Behind the Curtain: How Chiefs of Staff Drive Strategy Execution

This article is co-authored by Aaron Velek , Jessica Kraxberger , Shelby Stoddard , Mackenzie Lee , Clara Ma , and Harry Siggins .

The Chief of Staff role is often described as a force multiplier—a unique position that amplifies an organization’s ability to execute its strategy and achieve its vision. Yet, what does this look like in practice? How do Chiefs of Staff navigate the complexities of strategy execution, from aligning leadership teams to prioritizing competing goals, while keeping the organization adaptable and focused?

To explore this, we reached out to seasoned Chiefs of Staff and strategy leaders, posing seven key questions that delve into the heart of their strategic impact. Their responses revealed a treasure trove of wisdom, showcasing the nuanced ways they drive alignment, ensure accountability, and adapt to the ever-changing business landscape.

1. How do you measure progress towards the organization’s strategic goals, and what key indicators or metrics provide the best insights into success?

For Harry Siggins , tracking progress toward strategic goals is like operating a complex machine. Imagine the organization as a finely tuned engine, where OKRs act as the dials you adjust to optimize performance. "OKRs are your leading indicators," he explains, "showing whether you're making the right moves to execute your strategy. They're the early signals that tell you if the strategy is changing how the organization operates." But strategy execution doesn’t stop there. "KPIs are your lagging indicators – they reveal if those changes are delivering the intended results. Together, OKRs and KPIs paint a full picture of success, allowing you to see if you're both executing well and achieving the desired outcomes."

Clara Ma takes a similarly holistic approach but adds a layer of practicality rooted in real-time feedback. For her, strategic objectives come alive through an OKR framework, with each objective tied to 2-4 clear, measurable outcomes. "For instance," she shares, "if our goal is to expand into a new market, we define success with metrics like revenue growth, new customer acquisition, or partnerships in that region." To keep progress visible, Clara leans on dashboards and department-specific scorecards, but she knows numbers alone don’t tell the whole story. "Regular check-ins and conversations with team leaders help uncover roadblocks or opportunities that data can miss. It's about pairing the quantitative with the qualitative to guide our next steps."

Mackenzie Lee brings the perspective of someone immersed in the pulse of the executive suite. For him, progress is tightly linked to KPIs defined by the CEO and C-suite, each one anchored in the organization’s annual plan. "These could be anything from topline revenue and customer acquisition cost to Net Promoter Scores or retention rates," he notes. Mackenzie emphasizes that while these high-level indicators are crucial, they must cascade effectively through the organization to ensure every team understands their role in delivering on the broader strategy.

2.? What approach do you take to prioritize strategic goals, especially when there are competing demands for resources or shifting market conditions?

For Mackenzie, prioritization begins at the top with structured and intentional planning. "We hold dedicated strategic planning sessions on an annual and quarterly basis," he explains, "bringing the CEO and C-suite together regularly to set and agree on priorities." This disciplined cadence creates a strong foundation, ensuring that the organization is aligned on what matters most before diving into execution. Once priorities are set, they serve as the organization’s guiding framework, helping to steer decisions amidst the inevitable noise of competing demands.

Clara builds on this foundation with an approach that leverages her unique vantage point as a Chief of Staff. "Alignment with the executive team’s vision is always step one," she shares. From there, Clara uses her ability to see across teams to foster collaboration and resolve conflicts. Her decision-making lens? Impact versus effort. "I’m always asking: what initiatives will move the needle the most without pulling us in too many directions?" But Clara knows that even the best-laid plans need room to breathe. "Nothing ever goes perfectly to plan," she says, "so we have regular check-ins to revisit and adjust priorities as challenges or opportunities arise." For her, communication is key to building buy-in. "When the team understands the 'why' behind priorities, they’re far more connected to the bigger picture. That alignment keeps everyone focused on what truly matters."

Harry takes a broader philosophical approach, emphasizing the need for strategic goals to remain the organization’s north star. "When competing demands arise, I flip the conversation," he says. "Instead of asking how to juggle everything, we need to ask what’s so significant that it warrants diverging from our strategy." For Harry, this often highlights a deeper issue: generic goals that fail to address core challenges. "If your business-as-usual activities aren’t setting you up to achieve your organization’s purpose, that’s a red flag." His solution? Get laser-focused on identifying the real challenge and the most critical moves needed. But he’s quick to point out that strategy isn’t static. "It needs to be a living, breathing discussion. Build in the agility to adapt when true market shifts or significant changes occur. The key is knowing the difference between a legitimate need to pivot and simply losing focus."

3. How do you secure and maintain executive buy-in on the organization’s strategic vision, particularly when there are differing perspectives or priorities?

For Harry, securing executive buy-in begins not with plans and actions but with crafting a compelling strategic narrative. "It starts with answering three fundamental questions: Why do we exist, who do we serve, and what do we do best?" he explains. Harry likens the organization’s vision to a destination, where the "why" is the fuel and the purpose is the path guiding the way. This approach is particularly vital in growth-stage companies, where the vision can often feel far-off or abstract. "Purpose acts as a set of guardrails, making a lofty vision feel achievable and giving executives something tangible to rally around. It’s about anchoring everyone in the organization’s core reason for being."

Clara’s approach builds on trust, communication, and relentless focus on the big picture. "Alignment starts with open, honest conversations," she shares. "I facilitate discussions that use data to cut through competing perspectives and clarify trade-offs." Clara sees the Chief of Staff role as a bridge-builder, ensuring that every decision ties back to the organization’s top strategic goals. But for her, alignment isn’t achieved in a single meeting. "It’s in the follow-ups—those one-on-one check-ins where concerns can surface and be addressed early. By staying neutral and focused on what’s best for the organization, I was able to earn the trust of the leadership team." With that trust in place, Clara kept everyone rowing in the same direction, even when the waters got choppy.

For Mackenzie, buy-in is solidified through structure and consistency. "Written sign-offs, strategy retreats, and facilitated sessions are key tools," he explains. Mackenzie emphasizes the importance of clear communication, not just within the leadership team but cascading top-to-bottom throughout the organization. "A strategy isn’t real until everyone knows about it and understands their role in making it happen." By institutionalizing these practices, he ensures the strategic vision isn’t just agreed upon—it’s embraced and acted on at every level.

4.? What criteria or frameworks do you use to assess the relevance or potential impact of new opportunities on the organization’s existing strategic direction?

For Clara, assessing new opportunities requires a structured and data-driven approach. Her go-to tool? The RICE Scoring Model. "This framework evaluates opportunities based on Reach, Impact, Confidence, and Effort," she explains. "It’s invaluable for identifying high-impact opportunities with broad reach and strong feasibility, while deprioritizing less impactful ones." Clara highlights how these tools not only streamline decision-making but also help maintain focus on initiatives that truly move the needle. "In a world of competing priorities, frameworks like RICE ensure we make the best use of limited resources and keep aligned with our strategic goals," she says. It’s a method she’s refined and even shared in a recent LinkedIn post. Clara recently shared her expertise on prioritization frameworks in a LinkedIn article, offering insights into navigating competing priorities and staying focused on high-impact initiatives. You can check out her post here.

Mackenzie approaches prioritization with a multi-dimensional lens, plotting opportunities against four key factors: level of effort, level of impact, level of risk, and timeframe. "This method gives a clear visual representation of where each opportunity sits in relation to the others," he explains. By systematically evaluating these dimensions, Mackenzie ensures that decisions aren’t just reactive but deliberate and aligned with the organization’s strategic direction. It’s an approach that balances ambition with pragmatism, helping the organization focus on opportunities that maximize impact while managing risk effectively.

Harry takes a straightforward yet powerful approach to opportunity assessment. "I think of it like a modified Eisenhower matrix," he shares. "Instead of urgent versus important, I evaluate opportunities based on impact and effort." For Harry, this framework helps quickly identify whether a new opportunity requires a strategic pivot or a simple course correction. "Opportunities and challenges are often two sides of the same coin," he adds. "The key is having a consistent framework that cuts through the noise and lets you make decisions with confidence and speed." By keeping the process clear and consistent, Harry ensures that every decision reinforces the organization’s overarching strategic goals.

5. How do you communicate strategic progress to the executive team, and what mechanisms do you use to ensure that they are aligned and actively engaged with the strategy?

Effective communication with the executive team is rooted in clarity, consistency, and connection, in Clara Ma’s perspective. "Strategic updates need to tie directly to the overarching goals and be framed in a way that resonates with their priorities," she explains. Clara breaks progress into digestible pieces: what’s working, where the team is stuck, and what decisions or trade-offs need to be made. "I also make space for honest conversations. It’s crucial that leaders feel heard, even as we stay laser-focused on what’s best for the organization." To keep engagement high, Clara leverages dashboards for real-time visibility, along with structured weekly updates and quarterly reviews. "These checkpoints aren’t just about reporting progress—they’re about actively involving leaders in shaping the path forward. When they see the progress and have input, alignment becomes a natural outcome."

Harry takes a practical and disciplined approach to keeping the executive team aligned. "At Quantive, we held bi-weekly OKR check-ins where OKRs literally formed the agenda," he recalls. "If a topic didn’t connect to our strategic OKRs or wasn’t owned by a leadership team member, it was handled separately." This structure might sound rigid, but Harry found that it created incredible clarity. "Everyone knew exactly where we stood on strategy every single week. It kept the team focused on what really mattered and eliminated distractions."

For Mackenzie, the key lies in using a variety of communication tools to ensure comprehensive updates and alignment. "We rely on KPI dashboards, program and project management status updates, and RAG (Red, Amber, Green) statuses," he shares. Mackenzie also emphasizes the importance of retreat and offsite readouts to reinforce alignment. "These mechanisms provide a clear and consistent way to assess progress and keep the team engaged with the strategy."

6.? What role do you play in adapting the strategic vision when early indicators suggest a shift might be necessary to achieve the organization's long-term goals?

Running the OKRs program provided a unique vantage point that bridged short-term execution with long-term strategy for Harry Siggins. "I could see the immediate impact of our OKRs while tracking longer-term trends through our KPIs," he explains. This dual perspective allowed him to play a crucial role in flagging potential issues during weekly leadership meetings. "Rather than just reporting progress, I’d call out when metrics were moving in the wrong direction or when consistent blockers arose." By surfacing these insights, Harry enabled the leadership team to make informed decisions about whether a shift in strategy was necessary to stay on track with long-term goals.

Mackenzie views the role as a strategic sounding board for the executive team, with a strong focus on risk and blocker identification. "I help surface potential risks and barriers early, acting as an escalation point to ensure issues don’t derail progress," he shares. Mackenzie also emphasizes the role in helping executives think through the broader implications of potential changes. "I provide a space to evaluate different scenarios and weigh the trade-offs, ensuring that any adjustments align with the organization’s overarching vision." He contributions help leadership navigate the complexities of pivoting while maintaining strategic continuity.

Clara describes the role as being the "signal amidst the noise," synthesizing early indicators into actionable insights for leadership. "I keep a pulse on internal metrics, market shifts, and team sentiment, surfacing patterns that others might overlook," she says. Clara’s approach involves more than just identifying the need for change—it’s about facilitating clarity and alignment. "When a shift is necessary, I lead scenario planning and trade-off discussions, ensuring everyone understands the ‘why’ behind the adjustment." For Clara, the key is balancing agility with strategic focus. "By grounding decisions in our mission and supporting them with clear, adaptable plans, I help the leadership team evolve while keeping the organization unified and moving forward."

7.? How do you use OKRs to drive alignment and measure progress towards strategic goals, and what role do you play in ensuring OKRs remain relevant to the broader strategy?

For Harry, OKRs are less about rigid structure and more about driving meaningful outcomes. "We didn’t align OKRs to the org chart but to outcome hierarchies," he explains. "Each team had just one OKR per quarter, focused on what they could achieve in the next three months to support our strategic goals." By tying every OKR back to strategic pillars and themes, Harry ensured that OKRs remained tightly connected to the organization’s broader strategy. "It all comes down to the strategic narrative," he adds. "When you have a strong story about where you’re going and why, it’s much easier to ensure OKRs stay relevant and impactful."

Mackenzie highlights the importance of structure and cadence in using OKRs to drive alignment. "We start with annual OKR setting to align with the long-term strategy," he shares, "and then revisit them quarterly to ensure they’re still relevant and aligned with shifting priorities." This regular evaluation keeps the organization on track while providing the flexibility needed to respond to changes in the business environment.

Clara takes a dynamic and hands-on approach to leveraging OKRs for alignment and progress. "I work with leadership to define clear, ambitious objectives and measurable key results that tie directly to the company’s long-term goals," she explains. For Clara, the process doesn’t stop at setting OKRs. "I facilitate regular reviews to track progress, address roadblocks, and ensure key results remain meaningful." Flexibility is a cornerstone of her approach. "As business priorities shift, OKRs are adapted to stay relevant and continue driving alignment and impact across the organization."

In Closing

The insights shared by these accomplished Chiefs of Staff reveal the indispensable role they play in steering strategy and unlocking organizational potential. Whether it’s through effective use of OKRs, fostering executive alignment, or adapting to shifts in the business environment, their approaches offer valuable lessons for leaders at all levels.

As organizations continue to evolve, the Chief of Staff role will undoubtedly grow in significance, shaping not just how strategy is executed but also how it is envisioned and adapted. I hope these insights spark conversations within your own teams and inspire new ways to tackle strategic challenges.

What are your thoughts? How has your Chief of Staff—or a similar role—impacted strategy in your organization? Share in the comments below! ??