Certified: The GIAC GSTRT Audio Course

In this episode, we focus on a part of security leadership that is easy to underestimate until you have lived through a few failed rollouts: culture and constraints determine whether a strategy actually lands. You can have a technically sound plan, a strong control framework, and well-meaning people, and still watch the initiative stall because it clashes with how decisions are made, how incentives work, and what the organization can realistically absorb. Culture is not a soft topic in this context. Culture is the operating system of the organization, and your security strategy is an application that either runs smoothly on that operating system or crashes repeatedly in production. The goal here is to read the environment clearly, so you design strategies that fit the mission, fit the risk realities, and fit the human system that has to execute them.

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 identifying norms, incentives, and the stories people repeat, because those elements reveal what the organization truly values under pressure. Norms are the unwritten rules about how work gets done, such as whether teams prefer written decisions or hallway conversations, whether escalation is seen as helpful or as political, and whether the default is to move fast and fix later or to be careful and prove first. Incentives are what people are rewarded for, formally and informally, which may be very different from the values stated on posters. Stories are the repeated narratives about past successes and failures, like the time a security gate delayed a launch, or the time an outage caused public embarrassment, or the time a leader defended a team that made a good-faith mistake. These stories act like cultural memory, and they shape how people interpret new security initiatives. When you know the norms, incentives, and stories, you can predict adoption patterns and resistance points with far more accuracy than any policy document can provide.

Next, map decision styles, because security strategies fail when they assume decisions are made one way while the organization actually makes them another way. Some organizations are consensus-driven, where decisions require broad agreement and alignment across peer groups. Others are directive, where leaders set direction and teams execute with limited debate. Many are delegated, where leaders define objectives and constraints but expect teams to choose the implementation path. Each style has strengths and weaknesses, and none is inherently better for security, but each demands a different approach. In a consensus culture, you need early stakeholder involvement and shared language about tradeoffs, because surprises create backlash. In a directive culture, you need clear executive sponsorship and crisp accountability, because ambiguity causes local avoidance. In a delegated culture, you need guardrails, reference architectures, and measurable outcomes, because teams will interpret goals differently without shared constraints.

Once you understand decision style, assess constraints with the same seriousness you apply to threat modeling, because constraints define what is possible in the near term. Budget is an obvious constraint, but skills often matter more, because capability is the ability to execute reliably, not the ability to buy tools. Tooling constraints include what platforms exist, what is standardized, what is brittle, and what is already overloaded with integrations. Time is usually the most binding constraint, because teams are balancing delivery, operations, and incident response while you are asking them to adopt new controls. Constraints also include change windows, regulatory timelines, and the maturity of supporting functions like identity, asset management, and IT service workflows. If you ignore constraints, your strategy becomes aspirational and teams quietly work around it. If you respect constraints, you can design sequencing and pilots that build momentum while moving the organization toward stronger capability.

With constraints mapped, spot sacred cows and genuine third rails, because these are the points where well-designed strategies unexpectedly blow up. A sacred cow is an entrenched practice, system, or team that is protected by tradition or by perceived business necessity, even when it creates risk. A third rail is something that triggers immediate political consequences, such as challenging a key revenue system, changing an executive’s preferred workflow, or implying that a high-status team should follow a process they previously avoided. You do not need to accept these as permanent, but you need to recognize them early so you can plan your approach. Sometimes the right move is to work around a sacred cow while you build evidence and alliances for a later change. Sometimes the right move is to reduce risk through compensating controls rather than direct confrontation. The worst move is to stumble into these areas unintentionally and frame the conflict as a purely technical disagreement, because that misreads what is actually happening.

Alongside the minefields, discover motivators, because motivation is what turns compliance into sustained behavior. People may be motivated by recognition, where public credit and visible impact matter. Others are motivated by autonomy, where they value being trusted to choose implementation details within clear constraints. Many professionals are motivated by mastery, where they want to build skill and pride in doing things well. Purpose is also powerful, especially when teams can connect security outcomes to protecting customers, protecting colleagues, or preserving the organization’s ability to operate. These motivators are not abstract; they shape how you frame your strategy and how you design reinforcement mechanisms. A team that values autonomy will reject heavy-handed prescriptions but will embrace guardrails that allow creativity. A team that values mastery will respond to clear standards, practical training, and a sense of craft. When you align your approach to real motivators, you reduce resistance without manipulating anyone.

With motivators in mind, adapt messaging to match audience preferences, because the same message can sound helpful to one group and hostile to another. Engineers often respond to clarity, evidence, and practical constraints, while leaders often respond to risk framing, mission impact, and tradeoff visibility. Operations teams often want predictability, reduced toil, and clear escalation paths, because their pain is usually lived during outages and incidents. Legal and compliance teams often want traceability, defined responsibilities, and evidence expectations, because their risk is accountability. Your messaging should avoid jargon-heavy phrasing that forces translation, and it should avoid moralizing language that implies teams are careless or reckless. The core content can stay consistent, but the emphasis should shift to meet the audience where they are. When messaging is tuned, it becomes easier for leaders and managers to repeat it accurately, which is how strategies spread without distortion.

Now bring this into execution design by crafting pilots that respect bandwidth and risk tolerance, because pilots are where landable strategy becomes visible. A pilot should be small enough that it does not overload teams, but meaningful enough that it produces measurable outcomes and learnings. It should be scoped to a specific system, workflow, or team, with clear success criteria and a defined time window. Risk tolerance varies, so choose pilot areas where the organization is willing to experiment without fear of catastrophic blame if something needs adjustment. Pilots should also be designed to reduce the perceived cost of adoption by providing support, documentation, and quick feedback loops. The purpose of the pilot is not to prove that security is right; it is to prove that the strategy can work in the organization’s environment. When a pilot respects constraints and produces real outcomes, it creates credibility that unlocks broader adoption.

As you move from pilot to scale, align rewards and consequences to desired behaviors, because behavior follows reinforcement far more reliably than it follows persuasion. Rewards can be simple, like recognition for teams that adopt secure patterns, reduced friction for teams that follow standard processes, or prioritization support for teams that invest in foundational improvements. Consequences should be fair and consistent, and they should focus on protecting the mission rather than punishing individuals. If consequences are arbitrary or applied inconsistently, teams learn that the strategy is negotiable, and drift becomes normal. If rewards are absent and all attention goes to failures, teams learn that security only shows up to criticize, and motivation drops. Alignment also means ensuring that leadership performance expectations do not inadvertently punish secure behavior, such as rewarding speed without recognizing stability or safe delivery. When reinforcement matches the behaviors you want, adoption becomes self-sustaining rather than dependent on constant pushing.

Recruit cultural allies to sponsor adoption, because strategies land faster when they are carried by respected insiders rather than by a central security function alone. Cultural allies are people who are trusted, who understand local constraints, and who can translate your objectives into the language of their teams. They might be senior engineers, operations leads, product managers, or regional leaders, depending on the organization. The point is not to create a token champion program, but to build a coalition of credible sponsors who can validate the strategy and shape it to fit real workflows. Allies also help surface resistance early, because people tell insiders what they will not tell central leadership. When allies sponsor adoption, the initiative becomes part of the organization’s identity rather than an external imposition. That shift in ownership is one of the strongest predictors of long-term success.

Even with allies, anticipate friction and prepare respectful escalation paths, because not all disagreements can be resolved through informal alignment. Friction often comes from competing priorities, resource scarcity, unclear ownership, or differing interpretations of risk appetite. A respectful escalation path provides a way to resolve these conflicts without personal conflict or political theater. Respectful means you frame the issue as a tradeoff decision that requires leadership input, not as a failure by a team to comply. It also means you bring options, such as alternative timelines, compensating controls, or phased adoption, rather than presenting a single demand. Escalation should be used sparingly and predictably, because overuse teaches teams that every disagreement becomes a leadership battle. When escalation is clear and respectful, teams feel safer raising issues early, which prevents silent workarounds and late surprises.

To understand whether the strategy is landing, measure traction using participation and outcome signals rather than relying on anecdotes. Participation signals include adoption rates of standard patterns, completion of training updates, reduction in exception requests, and increased engagement in review sessions. Outcome signals include changes in incident patterns, improved recovery test results, reduced exposure pathways, improved time to detect and contain, and more consistent evidence quality during reviews. Traction measurement should be lightweight enough to sustain and meaningful enough to guide decisions, because noisy metrics create skepticism. You should also watch for lagging indicators, because some improvements take time to show in incident statistics, while leading indicators like workflow adoption can show progress earlier. Measurement is not about proving success; it is about steering. When you can see traction, you can decide where to accelerate, where to simplify, and where to invest.

As traction data comes in, iterate strategy based on authentic feedback, because culture-aware strategy treats feedback as operational input, not as resistance. Authentic feedback often includes uncomfortable truths, such as a requirement that adds too much toil, a control that conflicts with delivery reality, or a lack of clarity about ownership. The goal is not to appease every complaint, but to distinguish between feedback that reveals a real design flaw and feedback that reflects discomfort with change. Iteration might mean adjusting sequencing, improving documentation, refining success measures, or providing better tooling support to reduce friction. It might also mean clarifying non-negotiables tied to risk thresholds, so teams know what must be done even when it is inconvenient. When you iterate transparently, you build trust, because teams see that the strategy is responsive and grounded. Trust is what keeps people engaged through the messy middle of adoption.

To conclude, pick one initiative you are currently trying to drive and adjust it intentionally to align with the culture and constraints you have identified. That adjustment might be as simple as changing the way you frame the outcome, shifting the pilot scope to respect bandwidth, recruiting a stronger cultural ally, or redefining success measures so progress is visible and credible. The key is to treat culture as a real system you can observe and design for, not as a vague excuse for inertia. When your strategy respects decision styles, acknowledges constraints, leverages motivators, and provides fair reinforcement, it becomes landable, meaning it can be adopted without constant coercion. Landable strategies spread because they reduce confusion and create practical value while reducing risk. Over time, this approach turns security from a set of demands into a shared way of working that supports the mission under real conditions.