Certified: The GIAC GSTRT Audio Course

In this episode, we treat one-on-ones as leadership multipliers because they are one of the few places where you can build trust, remove friction, and shape future leaders in the same conversation. Many managers hold one-on-ones because the calendar says they should, but they run them as status updates, and that turns a high-leverage ritual into a low-energy routine. A well-run one-on-one is different because it creates psychological safety, surfaces blockers early, and converts ambiguity into commitments that actually move work forward. It also creates a private space where people can talk about concerns they will never raise in a group setting, which means it can prevent problems long before they become incidents or team conflicts. In security environments, where workload is heavy and interruptions are constant, one-on-ones are often the only consistent channel for aligning expectations and protecting people from burnout. The goal here is to build a repeatable structure that makes one-on-ones predictable, useful, and trust-building. When that structure is present, the meeting stops feeling like overhead and starts feeling like the place where momentum is restored.

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.

A strong first step is to set cadence, agenda, and expectations together, because one-on-ones fail when one person treats them as mandatory and the other treats them as optional. Cadence should match the reality of the work and the needs of the person, meaning some roles benefit from weekly rhythm while others can sustain a biweekly cadence if work is stable. The important part is consistency, because consistency is what builds trust and allows issues to be surfaced before they grow. Agenda should be co-owned, with the direct report bringing topics and the leader bringing a structure that ensures blockers, growth, and commitments are addressed. Expectations should clarify what the meeting is for, such as unblocking work, discussing priorities, addressing team dynamics, and investing in growth, rather than only reviewing tasks. It is also useful to agree on what one-on-ones are not for, such as surprise performance critiques or last-minute escalations that should have been handled earlier. When you set these expectations explicitly, you reduce anxiety because the person knows what will happen in the meeting and what the leader will do with what they share. Co-owning cadence and agenda also increases engagement because the direct report feels agency rather than feeling examined. Over time, this structure makes the meeting reliable, and reliability is what creates trust.

Starting with rapport matters, but it must be done with open, purposeful questions rather than with forced small talk that feels performative. Rapport is about creating a sense of safety and connection so real issues can be discussed, and the simplest way to do that is to ask questions that show you care about the person’s experience at work. Open questions might explore how they are feeling about workload, what has been energizing, what has been draining, and what is unclear right now. Purposeful questions also help you gather early signals of burnout, frustration, or confusion that could affect performance and retention. The key is to listen for meaning, not just for facts, because one-on-ones often reveal the difference between what is happening and how it is being experienced. In a security team, a person may say they are fine, but their tone and their pacing might suggest they are carrying too much. Rapport also means acknowledging wins and effort, not as flattery, but as recognition that helps people feel seen and keeps motivation stable. The goal is to create enough warmth that honesty feels safe, while keeping the conversation grounded in forward motion. When rapport is built consistently, the meeting becomes a place where reality can be spoken without fear.

A major value of one-on-ones is surfacing blockers early and committing to removal, because leaders often underestimate how much progress is lost to small frictions that no one escalates. Blockers can be technical, such as access delays, tooling problems, or dependency failures, but they can also be organizational, such as unclear decision rights, competing priorities, or lack of stakeholder responsiveness. The person doing the work often adapts silently by working around the blocker, which can hide the problem while increasing stress and reducing quality. A good one-on-one pulls blockers into the open, classifies them, and assigns action, including what the leader will do and by when. Commitment matters because trust grows when the leader follows through, and it shrinks when the leader nods and does nothing. Blocker removal is also a performance lever because removing one recurring blocker can free hours of productive capacity without any additional staffing. In security, where teams are often under-resourced, this is one of the fastest ways to improve throughput and morale simultaneously. The meeting should therefore include a dedicated moment for blockers, not as an afterthought. When people see blockers consistently addressed, they begin to bring them earlier, which prevents accumulation.

One-on-ones are also the right place to explore growth goals aligned to team outcomes, because growth is most effective when it is connected to real work rather than to generic training aspirations. Growth goals can include technical depth in a domain, improved communication skill, improved decision-making under uncertainty, or increased leadership capability through owning a program area. Alignment matters because the goal should both help the person and help the team, creating a shared purpose that makes investment easier. A growth discussion should identify the capability to build, what good looks like, and what practice will occur in the next few weeks, not someday. It should also include how the leader will support growth, such as providing opportunities to lead a meeting, own a decision narrative, or practice incident briefing. In security teams, growth can also include learning to translate technical risk into business impact, which is a career-accelerating skill. When growth is discussed regularly, people feel invested in, and that investment is a retention factor, especially in high-demand roles. It also grows leaders because people learn to own outcomes and to communicate clearly, which scales the team’s capability. Over time, growth alignment turns one-on-ones into a talent development pipeline rather than a maintenance ritual.

A practical example is converting a vague worry into specific action, because worry is common in high-stakes environments and it often hides actionable information. A person might say they are worried about an upcoming deadline, an audit, or an incident response readiness gap, but the worry may be diffuse and hard to address. The leader’s job is to help them name the worry precisely, identify what is within control, and convert it into a small set of specific next actions. That conversion might involve clarifying scope, identifying missing information, escalating a dependency, or breaking work into a sequence with clear definitions of done. It might also involve identifying whether the worry is about uncertainty or about capacity, because those require different fixes. When the worry is converted into action, the person experiences relief because they now have a path, and the leader gains clarity about what support is needed. This is not therapy; it is operational leadership applied to human experience. It also builds trust because the person sees that the leader takes concerns seriously and can turn them into progress. In security work, where uncertainty is constant, this ability to convert worry into action is one of the most valuable leadership skills.

Notes are essential because they turn one-on-ones from conversations into a system of commitments and follow-through, and follow-through is the core mechanism of trust. Notes do not need to be long, but they should capture the key points: what blockers were raised, what commitments were made, what growth goals were discussed, and what next steps were agreed. Notes also help you track patterns over time, such as recurring blockers, recurring stress signals, or repeated goals that are not progressing. In one-on-ones, memory is unreliable because leaders have many conversations, and relying on memory can unintentionally signal that the person is not important. Notes solve that problem by making the relationship visible and by enabling continuity across meetings. They also protect fairness because they ensure that commitments are followed consistently and that feedback is grounded in observed patterns rather than in recent impressions. Notes should also capture your own commitments, not only the direct report’s, because leadership accountability is part of the trust dynamic. When you revisit notes at the start of each one-on-one, you demonstrate seriousness, and seriousness is what makes the meeting feel worth attending. Over time, notes create a record of growth, which is valuable for both coaching and for career development discussions.

A common pitfall is allowing one-on-ones to become status-only meetings that drain energy, because status is easy to discuss but it rarely addresses the reasons status is stalled. Status-only meetings also duplicate information that could be shared through other channels, making one-on-ones feel like overhead rather than support. The cost is not just time; it is missed opportunity to discuss blockers, growth, and team dynamics that affect long-term performance. The solution is to treat status as context, not as the meeting’s purpose, and to shift quickly from what is happening to what is needed. If a person is delivering well, the one-on-one can focus more on growth and on removing obstacles that would make delivery easier. If a person is struggling, the one-on-one can focus on clarity, prioritization, and support rather than on reciting tasks. Status-only meetings often happen when the leader has no structure or when the leader is anxious about control, and structure addresses both by providing a predictable flow. Another sign of the pitfall is that the person begins to bring fewer topics because they assume the meeting will not help. When that happens, trust is already slipping, and the leader must rebuild usefulness by changing the meeting’s shape. One-on-ones should leave the person feeling clearer and lighter, not feeling like they performed for approval.

A quick win that improves one-on-one quality immediately is ending with agreed next steps, because it ensures the conversation produces action rather than evaporating. Next steps should include what the direct report will do, what the leader will do, and when each will be done, because trust depends on leader follow-through as much as on employee execution. The steps should be small enough to be realistic, but meaningful enough to reduce a blocker, advance a deliverable, or move a growth goal forward. Ending with next steps also helps the person leave with a plan, which reduces anxiety and increases momentum. It also provides a natural link to notes, because the notes become a commitment tracker that will be revisited next time. This practice prevents one-on-ones from turning into vent sessions with no resolution, while still allowing space for concerns to be heard. In security teams, where work is interrupt-driven, next steps create a stable thread that keeps progress from being lost between crises. It also helps leaders manage their own workload by making commitments explicit rather than vaguely promising to help. Over time, this habit alone can transform one-on-ones because it makes them reliably productive.

Conflict is inevitable in complex teams, and a one-on-one is often the safest place to navigate conflict if you use curiosity first. Curiosity means you ask for the person’s perspective, you seek to understand the underlying interests and constraints, and you avoid jumping to judgment before you have the full story. Many conflicts are driven by misaligned expectations, unclear roles, or conflicting priorities, and these can often be resolved by clarifying what each party is trying to achieve. In a one-on-one, you can help the person separate facts from interpretations, identify what evidence exists, and decide what a constructive next step looks like. Curiosity-first also helps de-escalate because people feel heard, and feeling heard reduces the need to defend. After understanding is established, you can shift to problem-solving, such as defining a shared outcome, proposing a communication plan, or agreeing on an escalation path if a decision is needed. The leader’s role is to help the person act professionally and effectively, not to take sides reflexively. You also want to watch for patterns, such as repeated conflict with a specific team, because patterns may signal a systemic issue like unclear decision rights or inconsistent standards. When you navigate conflict with curiosity, you model the behavior you want leaders in your team to adopt. This is how one-on-ones grow leaders: by teaching how to resolve friction without drama.

A practical preparation step is writing three questions for tomorrow, because good one-on-ones are built on intention, not on improvisation. The questions should be open enough to invite real answers and focused enough to surface what matters, such as what is the biggest blocker right now, what is unclear about priorities, and what would make you feel successful by next week. You might also include a growth-focused question, such as what skill you want to strengthen in the next month and what opportunity would help you practice it. Another useful question explores energy, such as what has been draining you most and what has been energizing, because energy is often the early signal of sustainability problems. Writing questions in advance reduces the chance that the meeting becomes status-only, and it ensures you address both execution and development. It also signals seriousness, because prepared questions show you are investing thought in the person’s success. Over time, a small set of consistent questions can become a template that keeps meetings productive even when you are busy. The goal is not to script the entire conversation; it is to ensure the meeting has purpose. When purpose is consistent, trust grows because the person sees the meeting is for them, not for the calendar.

A phrase to keep in memory is trust compounds through consistent follow-through, because it captures the mechanism that makes one-on-ones powerful. Trust is rarely built by a single supportive conversation; it is built by repeated evidence that commitments are honored, that problems are addressed, and that the person’s growth is taken seriously. Consistent follow-through means you do what you said you would do, you close loops on blockers, and you revisit prior commitments instead of letting them fade. This compounding effect is important in security teams because pressure can make people cynical, and cynicism grows when leaders talk but do not act. When follow-through is consistent, people become more honest, because they believe honesty will lead to help rather than to punishment. Honesty improves early warning signals, which improves operational resilience because problems are surfaced sooner. Follow-through also builds accountability because it creates a culture where commitments matter, and cultures where commitments matter tend to execute well. This phrase is a reminder that the one-on-one is not primarily about the conversation; it is about what happens after the conversation. If you want trust, you must build a pattern of action that validates the words.

As a mini review, keep cadence, blockers, growth, notes, and commitments linked as the core structure of a high-value one-on-one. Cadence provides consistency and predictability, which creates safety and early issue discovery. Blockers focus the meeting on removing friction, which increases throughput and reduces stress. Growth ensures the meeting invests in the future capability of the person and the team, turning one-on-ones into a leadership development engine. Notes preserve continuity and fairness, preventing promises from being forgotten and patterns from being missed. Commitments, especially leader commitments, turn the meeting into action and make trust compounding possible. When these pieces are present, one-on-ones become energizing because they produce clarity and progress. When they are missing, the meeting becomes draining because it feels like overhead and inspection. The review matters because one-on-ones are easy to do poorly by default, and the structure helps you do them well even when busy. If you can remember these five elements, you can run consistently useful meetings without needing elaborate preparation. That consistency is what makes the ritual a multiplier.

We will conclude by turning this into immediate action, because the value of one-on-ones is captured only when the next meeting is scheduled and the agenda is prepared together. Schedule the next one-on-one on a cadence you both agree is sustainable, and explicitly state the purpose so it is not mistaken for a status-only meeting. Prepare the agenda together by capturing the top topics, the current blockers, and one growth focus, and write them down so the meeting has a visible plan. Commit to ending with next steps that include your own follow-through, and then revisit those steps at the start of the next meeting to reinforce trust. This is the last paragraph and the conclusion, and it is the last required bullet: schedule the next one-on-one and prepare the agenda together, because one-on-ones only become leadership multipliers when they are consistent, purposeful, and backed by reliable follow-through.