The Evolution of the T-Shaped Skill Set: Building a High-Performance Box-Shaped Product Management Team

The concept of a T-shaped professional is a good one. It suggests the need for both a breadth (top of the letter “T”) and depth (central pillar of the “T”) of skills to excel in your role.

McKinsey & Company adds “For any given role, some skill requirements are universal. Every team member may need to be comfortable working with data, or solving problems in a structured way, for example. Beyond those basics, however, they will also want to develop a deeper understanding of topics that allow them to make a real difference in their job… The result is a T-shaped skills profile, with a broad set of generally applicable skills, supplemented by a spike of specific expertise.”

T-shaped skills are especially important in Product Management, a renaissance role that requires a mix of hard research/design/data/technical skills and softer collaboration/communication/consensus-building skills across diverse internal and external partners. In my product leadership roles, I work to develop both my own T-shaped skills and also to develop an organization of strong, diverse Ts that build something unique when combined together – the box-shaped product team – a synthesis of individual competencies that is more than the sum of its parts.

The Top of the T: The Default Product Manager Skill Set Curriculum

I love working in product management as it allows me to consistently leverage a highly diverse set of skills ranging from business strategy to experience design to quantitative analysis. There are parallels in my personal life. I’m a lifelong musician who started on the piano but then added guitar, bass, drums, production, vocals, and more. 

Even better, the diverse skills of the PM are constantly changing. A decade ago, the archetype product manager was an ex-Google engineer, immersed in coding and architecture. Half a decade later, the pendulum swung to customer-centric experience design. Things have shifted again and now I consider the product role fundamentally a data/business one, albeit one that requires a constant conversation with operational, technical, design, quantitative, and other specialized teammates.

I actively engage my teams in an ongoing dialogue to define and refine the contents/curriculum of this “top T”, and push to foster a culture of continuous learning and development of these different skills through various means including 1:1s, pairing, book clubs, external mentorships, online education, and more.

The Pillar of the T: Each Team Member’s Specialization

Beyond the foundational skills, I encourage every team member to cultivate deep expertise in specific skill segments of the Product Management curriculum that resonate with their interests and abilities.

Teams are better when we fully support – and enjoy – each team member’s natural strengths and talent. This is why they’re here. Peter Drucker perhaps went overboard here when he suggested “Focusing on strengths is development, whereas focusing on weakness is damage control” and “to focus on one’s weakness at work is misuse, if not abuse of the person”, but Drucker certainly knew where the upside was.

A case in point is my experience leading Viacom’s Social Data Product team. Each team member was encouraged to hone their unique strengths. Brian, with a technical predisposition, delved deep into algorithms alongside our data scientists. In contrast, Tanmay excelled in public speaking and presentation and refined those skills to perfection. The collective growth in individual specializations (plus foundational PM skills) up-leveled the overall impact of our team and both individuals to executive management roles.

A Super Team: A Symphony of Diverse Ts

The result of growing both the breadth and diverse depths of product management skills is a product team of specialized experts, with a common framework of foundational skills to get jobs done. The organization has superpowers all across the top of the T and teammates who are pursuing their passions, interests, and strengths. It’s a dynamic where every team member’s depth amplifies our collective capability, fostering an environment of shared learning and mutual growth.

Together we form a box shape that falls outside of the English alphabet, with a rising, rock-solid top-of-the-T with deep strength across multiple functional areas. 


In essence, the orchestration of T-shaped professionals into a cohesive unit is akin to a musical group of varied instruments creating a harmonious song. Each instrument, with its unique tone and timbre yet familiar with the score, contributes to the grandeur of the ensemble. Similarly, in the world of Product Management, the mix of shared skills and diverse specializations culminates in an organization that is skilled, innovative, and ready to tackle the multifaceted challenges ahead.

Healthcare Roadmaps: Crafting Unique Patient-Centric Healthcare Experiences Amidst Other Priorities

In my years leading product and technology teams across various healthcare companies, balancing unique patient experiences with the integrity of foundational medical care has always been a core focus. Our objective is clear: enhance the patient journey without compromising quality.

In healthcare, we cannot risk gimmicks as our customers – patients in pain – expect excellence. This blog post explores how to strike the right balance between supporting core healthcare experiences and building truly differentiated features while utilizing limited technology resources effectively.

Whether dealing with chronic health conditions (Parsley Health), depression/anxiety/PTSD (Mindbloom), poor sleep (Proper), or long-term back pain (Vori Health), there are lofty standards of patient care to meet and we cannot spend all of our time on delightful, yet risky, whiz-bang features. This said, without creating a truly differentiated and delightful patient experience, these nascent companies cannot get a leg up on the entrenched industrial healthcare complex or other venture-backed competitors.

The Nuance Between Product Vision and Product Strategy

When developing any product, it’s essential to have both a clear product vision of long-term goals as well as a product strategy of critical near-term milestones. 

The product vision sets your 5-10-20-year north star goals for the project. The product strategy is the collection of near-term milestones that allow you to continue on your journey toward the vision. The early strategic milestones in nascent companies are often behind-the-scenes moments like fundraising, key hires, or closing early sales deals. 

Said another way, you can’t be a visionary if you fail to survive your early journey. The good news is that you don’t always have to create a well-tuned finished product to achieve these early milestones – for example, your operational margins need not reach their long-term targets and your technology stack may have technical-debt-by-design in the early stages.

Although a polished product isn’t an immediate requirement, a compelling value proposition is vital to attract investment, secure talent, and build customer trust. Striking a balance between foundational robustness and innovative flair is essential. Striking a balance between innovation and sustainability/durability is crucial.

A Balanced Approach

Accepting both the need to differentiate and that the product isn’t “done” in these early years, I tend to advocate for the following resourcing mix when starting out in healthcare:

  • 30-40% for elevated activation/onboarding experience
  • 30-40% for core healthcare experience
  • 10-20% for high-value differentiated feature development

1. Elevating Onboarding/Activation Experience (30-40%) 

An effective onboarding process is foundational to be successful as you can’t have a healthcare business without patients. In most of my roles, we’ve created dedicated teams focused on moving users through the awareness > consideration > conversation > activation funnel.

Excellence here requires continuous testing, quality analytics, a learning culture, and a fastidious mindset of experimentation, iteration, and improvement.

At Vori Health, we took a number of steps to improve our onboarding funnels, including:

  1. Adjusting our technical architecture for agility, breaking these components away from our other core services to allow for faster development and deployment
  2. Investment in specialized analytics instrumentation, including privacy-compliant session recording and anonymized aggregate analytics
  3. A heavy focus on qualitative insight, through in-flow surveys and 1:1 interviews

We combined these approaches with deep cross-functional collaboration with our clinical and operational teammates to completely rethink the order of our onboarding sequence and drive a 700% improvement in our first-visit conversion rates.

2. Core Telehealth Experiences (30-40%) 

There are no shortcuts in healthcare once patients are onboarded and are receiving care. The patient/provider experience needs to work flawlessly and ensure patients have frictionless access to the care they need via common features like scheduling, messaging, video conferencing, care plans/notes, and other medical-specific features (i.e., lab, imaging, testing integrations).

In an early-stage healthcare company, these foundational (aka commodity) telehealth features rarely need to be differentiated.  As such, selecting a partner/vendor for these core telehealth services is a prudent path.  Some things to keep in mind as you review vendors:

  • Compliance features. HITRUST and SOC2, in addition to HIPPA
  • Mature developer documentation, APIs, and SDKs 
  • Realistic roadmaps juxtaposed with feature release notes that demonstrate a proven history of delivery
  • Robust partner integrations to share the load across the telehealth service landscape
  • Outstanding customer references
  • Strong revenues and/or investors to ensure the company is in it for the long haul

Interestingly, as your healthcare business grows, there are very compelling reasons to move away from vendor solutions, including costs as your scale, opportunities to differentiate your patient experience up and down the journey, and creating both small and large feature-specific operational efficiencies (at scale, every 1-2% efficiency boost has major impacts on COGS and margins).

3. Differentiated Feature Development (10-20%) 

Consumer-centered onboarding and standard telehealth features are unfortunately not enough to win for patients, payers, and investors.  As such, I always withhold a stream of technology resources to develop unique features that differentiate the company and build intellectual property/enterprise value. These features must address specific patient needs and leverage cutting-edge technologies. Here are a few recent examples:

Vori Health (Musculoskeletal care)

We built “Motion Guide”, a computer-vision-assisted physical therapy app that uses pose estimation ML models to track patient movement and then provide real-time and personalized corrective feedback.

Proper (Sleep health)

We built a sleep behavior tracker that helps customers understand sleep-impacting and sleep-promotion activities.  There are 101 sleep trackers on the market, so we build something new, based on the leading clinical evidence – cognitive behavioral therapy for insomnia (CBTi) – in a beautiful engaging package.

Selection of these product efforts and features is of course hyperspecific to each business and should be done with the very best product discovery/experimentation/validation rigor that Marty Cagan and others speak to so eloquently.  

Creating differentiation is both an art and a science and if you are relying only on gut instinct you are bound the fail. Sit with your customers, brainstorm widely, test ideas cheaply, prototype quickly, and keep iteration until you get closer to the truth. This is the fun stuff, for sure.

Striking the Right Balance

In conclusion, creating differentiated healthcare experiences while maintaining high standards requires a well-balanced approach to resource allocation. The mix of resources between activation, core experiences, and differentiated features should be an ongoing conversation without a one-sized-fits-all formula. To succeed, a combination of creativity, customer engagement, and rigorous testing is essential. If you’d like to discuss this topic further, feel free to get in touch.

Embracing Failure: Accelerating Product Development with Insight and Iteration

When building consumer and data products, product decisions are most often incorrect (up to 80-90% of the time!) As such, the key to successful product development lies in the ability to quickly gain insights and iterate.

Success isn’t found in initial perfection but in the adeptness to rapidly glean insights and iterate. Being wrong is not a setback but a stepping stone that propels the innovation engine.

It’s crucial to understand how wrong you are, why you’re wrong, and what the next iteration should entail. High-performing technical teams embrace failure, creating systems and processes to learn from mistakes, and shorten iteration cycles for faster progress. They are adept at engineering systems and processes that not only absorb mistakes but transform them into learning opportunities, accelerating progress.

In this blog post, I will share tips and strategies to enhance your iteration speed, foster a learning culture, and bolster technical efficacy

Cultivate a Learning Culture

Celebrate being wrong, but with the condition that the company learns from its mistakes. Encourage an environment where failure is seen as an opportunity for growth and improvement.

Maintain a Hypothesis Backlog

Create a backlog prioritizing and estimating hypotheses, treating them like a regular product backlog. Include detailed descriptions of each bet, strategies for validation, and the outcomes and learnings associated with each experiment.

Optimize Technical Architectures for Speed

During the early stages, prioritize speed over product fidelity, automation, and resilience. Choose technical architectures that support rapid iteration.

Avoid overbuilding backends for initial product iterations, as they are likely to change significantly.

Prioritize Analytics Instrumentation

Each product venture should include a ‘success metrics’ component, including an analytics tracking plan. This ensures the entire team understands what they need to measure and validates that the necessary data hooks are in place before launch.

Don’t Wait for Statistical Significance

It’s rare for an early product to accumulate enough usage for statistically significant insights. Therefore, don’t wait for it. Balance early data with heuristic instincts while keeping a close eye on biases. Don’t hesitate to make informed decisions based on the available information.

Document and Centralize Insights

Build a knowledge base to store outcomes from experiments. Treat these insights as invaluable resources for your organization. Encourage external teams, such as marketing, to contribute their experiment outcomes to this knowledge base. Invest time in structuring this repository effectively.

Share and Celebrate Outcomes

Embrace failures that lead to valuable insights. Share these learnings widely within the organization to foster a culture of continuous improvement.

Plan Next Iterations

Design subsequent sprints quickly based on the new insights gained. Roadmaps often require significant pivots as you accumulate more knowledge, so be open to adapting your plans accordingly.

Revisit Experiments Over Time

Consider repeating experiments when appropriate, as the outcomes can be influenced by factors such as user preparedness, technical feasibility, and changing foundational elements. What didn’t work previously may succeed now due to altered circumstances.

Monitor and Improve Iteration Cycle Time

Regard product iteration cycle time as a core company Key Performance Indicator (KPI) and actively work to enhance it over time.

By embracing failure, fostering a learning culture, and implementing efficient processes, your technical team can significantly improve product iteration speed. Remember that the path to success involves acknowledging mistakes, gaining insights, and continuously adapting based on newfound knowledge. With these strategies in place, your organization can thrive in the ever-evolving landscape of product development.

Whose Product is it Anyway? Nurturing the PM/CEO Relationship

In early-stage leadership product roles, the fit between the product lead and the CEO is paramount. When there is clarity and alignment, the product leader becomes supercharged. However, when this connection is lacking, it can lead to a breakdown.

In this article, I’ll explore tips on how to identify a strong product opportunity during the interview process and how to nurture the PM/CEO relationship for greater success.

Understand the CEO’s Vision for the Product Role

The product lead role is delightfully wide-ranging, requiring a diverse set of skills ranging from business acumen and strategy to technical delivery and operations. This broad scope is why I love working in product management. However, it is crucial to grasp which specific aspects of the product role the CEO expects you to emphasize. Having clarity on whether the role is more focused on vision/strategy or operational/services will set the stage for a strong partnership.

Recognize the CEO as the OG Product Lead

Almost universally, the CEO or Founder serves as the original product lead within their organization. They often have formal product management experience or assumed PM responsibilities during the company’s founding. Over time, the CEO’s role evolves to encompass fundraising, sales, talent management, and more. There comes a point when the product function should be professionalized under dedicated leadership, but this transition can be challenging for the CEO. It is critical to discuss expectations regarding this handoff and the division of labor moving forward. Expect some backseat driving or ‘takebacks’ in responsibility post-handoff. This transition must be discussed openly and continuously.

Manage Your Manager

The product role is highly collaborative, and at leadership levels, the responsibility for people/peer management often outweighs the ‘hard’ skills typically associated with an individual contributor PM (such as design, data, tech, road-mapping, etc.). Devote time to building relationships with your executive leader. I recommend a combination of dedicated 1:1 meetings and clear documentation at different altitudes, from up-to-date high-level product strategy documents to granular roadmaps. Humanize this relationship by creating an environment where you can discuss what’s going well and what needs further development. Prioritize conversations about “how we work together” as much as “what we’re working on.”

Keep Your Eyes Open

As a product leader, you have a unique perspective on the strengths and weaknesses of your executive leader. While you can nurture most relationships to success, some relationships cannot be improved. If you genuinely cannot regain confidence in your executive leader or restore the relationship, it may be a sign that you should start exploring new professional opportunities.

By focusing on these key aspects, you can strengthen the PM/CEO relationship and drive success in your early-stage leadership product role. Remember, the fit between the product lead and the CEO is essential for a thriving partnership. Open communication and mutual understanding are key ingredients for fostering that fit.

Supporting Sweet Dreams: A Product Journey from Concept to Impact with Proper Sleep + Behavior Tracking App

As the Product Management Leader at Proper, a Redesign Health portfolio company focused on sleep health, I had the incredible opportunity to spearhead the creation of a groundbreaking consumer-facing product that changed the way our customers understand and optimize their sleep. Our journey from ideation to delivery was a remarkable adventure that brought together sleep science, novel user-centric design, and our passion for enhancing people’s lives through better sleep.

Inception and Ideation

The journey began with a vision to empower our customers to take control of their sleep quality and duration with the most research-supported intervention for poor sleep, Cognitive Behavioral Therapy for Insomnia (CBTi) – and to promote our consumer products (evidence-based, premium sleep supplements).

The science is clear: behavior change changes sleep quality. We recognized the growing importance of sleep in overall well-being and were eager to provide a tool that allowed users to bridge the gap between their daily behaviors and the quality of their sleep. Our goal was to create an intuitive, data-driven app that helped users uncover new insight into how their daily routines impacted their sleep patterns.

The world didn’t need another sleep tracker; rather we needed to build a behavior tracker that used sleep tracking metrics as core outcomes.

Our product and design team conducted thorough market research, analyzing user needs, pain points, and existing solutions. Armed with insights, we embarked on an ideation process that encouraged diverse perspectives. The world didn’t need another sleep tracker; rather we needed to build a behavior tracker that used sleep tracking metrics as core outcomes. Brainstorming sessions and design thinking workshops with customers and clinicians fueled our creative process, leading us to a clear vision of the Proper Sleep + Behavior Tracker.

User-Centric Design and Iteration

To ensure our app truly resonated with users, we adopted a user-centric design approach. We engaged in user interviews, focus groups, and usability tests to gather feedback at every stage of development. This iterative process allowed us to refine the app’s features, user interface, and overall user experience.

The app’s core functionality was designed around the concept of self-reporting sleep-promoting and sleep-detracting behaviors. Users could effortlessly input behaviors such as bedtime consistency, media exposure before sleep, and dietary choices. These inputs, combined with sleep data from wearable devices or self-reported, formed the foundation for our data-driven insights.

In close collaboration with our product design partners, XXIX, we executed this vision with a novel visual identity that supported touch-friendly mobile inputs and circular, clock-inspired data visualizations.

The Proper Sleep + Behavior Tracker revealed correlations between sleep-promoting and sleep-impacting behaviors.

Testing and Validation

Testing was a pivotal phase of our product development journey. We created prototypes to simulate the app’s interactions and visualizations, seeking user feedback on usability, clarity, and overall appeal. Our team’s commitment to continuous improvement drove us to refine the app’s mechanics and aesthetics based on the invaluable insights from these tests.

During this phase, we fine-tuned the data algorithms that correlated sleep behaviors with sleep quality. Rigorous testing ensured the accuracy of our trend detection and data visualization components. Through this iterative process, we evolved from an initial concept to a robust product ready for deployment.

Delivery and Impact

The culmination of our efforts was the Proper Sleep + Behavior Tracking app — an elegant fusion of sleep science and user-centric design. The app empowered users to recognize the effects of their behaviors on their sleep quality and duration. Daily behavior inputs were artfully visualized alongside sleep data, providing users with real-time feedback on their sleep hygiene practices.

We optimized our data visualizations for both mobile and web devices, ensuring a seamless experience for users regardless of their preferred platform. Over time, the app’s trend analysis revealed patterns and correlations that allowed users to make informed decisions about their sleep-promoting and sleep-detracting behaviors.

The app was also leveraged by our team of Sleep Coaches, who worked 1:1 with Proper’s best customers to understand and improve their sleep outcomes.

In Summary

The Proper Sleep App represented more than just a technological innovation; it symbolized our dedication to improving lives through meaningful data insights. Our journey—from ideation to delivery—showcased the power of collaboration, user-centric design, and iterative development. The impact of the app extended beyond the digital realm, influencing positive behavioral changes and promoting healthier sleep habits.

As a Product Leader, being part of this journey has been a privilege. It reaffirmed my belief in the transformative potential of user-focused product development. The Proper Sleep + Behavior App not only enriched our product portfolio (supplementation is of course a data-backed, sleep-promoting behavior) but also enriched the sleep experiences of countless users. As we continue to evolve and innovate, this project remains a testament to our commitment to enhancing lives through thoughtful, data-driven solutions.