Productside Webinar

Writing Requirements That Actually Drive Outcomes

How to Connect Strategy, Discovery, and Execution Without Losing the Plot

Date:

05/07/2025

Time EST:

1:00 pm
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Product managers are under more pressure than ever to deliver business impact—not just backlog tickets. In this free webinar, Productside consultant Tom Evans will walk through the mindset and methods behind writing requirements that move the needle. You’ll learn how to go from vague asks to aligned user stories and manage shifting priorities without sacrificing outcomes. 

What You’ll Learn:  

  • How to align product requirements to measurable business and customer outcomes 
  • How to use your roadmap to drive discovery, not just delivery 
  • How story mapping turns epics into user stories with context 

Welcome and Introductions

Rina Alexin | 00:00–03:00
Hi everyone, and welcome to today’s Productside webinar, “Writing Requirements That Actually Drive Outcomes.” I’m Rina Alexin, part of the Productside team, and I’m so glad you’re joining us. We’re going to talk about something that every product manager deals with but few truly master—writing requirements that don’t just describe features but actually lead to business impact.

Before we dive in, please drop a hello in the chat and let us know where you’re joining from. We love seeing our product community connecting across the globe.

Tom Evans | 03:00–04:10
Thanks, Rina, and hi everyone! I’m Tom Evans, a senior product advisor here at Productside. I work with teams to align strategy, structure, and execution. Writing great requirements is one of those unglamorous but essential skills that separates good PMs from great ones.

About Productside and Session Overview

Rina Alexin | 04:10–06:00
If this is your first Productside session, a quick intro: we’re an outcome-driven product partner. We help product teams connect their work to measurable business results through training, advisory, and practical frameworks.

Today’s session is about translating strategy into clarity—how to write requirements that drive outcomes, reduce churn, and actually make development faster. We’ll share frameworks, examples, and common traps to avoid.

Why Requirements Often Fail

Tom Evans | 06:00–10:00
Let’s start with the pain point. Why do so many requirements fail? They’re too vague, too technical, or too focused on outputs instead of outcomes. PMs often write what they *think* engineering wants, not what the *business* needs.

You’ve probably seen these: “Add a button,” “Enable export,” “Refactor API.” None of those say why it matters. Requirements should always start with impact, not implementation.

Poll #1 – What Information Do You Include in Requirements?

Rina Alexin | 10:00–12:00
Let’s take our first poll: what do you usually include in your requirements? Is it user stories, acceptance criteria, business goals, or all of the above?

Tom Evans | 12:00–12:40
Interesting—looks like most of you said user stories and acceptance criteria, but not as many include the business context. That’s one of the biggest gaps we see in PM documentation today.

Framework #1 – The “Why–What–How–Measure” Model

Tom Evans | 12:40–17:00
Our first framework is called “Why–What–How–Measure.” It’s simple but powerful:
– **Why:** What’s the problem or goal?
– **What:** What’s the proposed solution?
– **How:** How will it work or be implemented?
– **Measure:** How will success be tracked?

This ensures your requirement tells a complete story—from purpose to proof.

Framework #2 – Context Before Content

Rina Alexin | 17:00–21:00
One of the biggest mistakes PMs make is jumping straight into the “what.” Context should always come first. Engineers and designers don’t just need instructions—they need understanding. When they see the bigger picture, they make smarter decisions even when trade-offs appear.

Poll #2 – Where Do Requirements Break Down?

Rina Alexin | 21:00–23:00
Next poll: where do your requirements usually break down? During handoff, during sprint planning, or during testing?

Tom Evans | 23:00–23:40
No surprise—most of you said “handoff.” That’s where intent gets lost. Requirements should make intent obvious, not just describe tasks.

Framework #3 – The “Outcome-Oriented Requirement”

Tom Evans | 23:40–29:00
Here’s the model we teach in Productside workshops: every requirement should tie directly to an *outcome*, not an output. That means you start from the metric or behavior you want to influence, then describe the feature that enables it.

Example: Instead of “Add an onboarding checklist,” write “Reduce user churn by helping new users complete first actions through a guided checklist.” That’s an outcome-oriented requirement.

Case Study – Turning Features into Outcomes

Rina Alexin | 29:00–33:30
We worked with a SaaS platform where PMs wrote pages of Jira tickets with zero impact linkage. We helped them rewrite 10 top features as outcome-based requirements. Within one quarter, adoption improved 15%, and engineering rework dropped by 25%. The difference? Clarity around the “why.”

Poll #3 – Who Reviews Your Requirements?

Rina Alexin | 33:30–35:00
Quick pulse check—who reviews your requirements before they’re finalized? Just engineers? Design? Stakeholders? Or no one?

Tom Evans | 35:00–36:00
About half said “engineering only.” That’s common, but ideally, requirements should be reviewed cross-functionally—especially with design and data partners.

Common Pitfalls in Writing Requirements

Tom Evans | 36:00–41:00
A few red flags we see all the time:
1. **Ambiguous ownership** – “We’ll figure it out later.”
2. **Too many edge cases** – Don’t write novels.
3. **No success metrics** – If you can’t measure it, you can’t manage it.
4. **Overly technical focus** – Write outcomes, not code specs.

Framework #4 – Aligning Requirements to Strategy

Tom Evans | 41:00–46:00
Every great requirement traces back to a business objective. The simplest way to connect the dots is a three-layer chain:
– Company goal → Product objective → Requirement.

When these align, prioritization becomes easier. It’s no longer about opinion—it’s about evidence.

Case Study – Aligning Teams with “One Requirement Language”

Rina Alexin | 46:00–51:00
A healthtech company we worked with had 12 PMs, each using different templates. We implemented the “Why–What–How–Measure” model across the org. Within two months, the engineering team reported a 40% improvement in clarity during sprint planning.

Poll #4 – How Long Should a Requirement Be?

Rina Alexin | 51:00–52:30
Let’s see what you think: how long should a requirement be? One paragraph? One page? Ten pages?

Tom Evans | 52:30–53:30
(Laughs) I love that someone said “as long as it takes.” In general, aim for one to two pages max, with the “why” taking up half that space.

Q&A and Closing Remarks

Rina Alexin | 53:30–58:00
Let’s get to a few questions. One from Jamie: “How do you handle requirements when leadership skips discovery?” Great one. Tom?

Tom Evans | 58:00–59:00
You anchor the conversation around risk. Show that unclear requirements lead to wasted time. Use AI tools to summarize assumptions fast—then validate them with data.

Rina Alexin | 59:00–60:00
Love that. Thanks to everyone who joined. You’ll get the replay, frameworks, and examples in your inbox tomorrow. And don’t miss our next webinar, “PMs and the AI Advantage.”

Tom Evans | 60:00–61:00
Thanks everyone—go write requirements that drive real outcomes!

Webinar Panelists

Tom Evans

Tom Evans, Senior Principal Consultant at Productside, helps global teams build winning products through proven strategy and practical expertise.

Rina Alexin

Rina Alexin, the CEO of Productside holds a BA with honors from Amherst College and an MBA from Harvard Business School. She is also a member of the AIPMM.

Webinar Q&A

Writing requirements that drive outcomes means going beyond feature lists or backlog items to connect every requirement to a measurable business and customer goal. As Tom Evans explained, the best PMs use Voice of the Customer, Jobs-to-Be-Done, and outcome trees to ensure that every user story ties back to why it matters — not just what it is
When executives or stakeholders demand specific features, PMs should redirect the conversation to outcomes and context. Evans suggests asking clarifying questions like, “Who is this for?” and “What problem does it solve?” These questions reveal the why behind the request and prevent teams from building solutions in search of problems. Using an outcome tree or story map helps stakeholders visualize alignment to strategic goals
Evans recommends keeping your requirements refined two to three sprints ahead—no more. Working too far ahead leads to stale, irrelevant stories, while working too close risks chaos. Regular discovery cycles, backlog grooming, and story-mapping sessions ensure requirements stay aligned to changing user needs and business goals
Before a developer writes a single line of code, the requirement should pass the “shared understanding test.” Evans emphasizes story mapping as the best way to create that alignment — bringing together PMs, engineers, UX, and QA to visually walk through the user journey. If everyone can explain why and how the user benefits, the requirement is ready. Clarity comes not from writing more — but from talking more
Use your roadmap as a discovery tool—not just a delivery tracker. Evans advises that PMs should constantly validate problems and desired outcomes in parallel with delivery. The key is an outcome-based roadmap — where near-term work focuses on delivery, and upcoming quarters emphasize discovery and validation. This approach keeps teams nimble and outcome-focused even as priorities shift