Riseplan from Roast & Rise

The Next Three Years: A Scenario Planning Sprint for Leadership

Map your market’s real futures and commit with clarity—before uncertainty chooses for you.

This sprint guides founders and executive teams to write sharp, industry-specific scenarios and make irreversible vs. reversible decisions visible. By the end, you’ll hold a tailored roadmap for immediate moves, smart wagers, and focused restraint.

Editorial still life of three slightly open scenario folders on a warm-lit surface, each folder casting a shadow, beside a minimalist orange accent—all objects, no people, conveying readiness for strategic work. — A cinematic workspace holds three carefully arranged, empty scenario file folders. Each folder is slightly open, allowing warm morning light to cast distinct shadows across a textured, neutral surface. The scene is minimalist, with a burnished orange accent strip bisecting the bottom edge—framing this as an artifact-driven journey. No labels or text. The composition is intentional and human in its sense of anticipation.

Course thesis

AI answers 'how'. Foresight answers 'then what'. This sprint gives leaders concrete ways to see—and act on—their market’s next moves before they're swept along for the ride.

What you leave with

By the end, you’ll have written three concrete scenarios for your market, built a clear decision map, and committed your leadership team to act on what’s next—not just what’s urgent.

For

Founders and executive teams responsible for high-impact strategic choices in fast-moving markets, with a vested interest in directing their own company's future.

Workflow

Strategic planning off-site or sprint: diagnosing change signals, scenario building, surfacing key bets, aligning on decisions, and publishing a shared, actionable roadmap.

Change

Shift from reactive AI-adoption and incremental planning to scenario-driven, irreversible-vs-reversible decision making and explicit commitment around what to build today, scan for tomorrow, and leave for later.

What you can do

Use these as checks while you move through the plan.

Generate two or three named, credible scenarios for your own industry’s next three years.

Identify and clearly label strategic decisions as reversible or irreversible.

Use a structured scenario canvas to map implications and plan concrete responses.

Build a one-page commitment sheet: what to build now, what to watch, what to defer.

Spot early-stage signals and avoid reflex execution on unproven bets.

Advance from leadership alignment to public action—without false consensus or vague intentions.

Chapters

Name the Real Uncertainties

Surface the true drivers of market disruption by naming—and filtering—the uncertainties that could upend your business in the next three years. Cut through clichés and list only the unknowns that force new strategic moves.

An editorial view of five blank index cards above a paper filter grid; three cards are distinctly circled, the others left aside. The composition is warm and clear, with soft shadows and no people, highlighting selection and judgment. — Five blank index cards, each resting above a paper checklist filter matrix, with three sharply circled. The rest are pushed aside. A single pencil lies parallel, signaling active selection. The light isolates the chosen cards, and a soft orange band gives editorial warmth. No visible text. The scene expresses both filtering discipline and the concrete physicality of 'real uncertainties.'

Why this matters in the workflow

Strategy sprints fail when the team starts from slogans or settles for best-guess forecasts. Most leadership teams list what’s popular, not what’s real. If you don’t sharpen your true unknowns now, every scenario will drift into fiction or fizzle into consensus. Real uncertainties give your sprint teeth—and set up concrete, credible scenarios.

The working model

The goal: a short, brutal list of what you don’t know, but must. These are the uncertainties that—if answered—would change what you build, where you hire, or how you invest. Filter ruthlessly.

Quality checklist

Uncertainty is specific—no handwaving or generic tech talk.

Item is outside your team’s direct control, but you can track signals.

Each item would fundamentally change a strategic choice.

There are no more than five uncertainties in the shortlist.

Each uncertainty has a clear impact sentence attached.

The list provokes debate—not just agreement.

Common mistakes

Listing tech hype or general AI trends as uncertainties.

Allowing the team to dodge uncomfortable or sensitive uncertainties.

Keeping weak or irrelevant items because of consensus.

Collecting too many uncertainties (more is not better).

Checkpoint

Can you clearly state three to five real uncertainties—each with sharp consequences—that go beyond industry platitudes?

Exercise

Cut Through the Noise—Draft and Filter Your Uncertainties

Step 1: Raw List

Spend 5 minutes dumping every uncertainty top-of-mind for your market, business, and customers. No editing.

Step 2: Apply the Filter

For each item, ask:

Does this uncertainty force different moves depending on how it resolves?
Is it outside our control, but visible by signals?
Would it move our biggest needle in three years?

Eliminate or rephrase anything that fails.

Step 3: Final Shortlist

Pick the 3-5 uncertainties that survive. Write a one-sentence impact for each (“If X happens, we…”).

Step 4: Save and Share

Capture the filtered list and impact notes in the provided template. Share with your team—invite challenge or add missing angles.

Use this at work tomorrow

Book 30 minutes with your exec team to capture and debate your true uncertainties. Leave with three to five you’d bet the next offsite on.

Write Your Scenarios—No Science Fiction

Draft sharp, credible scenarios for your company's real market—no trend-watching, no hype. Name each. Map drivers and consequences. Set trigger signals. These scenarios anchor every next decision—not as fantasy, but as working tools for the next three years.

Overhead editorial illustration of a physical scenario canvas split into three sections, each with a closed envelope, a stone, and a colored paper slip—arranged intentionally on a warm orange-lit surface, no humans present. — A large planning canvas is spread across a tabletop, divided into three bold sections. Each section holds grouped objects: a closed envelope (for scenario name), a smooth stone (driver), and a slip of colored paper (trigger signal). Ambient orange light draws attention to the composition’s structure and seriousness. The scene makes tangible the scenario design process and the selectivity of concrete, testable future bets.

Why this matters in the workflow

Strategy is only as real as its picture of tomorrow. Vague trends (‘AI everywhere’) and platitudes (‘the market will be disrupted’) dissolve in practice. A scenario worth using names the concrete paths your company might face—and gives leadership a shared language for bets, fears, and moves.

Scenarios are not endless wish lists. They are choices about which futures to rehearse, so you’re ready whether reality lands on ‘Eruption’, ‘Stalemate’, or ‘Broken Glass’. This chapter is about getting those futures down—truthfully.

The working model

Quality checklist

Scenarios are clearly named—memorable, not generic.

Each scenario is tied to a real, specific uncertainty.

Drivers and consequences are concrete and direct—no handwaving.

At least one observable, plausible trigger is identified per scenario.

No scenario is a disguised version of your current plan or wishes.

Common mistakes

Writing broad, generic scenarios with no anchor in reality.

Making all scenarios variants of the same outcome (e.g., all win paths).

Missing specific, observable trigger signals.

Focusing consequences on industry platitudes, not your business.

Naming too many scenarios—confusing action with exhaustiveness.

Checkpoint

Can you describe each of your three scenarios—including a trigger signal—in under one minute, to a skeptical colleague? If yes, move to the next chapter.

Exercise

Draft Three Plausible Scenarios With Triggers

Draft three written scenarios for your company’s market and workforce. Use the canvas to anchor each in a real uncertainty, flesh out key drivers, and map the consequences. Close each with at least one plausible trigger: a market, regulatory, or competitor event that would tip you into scenario monitoring.

Steps:

Pull your top 2–3 real uncertainties from the last session.
Name your scenarios—avoid jargon and broad verbs.
For each scenario, fill:

Main driver(s)
Concrete consequences (be specific to your P&L, customers, or team)
At least one observable trigger signal

Review with one colleague for plausibility. Ask: Could this be described to a new board member in under a minute? If not, cut and rewrite.

Estimated time: 15 minutes.

Use this at work tomorrow

Book 15 minutes: name your three real scenarios, write them up on the canvas, and share with one exec for honest pushback.

Sort the Decisions: Reversible vs. Irreversible

Surface and map every major upcoming leadership decision by how hard it is to reverse—then debate what that makes visible for your next moves.

Still life of two trays on a workspace—one with a stack of cards under bold orange light (irreversible), one with fewer cards in softer light (reversible). Colored pebbles beside trays hint at scenario links. No people, just intentional object placement. — A clean desktop holds two trays: one marked by orange lighting (irreversible), the other softly lit (reversible). Each tray contains a short stack of blank decision cards. Thin lines connect a few cards to colored pebbles nearby, denoting scenario dependencies. The arrangement makes the irreversible pile visibly heavier. The design underscores the weight of commitment versus agility.

Why this matters in the workflow

Every team makes bets. Some you can unwind. Some become your new North Star—or your deepest regret. Too often, executive teams lump every decision into a single pile, or dodge the discussion for fear of making things uncomfortable. That’s a risk you can’t afford in AI’s pressure-cooker market. This tool is your forcing function: make clear which choices you can walk back when the landscape changes, and which will set you on a path with no easy exit.

Irreversible doesn't just mean expensive. It means a move that commits you so completely—resources, reputation, contracts, talent—that reversal becomes impractical. By mapping these, you shift debates from ego-defending or optimism bias to actual consequence planning.

The working model

Quality checklist

Every major decision for the next 6–12 months is listed—no cherry-picking.

Each decision is honestly scored: you can explain why it’s reversible or not.

Scenario risks are clearly annotated and traced to your own scenarios, not just general trends.

Disagreements are captured—not papered over.

Map is versioned/date-stamped for visibility and review.

Common mistakes

Overestimating reversibility of talent, contract, or public moves.

Dodging debate by lumping tough calls into mushy middle categories.

Forgetting to link decisions to the scenarios you’ve written—losing all context.

Letting one strong voice sweep the room and shortcut debate.

Checkpoint

Is every major upcoming decision mapped, debated, and linked to a concrete scenario? Are reversibility risks visible to your leadership team?

Exercise

Map Your Next 6 Months of Decisions: Reversible or Irreversible?

Instructions:

Gather your current and upcoming major team decisions for the next 6–12 months. Use real examples—investments, hiring, deals, public projects.
For each decision, honestly score its reversibility: Can it be unwound quickly and cheaply if the future shifts?
Map each into one of two columns: Reversible or Irreversible. Push for candor. Defend your choices.
For each, annotate the relevant scenario(s) (from your last exercise) where the risk or commitment gets sharpest.
Run a five-minute team debate—what did you disagree about? Capture that. Then save your map for the next commitment round.

Output:

A completed Reversible vs. Irreversible Decision Map, with scenario annotations and discussion notes.

Plan 15 minutes—no shortcuts. Use the template below.

Use this at work tomorrow

Block 15 minutes with your team, list every high-stakes decision, and force clarity: which can you walk back, and which turn the ship for good?

Commit to Build, Watch, Not-Yet

Turn analysis into action. Build a one-page commitment sheet that calls the shots on what your leadership team will move on now, what must be watched for signals, and what stays locked until the facts change. Make outcomes public, attach names, and close the loop on paper commitment versus lived action.

Still life showing a sleek one-page sheet divided into three columns, each with blank cards and a token on top, under orange editorial light—emphasizing public, organized commitment. No people present. — A single, unmarked one-page sheet dominates a warm-lit desk, divided cleanly into three columns by orange and neutral lines. Each column contains a clipped stack of blank initiative cards, with a small brass token (signaling ownership) atop each stack. A date card sits visibly at one corner. The public, physical arrangement marks this as more than theory.

Why this matters in the workflow Analysis withers without a decision. Most scenario work drifts into slides—never the day-to-day radar.

A one-page commitment sheet is your forcing function. It translates scenarios and decision maps into public action: what you build, watch, or pause. Ownership, triggers, and timing move from theory to habit. The sheet is short on style, heavy on names, dates, and line items.

Done well, it becomes the agenda for your next board, LT, or all-hands. No hiding. Decisions and inaction both visible.

The working model The commitment sheet has three columns:

Build: What you will act on now. New products, reorgs, investments. Bold and clear.
Watch: What is plausible, not proven. Needs a trigger—a defined signal or event to take action.
Not-Yet: No motion, no budget, no half-moves. These are acknowledged but paused—until a circumstance changes.

Quality checklist

Every item is specific—no vague placeholders or jargon.

Each Watch item has an objective, observable trigger (not a subjective feeling).

Owners are named for every item.

At least one Not-Yet item has a clear trigger to revisit.

Sheet fits on one page; readable without explanation.

Document is circulated/shared, not private.

Common mistakes

Putting everything in 'Build' to avoid hard choices.

'Watch' items without clear or checkable triggers.

Column drift—untracked moving items between categories without review.

Unassigned ownership.

Sheet hidden in drive, never shared.

Checkpoint

Can you point to a current, circulated sheet showing what your team commits to build, watch, and not pursue? Is every item owned and linked to a trigger?

Exercise

Draft Your Build, Watch, Not-Yet Commitment Sheet

In the next 15 minutes, construct your draft one-page commitment sheet. Use this with your team—don’t polish for minutes, make the real calls.

Steps:

Pull up your scenarios and decision map from previous chapters.
List 3-6 key initiatives, investments, or capability bets you’ve debated.
Place each in one column: Build, Watch, Not-Yet.
For any Watch item, define a trigger event in plain language (objective, checkable).
Assign an owner for each line.
Set a date to review or report on each active (Build/Watch) item in the next 30 days.
Copy your output to a visible team space, or prep to circulate in your next exec/board pack.

Use this at work tomorrow

Draft your Build, Watch, Not-Yet sheet in your next exec sync and circulate before leaving the room.

Run the 30-Day Reality Loop

Close the loop: translate scenario plans from a one-off event into a real-time discipline. This chapter walks you through the first month of signal tracking, scenario testing, and decision adjustment—anchoring your strategy in the changing market, not in wishful thinking or static plans.

Editorial arrangement of an open logbook, blank signal tags, a marker, and a small analog timer on a warm-lit desk—no people, emphasizing monitoring, checkpointing, and disciplined review. — A scenario checkpoint logbook lies open on a desk next to a small stack of signal tags (like blank event tickets), each with an attached marker. A round, vintage timer sits beside the book. Warm orange light falls across the logbook, illuminating page divisions for date, signals, and adjustments. The scene is still but loaded with the expectation of update, showing the continuous loop of evidence and revision.

Why this matters in the workflow

Ideas fade. Markets don’t care about your scenario offsite outputs unless you catch live signals, adjust quickly, and use your commitments under real pressure. The 30-Day Reality Loop is how leadership teams keep scenario planning alive: testing for drift, forcing revision (or validation), and stopping strategy from calcifying until the next annual retreat.

This is not ritual. It’s a sharp instrument for surfacing missed signals, sunk-cost bias, and fear of admitting error. The loop builds a habit: watch, log, review, decide. Nothing soft, nothing ignored.

The working model

Quality checklist

Signals logged are specific and externally verifiable.

Adjustments tie directly back to scenario or commitment, not vague trends.

Each change is dated, owned, and followed up.

Log is shared and visible to all leadership; not buried in private notes.

Common mistakes

Recording opinions instead of concrete signals.

Letting scenario reviews drift into sporadic reporting instead of set intervals.

Ignoring signals that contradict current bets.

Reviewing but not updating commitments—stuck in observer mode.

Checkpoint

Have you completed at least one scenario log entry with real signals, assigned adjustments, and agreed on the next review date?

Exercise

Build and Run Your First Scenario Reality Log

Practical Steps

Copy the scenario checkpoint log template below.
For each scenario, note owner, review date, and core signals to track.
Gather 3-5 new market/industry signals from the past two weeks. Log which scenario(s) they relate to.
Assess each scenario: Does any commitment need an update, pause, or rethink based on these signals? List adjustments.
Date and annotate every change. Assign follow-up owner for next interval.
Share the log with your full leadership team.

You should be able to complete your first review log in under 15 minutes—with real signals, not just opinion.

Use this at work tomorrow

Lock in your team’s first 30-day scenario review—log live signals, debate what’s changed, and update your commitments before the next wave hits.

30-day path

Week 1: Run the uncertainties and scenario-writing workshops (2 focused half-days).

Week 2: Map out decisions and review them in a leadership debate session (1-2 hours).

Week 3: Finalize, publish, and assign the Build, Watch, Not-Yet commitment sheet.

Week 4: Run the first 30-day scenario and decision review—capture live signals, update as needed, and agree on next interval.

Success signals

Three sharply written future scenarios, named for your market and workforce.

A mapped, debated list of decisions, clearly split by reversibility.

A one-page commitment sheet, circulated and referenced in leadership meetings.

Scenario and decision checkpoints set and followed up within one month.

Observable shift in team discussion—from ‘what if’ guessing to visible consequence planning.

Reflection prompts

Where does this topic show up in real work?

What behavior should change first?

What evidence would prove this Riseplan worked?

Manager checklist

Choose one owner for the behavior change.

Use the exercise on live work.

Review the output before scaling the habit.

Decide what changes after 30 days.

Want this shaped around your company?

Risey can research your company foundation first, then build a version of this path around your real workflows, customers, and culture.

Start with your company