.
Why: This directly targeted the frustration of being ignored. By increasing response rates, we aimed to minimize the feeling of being left in the dark and foster reliable communication.
Increase the average "listing completeness score" for active apartment listings from X to Y, based on criteria derived from successful swappers.
Why: We observed that successful swappers provided comprehensive, clear information about their current home and their desired swap. This Key Result aimed to maximize the clarity and effectiveness of their listings, reducing miscommunication and increasing relevant interest.
Increase the percentage of new users who successfully complete key profile and preference setup essential for effective communication from X% to Y%.
Why: This focused on ensuring new users were set up for success from day one, minimizing early anxieties and guiding them towards behavior and communication best practices in the product.
These Key Results defined what success looked like for its users, leaving the team the autonomy to figure out the how. This approach, where the "meaning" of the problem precedes the "metrics" of success, which in turn precedes the "method" (the solutions), proved incredibly powerful.
The "How": Iteration, Empowerment, and Learning
With our OKR clearly defined, the team's work began. This wasn't a linear march from plan to execution; it was an iterative dance of discovery and delivery. We started by mapping out key user journeys, identifying specific points where communication broke down or could be enhanced.
Our process involved:
Design Sprint-Inspired Workshops: We held collaborative sessions to brainstorm a wide array of potential interventions. No idea was too small or too grand at this stage.
Quick Technical Spikes and Data Research: Before committing, we'd quickly explore the feasibility and potential impact of promising ideas, leveraging its data scientists to validate assumptions.
Solution Prioritization: We used frameworks like RICE (Reach, Impact, Confidence, Effort) and simple impact-effort matrices to prioritize. The goal was to find solutions that were impactful, feasible, and allowed us to learn quickly. We knew we had time for a few major changes, and we'd adapt if needed.
The solutions we ultimately pursued were diverse, reflecting the multi-faceted nature of communication:
For Messaging Responsiveness (KR1): We introduced "quick replies" within the messaging feature, allowing users to send pre-set responses (e.g., "Sorry, not interested. Your listing doesn’t match what I need.," "Tell me more") with a single tap. We also expanded unread notifications to include "unresponded messages," providing quick access to messages directly from the notification, minimizing friction for users to provide a response, even a brief one.
For Listing Completeness (KR2 & KR3): We revisited the onboarding flow and the apartment listing creation process. We integrated educational elements, showing new users examples of what successful swappers included in their listings and guiding them through "best practice" communication for their own home descriptions and swap preferences.
This autonomy over the "how" was incredibly motivating. It allowed us to be truly agile, to test, learn, and adapt. For instance, while quick replies had great initial traction, we observed their usage decline over time. Instead of clinging to a solution that was losing steam, we iterated, simplifying it down the line to more subtle, context-sensitive helpful tips and guidelines for message composition.
This flexibility is a core strength of the OKR approach: it's not about executing a fixed plan, but about achieving a desired outcome, allowing the team to discover the best path.
The cross-functional team – product, design, and engineering – collaborated closely throughout this process. The shared understanding of the problem, fostered during our initial research, meant that everyone was pulling in the same direction, contributing their unique expertise to solve the user's communication struggles.
The "Results": Tangible Progress & Broader Impact
The work done had a profound impact, not just on the specific Key Results, but on the overall user experience and even the broader health of the product.
Direct Impact on Key Results: We saw measurable improvements across the board. The percentage of initial messages receiving a response within 3 days saw a noticeable increase, significantly reducing the "ghosting" frustration. The average "listing completeness score" improved measurably, meaning users were providing richer, more effective information about their homes. And a higher percentage of new users successfully completed the essential setup tasks, indicating they were better setup for success from day one.
Smoother User Journeys: For its users, this translated into a less frustrating, more empowered experience. Interactions felt smoother, less like shouting into the void. Even if a swap didn't materialize immediately, users felt more in control, understanding that they had effectively communicated and received a response, rather than simply being ignored. This humanized the process, allowing users to better grasp that while their efforts were crucial, the ultimate success of a swap often hinged on timing as well.
Contribution to Company Goals: While the team's OKRs were focused on these specific behavioral outcomes, their success rippled upwards. The reduction in communication friction directly contributed to a measurable decrease in customer support complaints related to "unanswered messages" or "poor communication." This, in turn, positively influenced segmented NPS scores, as users felt more understood and supported, even when facing the inherent challenges of the housing market. It was a powerful testament to how focused team efforts can collectively drive significant company-wide improvements.
Key Learnings & Takeaways: The Power of Purposeful Autonomy
This experience is a memorable one for me regarding well-defined goals and empowered teams.
The biggest learning for us was the flexibility this approach afforded. Not having to plan months of features in advance, being okay with a solution not performing as expected (and adapting!), and knowing that multiple paths could lead to the desired outcome was liberating. It fostered a culture of continuous learning and experimentation.
Moreover, the engagement and initiative within the team soared. When everyone clearly understood the "meaning" behind the "metrics" and had true autonomy over the "method" – how they would contribute to achieving those goals – commitment and creativity flourished. It's simply motivating to work on problems you deeply understand and have the freedom to solve.
While this was a successful example, it also highlighted a crucial ongoing challenge: the long-term monitoring of solutions. What performs well during an OKR cycle might see usage change over time. You can't simply "set and forget" once a goal is achieved. Continuous monitoring of product analytics broadly is always important, ensuring that the positive changes implemented continue to deliver value.
Ultimately, this journey reinforced a core belief: in product development, true success isn't just about shipping features. It's about deeply understanding the human struggle, empowering users to make progress in their lives, and giving your team the clarity and autonomy to pursue those outcomes relentlessly.
Ultimately, our success wasn't measured by the features we shipped, but by the friction we removed from our users' lives. It’s a powerful reminder that true innovation lies in empowering progress, not just delivering outputs. So my challenge to you is this: Instead of hunting for the next big feature, go hunt for your user's biggest struggle. The value you uncover there will be immeasurable.
References & Further Reading:
Making Users Awesome: For inspiration on empowering users to become highly proficient and successful with your product, explore Kathy Sierra's work (e.g., Badass: Making Users Awesome).
Meaning, Metric, Method: The concept of "Meaning before Metric, Measure before Method" is eloquently articulated by Mike Burrows (e.g., Agendashift: Outcome-Oriented Change and Continuous Transformation).
Jobs-to-Be-Done (JTBD): For more on understanding customer "struggle" and "progress," explore the work of Bob Moesta (e.g., Demand-Side Sales 101). For a quantitative approach to identifying underserved needs and outcomes, delve into Tony Ulwick's Outcome-Driven Innovation (ODI) framework (e.g., Jobs to be Done: Theory to Practice).
Outcome-Oriented Goal Setting: The principles of focusing on measurable outcomes over outputs are central to modern product management. Jeff Gothelf (e.g., Sense & Respond, Who Does What by How Much?) is a leading voice in customer-centric OKRs and agile product development.
Product Strategy & Empowerment: For insights into building empowered product teams and defining clear product strategies, Melissa Perri (Escaping the Build Trap) and Marty Cagan (Empowered) offer invaluable perspectives.
