Episode 49 — Craft convincing business cases that secure funding and executive backing
In this episode, we focus on how to craft business cases that executives can endorse confidently, even when the subject is deeply technical and the benefits are partly about avoided loss. Security leaders often assume that the merits of a control are obvious, but executives are paid to make tradeoffs across competing needs, and they need a case that is clear, bounded, and credible. A good business case reduces uncertainty, makes the outcome measurable, and shows that you have thought through delivery reality, not just the target architecture. It also respects the executive mindset, which is typically oriented around mission impact, financial stewardship, operational continuity, and accountability. The goal is not to exaggerate risk or to dress technical work up as something it is not. The goal is to translate security improvement into a decision-ready package that fits the organization’s strategy, risk appetite, and funding rhythms.
Before we continue, a quick note: this audio course is a companion to our course companion books. The first book is about the exam and provides detailed information on how to pass it best. The second book is a Kindle-only eBook that contains 1,000 flashcards that can be used on your mobile device or Kindle. Check them both out at Cyber Author dot me, in the Bare Metal Study Guides Series.
Start by defining the problem, the desired outcome, and the success criteria in plain language, because clarity here sets the tone for everything that follows. The problem should describe the current condition, the failure modes you have observed or can reasonably anticipate, and why the current state is not acceptable under the organization’s risk thresholds. The desired outcome should describe the state you want the organization to reach, using observable terms such as reduced likelihood of unauthorized access, faster containment of incidents, improved recovery reliability, or improved evidence quality for audits. Success criteria should specify how you will know the outcome has been achieved, and those criteria should be measurable or at least verifiable through repeatable evidence. If success criteria are vague, the business case becomes a blank check, and that makes executives nervous. If success criteria are too detailed or too technical, you lose the executive audience and create the impression of complexity without control. A strong opening section creates a clean decision frame: this is the problem, this is what good looks like, and this is how we will prove progress.
Next, quantify impacts using ranges and conservative assumptions, because credibility is the currency of executive backing. Security benefits often involve probability, uncertainty, and avoided losses, so using ranges is more honest and more defensible than presenting a single precise number. Conservative assumptions matter because executives have seen optimistic projections fail, and they are trained to discount overly confident claims. Impacts can include estimated cost of downtime, estimated cost of incident response, estimated productivity loss, estimated compliance penalties, and estimated reputational damage, but you should be careful to explain which impacts are measurable directly and which are directional estimates. If you have internal incident history, use it to ground the ranges, because internal data is more persuasive than external anecdotes. If you do not have precise internal numbers, you can still frame the impact in operational terms, such as the number of hours a team is pulled off mission work during a high-severity incident, and then translate that into cost ranges. A well-quantified section signals that you understand uncertainty and are not trying to sell certainty you do not have.
After you establish impact ranges, translate technical benefits into financial and operational terms, because executives approve outcomes, not mechanisms. Technical benefits might include stronger access controls, better logging, reduced attack surface, improved detection fidelity, or stronger recovery procedures. Financial translation might include reduced expected loss from fraud, reduced costs associated with outages, reduced spend on incident response surge staffing, or reduced licensing costs through consolidation. Operational translation might include reduced escalation frequency, reduced mean time to restore services, faster onboarding of systems into standard controls, or reduced manual evidence collection effort during audits. The translation should be direct, not theatrical, and it should avoid the trap of implying that security eliminates risk entirely. Instead, show how the improvement reduces probability, reduces impact, and increases recovery speed, because those are realistic levers. Also make sure you explain operational friction honestly, because executives will discover hidden friction later if you do not, and that damages trust. When you translate benefits this way, executives can compare the security investment to other investments using a shared decision language.
Present options with costs, risks, and required resources, because a business case that offers only one path feels like a sales pitch rather than analysis. Options can include doing nothing, doing a minimal version, doing a phased approach, or doing a full capability build, and each option should have clear implications for risk and outcomes. Costs should include upfront costs and ongoing costs, including staffing, training, maintenance, and integration work. Risks should include delivery risks, such as adoption resistance, timeline uncertainty, tool integration complexity, and vendor dependency, as well as residual security risk if the option is insufficient. Required resources should be described in terms of people capacity and skill availability, not just budget, because skill constraints can be the real blocker. The goal is not to overwhelm the reader with detail, but to show that you have evaluated realistic paths and are recommending one with eyes open. Options also give executives a way to choose a risk posture deliberately, which increases buy-in. When leaders choose among options rather than being told what must happen, they tend to sponsor the outcome more actively.
Once options are clear, show payback, total cost, and opportunity costs, because executives make decisions in the presence of constraints. Payback can be expressed as expected savings or avoided losses over time, but again it should be framed as a range and grounded in conservative assumptions. Total cost should include the full lifecycle, because tools and programs are rarely one-time purchases, and hidden operational costs can exceed license fees. Opportunity cost is what you will not do if you fund this initiative, such as delaying another program or consuming scarce engineering capacity, and acknowledging it signals maturity rather than weakness. It is also helpful to show how the initiative might reduce opportunity cost elsewhere, such as by reducing the frequency of high-severity incidents that disrupt delivery, or by reducing audit fire drills that consume leadership attention. Executives often think in terms of portfolio, meaning they want to know how an investment changes the overall risk and delivery capacity profile of the organization. When you present payback, total cost, and opportunity cost together, you give leaders the full economic picture rather than a partial financial argument.
Include pilots, milestones, and evidence collection plans, because executives are more comfortable funding initiatives that have controlled validation steps. A pilot demonstrates that the capability can work in the organization’s environment and reveals adoption friction early. Milestones provide a structure for progress reporting and for staged decisions, so leaders can see value emerging rather than waiting for a big reveal at the end. Evidence collection plans matter because security improvements often involve control effectiveness and compliance readiness, and leadership needs to know how you will verify that the investment delivered the promised outcome. Evidence can include adoption metrics, reduction in specific incident types, improved response times, improved recovery test results, and improved audit evidence quality. The plan should state what will be measured, how often it will be reviewed, and who will own the measurement. This also protects the initiative from drifting into ambiguity, because measurement creates a shared definition of success. When pilots and milestones are included, the business case becomes a managed investment rather than a leap of faith.
Align the business case with strategy, risk appetite, and regulatory obligations, because alignment is what turns a security initiative into a business initiative. Strategy alignment means showing how the work supports the organization’s direction, such as enabling cloud expansion safely, supporting customer trust commitments, improving service reliability, or protecting critical intellectual property. Risk appetite alignment means you show how the initiative reduces risk that is currently above acceptable thresholds, or how it preserves acceptable risk while enabling growth. Regulatory alignment means you identify obligations that require certain controls, evidence, or reporting, and you show how the initiative supports readiness and reduces compliance exposure. This alignment should be explicit, not implied, because executives use alignment to justify decisions to boards, auditors, and external stakeholders. It also helps you avoid being seen as competing with business priorities, because you are connecting security work to business commitments and constraints. When alignment is clear, sponsorship tends to be stronger and more durable through leadership changes and shifting priorities.
Address objections upfront and propose mitigations and fallbacks, because executives will have objections, and you gain credibility by showing you have already thought them through. Common objections include budget constraints, staffing constraints, timeline skepticism, fear of operational disruption, and concern about vendor lock-in. Mitigations might include phased rollout, limiting initial scope, using pilots to validate adoption, building training into onboarding, or establishing clear decision points where leadership can adjust course. Fallbacks are alternative paths if assumptions fail, such as a smaller scope that still reduces high-risk exposure, compensating controls that reduce risk while longer-term work is delayed, or a contingency plan if a vendor cannot meet requirements. Addressing objections is not about being defensive; it is about being honest about delivery reality and showing that you can manage risk in execution as well as in design. Executives often sponsor leaders who demonstrate control over uncertainty, not leaders who pretend uncertainty does not exist. When objections are handled this way, the business case feels safer to approve.
To make this concrete, consider a business case for Privileged Access Management (P A M) that is framed around reducing fraud risk and downtime, not around implementing a tool. Privileged access failures can lead to high-impact events, including unauthorized changes, data exposure, service disruption, and persistent attacker access that is hard to remove. A P A M program can reduce those risks by enforcing stronger controls over privileged credentials, reducing standing privileges, improving auditability, and enabling faster containment when accounts are suspected of compromise. The business value can be expressed in reduced likelihood of high-cost incidents, reduced recovery time due to clearer access control and logging, and reduced audit remediation effort because evidence becomes more consistent. The cost side should include not just licensing, but integration work, workflow updates, training for administrators, and the ongoing effort to maintain privileged role definitions. The plan should include a pilot on the highest-risk systems and roles, with success criteria tied to adoption and measurable reductions in privileged access anomalies. When framed this way, the executive decision is about reducing a specific class of high-impact failure, and that is a decision leaders can endorse confidently.
A quick win that often increases funding confidence is staging funding with progressive checkpoints, because it converts a large commitment into a managed sequence of smaller decisions. Progressive checkpoints might include funding a pilot first, then funding expansion after success criteria are met, then funding optimization after adoption is stable. This approach reduces perceived risk for leadership, because they retain control and can adjust based on evidence. It also protects the delivery team from being forced into premature scale, because the pilot phase creates time to refine workflows and reduce friction. Staged funding should be tied to milestones that are meaningful, such as achieving coverage for a defined scope and demonstrating measurable impact, rather than to simple activity completion. It is important to define the checkpoint criteria clearly, because vague checkpoints can become political arguments later. When staged funding is used thoughtfully, it increases the chance of approval and increases the chance of long-term success, because the program grows based on validated learning.
A common pitfall is overpromising timelines while underestimating adoption costs, and this pitfall damages security credibility more than almost any technical mistake. Adoption costs include training, workflow changes, documentation updates, support load, exception handling, and the time it takes for behavior to stabilize. If you promise a fast rollout without acknowledging adoption friction, you create an inevitable gap between plan and reality. That gap leads executives to believe security cannot deliver, which makes future funding harder. The remedy is to plan with realistic sequencing, include pilots, and express timelines in terms of milestone readiness rather than calendar certainty. Also be honest about what you will stop doing to make room for the new work, because capacity tradeoffs are real and executives appreciate transparency. A credible business case does not promise perfection. It promises managed progress with measurable outcomes and clear decision points.
As a mini recap, a convincing business case consistently covers the problem, the options, the quantified impact, the costs, and the evidence plan, all tied to mission and risk realities. The problem and desired outcome are stated plainly, with success criteria that can be measured or verified. Impacts are quantified using ranges and conservative assumptions to preserve credibility and avoid false precision. Technical benefits are translated into financial and operational terms so leaders can compare investments across portfolios. Options include costs, risks, and required resources, so leaders can choose deliberately rather than being cornered. Evidence plans include pilots, milestones, and metrics, so progress can be tracked and funding can be staged with confidence. Objections are addressed upfront with mitigations and fallbacks to show execution risk is managed. When these elements are present, the business case becomes decision-ready.
To conclude, finalize the case with a crisp recommendation, a staged plan if appropriate, and a clear sponsor decision meeting where tradeoffs can be made explicitly. Finalizing means the document or narrative is consistent, assumptions are stated, success criteria are measurable, and the options are comparable. The sponsor decision meeting should be booked with the leaders who have the authority to approve funding, accept risk tradeoffs, and allocate delivery capacity, because partial sponsorship creates stalled execution. The meeting should be framed around decisions, not around information sharing, so you leave with an approved path, a defined checkpoint plan, and clear ownership. If leadership requests changes, treat that as part of the process and update the case quickly, because responsiveness builds trust. When you close the loop this way, you turn a well-argued security idea into an executive-backed investment that can be delivered and measured. That is how security initiatives become funded programs that improve mission resilience rather than unowned aspirations.