Work For Humans: Applying Product Management Tools for a Better Employee Experience

Guest: John Cutler | Host: Dart Lindsley
Release Date: December 24, 2024

Episode Overview

This conversation explores how organizations can harness product management principles to rethink and redesign the employee experience as a "product." Host Dart Lindsley and guest John Cutler, a product leader and organizational thinker, discuss moving beyond rigid command-and-control management models towards a more agency-driven, service-oriented mindset. The episode navigates the complexities of scaling personalized work experiences, balancing the needs of the company and employees, and the nuanced challenges of designing organizations that people truly want to be a part of.

Key Discussion Points & Insights

1. Framing Work as a Product

• Employees as Customers: Dart posits that, just like external customers, employees should be viewed as customers of the organization (02:19). Designing their experience should be as intentional as designing products for market.
• Challenge of Personalization: Employees want unique combinations of “jobs to be done.” There’s “about a billion combinations” of what people want from work, making scaling personalization challenging (02:19-04:09).

“In reality, in the math and the physics of business, employees are customers... What people want from work is very different from person to person.” — Dart Lindsley (02:19)

2. Complexity, Scale, and Organizational Design

• Relevant Dimensionality: John discusses how both product and organizational complexity grows as you add variety, leading to unsustainable models if unchecked (04:09-06:45).
• Team Size Sweet Spot: John suggests optimal autonomous teams are around 30-50 people—“less than the Dunbar number” and with “two or three layers max of hierarchy” to keep autonomy and psychological safety (06:46).

“You can create an environment that is a better product for the employees...and potentially a better product for the company that is creating this ecosystem.” — John Cutler (06:45)

3. Lessons from B2B and B2C SaaS

• Horizontal vs Vertical Products: Vertical products (focused on an industry) accrue complexity quickly; horizontals (spanning industries) still face hidden complexity due to varied use-cases and maturity (09:32-13:23).
• Feature Bloat Trap: Stuffing all features into one product often leads to unusability and customer dissatisfaction (11:58).
• Product Structure Shapes Org Structure: Early decisions about product direction (vertical/horizontal) “have far-reaching impact on your org design, the employee experience, what kind of org you need to build” (16:15).

“…These early decisions about where you put your product and what product you’re building probably have far reaching impact on your org design, the employee experience, [and] what kind of org you need to build..." — John Cutler (16:15)

4. Work as an Experience Offering, Not Just a Product

• Service vs. Product: Work isn’t a reproducible good; it’s a context-dependent, mass-customized experience more akin to “bouquet assembling”—each arrangement unique, requiring managerial “hunter-gatherer” skills. (29:31-33:10)
• Manager as Product Manager: Can every manager become a “product manager” of the employee experience? Dart wonders if this consciousness can be distributed at scale (33:10).

5. Real-World Stories: Santa Barbara’s AppFolio

• Community as Product: John recalls AppFolio’s focus on creating an environment where employees stayed for years, grew professionally, and built deep customer empathy by visiting actual sites—a deliberate, thoughtful “product” for employees (21:30-26:42).
• Context Matters: Attracting talent varies by region, company culture, and business model, sometimes requiring unique “marketing” just to attract employees to the company itself (26:42-29:31).

6. Product Management, Service Design, and the Limits of Analogy

• Surface Area and Holism: PMs might own a narrow slice (“surface area”), or face broader, holistic challenges—much like managers with varying degrees of scope and agency (33:10-36:38).
• Service Design Mindset: There’s a spectrum: some are laser-focused missile-style PMs, others (often service designers) view experience more organically and holistically (36:38-40:10).

“Most software as service companies are service ecologies. They’re not like a bunch of products. They’re literally a value network.” — John Cutler (38:00)

• Language Evolution: Sometimes the language of “product” is useful for creating organizational focus, even if it’s not a perfect fit (41:28-43:48).

“We almost need to just surf ideas while they’re happening because they’re at the right point in the way of ways.” — John Cutler (41:28)

7. Organizational Capabilities, Levels of Abstraction, and Strategy

• Punching Up in Abstraction: Strategic clarity often requires thinking at multiple levels—capabilities and “jobs to be done” nearly universal across firms, but tactical action is local and time-bound (45:42-50:06).
• Practice and Tools: Most people can learn to connect daily tasks to larger goals if they have the right exercises and models (50:06).

8. The “Justs, Buts, and Cans” Model (54:57-61:08)

• Gestures: Want overly simple solutions (“We just need to do X”).
• Butters: Get bogged down by complexity and endless objections (“But what about Y?”).
• Canners: Pragmatically acknowledge complexity but focus on the next actionable move.

“The ‘justers’ are too simple. The ‘butters’ are infinite... the ‘cans’ are, what’s the first step?” — Dart Lindsley (60:23)

• Practical advice: Always arrive with a proposal. Recognize beautiful complexity; don’t be paralyzed or get stuck at either extreme.

9. Empathy and Agency in Management (65:06-75:11)

• Empathy as a Core Skill: Essential for both product managers and managers designing experiences of work.
• Agency: The best PMs see themselves as having degrees of freedom to shape experiences; managers need to see themselves as environment-shapers, not just enforcers.

“There is a skill set around design that is investing a lot more mental calories in certain ideas... the effects of what you’re doing.” — John Cutler (75:11)

• Gardener vs. Controller: The future manager is a “gardener of experience,” stepping back from being a bottleneck and giving more agency to the team (79:44).

Notable Quotes & Moments

• On Purposeful Work:
  “I want to be a citizen of something... a participant in a community of people who's passionately solving these problems and having fun." — John Cutler (80:39)

• Scaling Product Mindset:
  “I do think you can scale this way of thinking... The limiter is that it involves a tool chest when you're talking about this type of work.” — John Cutler (82:03)

• On Misapplied HR Product Thinking:
  “Nobody ever hired their job to give them a better benefits portal. You hire your job to give you great work.” — Dart Lindsley (44:22)

• Beautiful Complexity: “Beautiful complexity is local and is bounded and is vibrant and emerges. And we can't plan it all out.” — John Cutler (61:08)

Timestamps for Important Segments

• Framing the Core Problem (02:19)
• Scaling Complexity & Org Design (04:09–06:45)
• Horizontal/Vertical Products & Feature Bloat (09:32–17:55)
• Team Size and Autonomy (06:46)
• Manager as Product Manager Discussion (29:31–33:10)
• Spectrum of Product Management & Service Design (33:10–40:10)
• Capabilities & Abstraction (45:42–50:06)
• “Justs, Buts, and Cans” Framework (54:57–61:08)
• Empathy, Agency, and the “Gardener” Manager (65:06–79:44)
• Closing “Job to Be Done” Reflection (80:39)

Conclusion: Practical Takeaways

• Intentional Design: The employee experience should be consciously designed and requires investment, not happenstance.
• Mindset Shift: Transitioning managers into product/service designers of work calls for training, support, and a rethinking of their load and agency.
• Complexity is Inevitable: Design for beautiful, bounded complexity, not sterile simplicity or paralysis by overthinking.
• Scalable Mindset: Not every manager needs to become a PM, but adopting elements—empathy, agency, systems-thinking—can vastly improve the employee and business outcomes.

Further Resources

• John Cutler: The Beautiful Mess (Substack)
• Host: Dart Lindsley (LinkedIn)