Chapter 24: Building the Implementation Roadmap - From Strategy to Action

Video: Recommendation & Implementation That Seals the Win: Make It Realistic, Visual & Unforgettable

Learning Objectives

By the end of this chapter, you should be able to:

• translate a strategy into a focused set of implementation workstreams;

• break strategic initiatives into specific and actionable steps;

• work backwards from the desired outcome;

• sequence activities based on priorities and dependencies;

• establish realistic timelines and implementation phases;

• assign clear ownership and accountability;

• identify the resources and capabilities required;

• distinguish activities, milestones, outputs, and outcomes;

• use leading and lagging indicators to monitor progress;

• establish decision gates and performance triggers;

• create a visual roadmap that demonstrates the recommendation is executable.

Why This Matters

Implementation is often one of the highest-weighted sections on a case competition scorecard. There is a good reason for that.

Anyone can recommend:

• enter a new market;

• launch a new product;

• transform the customer experience;

• automate operations;

• establish a partnership;

• build a digital platform.

The difficult part is explaining how the organisation will make it happen.

A strong implementation roadmap should show:

• what must happen;

• what happens first;

• what depends on what;

• who is responsible;

• how long it will take;

• what resources are required;

• how much it will cost;

• how progress will be measured;

• when management should proceed, adjust, pause, or stop.

Without this detail, a recommendation may sound attractive but remain theoretical.

Discover Your Mad Skills Principle

If you cannot explain how the strategy gets done, you do not yet have a complete recommendation.

Don't treat implementation as the administrative section at the end of the presentation. It is evidence that the strategy is realistic. The roadmap answers the judge’s question: “Can this organisation actually do what you are recommending?”

Deciphering Case Characteristics

Implementation should reflect the nature, urgency, and complexity of the case.

Turnaround Case

The roadmap may require:

• immediate cash protection;

• rapid cost controls;

• operational stabilisation;

• clear 30-, 60-, and 90-day actions;

• strong executive oversight.

Market-Entry Case

The roadmap may require:

• market validation;

• regulatory approval;

• local partnerships;

• hiring;

• channel development;

• launch and expansion gates.

Innovation Case

The roadmap may require:

• customer research;

• prototype development;

• testing;

• pilot launch;

• learning cycles;

• staged investment.

Digital Transformation Case

The roadmap may require:

• process redesign;

• technology selection;

• data preparation;

• systems integration;

• employee training;

• adoption management.

Operational Case

The roadmap may require:

• process mapping;

• bottleneck removal;

• supplier coordination;

• equipment or technology changes;

• performance testing;

• staged rollout.

Organisational Change Case

The roadmap may require:

• leadership alignment;

• stakeholder engagement;

• structural changes;

• skills development;

• communications;

• incentives;

• culture and adoption measures.

Do not automatically use a three-year timeline. A crisis may require days or weeks. A transformation may require several years. The timeline should emerge from what the strategy actually requires.

From Strategic Choice to Implementation

The strategy developed in Chapter 21 established:

• the objective;

• where to play;

• how to win;

• the required capabilities;

• the major initiatives;

• the trade-offs;

• the strategic guardrails.

The implementation roadmap converts those choices into action:

Strategic Objective → Outcomes → Capabilities → Workstreams → Activities → Dependencies → Owners → Resources → Milestones → KPIs → Decision Gates

This sequence keeps implementation connected to strategy.

Start With the End

Before listing activities, define the desired future state.

Ask:

• What will be different when the strategy succeeds?

• What result will customers experience?

• What capability will the organisation possess?

• What financial or operational result will be achieved?

• What evidence will show that the strategy is working?

For example:

“Within 24 months, the company will operate a profitable Western Canadian market-entry model with at least 2,000 active customers, acceptable customer-acquisition costs, and the capability to expand into a second regional market.”

Then work backwards:

Desired Outcome
← Performance Required
← Capabilities Required
← Major Workstreams
← Activities and Milestones
← Owners and Resources

Working backwards reduces the risk of including activities that do not contribute to the result.

Define the Future State

A future-state statement should describe more than a completed activity.

Weak:

“The new customer platform has been launched.”

Stronger:

“Customers can complete the purchase process through the new platform, employees can support it, adoption has reached the required level, and the platform is producing the expected efficiency and revenue benefits.”

The first statement describes an output. The second describes an operational outcome.

Build the Roadmap Around Workstreams

A workstream is a major area of coordinated implementation activity.

Depending on the strategy, workstreams may include:

• product or service development;

• technology;

• operations;

• people and capabilities;

• partnerships;

• customer acquisition;

• finance;

• legal and regulatory;

• stakeholder engagement;

• performance measurement.

A market-entry recommendation might use four workstreams:

1. Market and Offering

2. Partnership and Operations

3. Customer Acquisition

4. People, Governance, and Measurement

Workstreams make a roadmap easier to understand than one long list of unrelated tasks.

The Seven Implementation Questions

For each workstream or major initiative, answer:

What?

What must happen?

Use specific action language:

• negotiate;

• design;

• build;

• test;

• hire;

• train;

• launch;

• measure;

• expand.

Why?

Why is the action necessary?

Connect it to:

• the strategic objective;

• a customer need;

• a required capability;

• a risk;

• a dependency.

Who?

Who is accountable?

Identify a role, function, team, or external partner.

When?

When does the action begin and end?

Use realistic dates or periods.

How?

What resources, systems, partnerships, or capabilities are required?

How Much?

What financial or human resources are required?

How Will We Know?

What milestone or KPI will show that the action has been completed or the desired result achieved?

Activity, Output, Milestone, and Outcome

These terms are often confused.

Activity

Work being performed.

Train the regional customer-service team.

Output

The immediate product of the activity.

Twenty employees complete the training programme.

Milestone

A significant point indicating progress or readiness.

Customer-service team certified before pilot launch.

Outcome

The result created by the work.

Customer response time remains below the agreed service standard during the pilot.

A strong roadmap does not stop at activities. It shows the milestones and outcomes that determine whether the strategy is working.

Build Logical Implementation Phases

A phased roadmap helps show sequence and reduces complexity.

A useful structure is:

Phase 1: Align and Validate

Establish the foundations and test the critical assumptions.

Possible actions include:

• approve the strategic direction;

• appoint the implementation leader;

• confirm the business case;

• conduct detailed customer research;

• negotiate preliminary partnerships;

• establish baseline performance;

• define pilot success criteria.

Phase 2: Build and Prepare

Develop the capabilities and infrastructure required for launch.

Possible actions include:

• finalise the offering;

• build or configure technology;

• redesign processes;

• recruit and train employees;

• sign partnership agreements;

• prepare marketing and sales channels;

• establish data and reporting systems.

Phase 3: Launch and Learn

Introduce the recommendation on a controlled basis.

Possible actions include:

• launch the pilot;

• acquire initial customers;

• monitor service quality;

• gather customer and employee feedback;

• measure unit economics;

• resolve operational problems;

• assess performance against thresholds.

Phase 4: Scale and Optimise

Expand after the evidence supports further investment.

Possible actions include:

• expand geographically;

• increase capacity;

• automate selected processes;

• refine pricing;

• improve customer experience;

• strengthen partnerships;

• institutionalise successful practices.

The exact phases should reflect the case. Do not force every recommendation into this structure.

Use Time Horizons That Fit the Decision

“Short term,” “medium term,” and “long term” mean different things in different situations.

Case Type	Possible Time Horizon
Crisis response	Days, weeks, and months
Operational improvement	30, 60, and 90 days
Pilot programme	Months 0–3, 4–6, and 7–12
Market entry	Preparation, pilot, and expansion
Digital transformation	6, 12, 24, and 36 months
Long-term sustainability strategy	1, 3, 5, and 10 years

Avoid arbitrary labels such as “Year 1, Year 2, Year 3” unless the work genuinely requires that amount of time.

Sequence Activities Through Dependencies

Some actions cannot begin until others are completed.

For example:

Select Technology
→ Clean and Prepare Data
→ Configure System
→ Test Integration
→ Train Employees
→ Launch
→ Monitor Adoption

If training is scheduled before the system is sufficiently developed, the timeline may be unrealistic.

Dependencies may be:

Finish-to-Start

One activity must finish before the next begins.

Regulatory approval must be received before launch.

Start-to-Start

Two activities can begin together.

Product development and partner training can begin at the same time.

External Dependency

Progress depends on someone outside the organisation.

The launch depends on approval from a regulator or delivery from a supplier.

Resource Dependency

Several activities require the same limited people, capital, or technology.

The IT team cannot complete three system integrations simultaneously.

Making dependencies visible demonstrates that the timeline reflects execution reality.

Identify the Critical Path

The critical path contains the activities that determine the earliest possible completion date.

If one critical-path activity is delayed, the entire launch may be delayed.

Potential critical-path activities include:

• regulatory approval;

• technology integration;

• facility construction;

• partnership agreement;

• specialist hiring;

• supplier qualification;

• data migration.

You do not need to perform a full project-management calculation in every case. However, you should identify the two or three activities most likely to determine the overall timeline.

Ask:

“Which delay would delay everything else?”

Those activities deserve special attention.

Assign Real Ownership

Avoid statements such as:

• “Management will implement the strategy.”

• “The company will monitor performance.”

• “The CEO will oversee everything.”

Management is not a specific owner, and the CEO cannot personally run every activity.

Assign responsibility to the appropriate role or function:

• CEO or executive sponsor;

• Chief Financial Officer;

• Chief Operating Officer;

• VP Marketing;

• HR leader;

• IT director;

• project manager;

• regional launch team;

• external partner;

• implementation steering committee.

Ownership should reflect the work.

For example:

Activity	Accountable Owner
Approve investment and strategic guardrails	CEO and Board
Negotiate partnership agreement	VP Strategy
Prepare fulfilment operations	COO
Develop customer campaign	VP Marketing
Build financial reporting	CFO
Coordinate the roadmap	Implementation Lead

Use a Lightweight Responsibility Model

For complex recommendations, distinguish among:

• Accountable: Ultimately responsible for the result.

• Responsible: Performs or manages the work.

• Consulted: Provides expertise or input.

• Informed: Receives updates.

This is a simplified version of a RACI model.

Do not build a large responsibility matrix for every case. Use it when several functions or partners must coordinate.

Establish Governance

Governance explains how implementation decisions will be made.

A credible governance model might include:

Executive Sponsor

Removes barriers, protects resources, and maintains strategic alignment.

Implementation Lead

Coordinates workstreams, manages dependencies, and reports progress.

Workstream Owners

Deliver specific parts of the roadmap.

Steering Committee

Reviews performance, resolves cross-functional issues, and approves progression through major decision gates.

Review Rhythm

For example:

• weekly workstream meetings;

• monthly steering-committee reviews;

• quarterly board updates.

Governance prevents the strategy from becoming “everyone’s responsibility” and therefore no one’s responsibility.

Identify Resource Requirements

The roadmap should show what implementation requires.

Financial Resources

• initial investment;

• operating budget;

• contingency funding;

• external financing.

Human Resources

• existing employees;

• new hires;

• temporary specialists;

• training;

• leadership time.

Technology

• new systems;

• integration;

• data;

• equipment;

• cybersecurity.

External Support

• partners;

• suppliers;

• consultants;

• regulators;

• community organisations.

Organisational Capacity

• decision-making authority;

• change capability;

• available employee time;

• project-management capability.

A timeline that ignores resource limits may look organised while remaining impossible to execute.

Connect Costs to Activities

The implementation budget should align with the roadmap.

For example:

Workstream	Major Cost
Product and market adaptation	$60,000
Technology and data integration	$90,000
Partnership and operational preparation	$50,000
Pilot marketing and customer acquisition	$80,000
Total Initial Investment	$280,000

This creates consistency among:

• the strategy;

• financial case;

• implementation activities;

• timing;

• resource allocation.

If the financial model includes a cost that never appears in implementation—or the roadmap contains an expensive activity missing from the financial model—reconcile the difference.

Include a Contingency

Implementation rarely proceeds exactly as planned.

Where appropriate, include:

• budget contingency;

• schedule buffer;

• backup supplier;

• alternative channel;

• reserve staffing;

• fallback technology.

The contingency should respond to a realistic source of uncertainty. Do not add an arbitrary amount without explaining its purpose.

Select Implementation KPIs

KPIs should show whether implementation is progressing and whether the strategy is creating results.

Use several types.

Activity Measures

Show whether work is being completed.

Examples:

• employees trained;

• locations prepared;

• partner agreements signed;

• system modules completed.

Leading Indicators

Provide early evidence about future performance.

Examples:

• customer enquiries;

• trial registrations;

• conversion;

• adoption;

• employee readiness;

• system usage.

Operational Measures

Show whether the solution functions effectively.

Examples:

• delivery time;

• defect rate;

• service response time;

• capacity utilisation;

• order accuracy.

Financial Measures

Show whether the expected economics are emerging.

Examples:

• customer acquisition cost;

• contribution margin;

• incremental revenue;

• cost savings;

• cumulative cash flow.

Outcome Measures

Show whether the strategic objective is being achieved.

Examples:

• customer retention;

• market share;

• profitability;

• stakeholder impact;

• employee turnover;

• emissions reduction.

Avoid Vanity Metrics

A metric may be easy to count without showing whether the strategy is working.

Examples include:

• number of social media impressions;

• number of training sessions delivered;

• number of meetings held;

• number of downloads.

These can be useful activity indicators, but they are not sufficient outcomes.

Ask:

“If this metric improves, does it mean the strategy is succeeding?”

If not, pair it with a more meaningful measure.

For example:

• training completion and employee proficiency;

• website visits and conversion;

• app downloads and active usage;

• customers acquired and retained;

• revenue growth and contribution margin.

Establish Baselines, Targets, and Timing

A KPI is more useful when it includes:

• current baseline;

• target;

• measurement frequency;

• responsible owner;

• time frame.

For example:

KPI	Baseline	Target	Timing	Owner
Active pilot customers	0	1,200 minimum	Month 6	VP Marketing
Contribution margin per order	$28 current model	At least $28	Monthly	CFO
On-time delivery	Not available	At least 95%	Weekly	COO
Customer retention	Not available	At least 70%	Month 9	Customer Lead

Targets should connect to the assumptions and thresholds used in the financial case.

Build Decision Gates

A decision gate is a point where management reviews evidence before committing additional resources.

Possible decisions include:

• proceed;

• revise;

• delay;

• expand;

• pause;

• stop.

A gate should specify:

Timing

When will the review occur?

Evidence

What information will be available?

Threshold

What level of performance is required?

Decision

What happens if the threshold is met or missed?

For example:

At the end of Month 6, expand the pilot only if active customers exceed 1,200, contribution margin remains at least $28 per order, and service performance meets the agreed standard. If the customer threshold is missed but retention is strong, revise the acquisition strategy before committing additional expansion capital.

Decision gates connect implementation to uncertainty management.

Build Feedback Into the Roadmap

Implementation should not be a one-way path from launch to completion.

A practical cycle is:

Act → Measure → Learn → Adjust → Scale

Ask:

• What will the pilot teach us?

• How will feedback be collected?

• Who reviews the evidence?

• What can be changed?

• Which decisions are reversible?

• When will the organisation commit additional resources?

This is particularly important when customer response, technology performance, or stakeholder adoption is uncertain.

Worked Example: Partnership-Led Regional Entry

The meal-kit company has recommended a partnership-led pilot in Calgary.

Desired Outcome

Within 24 months, establish a profitable Western Canadian entry model with:

• at least 2,000 active customers;

• acceptable customer-acquisition cost;

• contribution margin of at least $28 per order;

• reliable regional fulfilment;

• evidence supporting expansion into a second market.

Workstream 1: Partnership and Governance

Owner: VP Strategy

Key activities:

• confirm partner selection;

• negotiate responsibilities and economics;

• establish service-level agreements;

• define customer-data access;

• create joint governance;

• approve pilot launch.

Workstream 2: Product and Customer Experience

Owner: VP Product

Key activities:

• validate regional customer preferences;

• adapt the meal offering;

• test packaging and delivery experience;

• redesign customer onboarding;

• collect pilot feedback.

Workstream 3: Operations and Technology

Owner: COO

Key activities:

• integrate ordering and fulfilment systems;

• establish inventory and delivery processes;

• test data exchange;

• train operational employees;

• monitor order accuracy and delivery performance.

Workstream 4: Customer Acquisition and Measurement

Owner: VP Marketing, supported by the CFO

Key activities:

• build the launch campaign;

• activate digital and partner channels;

• acquire pilot customers;

• monitor acquisition cost, conversion, retention, and margin;

• prepare expansion recommendation.

Implementation Phases

Phase	Timing	Major Milestones
Align and validate	Months 0–2	Partner selected, customer research completed, success thresholds approved
Build and prepare	Months 2–5	Agreement signed, offering adapted, systems integrated, employees trained
Launch and learn	Months 6–11	Pilot launched, service monitored, customer and financial evidence collected
Scale and optimise	Months 12–24	Offering refined and expansion initiated if decision-gate thresholds are achieved

Critical Dependencies

• The partnership agreement must be signed before system integration.

• System integration must be tested before employee training is completed.

• Operations must pass readiness testing before customer launch.

• Expansion cannot begin before the performance gate is reviewed.

Initial Investment

Implementation Area	Cost
Product and market adaptation	$60,000
Technology and data integration	$90,000
Partnership and operational preparation	$50,000
Pilot marketing and acquisition	$80,000
Total	$280,000

Decision Gate

At the end of the pilot, expansion proceeds only if:

• active customers exceed 1,200;

• contribution margin remains at least $28 per order;

• customer acquisition cost stays within the approved limit;

• customer retention meets the required threshold;

• on-time delivery remains above 95%.

The roadmap now demonstrates how the strategy moves from recommendation to controlled execution.

Visualising the Roadmap

A strong roadmap slide should help judges see:

• phases;

• workstreams;

• major actions;

• milestones;

• owners;

• decision gates;

• essential KPIs.

Roadmap Timeline

Best when the objective is to communicate phases and sequence.

Gantt Chart

Best when workstreams overlap and dependencies matter.

Swimlane Roadmap

Best when several teams or functions own different activities.

Milestone Path

Best when the implementation can be explained through a small number of critical events.

Pilot-to-Scale Funnel

Best when investment increases as evidence develops.

Choose the simplest visual that communicates the implementation logic.

Keep the Roadmap at the Right Level

A competition presentation is not a complete project-management plan.

Judges do not need:

• every meeting;

• every task;

• every internal approval;

• every minor dependency;

• every employee involved.

They do need:

• the major workstreams;

• the critical steps;

• realistic timing;

• clear ownership;

• major dependencies;

• costs;

• milestones;

• performance gates.

The slide should allow judges to understand how the project would move from today to the desired future state. It does not need to contain enough detail to manage every daily activity.

Winning the Room

A strong implementation explanation might sound like:

“We will implement the partnership-led entry through four coordinated workstreams over 24 months. During the first two months, the VP Strategy will finalise the partnership and validate customer requirements. From Months 2 to 5, Product and Operations will adapt the offering, integrate systems, and prepare employees. The pilot will launch in Month 6, followed by six months of customer and financial testing. Expansion will occur only if the pilot achieves at least 1,200 active customers, a contribution margin of $28 per order, and the required service and retention levels.”

This explanation shows:

• sequence;

• ownership;

• timing;

• coordination;

• milestones;

• control.

Coach’s Lens

I often ask teams:

“Could the judges visualise the organisation moving from today to the desired future state?”

If the answer is no, the roadmap may be too vague.

But do not confuse credibility with excessive detail. A competition slide should not attempt to replace a complete project plan.

The goal is to demonstrate that your team understands:

• what must happen;

• what happens first;

• who must lead it;

• what could delay it;

• what success looks like;

• when management must make the next decision.

Strong implementation is not a long list of tasks. It is a logical path from strategic intent to measurable results.

Common Mistakes

Starting With Activities Instead of Outcomes

Define the desired future state before listing tasks.

Vague Actions

“Improve operations” is not an implementation step.

Repeating the Strategic Initiatives

The roadmap should explain how the initiatives will be executed.

Arbitrary Timelines

Do not use a three-year timeline simply because it is familiar.

Unrealistic Speed

Account for hiring, approvals, technology, training, procurement, and stakeholder engagement.

No Ownership

Every major workstream needs an accountable owner.

Making the CEO Responsible for Everything

The CEO may sponsor the strategy, but functional leaders should own execution.

Ignoring Dependencies

Actions do not occur independently.

Ignoring the Critical Path

Some delays affect the entire roadmap.

No Resources

A plan without people, capital, technology, or capacity is incomplete.

Costs That Do Not Match the Financial Model

Reconcile the roadmap budget with the financial case.

Milestones Without Outcomes

Launching the programme does not prove it is creating value.

Too Many Activity Metrics

Measure adoption, performance, and outcomes—not only completed tasks.

Vanity Metrics

Impressions, downloads, or meetings do not necessarily demonstrate success.

No Decision Gates

Do not assume every phase should proceed regardless of performance.

No Feedback Loop

Implementation should allow the organisation to learn and adapt.

Too Much Detail

Focus on the elements required to establish feasibility and control.

An Unreadable Timeline

If the judges cannot follow the sequence, simplify it.

Mad Skills Drill

Take the recommendation developed in Chapter 22.

Part One: Define the Future State

Complete:

At the end of implementation, the organisation will…

Include:

• one strategic outcome;

• one customer or stakeholder outcome;

• one financial or operational outcome.

Part Two: Work Backwards

Identify:

• capabilities required;

• major workstreams;

• key activities;

• milestones;

• performance measures.

Part Three: Create the Workstreams

Develop three to five workstreams. Assign one accountable owner to each.

Part Four: Build the Phases

Organise the roadmap into phases that fit the case.

For each phase, identify:

• objective;

• major actions;

• start and end time;

• milestone.

Part Five: Identify Dependencies

List:

• two finish-to-start dependencies;

• one external dependency;

• one resource dependency.

Then identify the activity most likely to delay the entire roadmap.

Part Six: Estimate Resources

Identify:

• people;

• technology;

• partners;

• financial investment;

• organisational capacity.

Part Seven: Create the KPIs

Develop:

• one activity measure;

• one leading indicator;

• one operational measure;

• one financial measure;

• one strategic outcome measure.

Part Eight: Establish a Decision Gate

Complete:

At [time], management will proceed to [next phase] only if [thresholds]. If those thresholds are not met, it will [response].

Part Nine: Test the Roadmap

Ask:

• Does every workstream support the strategy?

• Is the sequence logical?

• Are timelines realistic?

• Is ownership clear?

• Do costs match the financial model?

• Are the most important dependencies visible?

• Do KPIs show outcomes rather than only activities?

• Can the organisation adjust as it learns?

Part Ten: Simplify

Remove one activity.

If the strategy can still succeed without it, the activity may not belong on the main roadmap.

Reflection Questions

1. Did you begin with the desired outcome or with a list of tasks?

2. Which workstream is most important to success?

3. Who is accountable for each major result?

4. Which activity is on the critical path?

5. Which external dependency creates the greatest uncertainty?

6. Does the organisation have sufficient people and capacity?

7. Do implementation costs match the financial analysis?

8. Which leading indicator will provide the earliest warning?

9. What milestone demonstrates readiness to launch?

10. What evidence is required before scaling?

11. What should management do if the thresholds are missed?

12. Can judges understand the roadmap within 30 seconds?

Chapter Summary

A strong implementation roadmap turns strategic intent into a controlled sequence of action.

It moves through:

Desired Outcome → Required Capabilities → Workstreams → Activities → Dependencies → Owners → Resources → Milestones → KPIs → Decision Gates

The roadmap should make clear:

• what happens;

• why it matters;

• who owns it;

• when it occurs;

• what it requires;

• how progress will be measured;

• when the organisation should make its next decision.

The goal is not to create a complete project-management manual. It is to demonstrate that the recommendation is realistic, coordinated, measurable, and adaptable.

Key Takeaways

✓ Begin with the desired future state and work backwards.

✓ Build the roadmap around a focused set of implementation workstreams.

✓ Distinguish activities, outputs, milestones, and outcomes.

✓ Use phases and time horizons that reflect the actual case.

✓ Make important dependencies and critical-path activities visible.

✓ Assign accountable owners rather than relying on “management.”

✓ Establish governance for coordination and decision-making.

✓ Identify the financial, human, technological, and external resources required.

✓ Reconcile implementation costs with the financial model.

✓ Use leading, operational, financial, and outcome measures.

✓ Avoid relying only on activity measures or vanity metrics.

✓ Establish baselines, targets, timing, and ownership for important KPIs.

✓ Use decision gates to control further investment and expansion.

✓ Build feedback and learning into implementation.

✓ Keep the roadmap visual, focused, and easy to explain.

Looking Ahead

Even a well-designed implementation plan can be disrupted by:

• weak customer adoption;

• cost overruns;

• technology failures;

• stakeholder resistance;

• supplier problems;

• regulatory delays;

• competitor responses.

The next chapter asks:

What could prevent the strategy from succeeding, how likely is it, how serious would it be, and what should the organisation do about it?

That is strategic risk management.