Mind the Gap: Strategy, Execution and Portfolio Management

Event Report

Speaker: Steve Jenner
Host: David Dunning, Co-founder, BIG CIC

Overview

This session concluded the BIG Conference series by focusing on portfolio management as a critical bridge between strategy and execution suited to finite delivery.

While earlier sessions explored strategy formulation and governance and risk perspectives, this final discussion examined how organisations make better investment decisions, prioritise work, and deliver measurable strategic contribution through portfolios of change.

Steve Jenner drew on extensive experience across government and the private sector, alongside insights from Managing Portfolios and Managing Benefits, to challenge some common myths about project failure and to set out a more disciplined, evidence-based approach to portfolio management.

Key Themes and Insights

1. The Reality of the Strategy Execution Gap

The session opened by questioning headline claims that most projects fail. Jenner argued that while such statistics are misleading – much of modern life depends on projects that clearly do succeed – there remains a genuine and costly gap between strategy and execution. When projects fail, the consequences can be severe, as illustrated by large-scale infrastructure programmes such as HS2.

The core issue is not project management capability alone, but weak connection between strategic intent, investment decisions, and delivery.

Editors note: Portfolio is a widely used term. At its most generic level, a portfolio simply means a deliberately managed collection of things, held together for a purpose. That definition is broader – and more useful – than any single professional or sector-specific use. Stripped of jargon, a portfolio is not a container or a reporting construct. It is a way of thinking and deciding that recognises interdependence, scarcity, and the need to optimise across the whole rather than any single part

2. What Portfolio Management Really Is

Portfolio management was positioned as a senior management discipline concerned with:

• Choosing the right initiatives, based on strategic objectives
• Doing them well, so that intended benefits are realised
• Doing them at the right time, given organisational capacity and constraints

Rather than focusing on “strategic alignment” as a tick-box exercise, Jenner emphasised strategic contribution – the specific, demonstrable impact an initiative will have on stated objectives.

Editors note: It would have been interesting to discuss how much cascading and development of projects to address objectives actually goes ahead, vs emergence of projects which claim their existence based on their opinion of their strategic alignment.

3. Objectives, Benefits, and Traceability

A central argument was that portfolios must start with clear objectives. Benefits act as the bridge between objectives and delivery, providing two-way traceability:

• From objectives to initiatives, via defined benefits
• From projects and programmes back to strategic objectives

Benefits that cannot be measured or linked to strategic objectives were described as, at best, weak and, at worst, a waste of scarce resources. This thinking aligns with PMI guidance and with public-sector principles adopted in jurisdictions such as New Zealand.

The discussion also connected this model to OKRs, highlighting a shared structure: objectives first, measurable results next, and initiatives last.

Editors note: “strategic objectives” literally means objectives pertaining to strategy. Strategic objectives are the specific outcomes an organisation must achieve to fulfil its purpose and realise its strategy.

The challenge for many organisations is that they do not have a developed, current, or agreed strategy. This does not mean that the organisation does not want to progress, and its board and senior managers may have goals, investment ideas, and opinions on mission critical objectives. Without a unified strategy and strategic objectives, agreeing on performance targets, responses to corporate threat and  opportunity is less easy to agree, communicate, cascade and control.

4. Risk and Return, Not Just Cost and Benefit

Drawing on modern portfolio theory, Jenner argued that investment decisions must consider both expected return and the risk that benefits will not be realised. Many business cases focus narrowly on costs and benefits, ignoring delivery risk.

Tools such as the BCG DICE model were presented as practical ways to assess achievability, taking into account factors such as team capability, leadership commitment, and project complexity.

Editors note: Should benefit be situated in the programme, project or management team which is realising the benefit? In the BIG Management Team – benefits are a key agenda topic for the Business as Usual Function.

5. One Portfolio Is Not Enough

Treating all initiatives as if they were directly comparable was strongly criticised. Instead, portfolios should be segmented into logical categories or “strategic buckets”, such as:

• Mandatory and regulatory work
• Cost reduction and revenue generation
• Strategic change aligned to specific objectives

The first strategic decision is how much resource to allocate to each bucket. Only then should initiatives compete within their category, using criteria appropriate to their purpose.

Editors note: The concept of “strategic buckets” sounds quite un-strategic – but is a sensible way to break a portfolio into manageable chunks.

• Clearly “Mandatory and regulatory work” is imperative and will cost what it costs.
• Cost reduction is opportunistic and benefit related
• Strategic change aligned to specific objectives – this is strategic if the objectives pertain to strategy

The remit for the portfolio must be clear – as in – is it just for / for all of

• Investment Management
• Mission critical objectives
• Cross functional change

Please see the discussion of Business Portfolio in the BIG BoK – which extends beyond just investment or change portfolio. There are also operational workloads – which may include changes and investments – which may or may not relate to strategy – e.g. IT, finance, HR, Revenue generation

6. Discipline in Decision-Making

A recurring theme was the need for consistency and discipline. Drawing on research and personal experience, Jenner described common behaviours that undermine portfolio effectiveness, including bypassing agreed criteria, political escalation, and the “conspiracy of continuation” that makes failing initiatives hard to stop.

Effective portfolios apply clear rules, transparent information, and the courage to make and revisit decisions.

7. Capacity, Dependencies, and Flow

The session highlighted how unrecognised dependencies and overloading scarce resources slow delivery across the whole system. Logical and logistical dependencies, particularly around specialist roles, create bottlenecks if too much work is started at once.

 Staggering initiatives, limiting work in progress, and focusing people on fewer priorities were shown to improve flow and outcomes. The phrase “slow is smooth, and smooth is fast” captured this principle succinctly.

Editors note: The discussion focused mainly on the layering of work from the portfolio onto the organisation and the discussion was about choices made between portfolio items rather than choices between operational workloads and portfolio tasks.

In reality organisations can make choices between operational, investment and change activity – but it is not clear in the Portfolio Forum where this decision making is ultimately made. In the BIG Body of Knowledge, in the content on Management Teams, it is noted that resource deployment is made by resource owners who may be deciding between operational work, product / asset development or other investment / change work from the portfolio projects / programmes. The implication is that disagreement is resolved by escalation though a clear accountability map.

8. Stage-Gated Funding and Incremental Commitment

Jenner challenged the idea that organisations manage risk effectively once full funding is approved. Instead, he advocated stage-gated funding, where continued investment is earned at decision points based on evidence.

Borrowing from poker rather than chess, this approach treats strategy execution as a series of informed bets, increasing commitment only as uncertainty reduces.

Editors note: The stage gating approach works with the resource allocation management concept in Management Teams.

9. Governance That Actually Works

Governance was framed around three responsibilities:

• Setting direction
• Making investment decisions
• Providing oversight throughout delivery

The issue is rarely a lack of governance structures, but how they are used. Culture, transparency, and willingness to act on information matter more than formal processes alone.

Editors note: The BIG BoK recognises that portfolio, programme and project governance needs to fit with strategy, operational cycles, Product and Management Teams. It also relies on Accountability Mapping, and availability of support to enable governance to be synchronised.

Discussion and Audience Questions

The Q&A explored practical challenges, including:

• Introducing portfolio management “by stealth” in low-maturity organisations

Editors note: Managing the connection from purpose to vision to strategy and delivery and back again requires a capable organisation. It requires support and funding from the highest levels of the organisation. In my experience, “by stealth” means to try to achieve some capability without the support it needs.

• Building common benefit frameworks to improve comparability and transparency

Editors note: Where should benefits ultimately be managed? In the beneficiary team, or the delivery team?

• Engaging senior leaders by giving them the information they actually need to make decisions

Editors note: The BIG BoK operationalises information need for accountability, governance and assurance – and works back from what is needed for decision making to what is compiled and collected.

• Determining weightings between different portfolio segments through facilitated, collective decision-making

Editors note: This is interesting – but the weightings need to translate to resource allocation and actual time spent by people.

A recurring message was that successful portfolio management adds value to both executives and delivery teams by clarifying priorities, surfacing constraints, and improving decision quality.

Editors note: The measure  of success must be increased achievement of objectives – in line with the benefits expected from Portfolio Management.

Conclusion

The session reinforced that portfolio management is not an administrative overlay, but a core leadership capability. When done well, it connects purpose to delivery, balances ambition with capacity, and turns strategy into tangible results.

The discussion closed with a clear challenge: organisations already have most of the tools they need. What is required now is discipline, transparency, and sustained attention to making better decisions about what to do, what not to do, and when to act.

Editors note: We discussed prioritising between projects, but did not really address what is covered in management teams. This session concentrated on portfolio management of the projects / programmes initiated for a collection of objectives – which may or may not be strategic.

How does portfolio management fit into business integrated governance?

Portfolio management sits at the centre of business integrated governance. It is the mechanism that turns intent into controlled action and makes governance real rather than ceremonial. A useful way to think about it is this:

Integrated governance answers three questions – what are we trying to achieve, how will we oversee it, and how do we know it is working. Portfolio management is where those questions are continuously tested against real investment decisions.

First, portfolio management translates direction into choices.

Boards and executives set purpose, strategy, risk appetite, and policy. On their own, these are statements of intent. The portfolio converts them into explicit decisions about what will and will not be funded, in what order, and with what level of commitment. This is where governance stops being abstract. Every approved initiative is a governance decision.

Second, it integrates risk, value, and capacity.

Traditional governance often treats these as separate conversations – strategy in one forum, risk in another, delivery somewhere else. Portfolio management brings them together. Each investment is assessed not just for alignment, but for expected strategic contribution, achievability, risk to benefits, and impact on constrained resources. This is integrated governance in practice: trade-offs are visible and explicit.

Third, it provides the control layer between board and delivery.

Business integrated governance does not mean boards micromanage projects. The portfolio provides the delegation boundary. The board governs through portfolio principles, decision criteria, thresholds, and stage-gates. Management operates within those guardrails. When something escalates, it is because portfolio signals say it should, not because someone shouts loudest.

Fourth, it enables evidence-based assurance.

Assurance in an integrated governance model is not about periodic status reports. It is about confidence that the organisation is investing in the right things and stopping or reshaping work when assumptions no longer hold. Portfolio-level measures – strategic contribution, benefit confidence, risk exposure, and dependency pressure – give governing bodies forward-looking insight, not just hindsight.

Fifth, it closes the loop between strategy, execution, and learning.

Integrated governance requires feedback. Portfolio management provides it. When initiatives underperform, the question is not only “what went wrong in delivery?” but “what does this tell us about our strategy, assumptions, or risk appetite?” Over time, the portfolio becomes the organisation’s learning system.

BIG and Portfolio Management

In short

Portfolio management is not an add-on to business integrated governance – it is the way to make and manage investment choices.

BIG is the operating system that makes it work. Without a disciplined portfolio, governance fragments into policies, committees, and reports. With it, governance becomes a coherent, continuous process that connects purpose, strategy, risk, investment, and delivery.

Here is the simplest way to see the difference.

Portfolio management decides what we invest in and in what order. It provides structure for prioritisation, sequencing, stopping work, and balancing risk and return across initiatives. It is excellent at turning strategic intent into a coherent set of authorised investment / cross functional change actions.

Business integrated governance decides who is accountable for outcomes and how decisions are made across the whole system – including investment / cross functional change actions – but also across operations and value creation. It connects purpose, strategy, risk, operations, assurance, and delivery into a single decision logic. Portfolio management operates inside that logic;

There are five reasons portfolio management on its own is not enough.

First, portfolio management needs authority it cannot generate itself.
A portfolio can recommend stopping a project, rebalancing investment, or protecting capacity. But an integrated governance framework gives that recommendation legitimacy across silos – strategy, finance, risk, operations, and HR. Without it, portfolio decisions are easy to bypass.

Second, portfolios assume clarity they do not define.
Portfolio management assumes strategic objectives, risk appetite, and decision rights already exist. Business integrated governance is what defines and sustains them. When these are weak, the portfolio is forced to guess, negotiate, or improvise.

Third, portfolios focus on change, not the whole enterprise.
Most portfolio models focus on projects and programmes. Business integrated governance also covers business as usual, regulatory obligations, and mission-critical objectives. Without that wider frame, portfolio optimisation can unintentionally undermine operational resilience or compliance.

Fourth, assurance and learning sit outside the portfolio.
Portfolio management tracks performance and risk, but it does not by itself integrate assurance, audit, or executive learning. Integrated governance ensures that what the portfolio reveals actually informs strategic and operational decisions, rather than remaining as reporting.

Fifth, culture and behaviour are governed above the portfolio.
Integrated governance sets the norms for transparency, escalation, and decision discipline. Without these, portfolio management becomes a technical exercise fighting political behaviour. With them, portfolio management becomes a trusted decision-support function.

The practical test is this: If a portfolio says “this should stop” or “this cannot start yet”, and the organisation can simply ignore it, then you do not have business integrated governance – you have portfolio mechanics without authority.

So the short answer is:
Portfolio management is a critical component of business integrated governance, but it cannot replace it. Integrated governance provides the legitimacy, coherence, and accountability that allow portfolio management to work as intended.

See the session Introduction here:

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