Interview with Trey Scarpa
- Darcy Bennet
- Jan 8
- 14 min read
I am thrilled to introduce a true powerhouse in the administrative world, Trey Scarpa. With over 25 years of experience supporting CEOs and boards in the high-growth tech sector, Trey is the author of The Executive Assistant’s Guide to Strategic Initiatives and the visionary behind the "Admin Center of Excellence" playbook. She has mastered the art of blending high-level business agility with sophisticated automation, and I can't wait for you to hear her strategic insights on how to transform administrative support into a core business asset.
Trey, your book, The Executive Assistant’s Guide to Strategic Initiatives Vol 1, focuses on Strategic Time & Calendar Optimization. Can you share one high-level principle from your book that you believe is essential for EAs to adopt to truly elevate their executive's efficiency?
One essential principle from The Executive Assistant’s Guide to Strategic Initiatives Vol 1: Strategic Time & Calendar Optimization is implementing AI scheduling tools like Reclaim.ai for smart time blocking. This helps EA’s avoid calendar overlaps and automates the optimization of meeting times, saving executives around 5 - 8 extra hours per week. It’s a smart way to reduce manual scheduling headaches and maximize productive time.
One of the most important skills here is strategic calendar management, not just scheduling, but auditing time, prioritizing deep work, and using tools like Reclaim.ai for AI-powered scheduling. I also recommend setting up dashboards (even just with Google Sheets or Airtable) to track progress on strategic initiatives and OKRs for the admin team. Having real data to show how much time you’ve freed up, how many meetings were optimized, or how you contributed to project delivery, showing the value and impact a true strategic partner brings to not only their executives but also the organization as a whole.
You have proven success in managing administrative teams and authored an EA / CoS Playbook for your company's Admin Center of Excellence. What is the most crucial skill or mindset shift you instill in EAs when you train them to move from a support role to a strategic business partner?
The biggest mindset shift I encourage is to stop seeing yourself as “just support” and start thinking of yourself as a true strategic partner. Someone who has a seat at the table and helps drive the business forward. It’s about being proactive rather than tactical or reactive. Instead of waiting for tasks, you’re anticipating needs, analyzing how your executive spends their time, and suggesting improvements that align with company goals.
When EAs adopt this mindset, they’re able to tie their work directly to business objectives, like increasing the percentage of strategic time for executives, improving OKR alignment, or reducing meeting overload. The KPIs might look like “hours of deep work protected,” “number of low-value meetings eliminated,” or “intake deflection rate” from better meeting intake forms. The ROI for the executive is massive: more focus, less burnout, and a clear sense that their top priorities are always front and center, thanks to their EA acting as a true strategic partner.
Your expertise includes Automation Uplift, where you integrate tools like Notion, Calendly, and AI scheduling to reduce executive admin burden by 40%. Can you describe a specific, measurable result you saw after implementing that automation, and what advice you have for EAs wanting to start integrating AI tools?
One of the most impactful projects I led was rolling out Notion for executive project tracking, Calendly for automated meeting scheduling, and Reclaim.ai AI to smartly block time for deep work and priorities. Before automation tools like these, my entire executive team was drowning in emails and status update meetings.
After rolling out these tools, within a few months, we tracked a 40% drop in admin workload for the Executive team. Using Notion to centralize project status, which eliminated a bunch of unnecessary meetings, Calendly took over booking logistics, drastically reducing back-and-forth emails. Reclaim.ai created smart buffers and blocked deep work time, which increased the executive’s focused hours by nearly 30%.
The strategic initiatives here included “Increase executive strategic focus time” and “Automate repetitive admin workflows.” Our KPIs were things such as “admin hours saved per month,” “number of meetings scheduled via automation,” and “percentage of calendar time dedicated to high-priority initiatives.” For OKRs, we set goals like “Reduce executive admin time by 40% in Q1” and “Increase deep work hours to 8 to 10 hours per week.” The ROI was clear: the executive had more bandwidth for core business strategy, made faster decisions, plus, the admin team got to focus on higher-impact work instead of chasing emails or calendar invites.
For EAs wanting to dive into AI and automation, my advice is to identify the most repetitive, time-consuming tasks first and tackle those with simple tools. Reclaim.ai is a great starting point, while Notion or similar platforms can organize projects and reduce meeting overload. Then, explore AI schedulers that can help protect your executive’s focus time without your constant intervention. Don’t forget to measure your impact with KPIs or time audits. It’s the best way to prove value and get buy-in for more automation. Start small, test, and soon you’ll be turning your executive’s calendar from chaos into a strategic asset!
As a highly trusted EA for discretion and executive readiness, can you share your philosophy on handling highly confidential information and preparing an executive for critical board meetings or investor relations discussions?
My philosophy is all about trust, discretion, and precision. As an EA, you become a gatekeeper, not just of information but of your executive’s time and focus. Preparing an executive for high-stakes board meetings or investor discussions is about being proactive and thorough. I work with the executive team to map out key objectives and provide clear, concise briefings well in advance, often using dashboards in Notion to track talking points, Q&A prep, and relevant metrics tied to OKRs outlined by not only your executive but the entire C-Suite. This enables everyone involved to walk in fully aligned and confident, knowing they have the right data and strategic context at their fingertips. It’s not just about managing logistics; it’s about ensuring they’re mentally and strategically ready to lead those critical conversations.
You created templated board briefings to ensure 100% on-time delivery and actionable insights. What details did you incorporate into the template itself to ensure the information was not only delivered promptly but was truly valuable and actionable for the board?
A briefing doc for BoD, QBRs, ELT, etc., are mandatory for all meetings my executive team is asked to attend. When I created my templated board briefing doc, my goal was to make sure every meeting was not just on time, but packed with clear & actionable insights. I included a structured summary right at the top, highlighting the meeting’s objectives, strategic initiatives, and any urgent decisions needed. Every section has a clear owner, so it is obvious who is responsible for each deliverable (even for follow-ups). I also built in KPIs, OKRs, and ROI analysis for each topic, so the executive team, the board or anyone attending the meeting could instantly see what was working, what needed attention, and how everything ties back to the goals outlined by the BoD, the executive team and individuals within the org. This format keeps the discussions focused and helps everyone walk in feeling confident and prepared.
Having a consistent framework means we never miss a detail and everyone involved has what they need to make fast, informed decisions. Plus, it makes collaborating with leaders across the org so much easier since everyone knows exactly what info was expected and by when.
Board of Directors Briefing Template:
1. Executive Summary
Meeting Objective(s):
Key Decisions Required:
Date & Owner:
2. Strategic Initiatives Update
Initiative Name:
Initiative Owner:
Progress (KPIs/OKRs):
Recent Wins & Challenges:
Next Steps & Timeline:
3. Financial Highlights
Key Metrics (Revenue, Expenses, Runway, etc.):
Variance from Plan:
ROI Analysis:
Action Items:
4. Operational Updates
Major Milestones Achieved:
Risks & Mitigations:
Owner(s):
5. Board Action Items & Requests
Actions Needed from Board:
Responsible Party:
Due Date:
6. Appendix
Supporting Data/Charts:
Links to Detailed Reports (Notion, Google Drive, etc.):
Contact for Questions:
Strategic Initiatives: List Each with Owner
KPIs / OKRs: List Key Metrics & Targets
ROI Summary: Short Analysis per Initiative
Deliverables: Who, What, When
This structure keeps everyone aligned, deadlines clear, and ensures every board briefing is both timely and genuinely valuable.
With an extensive background in workflow optimization across high-growth technology companies, can you walk us through a cross-functional workflow you identified as problematic and the systematic approach you used to fix and optimize it?
Despite having talented teams, cross-functional collaboration often breaks down as the company scales. At one startup I worked at, the executive team noticed repeated issues with product launches stalling across the Product, Marketing, and Customer Success divisions. Updates were scattered between emails and Slack, accountability was non-existent, and deadlines were consistently missed. With my background in workflow optimization, I was asked to help find a solution for this specific issue. Working closely with the leadership team, here’s the approach I took:
Step 1: Diagnose the Workflow Bottleneck
Mapped the entire product launch process from ideation to post-launch support, interviewing stakeholders from each team to pinpoint handoff issues and recurring communication gaps.
Identified root causes: Siloed communications, lack of a single source of truth, and unclear ownership of deliverables.
Step 2: Design a Systematic Solution
Centralized project management: Introduced Asana as the unified platform for all launch-related tasks, timelines, owners, and dependencies.
Built a cross-functional launch template: Every deliverable, stage, and owner was mapped out, so expectations were crystal clear.
Created a real-time Notion dashboard: This acted as our central hub for documentation, updates, and executive visibility.
Step 3: Automate & Enhance Accountability
Automated task triggers: For example, when the product hit “Ready for Marketing” in Asana, it auto-notified the marketing team, spun up campaign prep tasks, and updated Notion—removing lag and manual follow-ups.
Approval checklists: Key milestones included automated approval steps, drastically reducing errors and last-minute surprises.
Step 4: Establish Clear Cadence and Metrics
Instituted bi-weekly cross-functional syncs: Focused not just on status updates but on proactively surfacing roadblocks and reallocating resources as needed.
Defined KPIs for success:
Average days from ideation to launch
Percentage of on-time deliverables
Cross-functional satisfaction scores
Reduction in post-launch errors
Step 5: Track Impact and Iterate
Continuous feedback loop: Used survey data and performance metrics to fine-tune the process.
Executive reporting: Leveraged Google Sheets to provide transparent, real-time reporting on OKRs and KPIs for leadership.
Set ambitious OKRs: “Reduce launch cycle time by 30% in Q3,” later evolving to “achieve 90% on-time launch deliverables by Q4.”
Results & ROI
Launch timelines improved by 35%, with far fewer last-minute fire drills and a smoother handoff between teams.
Team satisfaction scores rose, as roles and timelines were clear and everyone had visibility into the process.
Executives gained real-time insight into launch status and ROI, enabling more agile decision-making and resource allocation.
Faster time-to-market and higher campaign success rates became the new normal.
By taking a strategic and tech-enabled approach, an executive assistant can transform a broken process into a transparent and automated process.
You have a proven background executing a broad range of events and projects (manage, plan and execute) all within the required budget and time frame. Can you describe a high-stakes corporate event you managed, detailing how you leveraged project management tools to keep all stakeholders aligned and on budget?
One of the most high-stakes corporate events I managed was a global Presidents Club sales event, also known as the Sales Excellence Club, which I developed and executed from start to finish. This event was truly a highlight, bringing together 150 top-performing attendees and their significant others from around the world with a $500,000 budget.
The agenda was carefully curated to balance business and leisure which included meetings, receptions, themed dinners, leisure time including various activities, and live performances. The goal was to create an environment that fostered strong networking opportunities while also giving attendees a chance to relax and recharge.
To keep everything on track, I leveraged several project management tools to ensure all stakeholders were aligned and the event stayed within budget. For scheduling and task management, I created a task tracking form to break down the event into phases and assign responsibilities (if required) clearly across teams and individual contributors. This helped me monitor progress in real-time and quickly address any issues.
For budget tracking, I maintained a detailed spreadsheet integrated with our project timeline, which let me forecast expenses and adjust allocations proactively. Regular check-ins and status reports kept our leadership team and vendors in sync, ensuring transparency and smooth communication.
A basic task tracker will give you a clear overview of progress and help keep all stakeholders aligned and the budget in check. The task tracker will be added as a link at the end of the interview.
Overall, the combination of detailed planning, leveraging technology, and proactive stakeholder engagement allowed me to deliver a memorable, seamless event that met all objectives within the required timeframe and budget. It was incredibly rewarding to see attendees enjoy the perfect blend of business excellence and island hospitality
You've authored and published over 25 articles on EA / CoS best practices, productivity, and career development. How has having this recognized online presence and sharing your knowledge professionally enhanced your effectiveness in your day-to-day role?
From a personal perspective, authorship and active engagement in the EA / CoS community have been transformative for my career. Publishing over 25 articles on best practices, productivity, and career development wasn’t just about sharing tips, it was about opening up a dialogue within the global network of fellow professionals and executives. My recognized online presence has been a catalyst for building relationships and driving both personal and organizational growth. Most importantly, sharing knowledge online has deepened my sense of purpose. Seeing my work help others grow in their careers, or inspire new approaches within their organizations, is deeply rewarding. It keeps me learning, evolving, and energized to bring fresh ideas into my own role every day.
Each outline has sparked new conversations and connections on LinkedIn and these relationships have become incredible resources. I’ve had the privilege to connect with other EAs, Chief of Staff and C-Suite executives from newly formed startups to Fortune 100 companies across the globe. I regularly exchange insights on workflow optimization, strategic planning, and executive partnership. I’ve been invited to co-host webinars and participate in expert panels, further expanding my network and perspective. When I encounter a new challenge in my day-to-day work, I have a trusted circle of peers to brainstorm solutions with or benchmark best practices.
The credibility that comes from a recognized online presence has also strengthened my internal influence. Executives and teams see me not just as an administrative partner, but as a thought leader and strategic resource. Each article and especially my book, The Executive Assistant’s Guide to Strategic Initiatives, have helped position me as someone who brings more than operational support, I bring a strategic, big-picture mindset to the table. This trust has led to more meaningful involvement in high-impact projects and strategic initiatives, where my perspective is sought out early and often. It’s a key reason why I’m able to deliver such impactful results and why I’m passionate about helping others in our profession do the same.
Your software skills list is incredibly comprehensive, covering both legacy and modern tools. How do you approach the continuous process of lifelong learning and deciding which new applications or platforms are worth investing your time in mastering?
Lifelong learning is an intentional, strategic process for me. This approach ensures I’m not just keeping up, but constantly elevating the level of support and impact I deliver as an EA / CoS. And it’s one of the reasons I’m passionate about helping others in our field embrace new tools and continuous learning as keys to both personal and professional success.
For me, staying current with both legacy and modern software isn’t just about technical proficiency, it’s about bringing strategic value to my job, my executive team I support as well as the organizations I work for. Here’s how I approach it, both personally and professionally:
Curiosity Driven Learning: I’m naturally curious, and I make it a point to stay plugged into EA / CoS forums, LinkedIn groups, and newsletters. These channels are goldmines for learning about emerging tools. Through the platforms I am active on and my connections, I often hear first-hand which apps, platforms and software are transforming workflows or addressing pain points.
Needs First: With so many new apps, software or platforms launching every day, I’m selective. I start by mapping tools to business needs. If a tool can solve a recurring challenge, automate a manual process, or enhance collaboration, it grabs my attention. For example, when I noticed cross-team project tracking was a bottleneck, I invested time mastering Asana and Notion, which ultimately transformed our workflow.
Test & Assess: Before fully investing in a new app, software or platform, I’ll test it out on a small project. This lets me assess and evaluate the product based actual impact. I also leverage my network to get quick demos or insights, which helps me evaluate whether a tool is worth a deeper dive.
Knowledge Sharing: My LinkedIn articles and my book, The Executive Assistant’s Guide to Strategic Initiatives, have actually fueled my learning process. Writing and sharing my findings push me to stay ahead of the curve, so I’m always experimenting with new apps, software and platforms. The feedback and comments from my network often point me toward tools or features I might have missed.
Commitment to Continuous Growth: I carve out regular “learning time” each month, whether it’s a webinar on AI productivity tools, a LinkedIn Learning course, or just exploring new app updates. This habit not only keeps my skills sharp but also inspires new ways to streamline processes and deliver value.
Finally, Trey, given your focus on maximizing efficiency and strategic output, what is your personal approach to self-care? What methods do you rely on to manage your own time and energy to prevent burnout and maintain your high level of performance?
I’ve learned over the years that self-care isn’t a luxury, it’s essential to sustaining high performance and preventing burnout. What has truly reinforced this for me personally is my experience with a triple negative breast cancer diagnosis as well as the sudden death of my mom. Facing such a serious health challenge underscored how crucial it is to prioritize health and well-being, not just for myself but for the people and teams who rely on me. It’s a powerful reminder that maintaining physical and mental wellness is foundational to being able to deliver at a high level consistently. Here’s how I personally approach managing my time and energy to stay sharp and energized:
Intentional Time Management: I’m very intentional about setting clear boundaries between work and personal time. Whether it’s turning off notifications after hours or blocking out focus time during the day, I protect my energy to deliver my best. I use calendar tools not just to schedule meetings but to reserve “deep work” and “recharge” periods. This structure helps me avoid multitasking overload and maintain clarity on priorities.
Breaks and Reset Rituals: Throughout the day, I build in short mindful pauses, whether a quick stretch, breathing exercises, or a moment away from screens. These micro-breaks reset focus and reduce stress, enabling sustained productivity without fatigue.
Hobbies that Recharge: Outside of work, I’m passionate about landscape photography. Getting out into nature with my camera is not only a creative outlet but a powerful way to decompress and reconnect. Exploring natural environments sharpens my attention to detail and patience, qualities that translate back into my professional role. It also reminds me to appreciate the bigger picture, which is invaluable when managing complex, strategic initiatives.
Physical Wellness: Regular exercise, nutritious meals, and adequate sleep are pillars of my self-care routine. After my diagnosis, these habits became non-negotiable. When my body feels strong and rested, my mental stamina and decision-making improve dramatically.
Leverage Strategic Delegation & Tools: I rely on delegation and technology to manage routine tasks, freeing up time for high-impact work and self-care. This also models healthy workload management for my teams and executives.
Balancing high performance with self-care is a dynamic, ongoing process that requires discipline, creativity, and self-compassion. My journey with triple negative breast cancer has made me even more committed to protecting my health and well-being as the foundation for professional success. By nurturing my passions like landscape photography, staying mindful of my energy, and honoring my body’s needs, I’m able to consistently bring my best self to the strategic initiatives and executive partnerships I support.
__________________________________________________________________
With over thirty years of experience as an Senior Executive Assistant, and twenty-five of those years spent also serving as a hybrid Senior Executive Assistant and Chief of Staff, Trey’s professional journey is a testament to the power of commitment, resilience, and the art of balancing multiple roles in the fast-paced world of Silicon Valley’s technology sector.
Trey’s dual role as both Senior Executive Assistant and Chief of Staff is a rare combination—one that requires a unique blend of skills. As an Senior Executive Assistant, she mastered the art of managing schedules, projects, and communications with precision and grace. As a Chief of Staff, she became a trusted advisor and strategic partner to executives, seamlessly bridging the gap between visionary leadership and practical execution. Whether orchestrating complex meetings, managing confidential initiatives, or handling sensitive negotiations, Trey’s steady presence has always been an anchor in the midst of chaos.
Today, Trey Scarpa shares her insights, lessons, and stories with the next generation of administrative professionals and leaders. Her hope is that by sharing her journey, she can encourage others to embrace the challenges and opportunities that come with supporting those who shape the future. For Trey, being an Senior Executive Assistant and Chief of Staff is more than a career—it is a calling, and a privilege she is honored to fulfill.
Connect with Trey on LinkedIn: https://www.linkedin.com/in/treyscarpa/
Comments