Episode 25 — Drive change with executive sponsorship and visible early wins
In this episode, we focus on how real organizational change actually gets traction, which is securing executive sponsorship and producing visible early wins that make the change feel credible. Most security and resilience programs fail not because the ideas are wrong, but because the organization cannot feel the value quickly enough to stay committed. People are busy, priorities compete, and the default state of any system is to resist disruption, even when disruption is beneficial. Executive sponsorship matters because it supplies authority and air cover, and early wins matter because they supply evidence and belief. When those two pieces work together, you can accelerate adoption without relying on heroic effort from a small team. The aim is to make change move through the organization like a supported initiative with proof behind it, not like a personal crusade that fades when attention shifts.
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Selecting the right executive sponsor is the first strategic decision, and it should be made with more rigor than simply choosing the most senior person who will take the meeting. You want a sponsor with authority to allocate resources, remove blockers, and set expectations across leaders who do not report to you. Authority without credibility is weak, because people will comply superficially while resisting privately. Credibility is earned through the sponsor’s track record, their understanding of the business, and the respect they command in cross functional settings. Commitment is the third requirement, because a sponsor who agrees in principle but disappears in practice will not provide the consistent support needed when resistance appears. You should look for a sponsor who can show up predictably, ask hard questions, and make decisions that protect the initiative. In mature organizations, the best sponsor is not always the highest ranking, but the one who can translate outcomes into business value and hold peers accountable.
It also helps to understand what a sponsor is not. A sponsor is not a ceremonial name on a slide, and they are not a passive approver of budget. A sponsor is an active force who provides legitimacy to the work and makes it safe for others to invest effort. That means they must be willing to use their influence, not just their title, and they must care enough to engage when the initiative hits friction. The sponsor should also have a natural connection to the outcomes you are targeting, because that connection makes their advocacy authentic. If the change is about reducing outage impact, a sponsor close to operations or product reliability may be stronger than a sponsor who is only loosely connected. If the change is about reducing contractual risk or regulatory exposure, a sponsor with strong business governance influence may be the right fit. The better the fit, the less persuasion you need, because the initiative aligns with what they already value.
Once the sponsor is selected, align the vision to concrete, measurable business outcomes, because executives support results, not abstract programs. Vision is useful only when it clarifies what will change in the business, by when, and how you will know it changed. If the vision is framed as improving security posture, it will compete poorly against revenue, delivery, and customer commitments, because it sounds like a cost center story. If the vision is framed as reducing loss, reducing downtime, improving customer trust signals, or increasing delivery confidence, it becomes part of business performance. Measurable outcomes also protect you from drifting into work that feels good but does not move the business. They make it possible for the sponsor to advocate clearly, because they can speak in the language of risk, cost, speed, and reliability. This alignment is also how you avoid creating a disconnect between what you promise and what you can actually demonstrate, which is a common credibility trap for security initiatives.
Business outcomes need to be chosen carefully so they are both meaningful and measurable within the time horizon where you need momentum. A multi year transformation may be real, but if the first evidence of value arrives eighteen months later, the initiative will be exposed to leadership changes and competing crises. Good outcomes often include leading indicators as well as lagging indicators, because lagging indicators can take time to move. For example, reducing incident impact is a lagging indicator, but reducing time to detect or time to contain can be leading indicators that show progress earlier. The point is not to game metrics, it is to build a measurement story that shows the initiative is changing behavior and capability, not just producing artifacts. When you select outcomes that can be demonstrated early, you make it easier for the sponsor to defend the work during budgeting conversations. You also make it easier for teams to believe the effort matters, which is necessary for adoption.
With outcomes in place, identify quick wins that validate the strategy publicly, because private success does not create organizational momentum. A quick win is not a random easy task, it is a small deliverable that proves the strategy is working and that the organization is safer or more reliable because of it. The win should be visible to the people whose behavior you need to change, and it should connect directly to the outcomes so it does not look like a distraction. Ideally, the win also reduces pain that people already feel, because pain relief is one of the fastest ways to build support. Quick wins should be selected with an understanding of perception, because the organization will judge the initiative based on what it can see, not on what you know is happening behind the scenes. When you choose wins well, you create a narrative of progress that is hard to dismiss. That narrative is what turns early adoption into broader adoption.
Quick wins also need to be framed carefully so they do not sound like victory laps for normal operations. If the win is presented as a technical improvement without context, many stakeholders will not understand why it matters. If the win is presented as evidence of an outcome moving, it becomes legible and valuable. For instance, a change that reduces exposure time for critical weaknesses becomes compelling when you can show that patch cycle time dropped measurably in a high value system. A change that improves detection becomes compelling when you can show that alert fidelity improved and response time decreased. The win should also be repeatable, because a one off success can be dismissed as luck. When a win can be replicated across teams, it becomes a template, and templates are how change scales. Quick wins are not about celebrating, they are about proving.
Piloting changes in low risk areas is one of the most reliable ways to gather proof while minimizing collateral damage. A pilot is a controlled experiment that tests whether your proposed change produces the intended outcome in a real environment. Low risk does not mean unimportant, it means the blast radius is manageable if the pilot reveals unexpected issues. Pilots should be chosen so they reflect real work patterns, because proof gathered in an artificial environment does not persuade skeptical teams. A strong pilot has clear success criteria tied to the outcomes, and it has an agreed timebox so it does not become a permanent trial. When pilots succeed, you gain evidence, stories, and data that can be used to persuade others. When pilots struggle, you gain insight into the friction points you must solve before scaling. Either way, the pilot creates learning that is grounded in reality rather than opinion.
Pilots are also a social tool, because they reduce the emotional risk of change for the broader organization. Instead of asking everyone to commit to a new way of working, you ask one area to try it with support. That makes resistance less defensive, because people are not being forced to accept an unknown change at scale. It also gives you a chance to build champions inside the pilot group, because the people who experience success firsthand become credible advocates. The pilot should include enough stakeholders to reflect the cross functional nature of the work, but not so many that coordination overwhelms it. The best pilots feel like a practical improvement, not like a research project. When the pilot is complete, you should be able to point to what changed in process, what changed in behavior, and what changed in measurement. That combination is hard to argue with, and it becomes the backbone of your scaling plan.
As pilots and quick wins produce results, broadcast progress regularly, because silence invites doubt and forgetfulness. Broadcasting is not bragging, it is a way to keep the initiative present in the organizational mind and to reinforce that the change is real. The broadcast should include both stories and numbers, because numbers show movement and stories help people picture how the change affects their daily work. The most effective stories are simple, describing a before state, an intervention, and an after state that maps to the outcome. The numbers should be chosen so they are stable and meaningful, not vanity metrics that spike briefly. Regular cadence matters, because irregular updates feel like sporadic bursts of activity rather than sustained progress. When progress is communicated consistently, it becomes easier for the sponsor to advocate and easier for teams to align. Communication is part of the change mechanism, not an optional extra.
Progress communication also benefits from being honest about what is still hard. If every update is framed as flawless success, stakeholders will assume the initiative is either superficial or hiding problems. A credible broadcast includes wins, current focus, and the next obstacles being addressed, because that shows the initiative is being managed like a real program. It also sets expectations that scaling will require ongoing effort, which reduces shock when challenges appear. Stories should be attributed to the work rather than to individual heroics, because change that depends on heroes does not scale. Numbers should be tied to outcomes and should be explained in plain language so non technical stakeholders can understand their meaning. When you communicate this way, you build trust in the initiative itself, not just in the people running it. That trust matters because programs often outlive individual contributors, and the organization needs to believe the change is durable.
Removing obstacles is where sponsor influence becomes decisive, because many blockers cannot be solved within a single team’s control. Obstacles often appear as competing priorities, unclear decision rights, resource constraints, or entrenched process requirements that slow change. The sponsor provides an escalation pathway that can resolve these issues without turning them into political battles. The key is to use escalation intentionally, not as a threat, but as a way to align leaders around the agreed outcomes. When the sponsor can clarify that the initiative is a priority and that tradeoffs must be made, teams are more willing to adjust. Sponsor influence also helps when you need cross functional cooperation, because it can remove the fear that helping will hurt a team’s local goals. The sponsor can also protect the initiative from churn, ensuring that early wins are not used as an excuse to withdraw support too soon. This is why sponsor commitment matters, because obstacle removal is not a one time event.
Obstacle removal should be paired with clear problem statements so the sponsor can act effectively. If you bring a vague complaint, you will get vague support, and the blocker will remain. A useful pattern is to describe the obstacle in terms of what outcome it is preventing, what decision is required to remove it, and what tradeoff will occur when it is removed. This turns escalation into a decision request rather than a venting session. It also respects the sponsor’s time and strengthens the partnership, because the sponsor sees that you are managing the program with discipline. When obstacles are removed quickly, teams begin to believe that participating in the change is worth it, because they see that leadership is serious. That belief is itself a form of momentum, because it reduces cynicism and increases willingness to adopt. Sponsor influence is most valuable when it makes the path smoother for those doing the work.
A major pitfall is declaring victory before behaviors truly change, because early wins can create a false sense that the transformation is complete. A quick win might prove a tool can work or a process can be followed once, but sustained behavior change requires repetition, reinforcement, and integration into normal operations. If you declare victory too early, attention shifts away, and teams revert to old habits because the environment pulls them back. This is especially common when an initiative delivers a visible artifact, such as a dashboard or a new policy, and leadership assumes the artifact equals adoption. Real change shows up when people make different choices under pressure, not when they can point to a document. Avoiding this pitfall requires measurement over time and continued storytelling that highlights behavior and outcomes, not just deliverables. Early wins are the start of momentum, not the end of the journey.
Behavior change becomes durable when it is supported by incentives, training, and process integration, even if those elements are light. People must know what the new behavior is, why it matters, and how to perform it without excessive friction. If the new path is harder than the old path, adoption will stall unless the organization actively removes friction or adds strong motivation. This is another place where sponsorship matters, because sponsors can align incentives and set expectations that reinforce the new way of working. You also need to be careful that early wins do not create resentment, especially if they appear to favor one group while imposing burden on another. A coalition of champions helps here, because champions can translate the change into local value and can surface resistance early. Sustained change is built from many small reinforcements that make the new behavior feel normal. Declaring victory should be reserved for the point when the organization can sustain the behavior without constant program effort.
Building a coalition of champions across critical functions is how you scale beyond the initial pilot group. Champions are not just supporters, they are people who can influence peers and adapt the change to local realities without breaking the outcomes. You want champions in areas that will be affected by the change, such as operations, engineering, identity, risk, legal, and customer facing leadership, depending on the initiative. The coalition should include both formal leaders and informal leaders, because informal leaders shape daily behavior. Champions help by modeling the change, answering questions in context, and providing feedback about friction that the central team might not see. They also help prevent the initiative from being labeled as a security project, because coalition membership signals shared ownership. When champions speak positively about a change, it carries more weight than when the program team speaks positively about itself. Coalition building is one of the most reliable ways to turn early wins into cultural shift.
A useful scenario is converting a resistant team with a targeted pilot, because resistance is common and often rational. Teams resist when they believe the change will slow delivery, add bureaucracy, or expose them to blame without support. A targeted pilot can address those fears by choosing a scope that matters to the team and by measuring results that reflect the team’s goals as well as the program’s outcomes. You might select a low risk service or workflow that the team owns, and propose a small change that reduces pain, such as clearer ownership, faster approvals, or reduced rework. The pilot should be framed as a collaboration with explicit success criteria, not as an audit. As results appear, you use both the team’s story and the numbers to show that the change helped them, not just the organization. When a previously resistant team becomes a champion, their credibility becomes a powerful amplifier, because others know they were not easily convinced.
In that scenario, the sponsor’s role is to make it safe for the pilot to happen and to ensure the team is not punished for participating. The sponsor can clarify that the pilot is an investment in improvement, not a trap for performance evaluation. The program team can then provide practical support, such as templates, coaching, and help removing friction, so the pilot group does not feel like they are carrying extra weight alone. The pilot results should be shared in a way that respects the team, focusing on what was learned and what improved rather than on what was wrong before. This protects relationships and increases willingness to participate across the organization. If the pilot reveals issues, you treat them as design feedback rather than as failure, and you adjust before scaling. The combination of sponsor support, respectful collaboration, and measurable outcomes is what converts resistance into partnership. Once partnership exists, scaling becomes far easier.
A practical exercise is scripting a sponsor update that highlights tangible wins, because sponsor communication is a lever for visibility and momentum. The update should open with the business outcome and whether it is moving, then summarize the most concrete wins with both a short story and a metric. It should also name the next pilot or scaling step, so the sponsor can see the path forward rather than a collection of disconnected wins. Obstacles should be stated as decision requests, not as complaints, because sponsors are most effective when they can act on clear asks. The tone should be confident but not triumphal, because credibility is reinforced when progress is communicated with realism. A good sponsor update is also short enough that it can be forwarded without editing, which increases reach. When you practice this, you make sponsorship easier, because you are giving the sponsor a clean narrative they can use in leadership settings.
Keep the memory anchor in mind: visible wins create momentum and belief. Momentum matters because it reduces the activation energy required for people to try the new behavior, and belief matters because people will not invest effort in a change they think will vanish. Visibility is not about marketing, it is about making the change legible, so that participants can see the cause and effect. Wins that are visible and connected to outcomes create a story that the organization can repeat, and repeated stories become shared understanding. That shared understanding makes adoption feel less risky, because people know what success looks like and they have evidence it is achievable. Over time, visible wins shift the narrative from why are we doing this to how do we scale it responsibly. When belief is present, obstacles become solvable problems rather than reasons to give up. This is why early wins are not optional, they are the fuel.
As a mini review, driving change at organizational scale requires a sponsor who has authority, credibility, and commitment, because the sponsor provides legitimacy and removes blockers that teams cannot remove alone. The vision must be aligned to measurable business outcomes so leadership can support it as performance improvement rather than as abstract risk work. Quick wins should be selected to validate the strategy publicly, and pilots should be run in low risk areas to gather proof and refine the approach. Progress must be broadcast regularly using stories and numbers so momentum stays alive and belief spreads beyond the initial group. Obstacles should be removed through sponsor influence and clear escalation pathways, and you must avoid declaring victory before behaviors truly change. A coalition of champions across critical functions is what scales the change and makes it durable. These elements reinforce each other, turning early proof into sustained adoption.
To conclude, pick one quick win that is directly tied to a measurable outcome, design it as a small pilot with clear success criteria, and brief your sponsor today with the plan and the expected evidence. The brief should make it easy for the sponsor to advocate by naming what will improve, how it will be measured, and when the first proof will be visible. As the win lands, share it in a way that highlights both the human story and the metric, because that combination creates belief. Use the sponsor to remove the first obstacles quickly, because early friction is where momentum dies. Then expand through champions who can carry the change into their functions with local credibility. When you do this well, change stops feeling like an uphill push and starts feeling like a supported movement with proof and leadership behind it. That is how you accelerate meaningful security improvement without exhausting the team or losing focus.