Product Therapy: "Coaching Roadmaps"

Host: Christian Idiodi
Guest: Leah Hickman (SVPG Partner)
Date: November 13, 2025

Episode Overview

In this episode, Christian Idiodi and Leah Hickman dive deep into the world of product roadmaps—one of the most contentious, misunderstood, and critical artifacts in product development. They explore the behavioral, mindset, and cultural dimensions that inform how teams approach roadmaps, common dysfunctions, and strategies for coaching leaders and teams toward more effective, outcome-oriented roadmap practices.

Key Discussion Points & Insights

1. Why Are Roadmaps Loved and Hated?

• Roadmaps as Communication Tools:
  • Executives and stakeholders want to know what is being worked on and when it's coming.
  • “People love roadmaps because it gives them a view into the work that's being done and when it's going to be delivered.” — Leah [01:13]
• But Also Commitment Traps:
  • Roadmaps imply commitments to solutions and dates that are often unvalidated and based on shaky assumptions.
  • “The moment your roadmap becomes a promise rather than a hypothesis, you've kind of lost room to learn.” — Christian [08:47]
  • Stakeholders interpret dated roadmaps as guarantees, damaging trust when reality changes.

2. Problems With Traditional Planning

• Output-Driven vs. Outcome-Driven:
  • Traditional roadmaps list features and dates; they often fail when features have little impact or are based on guesses, not validated insights.
  • “Most traditional roadmaps, what by when, are wasteful. They are not bad, but … most of the things on your roadmap will fail.” — Christian [02:47]
• Lack of Discovery and Real Ownership:
  • Many roadmaps originate from leadership or stakeholders, not from the teams doing the work, causing disconnect and harming product quality.

3. What Does a Good Roadmap Look Like?

• Outcome-Based Roadmaps:
  • Focus on business goals, customer problems, and measurable objectives, not just features.
  • “A good outcome-based roadmap is based on the outcomes or objectives that the team is working on, how we're going to quantify success.” — Leah [05:31]
• Features as Hypotheses:
  • Features are “candidates,” not certainties—subject to validation and change after experiments and learning.
• Sequencing and Empowerment:
  • Teams should align work to outcomes and decide on the solutions tested to reach those goals.

4. The Date Debate: Commitments vs. Timeframes

• No Absolute Dates—Timeframes Are Safer:
  • “I would never commit to a date. I commit to a timeframe, but I would not commit to a date.” — Leah [09:54]
  • Dates are for marketing launches or when dependencies genuinely require them (“high integrity commitments”), not by default.
• Pushing Back on Dates with Executives:
  • Executive need for dates is often about control, but such control is usually false and counterproductive.
  • “A roadmap is a perceived tool of control ... It's false control.” — Leah [12:37]

5. Coaching Executives & Building Trust

• Shifting Executive Focus:
  • Change the conversation from controlling feature delivery to controlling strategy, vision, and desired outcomes.
  • “Control the strategic context … Align on what the product vision is, what the product strategy is, what the priorities for the business are. … Give the teams the capability to build the right product to deliver on those results.” — Leah [13:40]
• Trust Must Be Earned via Results, Not Outputs:
  • Teams earn credibility by demonstrating value delivery, not just by shipping on time.

6. Roadmap Dysfunction: Common Anti-Patterns

• Stakeholder/Executive-Driven Roadmaps:
  • Product becomes an order-taker; no validation of ideas or alignment with outcomes.
• Quarterly “Fill the Bucket” Roadmaps:
  • Capacity-driven, not problem-driven—focused on how many tickets can fit, not what matters most.
• Feature Factories:
  • Just lists of outputs, detached from why the work matters.
  • Test: “Why are you working on this?” “Because it’s on the roadmap.”

7. Ownership and Team Dynamics

• Who Owns the Roadmap?
  • Ideally, the product manager, but real empowerment means teams co-own the problem and path to the solution.
  • Roadmap structure influences whether a team is empowered (problem-solving) or a delivery factory.

8. Transitioning to Outcome-Based Roadmaps

• Transitional Roadmaps:
  • Even if handed feature lists, ask “why,” reframe in terms of problems and objectives, and present features as candidates with attached outcomes/metrics.
  • “It changed the conversation … a transition to being more outcome driven.” — Leah [21:58]
• Coaching Teams:
  • Annotate why every item exists and how success will be measured.

9. Roadmaps vs. OKRs

• Alignment, Not Competition:
  • Outcome-based roadmaps and OKRs can and should work together—roadmaps answer the “how,” OKRs clarify the “what” and “why.”
  • “Your objective is your problem to solve. Your key results are your measurement of success. … Then underneath that you articulate the feature candidates.” — Leah [25:27]

10. The Role of Vision and Strategy

• Outcome Roadmaps Need Direction:
  • Without vision/strategy, roadmaps become tactical. Strong roadmaps derive from prioritized strategic problems, tied to overall product vision.

11. High Integrity Commitments

• When Dates Matter:
  • Separate feature guesses from real, validated, time-sensitive commitments (“high integrity commitments”).
  • “I want those high integrity commitments to be few and far between. … I don't want a whole roadmap of high integrity commitments. Because what is that? That's a feature-based roadmap.” — Leah [30:12]
• Prerequisites:
  • Discovery is done; commitments are made by builders, not imposed from above.

12. Navigating Stakeholder Politics & Building Credibility

• Output ≠ Value:
  • Hitting dates is less important than achieving intended impact. Prioritize conversations about value over deadlines.
  • “Would you rather me deliver something that has no value by that date, or would you rather have me deliver something that has value … because you allowed me to have some time to build the right thing?” — Leah [33:39]
• “Yes, and…” Stakeholder Engagement:
  • Don’t just say “no”—ask for reasoning, connect their suggestions to underlying problems and business objectives.

Memorable Quotes & Moments

• On the Fundamental Roadmap Trap:
  • “The second you put a date beside an idea, it turns from an idea into like a commitment, a promise, an expectation.” — Christian [02:47]
• On Changing What You Control:
  • “Change what you control. Don't worry about controlling the features … Make sure that you control the strategic context.” — Leah [13:40]
• On Roadmaps Aligning Teams:
  • “A good roadmap aligns a team around purpose. And probably a bad roadmap just assigns them work to do.” — Christian [27:12]
• On Building Team Ownership:
  • “If I give you the solution, you become a delivery team or a feature team. If I give you the problem, I empower you.” — Christian [20:23]
• On Transitioning Roadmaps:
  • “All of that can be done by asking the questions, right? Like why, why do we need to have this kind of capability, what problem is it going after? What's the value to the customer?” — Leah [21:58]

Actionable Takeaways

Timestamps indicate where themes are discussed.

Roadmapping Best Practices

• Ask "Why" for Every Feature ([36:00])
  • Before working on a feature, articulate the problem to solve and how success is measured.
• Annotate Roadmaps with Outcomes ([36:32])
  • Don’t just list tasks—always add the intended value or impact next to each.
• Push for Outcome-Based Thinking ([05:31], [08:47])
  • Shift away from outputs and deadlines toward solving key problems with measurable results.

Coaching & Organizational Change

• Push Back Thoughtfully on Date Requests ([09:54])
  • Offer timeframes when possible and explain the risk and tradeoffs of fixed dates.
• Build Credibility Through Impact, Not Outputs ([32:50])
  • Deliver value and earn trust to move stakeholders away from purely output-driven pressure.

Managing Stakeholders

• Engage Don't Reject ([35:29])
  • Use “Yes, and…”—ask stakeholders to clarify the value and problem, turning requests into insights and discovery opportunities.
• Change the Conversation Upstream ([13:40])
  • Help leaders focus on vision, strategy, and accountability for outcomes—rather than micromanaging features or schedules.

Notable Segment Timestamps

| Topic | Timestamp | |------------------------------------------------------|-------------------------| | Definitions: Why roadmaps are loved/hated | [01:13] – [02:47] | | The trap of feature-based roadmaps | [02:47] – [05:31] | | Anatomy of an outcome-based roadmap | [05:31] – [08:47] | | The date and commitment dilemma | [09:54] – [10:55] | | Coaching executives and shifting conversations | [12:37], [13:40] | | Roadmap anti-patterns | [16:16], [18:47] | | Who owns the roadmap? | [20:10], [20:23] | | How to transition toward outcome-driven thinking | [21:58], [24:20] | | Roadmaps and OKRs | [25:27] | | Roadmaps, vision, and strategy | [28:45], [28:50] | | High Integrity Commitments & when dates matter | [29:47], [30:12] | | Credibility, stakeholder politics, and trust | [32:50], [33:39] | | Practical roadmap transformation advice | [35:53] – [36:32] |

Final Advice: Starting Today

• “If they have features on their roadmaps right now, ask the question why? And articulate, what problem are we trying to solve and how am I going to measure success?” — Leah [36:00]

• “Never tell people what you're working on without telling them why you're doing it. And you've got to annotate your roadmaps with outcomes.” — Christian [36:32]

Tone Note

The conversation is candid, relatable, and a bit playful, mixing tough love critique of common practices with pragmatic, experience-based guidance. Both speakers share stories and actionable tips, keeping the mood light even as they challenge the status quo.

For more, visit svpg.com or attend their workshops.

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