Agenda | Shyft PM

A two-day workshop that reinforces the core craft of product while embracing new, AI-powered ways of working

AGENDA

MODULE 1: Opening & Modern PM Foundations

OVERVIEW
Sets the tone and shared context for everything that follows. Before diving into skills and frameworks, participants need a common understanding of what product management actually demands right now — especially as AI reshapes how PMs work without changing what they're ultimately accountable for. Ends with a practical AI-in-practice framework and a personal self-assessment that each participant will carry through both days.

TOPICS

Welcome, introductions, and workshop goals — establishing the group contract
How AI is changing the work of product management — speed, synthesis, generation — and what it doesn't change
What PMs are truly accountable for: outcomes, not outputs
The 5 Dimensions of Great Product Managers: Know Your Customer, Connect Business & Technology, Think with Clarity, Lead with Influence, Drive Execution
AI in practice: a working framework for when to use it, what to use it for, and where to keep humans in the loop

LEARNING OBJECTIVES

Articulate what product managers are uniquely accountable for in the AI era
Describe how AI changes PM workflows without replacing PM judgment
Use the 5 Dimensions as a shared framework for the workshop and beyond
Apply a practical decision framework for when and how to use AI in your own PM workflow
Identify 1–2 personal development priorities to focus on through the two days

ACTIVITIES

5 Dimensions self-assessment: participants rate themselves honestly across all five areas, then share one strength and one growth area with the group. Creates psychological safety early and surfaces the diversity of experience in the room — which becomes a resource throughout the workshop.

MODULE 2: Knowing Your Customer (When Everything Is Moving Fast)

OVERVIEW
Customer understanding is the foundation of every good product decision — but it's increasingly at risk. AI tools generate plausible-sounding customer insights at scale, and speed pressure makes it tempting to skip real discovery. This module reconnects participants to the discipline of problem-first thinking and gives them tools to apply it even when time is short and data is abundant. The activity is redesigned to make the AI-insight trap experiential, not just conceptual — participants have to interrogate synthesized data before they can trust it.

TOPICS

Customer discovery foundations refresher: what good looks like and why it still matters
The AI-insight trap: how to use synthesized data without losing real customer understanding
Solution-first vs. problem-first thinking: how teams default to solutions and how to interrupt that pattern
Personas and journey mapping as thinking tools, not just deliverables
Defining the core problem clearly enough that a team can act on it

LEARNING OBJECTIVES

Distinguish between real customer insight and AI-generated synthesis — and know when each is sufficient
Interrogate synthesized customer data: identify what to trust, what to probe, and what to discard
Apply problem-first thinking to interrupt solution bias in their team
Build a useful persona and journey map that surfaces the real job to be done
Write a clear, specific problem statement that anchors product decisions

ACTIVITY
Part 1 — AI Insight Audit (~20 min) Teams receive an AI-generated Customer Intelligence Summary for their challenge company and audit it against three questions: What do we believe? What do we need to verify? What do we distrust? Quick share-out: one insight each team would act on, one they wouldn't trust without real research. Facilitator debrief on what the audit revealed.

Part 2 — Build Your Customer Foundation (~35 min) Using the audit as a lens, teams build their own customer understanding:

Persona (12 min) — primary user, context, motivation, constraint
Journey Map (15 min) — current-state experience, top 3 friction points, 1 moment of delight
Problem Statement (8 min) — structured "[Persona] struggles with [problem] because [root cause], resulting in [impact]" — compared against the AI summary's version

Part 3 — Share-Out & Carry Forward (~5 min) Each team shares their problem statement. One word of feedback from the group. This output carries directly into Module 3 and anchors the Day 2 roadmap and capstone.

MODULE 3: Strategy & Judgment Under Speed

OVERVIEW
Speed is no longer an excuse for poor decisions — in many ways it raises the bar for judgment. This module addresses one of the hardest things PMs do: making high-quality strategic choices with incomplete information, under pressure, when AI can generate a dozen plausible options in seconds. The focus is on the human skill of judgment: what it is, how to build it, and how to apply it to set a clear strategic direction.

TOPICS

Decision-making with incomplete information: what makes a decision good, not just fast
Prioritization as strategy: how what you choose not to do defines your product as much as what you build
AI as option-generator, PM as decision-maker: where the boundary is and why it matters
Product vision: what it is, what it isn't, and why vague vision costs teams dearly
Strategic bets: how to articulate a directional commitment the team can act on
The one-page strategic brief as a forcing function for clarity

LEARNING OBJECTIVES

Make and defend a strategic decision with incomplete information using a structured approach
Distinguish between a prioritized backlog and a product strategy
Write a product vision that is specific enough to guide decisions and inspire a team
Articulate 2–3 strategic bets that connect customer insight to business outcomes
Produce a one-page strategic brief that will anchor Day 2 work

ACTIVITY
Strategic brief build: teams take their customer work from Module 2 and develop a one-page strategic brief — product vision, 2–3 strategic bets, key assumptions, and definition of success. This is the core Day 2 input and the through-line deliverable for the capstone presentation.

DAY 1 CLOSE: Reflection

OVERVIEW
Roadmaps are one of the most misunderstood tools in a PM's kit. They're too often treated as commitments when they should be communication tools — and too often filled with features when they should be filled with direction. This module reframes what a modern roadmap is for and gives participants a practical structure for building one that holds up when things change (which they always do).

TOPICS

What modern roadmaps are — and what they are not (not a promise, not a project plan)
Balancing direction and flexibility: how to commit to outcomes without over-committing to solutions
Now / Next / Later as a framework for adaptive planning
Turning vision and strategy into themes, initiatives, and learning bets
How AI and faster shipping cycles change the planning rhythm — and what that means for roadmap format
Pitching a roadmap to executives: what they actually need to see

LEARNING OBJECTIVES

Explain the difference between an outcome-based roadmap and a feature list
Build a Now / Next / Later roadmap from a strategic brief
Articulate the rationale behind roadmap priorities to a skeptical executive audience
Identify where their current roadmapping practice is strongest and where it needs to evolve

ACTIVITY
Roadmap build and executive pitch: teams take their Day 1 strategic brief and build a Now / Next / Later roadmap. They then present it to a mock executive panel (played by peers and JJ) and field tough questions. Structured feedback on both the roadmap and the pitch follows.

MODULE 4: Adaptive Roadmapping in the AI Era

OVERVIEW

Roadmaps are one of the most misunderstood tools in a PM's kit. They're too often treated as commitments when they should be communication tools — and too often filled with features when they should be filled with direction. This module reframes what a modern roadmap is for and gives participants a practical structure for building one that holds up when things change (which they always do).

TOPICS

What modern roadmaps are — and what they are not (not a promise, not a project plan)
Balancing direction and flexibility: how to commit to outcomes without over-committing to solutions
Now / Next / Later as a framework for adaptive planning
Turning vision and strategy into themes, initiatives, and learning bets
How AI and faster shipping cycles change the planning rhythm — and what that means for roadmap format
Pitching a roadmap to executives: what they actually need to see

LEARNING OBJECTIVES

Explain the difference between an outcome-based roadmap and a feature list
Build a Now / Next / Later roadmap from a strategic brief
Articulate the rationale behind roadmap priorities to a skeptical executive audience
Identify where their current roadmapping practice is strongest and where it needs to evolve

ACTIVITY

Roadmap build and executive pitch: teams take their Day 1 strategic brief and build a Now / Next / Later roadmap. They then present it to a mock executive panel (played by peers and JJ) and field tough questions. Structured feedback on both the roadmap and the pitch follows.

MODULE 5: Influence & Storytelling

OVERVIEW

PMs lead without a title. Their ability to move people — executives, engineers, designers, stakeholders with competing agendas — is what separates good product managers from great ones. This module gives participants a practical model for influence and a storytelling structure that works across different audiences, paired with live practice so they leave with more than theory.

TOPICS

Leading without authority: what influence actually is and how PMs build it over time
Stakeholder mapping: who matters, what they care about, and how to approach each
The narrative structure for product: situation → insight → recommendation → ask
Tailoring your story for executives vs. teams vs. cross-functional partners
Anticipating and addressing objections before they become blockers
What makes a product story compelling vs. merely informative

LEARNING OBJECTIVES

Map the key stakeholders for a real initiative and identify the right influence approach for each
Structure a product narrative using the situation → insight → recommendation → ask framework
Tailor the same core message for at least two different audiences
Deliver a short product pitch and receive structured, actionable feedback

ACTIVITY

Stakeholder mapping: participants map the real stakeholders for their challenge product, identify their concerns, and draft an influence approach for the trickiest one.
Role play and pitch: pairs practice a difficult stakeholder conversation using their actual challenge context. Then each participant delivers a short (3–5 min) product narrative to the group. JJ coaches in real time; peers give feedback using a shared rubric.

MODULE 6: Connecting Business & Tech

OVERVIEW

The best PMs can walk into a business conversation and a technical conversation and be credible in both. This module focuses on the bridge — how to develop enough fluency in business economics and engineering constraints to make better decisions, communicate more clearly, and earn trust from both sides of the table. AI-related trade-offs are woven in as a practical lens throughout.

TOPICS

What business acumen actually means for a PM: P&L, unit economics, and strategic trade-offs
What technical acumen actually means for a PM: constraints, debt, architecture decisions at a conceptual level
How business and technical constraints interact — and why PMs are uniquely positioned to navigate them
AI-specific trade-offs: cost, latency, accuracy, explainability, and when they matter
Presenting trade-off recommendations with confidence and clarity

LEARNING OBJECTIVES

Identify the key business and technical constraints affecting a product decision
Reason through a trade-off — including AI-related ones — using a structured approach
Present a trade-off recommendation to a mixed business/technical audience with confidence
Describe where their current business and technical fluency is and what they want to develop further

ACTIVITY

Trade-off scenarios: teams work through 2–3 realistic scenarios involving tough business/tech trade-offs — including at least one AI-specific decision. Each team presents their recommendation and reasoning to the group. Structured debrief focuses on clarity of thinking and confidence of delivery, not just the "right answer."

CAPSTONE: Product Brief & Individual Commitments

OVERVIEW

The capstone is where everything threads together. Teams present the full arc of their work — customer insight, vision, strategy, roadmap, and key trade-offs — as if pitching to a real leadership team. Then individuals step back from the team work and make personal commitments: specific, written, public promises about what they'll do differently in the next 90 days.

TOPICS

Full product brief presentation: customer, vision, strategy, roadmap, trade-offs
Structured peer feedback using the Skeptic / Ally / Clarifier model
Individual development commitments: the 5 Dimensions focus, AI and experimentation practice, communication clarity
Closing reflection: what shifted, what's next, how to keep the momentum

LEARNING OBJECTIVES

Deliver a cohesive, confident product brief that connects customer insight all the way through to trade-off decisions
Give specific, actionable feedback as a Skeptic, Ally, and Clarifier
Leave with a written 90-day development commitment across three dimensions: a 5 Dimensions focus, a practice around AI and experimentation, and a communication goal
Name what genuinely shifted for them over the two days — not just what was interesting

ACTIVITY

Team presentations: each team presents their full product brief (15–20 min). Peers are assigned roles — Skeptic (challenge the assumptions), Ally (build on the strengths), Clarifier (ask the questions that sharpen the thinking) — and give structured feedback after each presentation.
90-day commitment cards: each individual writes three commitments — one dimension of the 5 Dimensions they'll intentionally develop, one way they'll use AI and experimentation more thoughtfully, and one way they'll communicate direction more clearly with their team. Shared with the group for accountability.

Day 1: Foundations, Customers, Strategy & Judgment

Module 1: Opening & Modern PM Foundations

Module 2: Knowing Your Customer (When Everything Is Moving Fast)

Module 3: Strategy & Judgment Under Speed

Day 1 Close: Reflection

Day 2: Roadmaps, Influence, Business & Tech, Capstone

Module 4: Adaptive Roadmapping in the AI Era

Module 5: Influence & Storytelling

Module 6: Connecting Business & Tech

Capstone: Product Brief Presentations & Commitments

Back to Workshop Overview

A two-day workshop that reinforces the core craft of product while embracing new, AI-powered ways of working

Welcome, introductions, and workshop goals — establishing the group contract

How AI is changing the work of product management — speed, synthesis, generation — and what it doesn't change

What PMs are truly accountable for: outcomes, not outputs

The 5 Dimensions of Great Product Managers: Know Your Customer, Connect Business & Technology, Think with Clarity, Lead with Influence, Drive Execution

AI in practice: a working framework for when to use it, what to use it for, and where to keep humans in the loop

LEARNING OBJECTIVES

Articulate what product managers are uniquely accountable for in the AI era

Describe how AI changes PM workflows without replacing PM judgment

Use the 5 Dimensions as a shared framework for the workshop and beyond

Apply a practical decision framework for when and how to use AI in your own PM workflow

Identify 1–2 personal development priorities to focus on through the two days

ACTIVITIES

5 Dimensions self-assessment: participants rate themselves honestly across all five areas, then share one strength and one growth area with the group. Creates psychological safety early and surfaces the diversity of experience in the room — which becomes a resource throughout the workshop.