A while back, I was advising a founder who, on paper, had everything dialed in: strong traction, sharp team, clear roadmap. But every working session felt like a fire drill. He was constantly behind, buried in Slack threads and email chains. Strategic planning turned reactive. Critical hires kept stalling, not because he didn't care, but because he was overwhelmed.
I suggested bringing in an Executive Assistant. At first, he brushed it off, worried it was too early or that onboarding someone would just create more work. But the symptoms were clear, and I'd seen how transformative the right EA could be. So we helped him scope the role and run the search.
Two weeks after onboarding, the difference was night and day. Meetings were prepped, decisions moved faster, and the founder himself was sharper (less reactive, more present, more effective). It wasn't just that things were getting done. It was that the business could finally move forward at the pace it needed.
That experience cemented a truth I've seen play out again and again: a great EA isn't a luxury; they're a lever.
Here's what that looks like in practice and how to get it right.
The Real ROI of an Executive Assistant
If I had to boil it down to one line, it's this: a great Executive Assistant gives leaders back their most valuable asset: time.
That's not just about calendar management. It's about mental space, decision-making capacity, and strategic availability. When you've got a smart, proactive EA filtering out noise, managing details, and keeping communication flowing, the ripple effect is huge. Founders spend less time firefighting and more time building. Executives stop playing email tag and start closing meaningful deals.
I once spoke to a COO who brought on an EA right as their company hit Series B. He told me, "Within a month, I wasn't just more productive, I was more present. I had time to coach my team, talk to customers, and actually think ahead for once."
The ROI of an EA shows up in meetings that don't get rescheduled, decisions that don't get delayed, and leaders who stay in the driver's seat.
So what exactly does that look like in practice? Let's break it down.
Why Every Growth-Minded Business Needs an EA
When you're scaling a business, time isn't just scarce; it's expensive. And yet, research from Harvard Business Review found that executives spend nearly 23 hours a week in meetings. Add in inbox management, admin coordination, travel logistics, and follow-ups, and it's easy to see how leadership time gets consumed by tasks that don't require leadership.
That's where an Executive Assistant comes in – not as a helper, but as a strategic operational layer. A good EA is a force multiplier. A great one is a firewall, a fixer, and a trusted right hand. And in a post-remote world, the value of that role is only growing.
Remote and hybrid work has created more complexity in calendars, communication, and cross-functional workflows. What used to be solved by dropping by someone's desk now takes a Slack thread, two emails, and a 30-minute Zoom call. Without someone to orchestrate that complexity, executives lose leverage. And businesses lose momentum.
Another founder I know delayed hiring an EA until his team crossed 40 people. Once he finally did, he told me he'd been making a $200,000 mistake. A result of his personal inefficiency had stalled decisions, delayed hires, and drained his leadership energy for months.
In short, it's not just about getting help; it's about protecting your time, your clarity, and your leadership effectiveness when your business needs it most.
What an Executive Assistant Actually Does Day to Day
The biggest misconception about Executive Assistants is that they're just calendar and travel coordinators. In reality, a high-performing EA functions like an operations partner embedded directly into the executive's workflow. Their day-to-day impact touches nearly every corner of the business.
Mastering the Calendar and Inbox
This is the most visible part of the job, but also one of the most strategic. A great EA doesn't just schedule meetings; they defend time, optimize the flow of a leader's week, and ensure the right conversations happen at the right cadence. The same applies to email; they triage, prioritize, draft responses, and escalate only what truly matters.
Preparing Leaders for High-Stakes Conversations
EAs often manage briefing docs, prep materials, and follow-up communications for key meetings. Whether it's a board call or a client pitch, they ensure leaders show up prepared and stay focused on outcomes, not logistics.
Coordinating Projects Across Teams
Think of them as the connective tissue between executive decisions and execution. EAs track action items, chase down updates, and help close the loop on cross-functional projects that might otherwise drift.
Managing Executive Visibility and Communication
From ghostwriting updates to liaising with investors, clients, or internal stakeholders, many EAs handle sensitive communications. This requires sound judgment, impeccable discretion, and a sharp understanding of voice and tone.
Providing Strategic Support Behind the Scenes
At the higher end, some EAs operate in a Chief of Staff–adjacent capacity, helping with research, handling special projects, or supporting OKR tracking and business planning.
One of the best EAs I've seen operated with the rhythm and trust of a business partner. She anticipated her exec's needs two steps ahead, protected his schedule like a hawk, and ran point on internal follow-through with surgical precision.
How to Set Your Executive Assistant Up for Success
Hiring a great Executive Assistant is only half the equation. The other half? Giving them the clarity, structure, and support they need to actually thrive in the role. These are the key pillars:
Clarify the Role Early and Often
One of the most common reasons EA relationships fail is scope creep, or worse, scope confusion. Is your EA managing your calendar, or are they also expected to handle internal operations? Are they booking travel, or leading prep for investor meetings?
Define what success looks like from day one. Create a clear role scorecard, walk through responsibilities together, and revisit expectations regularly. Ambiguity breeds underperformance.
Prioritize Work Style and Communication Fit
A resume can show experience, but it won't tell you how someone responds to pressure, communicates over Slack, or adapts to your quirks. Chemistry and compatibility matter just as much as skill.
I once worked with a CEO who had churned through two EAs in a year. Both competent, but neither able to match his breakneck pace or love for verbal communication. The third was a former agency EA who thrived in chaos and used voice notes to keep things moving. Total game-changer.
Build for Remote-Ready Support
Many Executive Assistants work remotely, especially in scaling or distributed teams. That flexibility works, but it raises the bar on systems and communication. Document your tools, workflows, and decision-making norms. Use async updates and shared dashboards. Grant appropriate access to calendars, inboxes, and files (with clear boundaries).
Remote EAs can be just as effective as in-person support, but only if you build the infrastructure intentionally.
Invest in Compensation and Career Development
Treat this like the high-leverage hire it is. Pay competitively. Offer feedback and growth. Some EAs go on to become Chiefs of Staff or ops leads. Others stay in the EA role long-term, but either way, retention comes down to respect, challenge, and career visibility.
Common Pitfalls When Hiring EAs And How to Avoid Them
Even the most experienced founders and execs can stumble when integrating an Executive Assistant into their workflow. These are the most common failure points and how to sidestep them.
Inadequate Onboarding and Training
Assuming your EA will "figure it out" is one of the quickest ways to derail the hire. Even highly seasoned EAs need context: your preferences, your priorities, your style of thinking. A structured onboarding process (complete with weekly check-ins, shadowing sessions, and documentation of systems) goes a long way.
Over-Managing or Under-Trusting
The point of hiring an EA is leverage. If you're still triple-checking their calendar invites or rewriting every draft email, you haven't actually created leverage; you've created duplication.
Start small if needed, but start delegating fully. Create a "decision budget": a clear list of tasks and scenarios where your EA can act without approval. Build trust with clear boundaries, not constant oversight.
Ambiguity Around Access and Boundaries
Do they have full access to your inbox? Can they reschedule board calls? Are they looped into hiring decisions? These are decisions that should be made explicitly, not discovered by accident.
Burnout from Poorly Scoped Roles
Executive Assistants are often highly capable generalists. That's a blessing and a risk, because it's easy to start piling on extra projects, team support, or company-wide coordination tasks without re-scoping the role or adjusting expectations.
Keep an eye on bandwidth. If your EA starts becoming your de facto ops lead, it may be time to rethink the structure or hire additional support.
Executive Support That Moves the Needle
An Executive Assistant isn't just a logistical asset; they're an operational amplifier. They create space for strategic thinking, protect leadership focus, and drive momentum across teams. When scoped right and matched well, they don't just make your life easier; they make your company sharper, faster, and more resilient.
We've covered what EAs actually do, how to set them up for success, and where teams most often go wrong. The takeaway is simple: this is a role worth investing in. Early, seriously, and with clarity about the kind of impact you want it to have.
A Strategic Hire That Pays for Itself
Hiring an Executive Assistant isn't about finding someone to "take things off your plate." It's about finding the right person to manage the right things, in a way that matches your working style, your business needs, and your long-term goals.
That's where a partner like Somewhere can make all the difference.
Somewhere specializes in helping startups and growth-stage companies find executive support talent that clicks with your leadership rhythm. Whether you need someone remote, hybrid, full-time, or fractional, Somewhere handles the sourcing, vetting, and placement process with a level of care most internal teams can't match.
If you're serious about hiring an EA who will drive real leverage, reach out via the contact form below. The right assistant can change how you lead. Somewhere can help you find them.
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