Delivery managers face unprecedented complexity in today’s enterprise environment. C-suite executives demand predictable outcomes while navigating market disruption, technological acceleration, and shifting customer expectations.

Traditional planning methods collapse under this pressure, leaving organisations and delivery managers vulnerable.

For delivery managers, relying on traditional ‘predict-and-plan’ methods feels like building castles on sand. The answer isn’t more detailed planning; it’s a fundamental change in mindset. These five tips are aimed at transformation leaders striving for excellence in enterprise delivery. If you are

• Deliver Managers and Senior Delivery Managers oversee complex portfolios.
• Digital Transformation Directors and Programme Leads
• Enterprise Agile Coaches and Organisational Change Leaders
• C-level executives sponsoring large-scale delivery initiatives

Enjoy your reading and explore more content at pawelrola.com

The illusion of certainty vs the reality of complexity

Traditional project planning often assumes a high degree of predictability and stability. It aims to eliminate or reduce uncertainty through exhaustive upfront analysis, locking down scope, time, and cost in the infamous “Iron Triangle.” This works well for simple domains (Boone 2007). However, in complex or complicated domains, where typical “knowledge work ” is associated with delivering a product or service, uncertainty isn’t an anomaly; it’s the default state.

As a leader, I have seen leading enterprises adopt business agility (K. Beck 2001) to thrive in complex domains. Through my work with Fortune 500 companies, I’ve observed that delivery leaders who master adaptive planning principles consistently outperform traditional project management approaches in value delivered.

The Delivery Manager must recognise that the agile mindset is advantageous, not limiting. Three planning-related truths relevant for Delivery Managers in most situations are:

• We can’t know everything beforehand. Detailed requirements identified months before development often turn out to be incorrect, incomplete, or irrelevant once real-world delivery begins.
• Change is inevitable. Markets shift, competitors act, and users alter their preferences and behaviours. Feedback regarding the outcome of the service or product should influence our direction.
• The ability to learn quickly and effectively is the key competency. The main result of early short iterations isn’t just a working product; It is validated learning about what truly works, and what the user or customer needs and expects.

How does a Delivery Manager plan in uncertainty?

Delivery managers plan differently from traditional project managers. Planning in uncertainty requires an agile mindset. Delivery managers operating in an uncertain environment must shift their focus from prediction to adaptation, from certainty to confidence levels, and from rigid execution to empirical control. Below, you will find five pieces of advice for planning in uncertainty by delivery managers, along with actionable steps you can implement.

Regular cadence & feedback loops

Prioritise establishing a sustainable delivery rhythm. Plan thoroughly only for the immediate, predictable horizon. Use short feedback loops to test assumptions. Implement feedback mechanisms that link operational delivery directly to strategic results. Concentrate detailed planning on short-term value horizons.

Implementation Strategy:

• Design feedback loops that provide strategic intelligence to leadership teams
• Build organisational and team capabilities for rapid delivery
• Create stakeholder engagement frameworks that align operational delivery with strategic objectives
• Establish delivery governance that empowers teams whilst maintaining executive oversight
• Implement rhythm-based reporting that connects daily operations to the cadence of monitoring business outcomes.

High-level direction & probabilistic forecasting

Develop a Product Vision and set outcome-oriented goals like Objectives & Key Results (OKRs) (Plewniok 2023). These will serve as your guiding principles for decision-making processes under uncertainty. Create a high-level roadmap illustrating themes, outcomes, or epics in a likely sequence. Treat dates as forecasts, not commitments, especially those far in advance. Maintain transparency for strategic topics across the portfolio. Use Monte Carlo simulations or other methods to model the probability of different outcomes and express confidence in delivery.

Implementation Strategy:

• Shift portfolio discussions from focusing solely on delivery dates to emphasising strategic value optimisation and strengthening competitive positioning.
• Use forecasting methods that give leadership risk-adjusted confidence in delivery for strategic initiatives.
• Establish outcome-focused prioritisation frameworks that align resource distribution with strategic objectives.
• Create executive dashboards that visualise management information, such as probability ranges, strategic risks, and opportunity costs across the delivery portfolio.
• Adopt an evidence-based approach to guide meaningful change.

Flow optimisation

Focus on optimising the flow of value, if possible, throughout the value chain. Manage work in progress (WIP) limits and potential bottlenecks. Visualise workflow (Kanban boards) to identify and resolve impediments quickly. Prioritise ruthlessly based on value, risk, and learning potential.

Implementation Strategy:

• Implement portfolio-grade flow analytics that connect operational efficiency to key business metrics, such as financial performance and customer satisfaction.
• Establish impediment removal processes that improve the flow of the value creation process.
• Deploy strategic prioritisation that helps to optimise portfolio value delivery.
• Design flow governance models that balance team autonomy with strategic alignment and regulatory compliance

Embracing learning

Validated learning is essential for delivering the right value. The plan is a living artefact. Adapting the plan based on new information isn’t failure; it’s expected.

Implementation strategy:

• Support a learning culture that accelerates innovation. More on that topic here (Rola 2024)
• Develop adaptive governance frameworks that enable course correction whilst maintaining stakeholder confidence.
• Create a set of learning-driven performance metrics.

Incremental value delivery

Value is delivered continuously in small increments. Each iteration should produce something shippable that delivers tangible benefit or learning. This helps to manage delivery better and provides early ROI.

Implementation Strategy:

• Establish market validation procedures that gather customer feedback and competitive insights before full-scale investment.
• Create portfolio-level release governance that improves innovation speed while maintaining necessary regulatory compliance.
• Monitor the value or outcome realisation that links incremental deliveries to achieved results.
• Establish effective stakeholder communication that shows ongoing progress.

Delivery Manager is a navigator, not a fortune teller.

The Agile mindset transforms the Delivery Manager’s role from a fortune teller attempting to predict an unpredictable future into a skilled navigator. It’s about setting a clear direction, equipping the team, establishing effective feedback mechanisms, and making constant, informed course corrections based on the realities encountered. Planning in uncertainty isn’t about eliminating the unknown but building resilience, adaptability, and a learning culture.

By embracing this mindset, you stop fighting uncertainty and start leveraging it as a source of insight and opportunity. You move from the stress of defending an inevitably wrong plan to the confidence of steering effectively towards valuable outcomes.

If you found this article helpful, explore more content at pawelrola.com. Feel free to contact me via LinkedIn or the website.

Let’s work together to bring the organisations of the future.

Bibliography

Boone, David J. Snowden and Mary E. 2007. “A Leader’s Framework for Decision Making.” HBR.

K. Beck, M. Beedle, A. van Bennekum, A. Cockburn, W. Cunningham, M. Fowler, J. Grenning, J. Highsmith, A. Hunt, R. Jeffries, J. Kern, B. Marick, R. Martin, S. Mellor, K. Schwaber, J. Sutherland, and D. Thomas. 2001. Manifesto for Agile Software Development. http://www.agilemanifesto.org/.

Plewniok, Natalia. 2023. How to use the OKR technique to achieve business goals. 23 3. https://www.meirik.com/articles/how-to-use-the-okr-technique-to-achieve-business-goals.

Rola, Pawel. 2024. pawelrola.com. 10 12. https://pawelrola.com/leaders-business-innovation-improve-pratice/.