Evaluating Digital Initiatives in the Age of AI

In today’s fast-evolving digital landscape, AI and data-driven practices are rapidly becoming indispensable tools for digital transformation. Yet many organisations struggle to evaluate which digital initiatives to prioritise to secure future growth. This training focuses on how to evaluate and prioritise digital initiatives, distinguishing quick wins and strategic bets, using structured frameworks and AI-enabled tools. The programme is highly practical, combining guided demonstrations, discussions, and hands-on exercises.

Join us to strengthen your ability to navigate digital transformation with confidence. This training will equip you with practical techniques and hands-on experience to effectively prioritise digital initiatives and drive future growth. Don’t miss this opportunity to elevate your organisation’s digital capabilities and make smarter, data-driven decisions.

By the end of the training, participants will be able to:

1. Describe the difference between quick wins and strategic bets in delivery contexts.
2. List key frameworks and models used for evaluating and prioritising initiatives.
3. Differentiate between tactical and strategic initiatives based on business impact and time horizon.
4. Classify AI applications that support initiative evaluation and decision making.
5. Apply evaluation frameworks to real or simulated digital initiatives.
6. Demonstrate the use of AI tools to accelerate the process.
7. Develop a balanced product portfolio plan that integrates both quick wins and strategic bets.
8. Justify prioritisation decisions.
9. Collaborate effectively during evaluation discussions to reach consensus on priorities.
10. Defend strategic decisions with evidence-based arguments.
11. Motivate peers to adopt an AI-enhanced approach to accelerate and facilitate evaluations.
    

This training is addressed to:

• Company Owners and C-Suite Executives (CEOs, CFOs, COOs, CIOs, CTOs, CCOs)
• Delivery and Operations Managers, from any department/function, seeking to improve efficiency,
• alignment, and impact in execution
• Heads of Innovation and Transformation Leads exploring how AI can accelerate digital delivery
• Product Managers and Product Owners involved in digital delivery and transformation initiatives
• Product Leaders, Portfolio Managers, and Strategy Managers responsible for prioritization and investment decisions
• Other professionals involved in digital transformation, product planning, or AI-driven business improvement

All participants should be currently employed.

*The number of participants is restricted to 28.

1. Framing: Quick Wins vs. Strategic Bets (30 min)

• Define “quick wins” (short-term, low-effort, immediate-value initiatives) and “strategic bets” (long-term, high-impact initiatives).
• Discuss why balancing both is key in digital transformation.
• Identify common delivery challenges in prioritisation.

2. Evaluation Capabilities (45 min)

• Explore core assessment capabilities such as data analytics, CX (customer experience) insights, and delivery performance metrics.
• Discuss data quality, integration, and accessibility challenges.

3. Evaluation Frameworks (1 h)

• Use evaluation frameworks (Effort vs. Impact Matrix, ROI Horizons, Strategic Alignment Mapping).
• Apply structured models to compare initiative value, feasibility, and alignment.
• Define ROI (Return on Investment) horizons – short-, medium-, and long-term payoff categories.
• Conduct Strategic Alignment Mapping to link initiatives with business objectives and measurable indicators (KPI, Key Performance Indicators).

4. Hands-on exercise: classify initiatives and debate tradeoffs (45 min)

• Guided exercise using frameworks learned.
• Case Study: Classify 6– 8 sample initiatives into quick wins and strategic bets.
• Group debate on trade-offs between speed, risk, and resource allocation.
• Capture key lessons about portfolio balance.

5. Communicating Prioritization Decisions (30 min)

• Present prioritisation outcomes effectively to stakeholders.
• Address typical objections and defend prioritisation rationale.

6. Apply AI tools as speed accelerators in decision-making (1 h & 15 min)

• Explain how AI enhances speed, consistency, and insight in evaluating initiatives.
• Demonstrate how AI tools assist with prioritisation and decision support. .
• Introduce common AI use cases such as:
  • Customer feedback analysis and theme extraction.
  • Portfolio review and rebalancing.
  • Stakeholder communication drafting.
• Provide sample AI prompts for continued practice.

7. Hands-on exercise: classify initiatives and debate trade-offs (30 min)

• Practice applying AI tools to real or sample product data.
• Conduct practical AI exercises such as:
  • Customer feedback summarisation and classification into quick wins vs. strategic bets.
  • Stakeholder role-play simulations (e.g., CFO or customer perspectives).
  • Portfolio balance check to assess initiative mix and recommend rebalancing.
• Compare AI-generated material and insights with team reasoning.

8. Avoid over-indexing on one side (30 min)

• Recognise portfolio imbalance risks (too tactical vs. too visionary).
• Discuss signals of imbalance and how to correct them.

9. Wrap-Up and Discussion (15 min)

• Recap of key learning points.
• Q&A and participant reflections.

Our services include:

• Handouts, including the hard copy presentation, examples, case studies, exercises, and additional notes if applicable.
• Stationery, such as pads, pens, and files.
• Drinks (coffee, tea, etc.) and a buffet lunch.
• A fully equipped training room with WiFi access.
• Certificate of completion.

If you wish to register for the seminar, please complete the registration form

Once your registration is submitted, you will receive an email stating how to proceed with your HRDA registration through the Ermis platform. Upon completion of this step, you will receive a confirmation email which will include the participation fee, including any discounts, if applicable. Kindly note that the payment should be settled at least two days prior to the seminar’s date for your registration to be confirmed.

The programme has been approved by the HRDA. Enterprises participating with their employees who satisfy HRDA’s criteria, are entitled to subsidy. Please note that there are limited seats available, therefore enroll in this seminar as soon as possible.

If you do not receive our confirmation e-mail regarding your registration, your participation cannot be guaranteed.

Cost

€150 net investment after the HRDA subsidy (€120) for all eligible participants

€270 + VAT (19%) for all participants who are not eligible for the HRDA subsidy.

Last Date for 10% Early Bird Discount: 26/02/2026

Extra discounts may apply to the initial price, before the VAT and HRDA subsidy. Please view options below.

Note

We do not provide a soft copy of the presentation for face-to-face seminars. However, if you would like to request one, please contact us. We may be able to provide it, subject to approval. In this case, the cost of the soft copy will be €50 for participants who have already attended the relevant training, or €100 for those who have not. 
 

HRDA Note

All individuals who wish to attend our HRDA approved training courses, should not only fill out our registration form, but also complete the registration process through the ERMIS platform in order to be approved by the HRDA. Regardless of whether they are claiming the HRDA subsidy or not, each participant will need to complete their registration through ERMIS as a physical person and then register to our training in order to be able to attend (either as an employee whose company is claiming the subsidy or as an individual who is not claiming the subsidy). Please reach out to the HRDA Ermis officers on 22 390 300 for more details regarding the registration as a physical person.

Discounts available

• For three or more (3+) participants from the same company, a 10% discount is available on the total cost, before the VAT and HRDA subsidy. This discount only applies for participants who enroll in the same seminar, on the same day. This discount can only be combined with the early bird discount and the HRDA subsidy, when applicable.
• For individuals/legal entities who/which register in more than two (3+) seminars during the same semester (January-June & July-December), a 10% discount is available on the total cost, before the VAT and HRDA subsidy. This discount only applies for individuals/legal entities who/which enroll in more than two (3+) seminars during the same semester, on the same day. This discount can only be combined with the early bird discount and the HRDA subsidy, when applicable.
• There is a 10% discount for alumni members. This discount should be applied before the VAT and HRDA subsidy and can only be combined with the early bird discount and the HRDA subsidy, when applicable. For more information on our alumni scheme, click here.
• There is a 10% early bird discount on selected seminars for participants who enroll in a training course until a specific date which is stated above. This discount should be applied before the VAT and HRDA subsidy and can only be combined with the HRDA subsidy, when applicable
• HRDA subsidy for all HRDA approved seminars. 
• Please note that while participants may qualify for multiple discounts, a maximum of two discounts, up to a total of 20%, can be applied per registration.

Contact

For any queries, please contact KPMG Academy on +357 22 207 460 or at academy@kpmg.com.cy

CPD

This seminar may contribute to Continuing Professional Development requirements. At the end of the seminar participants will be given a certificate of attendance confirming the total number of training hours (6 CPD).

George Constantinou
Senior Manager, Technology Consulting, KPMG in Cyprus

George is a Senior Manager in Technology Consulting at KPMG in Cyprus, bringing extensive experience in project management, technical delivery leadership, quality assurance, and largescale testing across EMEA, APAC, and NALA. With a strong foundation in DevOps, agile transformation, and software delivery excellence, he specialises in designing testing strategies, implementing automation frameworks, and ensuring that complex technology programmes deliver highquality outcomes efficiently and reliably.

He has led major initiatives across the pharmaceutical, energy, financial services, insurance, telecom, and public sector, managing crossfunctional teams and coordinating with global stakeholders to drive successful implementations. His work spans S/4HANA programmes, digital transformation strategies, CI/CD pipeline design, cloud migration, managed services, and enterprisewide rollout management.

George’s focus is on elevating delivery quality, reducing inefficiencies, and embedding automation and “shiftleft” practices to optimise the SDLC. Through his leadership, he enables organisations to modernise their delivery models, strengthen operational resilience, and achieve measurable improvements in speed, consistency, and customer value.

Rasha Abou Shakra
Manager, Technology Consulting, KPMG in Cyprus 

Rasha is a Manager in Technology Consulting at KPMG in Cyprus, holding an MSc in Computer and Communication Engineering and bringing over 10 years of experience in technology consulting, digital transformation, product ownership, and application delivery. With a strong foundation in agile practices and technical leadership, she balances strategy with execution, leading end-to-end transformation initiatives from assessment and roadmap definition to delivery and go-live.

She has extensive experience across the energy, financial services, insurance, telecom, and payments sectors, bridging business and technology to deliver scalable, user-centric solutions.

Rasha currently leads the local adoption of Microsoft Copilot as the appointed Cyprus Lead and contributes to KPMG’s global Copilot Champion network, driving AI-enabled productivity and transformation. Her work focuses on aligning business strategy with technology execution to create measurable impact, improve operational efficiency, and enable sustainable change.