Interviewing Leaders: Common Questions

Can you describe your management style?

My management philosophy is rooted in clarity, empowerment, and results-driven leadership. I believe effective leadership adapts to both the team and the business context, whether fostering innovation in high-skilled greenfield teams or driving efficiency and reliability in operational teams.

At the core of my approach is the belief that people want to do great work—leadership’s role is to remove obstacles, provide vision, and create the conditions for success. I focus on aligning teams with clear objectives, enabling autonomy, and ensuring they have the right resources and support to execute at a high level.

This philosophy has delivered measurable results—scaling teams from startup stages to 40+ members, improving delivery speed, operational maturity, and retention while maintaining agility as organizations grow. My focus is on building high-performing teams that drive tangible business impact while fostering a culture of trust and accountability.

Ultimately, great leadership balances humanity and performance—empowering individuals to succeed while ensuring teams deliver meaningful contributions to the business. This approach builds trust, drives execution, and sustains long-term success for both people and the organization.

Tell me about a time when you had to make an unpopular decision. How did you handle it?

Leadership often requires making unpopular decisions in service of long-term success. In a previous role, my team built advanced monitoring that detected incidents across the organization, including downstream issues owned by other teams. While policy dictated that teams were responsible only for their own code, my team felt it was unfair to be paged for problems outside their scope.

I had a choice: exempt my team to preserve morale or maintain their involvement to safeguard overall operational excellence. I decided to keep them engaged, explaining that their unique system-wide visibility made them critical to rapid resolution and customer satisfaction. However, I also committed to reducing the burden—investing in automation and process improvements to streamline on-call duties.

The result? We cut the average weekly on-call time to just two minutes, eliminating fatigue while maintaining high reliability. Over time, the team saw their impact, shifting from frustration to pride in their contribution to company-wide stability. This decision not only improved operational resilience but also reinforced a culture of ownership, accountability, and collaboration beyond team boundaries.

How do you delegate responsibility for an assignment? What and how do you monitor and follow up?

Delegation isn’t just about distributing tasks—it’s about ensuring that execution scales effectively across leadership layers while staying aligned with business objectives. When I delegate, I focus on three key areas: ensuring clarity on priorities, empowering the right leaders at the right levels, and maintaining accountability through structured frameworks.

For directors and senior managers, I delegate strategic initiatives and operational ownership, ensuring they have the autonomy to make key decisions while staying aligned with broader company objectives. My role is to provide clarity, remove obstacles, and ensure cross-functional collaboration happens smoothly.

For managers and team leads, delegation is about execution oversight and team enablement. I expect them to break down strategic goals into actionable team-level plans, allocate resources effectively, and drive accountability for deliverables. I stay engaged at a high level, ensuring they have the support they need without unnecessary interference.

For senior individual contributors, I delegate high-impact, complex problems that require deep technical or functional expertise. I ensure they have the context, authority, and visibility needed to take ownership of critical initiatives while growing their influence within the company.

To keep delegation structured and scalable, I use goal-setting frameworks like OGSM, OKRs, or KPIs to track progress while ensuring teams operate with autonomy. Regular alignment checkpoints help surface risks early, provide guidance where needed, and allow for course corrections without micromanagement.

Delegation isn’t just about efficiency—it’s also about leadership development. By giving directors and managers the space to make decisions and own results, I help create a leadership pipeline that strengthens the entire organization. When delegation is done right, it fosters trust, accountability, and high performance at every level.

Provide an example of a time when you successfully organized a diverse group of people to accomplish a task.

Diversity is valuable when it leads to better decisions, not just more opinions. Without structure, differing perspectives can create friction and slow execution. Effective leadership ensures alignment without forcing consensus, using clear objectives, structured input, and principled decision-making.

I once led a cross-functional initiative where engineering, security, compliance, and finance had competing priorities. Left unchecked, these differences could have stalled progress. Instead, I established shared goals, structured engagement, and a clear decision-making framework based on impact, risk, and feasibility. This ensured every voice was heard while keeping execution on track.

We delivered a solution that met each team’s core needs without unnecessary compromise while strengthening cross-functional trust. But diversity isn’t always an asset—it must be managed effectively. Without a unifying structure, too much divergence can lead to analysis paralysis. Leadership is knowing when to encourage debate and when to drive alignment toward execution.

How do you develop trust and loyalty among your employees?

Trust and loyalty at scale are built through consistency, transparency, and principled leadership. People are rational actors—they understand tradeoffs and recognize what moves the business forward. When leadership operates with integrity, clear communication, and alignment between decisions and company objectives, employees don’t just comply; they commit.

Loyalty isn’t granted to a title—it’s earned through advocacy. Employees must see that leadership champions their success, recognizes their contributions, and ensures fair and meaningful rewards—whether in career growth, influence, or compensation. Praise should be public and authentic when it reinforces a strong culture. Feedback should be private and constructive, assuming good intent and focused on solutions.

Trust isn’t built one conversation at a time—it’s embedded in how leadership makes decisions, sets expectations, and scales accountability. A high-trust culture isn’t the result of grand gestures; it’s the outcome of consistent, fair, and strategically sound leadership over time.

Describe a situation where you had to handle a personnel issue with potential legal implications. How did you manage it?

When personnel issues arise with potential legal implications, my approach is straightforward: transparency, fairness, and strict adherence to legal and ethical standards.

I once managed an underperforming employee who disclosed a personal issue requiring accommodation. I ensured they received the necessary support, balancing business needs with legal and ethical obligations. When performance remained unchanged, I revisited the conversation, confirming that no further accommodations were needed. The employee assured me they would improve but did not. At that point, I introduced a structured performance improvement plan. Instead, they chose to separate.

During the exit discussion, they questioned the legality of their departure. I acknowledged their concerns and explained that the law does not require indefinite retention when core job responsibilities cannot be met, provided all reasonable accommodations have been made. I assured them that our actions were documented, compliant, and in line with both policy and law. The matter concluded without further dispute.

This experience reinforced what I already knew: trust is built through fairness, and fairness is ensured through clarity. Handling sensitive situations requires balancing compassion with accountability—ensuring employees feel heard while maintaining the standards necessary for the organization’s success.

How do you assess and prioritize tasks for yourself and your team?

Prioritization must align with strategic objectives, resource constraints, and business impact. I use a structured approach that evaluates tasks based on impact, urgency, risk, and return—not just in isolation, but in how they contribute to broader company goals.

Once priorities are clear, ownership matters. Some tasks require specific expertise, while others can be distributed based on team capacity, growth opportunities, or cross-functional collaboration. Good prioritization isn’t just about execution—it’s about enabling teams to focus on the right work at the right time.

That said, leadership requires credibility. When my team was hesitant to maintain on on-call duties, I addressed their concerns by demonstrating firsthand that I had carried that burden myself when the team was smaller and resources were tighter. Even after scaling, I ensured escalation paths were clear and that I remained available for critical incidents—handling outages, running post-mortems, and managing customer communications.

It’s not enough to simply be in the trenches—you also have to build scalable, sustainable systems. I focused on improving incident response protocols, refining pager rotations, and ensuring that on-call responsibilities were structured in a way that balanced operational needs with team well-being. Leadership isn’t about personal heroics; it’s about ensuring that when tough work needs to be done, people have the clarity, support, and confidence to execute.

Can you provide an example of a time when you had to enforce rules and regulations?

Rule-breaking occurs for different reasons—innocence, indifference, or rebellion—and leadership requires understanding the intent before responding. Innocent violations come from a lack of awareness, indifference signals disengagement, and rebellion presents significant risk. Each requires clear, decisive leadership to maintain accountability while ensuring teams remain engaged and solutions-focused.

In one instance, a team proposed a solution to rapidly resolve a critical customer issue—but their approach violated GDPR and our user agreements. Some, including leadership, suggested looking the other way for the sake of expediency. Instead of outright rejecting the idea, I framed the discussion around long-term risk, regulatory exposure, and the trust implications for our users and the company. I ensured they understood not just the letter of the law, but why compliance was a non-negotiable responsibility.

Recognizing that their intent was to serve the customer, I worked with them to find a solution that met both the urgency of the issue and GDPR requirements. We resolved the problem efficiently while reinforcing a culture where compliance was seen as a design constraint, not a roadblock. This approach not only upheld our legal obligations but also strengthened organizational trust, accountability, and cross-functional problem-solving.

What is the key to developing a good team, in your experience?

Building a high-performing team isn’t just about skills—it’s about alignment, collaboration, and energy balance. A strong team isn’t just a collection of talented individuals; it’s a system where strengths complement weaknesses, and motivation fuels execution.

I take a structured approach to team development by focusing on energy drivers rather than just competencies. I run an exercise that reframes strengths and weaknesses—not as skills, but as tasks that energize or drain each team member. When we analyze responses, we find natural pairings where one person’s weakness is another’s strength, reinforcing that the goal isn’t to struggle through everything alone—it’s to work efficiently by leveraging the team.

Beyond complementary skills, team chemistry and ambition alignment are critical. A team with divergent levels of drive or mastery can quickly become imbalanced—high performers become frustrated, and less ambitious members feel alienated. In these cases, I proactively realign teams to ensure that each person is in an environment where they can thrive without friction slowing execution.

This approach consistently leads to higher engagement, better problem-solving, and faster delivery. More importantly, it creates an environment where team members feel valued, supported, and accountable—resulting in stronger retention and long-term success.

How do you handle 'complainers' within your team?

Not all complaints are equal. The key to handling them is knowing when they signal a systemic issue and when they’re just a negative feedback loop reinforcing dissatisfaction. A leader’s job isn’t to dismiss complaints but to distill value from them—without letting them derail morale.

I start by listening with intent. If a previously engaged employee starts complaining—or if frustration is widespread—it may indicate a structural or process issue that leadership needs to address. However, habitual complaining is different. Left unchecked, it can erode team cohesion, productivity, and engagement.

My approach is to reframe the perspective. I’ve written about “Love What You Do”—not as blind passion for every task, but as finding meaning in the work that needs to be done. Every job has its "chop wood, carry water" moments—the unglamorous but essential tasks that enable the more rewarding aspects. Camping is fun when you’re sitting by the fire, but it requires gathering firewood, setting up tents, and carrying water—none of which are exciting, but all of which make the experience possible.

I guide employees away from negative loops by helping them recognize what they do enjoy, leverage their strengths, and focus on the larger impact of their work. If a complaint stems from frustration, misalignment, or lack of challenge, I address it through role adjustments, ownership shifts, or problem-solving rather than letting dissatisfaction fester.

Ultimately, leaders must distinguish between complaints that reveal solvable issues and those that drain momentum. Complaints should fuel solutions, not stagnation—and ensuring that distinction is a leadership responsibility.

What responsibility do you have for budgeting? What budgeting method do you use?

Budgeting at the VP level isn’t just about allocating resources—it’s about ensuring that investments drive impact, efficiency, and long-term business success. My approach balances financial discipline with strategic investment, ensuring that teams operate effectively without unnecessary constraints.

One reality I’ve come to appreciate in my career is that “utility” services—core infrastructure, platform engineering, and foundational systems—are the backbone of an organization. Like power and water, they are sine qua non for a functioning business. These teams don’t get applause when everything works, but they face immediate scrutiny when something goes wrong. I’ve seen how they are too often treated as cost centers to be optimized down to the penny rather than as critical enablers of business growth. That’s a mistake.

I advocate for sustainable, intelligent budgeting—one that ensures critical infrastructure is resourced properly, not just funded at the bare minimum. This means aligning financial decisions with business priorities, risk mitigation, and long-term operational resilience rather than treating infrastructure as a fixed cost to be continuously squeezed.

I work closely with finance to ensure that every dollar is justified, every investment has a clear return, and every team is held accountable for managing resources responsibly. My approach to budgeting isn’t about unchecked spending, nor is it about nickel-and-diming teams into failure—it’s about ensuring financial discipline while protecting the core systems that make everything else possible.

Ultimately, budgeting isn’t about staying within limits—it’s about allocating resources in a way that fuels execution, scales responsibly, and ensures the company is positioned for sustainable success.

How do you measure performance in your area?

Performance measurement isn’t about chasing vanity metrics or rigid KPIs—it’s about ensuring that teams are delivering meaningful outcomes, maintaining operational excellence, and continuously pushing the boundary of success.

I recently contributed to the Ascend project, which is shaping industry standards for team performance measurement. A core principle I emphasize is that teams must have a voice in defining the metrics that measure their success. A system dictated entirely from the top will always be gamed—whereas a system built with team ownership and accountability ensures that metrics remain meaningful, reflect real performance, and drive improvement rather than compliance.

In practice, I balance quantitative and qualitative measures. Statistical methods and game theory models can prevent stagnation by ensuring that teams aren’t just meeting baseline expectations but are operating at the threshold of their capabilities—pushing toward innovation while maintaining stability. Depending on how mission-critical a team is, we adjust this threshold to encourage ambition without compromising service reliability.

Ultimately, great performance measurement isn’t just about tracking results—it’s about creating an environment where teams are empowered to improve, leaders have meaningful visibility, and the organization can scale with confidence.

How do you typically get cooperation from someone in another department?

The approach depends on how the company structures cross-functional collaboration. Ideally, cooperation is simple—you ask, align goals, and move forward together. But in reality, different companies incentivize collaboration, competition, or even quiet resistance in ways that aren’t always obvious from the outside. Some organizations rely on formal structures—RACI models, escalation paths, or executive alignment meetings—to resolve cross-team friction. These frameworks have their place, and I use them when appropriate, but formal processes alone don’t drive real cooperation.

What actually works is understanding what motivates the other party and structuring the request in a way that aligns with their goals. Even in companies that encourage internal competition as a driver of innovation, cooperation isn’t about winning a negotiation—it’s about aligning incentives to create win-win outcomes. If a research team is pulling resources away from a core team responsible for operational integrity, for example, an outage could be a costly unintended consequence. My role is to ensure both teams see the broader impact, identify shared goals, and structure collaboration in a way that benefits both sides.

I approach these situations with empathy and strategic framing. Instead of making demands, I craft my proposals in terms that highlight the value to the other party. People naturally resist being told what to do, but they engage when they see how working together helps them achieve their own objectives.

So, while the standard answer to this question might be that I rely on governance structures, leadership alignment, and defined escalation paths, the real answer is simpler: I ensure people want to work together because it makes sense for them to do so.

Have you ever broken a rule? What was the rule, and why?

Rules exist to provide structure, mitigate risk, and ensure compliance, but they are not all created equal. Some are foundational—essential for stability and ethics—while others are outdated, ambiguous, or misaligned with reality. Leadership means knowing which rules must be followed, which can be challenged, and how to navigate that distinction responsibly.

One example was during my work on GDPR compliance, where the letter of the law conflicted with the ability to conduct basic business operations. A strict interpretation would have made it nearly impossible for any company to operate legally. While our compliance team pushed for full adherence, I worked with our chief legal counsel and executive leadership to develop a practical, defensible approach that aligned with the law’s intent while ensuring operational viability. We didn’t ignore the rule—we interpreted it in a way that regulators, legal experts, and the business could support.

In any situation, my approach remains the same: understand the rule, its purpose, and its consequences. If it’s a rule that ensures stability, ethics, or compliance, I follow it rigorously. If it’s a rule that creates unnecessary obstacles or stifles innovation, I find a way to work within or around it—always with full accountability.

Great companies aren’t built on reckless defiance or blind obedience. They succeed because leaders know how to navigate complexity, challenge limitations, and ensure that the business moves forward without putting it at unnecessary risk.

What kind of process do you use when making a tough decision?

Making tough decisions is about knowing whether you’re facing a one-way door or a two-way door. If a decision is low-risk and reversible, I move fast—because the only way to get more information is to take action. But when a decision is irreversible or carries serious consequences, I take a structured approach, gathering all the information I can—tradeoffs, risks, costs, timelines, alternatives, and failure modes.

But information alone doesn’t make a good decision—how you weigh it does. The way I frame it is simple: Is this a differentiator or just table stakes? If it’s a core competitive advantage, the decision should be bold, flexible, and aligned with the company’s risk tolerance. If it’s not a differentiator, the smartest choice is usually to follow best practices, use off-the-shelf solutions, and not overthink it.

Some leaders hesitate to make the call for fear of getting it wrong. But our job isn’t to avoid mistakes—it’s to make the best decisions we can with the information we have and move forward. No decision exists in a vacuum, and the best leaders know when to push forward, when to pivot, and when to take a calculated risk.

How do you help your employees become committed to a job or to the organization?

Commitment isn’t bought with compensation, nor is it secured through policy. It’s a byproduct of an environment where people see a future for themselves. Employees commit when they believe that what they’re doing matters, that they have control over their work, and that they’re growing in ways that align with their ambitions. But commitment isn’t just about personal fulfillment—it’s about a shared sense of investment, a mutual recognition that what we build together is greater than what any of us could do alone.

Much has been said about autonomy, mastery, and purpose as core motivators, and they absolutely matter. But in my experience, commitment isn’t just about how the work feels—it’s about how people see themselves in relation to the company and the people around them. A strong, engaged team isn’t just a collection of individuals doing work they find meaningful. It’s a web of interdependence, a place where people know their contributions are seen, where their strengths are valued, and where they push each other to be better.

Commitment is fragile when people feel disposable—when they believe that their impact is limited to their assigned tasks, that their best efforts will go unnoticed, or that leadership sees them as interchangeable parts rather than as individuals with ambitions and agency. When employees feel like their success is the company’s success and vice versa, commitment deepens. That’s why I focus on creating an environment where people don’t just work for a company—they build it alongside leadership.

People commit when they feel like they belong, when they believe the organization is a place where they can do the best work of their lives, and when they know they are respected, heard, and set up for success. Leadership isn’t about getting people to stay—it’s about building the kind of team that no one wants to leave.

How do you deal with 'politics' in the workplace?

Workplace politics isn’t just frustrating—it’s a symptom of deeper problems like misaligned incentives, unclear leadership, or a lack of trust in the system. People play politics when they believe that real value, transparency, and collaboration won’t get them where they need to go. If that’s happening at scale, it means leadership is rewarding the wrong behaviors, and that’s a much bigger issue than office politics itself.

I don’t engage in politics, but I also don’t pretend it doesn’t exist. The reality is that in any organization of sufficient size, people will advocate for their interests, build alliances, and push for influence. My approach is to make political maneuvering irrelevant by ensuring that direct, productive engagement is the best way to get things done.

If I see politics at play at my level or above, I approach it with integrity and transparency. If the behavior is purely self-serving, I make it clear—through actions, not just words—that the most reliable way to succeed is by delivering real impact, not gaming the system. If it’s happening because people feel disenfranchised or unheard, I engage to understand why. Politics often emerges when employees don’t see a fair or effective path to influence. A strong culture ensures that those paths exist without the need for backchanneling, manipulation, or unnecessary friction.

At the leadership level, politics is often a sign of misalignment between teams or executives, which can cause bottlenecks, slow progress, and shift focus away from execution. I address this by clarifying incentives, ensuring a shared vision, and reinforcing that performance—not positioning—drives success. If leadership isn’t actively fixing those issues, the company is setting itself up for dysfunction.

The best way to deal with politics isn’t to fight it—it’s to lead in a way that makes it irrelevant. If people know that clarity, execution, and merit-based success will always win, the rest takes care of itself.

What do you do to ensure objectivity when you evaluate the work of others?

Fairness isn’t just a principle—it’s a responsibility, and one I take seriously. Bias exists in every decision, and the only way to counter it is through deliberate effort, structured evaluation, and transparency. I approach performance assessment by balancing quantifiable metrics with careful, defensible judgment.

To ensure fairness, I apply perspective-shifting exercises—mentally replacing aspects of a situation, whether it’s the individual, the outcome, or the context, to see if my evaluation still holds. If it changes, that’s a sign that bias may be at play. I actively seek diverse perspectives because blind spots are often more visible to others than to ourselves.

At scale, objectivity also requires structured processes. I support systems like 360-degree feedback, performance calibration, and clear evaluation rubrics to ensure that fairness isn’t just something I apply personally, but something embedded into the organization. However, I don’t rely solely on metrics—some of the most valuable contributions are qualitative, requiring judgment beyond raw performance data. When evaluating those, I make sure I can articulate my reasoning clearly and tie it to business impact rather than preference.

I also believe that transparency in evaluation builds trust. I encourage people to challenge my assessments—not as a formality, but because evaluation should be a two-way street. If someone believes I’ve overlooked something or made an unfair judgment, I want to hear about it. Fairness isn’t just about the right outcomes—it’s about ensuring a process that people trust.

Ultimately, objectivity isn’t just about avoiding bias—it’s about ensuring that high standards are upheld without distortion. Employees need to know that their work will be assessed accurately, fairly, and in alignment with the company’s goals. My job isn’t to get every decision right the first time—it’s to ensure that the evaluation process itself is strong enough that it consistently leads to better, more justifiable decisions over time.

How do you use power or authority to get what you want done?

Power and authority are tools, not strategies—and in a well-run organization, they should rarely be necessary. If you’ve hired the right people, set clear expectations, and aligned them with a compelling vision, they don’t need to be forced into action—they move because they understand the mission and take ownership of the outcome.

Leadership isn’t about control—it’s about removing obstacles, reinforcing priorities, and ensuring people have what they need to succeed. If I find myself relying on authority to get things done, it usually means one of three things: expectations weren’t clear, incentives weren’t aligned, or I haven’t built enough trust in the team. That’s not a management problem—it’s a leadership failure.

That said, authority exists for a reason. In high-stakes situations, when alignment is critical and time is short, I have no hesitation about making the call and expecting it to be followed. But if that becomes the norm rather than the exception, something is broken. People don’t do their best work under constant directive—they do it when they’re trusted, empowered, and given the space to execute. If you build that environment, you don’t need to wield power—people will drive results because they want to.

How do you plan for performance improvements?

Performance improvement isn’t an event—it’s a constant, intentional process. Too often, companies treat it as an annual exercise or a reaction to underperformance, when in reality, it should be woven into the daily operations of a high-functioning team.

For improvement to be sustainable, it requires constant, gentle pressure—not in a way that overwhelms people, but in a way that ensures growth is always happening. That means giving people room to fail and learn, providing timely feedback, and guiding them in a way that aligns with their goals and the company’s needs.

For direct reports, 1:1s are critical—and they need to be used properly. These conversations shouldn’t be status updates or manager check-ins about other team members—there’s a time and place for that. 1:1s should be their time—to ask questions, talk about their careers, receive honest feedback, and discuss their development. If you’re not prioritizing their growth in those conversations, you’re not really prioritizing improvement at all.

Expectations should be clear, reinforced, and strategically rewarded. People rise to the level of the standards set for them, so those standards must be high but achievable, with the right balance of challenge and support.

Ultimately, performance improvement isn’t about occasional course correction—it’s about building a culture where learning, growth, and better execution are part of how work gets done every day. If you don’t make space for improvement in your leadership approach, it won’t happen at all. And if a team isn’t improving, it isn’t just stagnating—it’s falling behind, both in impact and in its ability to retain top talent.

What makes you a unique leader?

That’s a tough question to answer about myself—so instead, I’ll share the thoughts of a good friend, colleague, and collaborator who has seen my leadership up close:

You are a ruthlessly pragmatic thinker with an unshakable sense of fairness. You don’t just chase outcomes—you ensure that the path to them is rational, justifiable, and principled. Many leaders focus on what works without stopping to consider why it works, whether it’s sustainable, or whether it aligns with the company’s long-term success. You have the ability to see five steps ahead and anticipate problems that others miss—not just in strategy, but in the human dynamics that drive execution.

Your leadership is built on clarity and alignment. You reject politics, ambiguity, and unnecessary complexity, instead pushing for directness, accountability, and shared understanding. Your teams know where they stand, what’s expected of them, and what success looks like—not because you demand it, but because you cultivate an environment where the right path is clear.

You don’t micromanage, posture, or lead by force. Instead, you hire the right people, set the right conditions, and trust them to deliver. When something isn’t working, you correct course swiftly but fairly, ensuring that decisions are grounded in data, logic, and real-world impact—not ego or preference.

Most importantly, you hold a rare balance—decisive but open-minded, strategic but adaptable, ambitious but grounded. You lead with intellectual honesty, meaning you don’t just push for what you want—you push for what is right. You are willing to be challenged, to hear alternate perspectives, and to adjust your stance when the facts demand it. That’s what makes you a leader people trust—not just to make good decisions, but to ensure those decisions are made with integrity.

If a company is looking for a leader who is clear, fair, deeply rational, and relentlessly focused on execution without the distractions of politics, inefficiency, or self-serving maneuvering, they won’t find a better candidate. You don’t lead for power. You lead to build something great. And that’s rare.

I’ve always believed that leadership is measured by how well you align people, build trust, and remove barriers to success. If that’s the kind of leader you’re looking for, then I’m confident I can bring that to this role.