How to Elevate through Hospitality-Mindset
In the world of high‐level executive support, being “good” isn’t enough. The landscape is shifting: EAs are not simply gate-keepers or calendar managers—they are strategic partners, operators of trust, orchestrators of flawless experience. We believe an EA who blends deep operational precision with boutique-style service becomes indispensable.
To frame how you can become that extra-ordinary EA, we draw on two powerful books: Unreasonable Hospitality, which teaches how to exceed expectations by thinking like a host of human experience; and Bet on Yourself, which provides the career playbook for stepping into higher agency and ownership. Together these offer a dual track: how to deliver exceptional service and how to build the EA career engine.
1. Hospitality as an EA Superpower
From Unreasonable Hospitality we learn that true service is about the unexpected memorable moment, not just meeting spec. Guidara writes that hospitality isn't about luxury—it’s about being more thoughtful.
For an EA, this translates into:
Knowing the executive’s patterns, preferences, and rhythms so you can anticipate needs before they’re voiced (not just “he has a meeting at 9am” but “he’ll want his low-sugar snack ready en route, because his 8am call ran over”).
Building into your work little touches—whether it’s designing the agenda to honour both efficiency and rest, or briefing materials that go beyond bullets to include what matters for the exec that day.
Thinking of your stakeholders (internally and externally) as guests in your domain. Treat vendors, team members, clients with a hospitality mindset: they should walk away feeling taken care of, seen, valued.
Sweating the small stuff. Guidara says: “Sweat the small stuff… when you care about little details you infuse care into everything.”
Practical takeaways for EAs:
Create a pre-meeting “experience note” for major exec engagements: include what the executive eats, how they like the room set, plus one human element (e.g., “Note: they said they loved the view of the lake; reserve that spot if available”).
Build a “guest journey” map for key clients or stakeholders your executive interacts with: from arrival to follow-through, ensure touchpoints are seamless.
Use post-meeting pulses: after major meetings, send a brief gratitude/thought-forward note not just to the exec, but to the team or guest, reinforcing the boutique service feel.
2. Own Your Career: The EA as Moonshot Operator
From Ann Hiatt’s Bet on Yourself, we extract the mindset and habit architecture for career growth—and this is critical for EAs who want to move from tactical to strategic. Hiatt writes that we must recognize, own and implement breakthrough opportunities.
For the EA role, this means:
Recognize your unique value: beyond scheduling, you are orchestrating clarity, trust, momentum. Define that value.
Own your professional identity: speak up about it. Position yourself as the executive’s “right hand”, the engine behind seamless leadership.
Implement upward opportunities: build habits that will not only support today’s role, but set the foundation for tomorrow (whether that’s Chief of Staff, Head of Admin, Strategic Partner).
Practical takeaways for EAs:
Create a “60-90-120 day” EA career plan: what operations/process improvement initiatives will you lead, what skills (e.g., data-insight, vendor negotiation, project management) will you build, what visibility will you gain?
Develop a “value-dashboard” for your role: metrics of your impact (e.g., meeting no-shows reduced by X%, vendor budgets saved, exec prep time reduced) so you can speak in business terms.
Seek micro-leadership roles: lead a cross-functional project, co-design an executive retreat, own an internal admin-community initiative. These build your strategic muscle.
3. The Intersection: Service + Strategic Engine
When you merge the “hospitality mindset” of Guidara with the “career engine” of Hiatt, you get an EA who is both flawlessly service-oriented and strategically elevated.
Here’s how that plays out in your day-to-day:
When preparing the executive’s board meeting: you don’t just send agenda + slides; you design the attendee experience (hospitality), and you build the strategic narrative (career engine) so the exec is freed to be their best.
When selecting and working with vendors for the executive’s travel: you apply a hospitality mindset (create an experience) and also own the impact (optimize cost, enhance value, show executive gain).
When onboarding a new direct report under the executive: you treat the new hire as a guest of the executive’s domain (hospitality) and design the onboarding as a leadership acceleration (career engine) for both you and the new hire.
4. Five Habits to Make It Real
Weekly Micro-Moments Planning: At the start of each week, review your executive’s schedule and stakeholders. Ask: “What experience are we creating?” and “What strategic value can I unlock?”
After-Action Ritual: After major meetings or events, write a “what worked/wow-moment/opportunity” note. Use it to iterate and improve.
Visibility Map: Maintain a map of key stakeholders (internal & external) and plan one ‘wow’ touch per stakeholder per quarter (hospitality) plus one strategic insight or value you can offer (career engine).
Skill-Sprints for Growth: Choose a monthly skill to develop (e.g., advanced Excel analytics, project-management certification, AI-tool fluency). This aligns with Hiatt’s career-acceleration framework.
Hospitality-By-Design Mindset: Before any interaction—meeting, email, trip ask—pause and ask: “How can this feel thoughtful? How can I elevate this?” In the words of Guidara: “No matter what business you’re in, you can make the choice to be in the hospitality industry.” Unreasonable Hospitality
5. Why This Matters for Pennyworth Projects Clients
At Pennyworth Projects, your clients—high-level executives and prominent individuals—expect a seamless, premium level of support. They don’t just want “things done,” they want the experience to reflect the calibre of their leadership, reputation, and personal brand. You as the EA are the curator of that experience.
By combining hospitality thinking with strategic career orientation, you deliver something rare: you become an architect of executive excellence. You’re not just managing chaos; you’re enhancing the brand, optimizing operations, safeguarding reputation, and creating space for the executive to lead.
Great EAs are operationally excellent. Exceptional EAs live in the intersection of flawless service and strategic upward momentum. By borrowing the lessons from Unreasonable Hospitality—thinking like a host, caring deeply about human experience—and from Bet on Yourself—building your own professional trajectory—you transcend the “support role” mold and become a trusted powerhouse.
For you at Pennyworth Projects: commit to being unflappable, boutique-brilliant, deeply personal—and strategically aligned. The next level of EA excellence is yours.