Hire the Right Executive Assistant — and Make Sure it Actually Works
Expert guidance through your EA hire and a structured 90-day launch — so the right candidate becomes the right partnership.
Whether you're about to hire your next executive assistant or trying to make the one you just hired actually work — most EA relationships fail in the first 90 days. Not because the candidate was wrong, but because no one defined the role, screened for actual fit, or built the working relationship before the honeymoon ended.
You don't have time to figure out how to hire an executive assistant on your own — or to diagnose why your current one isn't working out. We've spent 18 years inside executive offices. We know what to look for when hiring an EA, what breaks in the first 90 days, and how to fix it. We advise the hire and coach the launch, so your EA is operational in 30 days and indispensable in 90.
How We Work With You
Phase 1 — Define the Role (Weeks 1–2)
Before we look at a single candidate, we figure out what you actually need. Most founders hiring an EA — or partners hiring a chief of staff — hire the role they think they need, not the one their day-to-day demands. We map your workload, identify what only you can do, and build a role description, scorecard, and screening criteria around protecting that work. You leave Phase 1 with a hiring profile that reflects how you actually lead.
Phase 2 — Find and Screen the Right Candidate (Weeks 2–6)
You'll run the posting and initial screening — that's faster and cheaper when it's coming from your team. We make sure you're set up to do it well. Before you post, we help you shape the job description, define screening criteria, and build the interview structure so you're filtering for the right things from the start.
Once you have your top candidates, we step back in. We assess your finalists through two in-depth profile assessments built specifically for EA fit, sit in on or review final-round interviews, and give you a clear read on each candidate — strengths, risks, and how they'd actually perform in your role, not a generic one. You make the call. You make it with expert input, not gut feel.
Phase 3 — Coach the Partnership Into Place (First 90 Days Post-Hire)
The hire is the start, not the finish. The first 90 days with a new executive assistant determine whether the partnership produces real leverage or quietly stalls. Six executive assistant integration coaching sessions across that window — with you, with them, and together — to install communication rhythms, decision authority, and real delegation habits. By day 90, you have a partnership that runs without your constant supervision.
What This Costs You If You Skip It
A bad EA hire isn't a $90K salary mistake. It's six months of lost executive time, a redo search, severance, and the cognitive tax of managing a role that should be reducing your load. Most founders we work with have been through this once already. They don't want to do it again.
What You Get
For You:
Optimized Leverage
A hire you're confident in.
An EA who's productive in 30 days.
A delegation system that holds.
10+ hours back per week, on average, by day 90.
For Your Future EA:
A Proven Process for Support Success
A clear role, defined success metrics, and a coach in their corner during the first 90 days as a new executive assistant — the hardest stretch.
They show up proactive instead of reactive.
Engagement Options
We work with leaders at two entry points, depending on where you are in the process:
Full Partnership Engagement: For leaders hiring an EA in the next 90 days.
Integration Coaching Only: For leaders who've already hired (or are about to) and need to make the partnership work.
Not sure which fits? We can explore that together on a strategy call.
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For leaders hiring an EA in the next 90 days. Includes role design, search advisory, finalist assessments, and the full 90-day integration coaching.
Best for: You haven't hired yet, or you're about to start the search.
Investment: starting at $6,500
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For leaders who've already hired (or are about to) and need to make the partnership work. Six executive assistant integration coaching sessions across the first 90 days — covering communication rhythm, decision authority, and delegation habits with you, your EA, and together.
Best for: Your new executive assistant isn't working out the way you hoped, or you want to onboard them right from day one.
Investment: starting at $3,000
Real-World Outcomes:
"I got 10 hours back — and I finally stopped second-guessing my EA."
Founder, professional services firm: Hired the right EA, wrong structure. Her new executive assistant wasn't working out — until four coaching sessions in, when communication rhythm and delegation system locked.
"We bypassed the six-month learning curve entirely."
Managing partner, high-stakes Chief of Staff/EA hybrid hire: We shaped the search criteria, assessed the finalists, and coached the launch.
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The first 90 days are the highest-leverage window — and the most commonly wasted. A successful onboarding requires three things most leaders skip: a clear role definition with success metrics, a defined communication rhythm (not ad-hoc check-ins), and explicit decision authority so your EA knows what they can move on without asking. Our integration coaching installs all three across the first 90 days.
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Beyond the obvious (organization, communication, discretion), the real differentiator is fit with your leadership style — how you make decisions, how you process information, and how much ambiguity you tolerate. A strong EA for a fast-moving founder will struggle for a methodical managing partner, and vice versa. We use two profile assessments to screen finalists for that specific dimension.
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Usually fix it, if you're inside the first 6 months. Most EA relationships that fail aren't candidate problems — they're structure problems. No clear priorities, no delegation system, no feedback loop. Before you start a second search (which costs you another 3–6 months), it's worth diagnosing whether the issue is fit or framework. Our Integration Coaching engagement is built for exactly this.
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With structure: 30 days to operational, 90 days to indispensable. Without structure: 6+ months, if it works at all. The variable isn't the candidate — it's whether the leader has built the scaffolding for delegation before day one.
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Different roles, often confused. An EA protects your time and runs your operating rhythm. A chief of staff owns initiatives, manages cross-functional projects, and operates with strategic authority. Some hires are hybrids — and those are the hardest to get right because the role definition usually isn't. Phase 1 of our engagement clarifies which one you actually need before you post anything.
Frequently Asked Questions
Ready to Get This Hire Right?
Book a 30-minute strategy call. We'll walk through your current situation, where the last hire broke down (or why you haven't hired yet), and whether this is the right fit. No pitch — just a clear read on whether we can help.