The Roles Nobody Writes a Hiring Plan For (Until Something Breaks)
Most companies have a plan for hiring engineers. They have a plan for hiring salespeople. Ask about the plan for hiring the executive assistant who keeps the CEO’s week from collapsing, and you’ll usually get a shrug and a job board posting written in forty minutes.
Then the person leaves. And for the next six weeks, three directors are scheduling their own meetings, the board deck is late, and nobody can find the vendor contract from last March.
That’s the gap. Executive support, office administration, project coordination, and chief of staff roles are the connective tissue of an organization, and they’re consistently the roles companies hire for with the least structure.
At Career Image Solutions, we’ve supported more than 100 businesses in Baltimore and the surrounding counties — Howard, Anne Arundel, Baltimore County, Carroll, and Harford — and the pattern holds almost everywhere. Here’s what we’ve learned about getting these hires right.
Why these roles are harder to fill than they look
There’s a persistent belief that administrative and support hiring is easy because the résumés look similar. Ten years of calendar management, some travel booking, a few tools listed at the bottom. Pick one.
But the résumés looking similar is exactly the problem. The skills that separate a good executive assistant from a great one barely show up on paper. Judgment. Knowing which of the day’s four fires matters. The ability to say “I don’t think you should take that meeting” to someone who outranks you by four levels and be right.
You can’t screen for that with a keyword filter.
The same is true across the board:
An office administrator at a 40-person company is doing something fundamentally different from one at a 400-person company. The first is improvising systems. The second is running them. Hire the wrong profile and you get someone either paralyzed by ambiguity or bored by structure.
A project coordinator lives or dies on their ability to chase people without being annoying. That’s a social skill, not a technical one, and no certification measures it.
A chief of staff is the hardest of the four, because the role means something different at every single company. At one, it’s a strategic partner running cross-functional initiatives. At another, it’s an elevated executive assistant with a better title. Both are legitimate. But if the hiring manager wants the first and the candidate expects the second, you’ve got a resignation in eight months.
Start by writing down what the person will do
This sounds obvious. It is almost never done.
Before you look at a single candidate, write out the ten things this person will spend the most time on in their first six months. Not responsibilities — tasks. “Manage the executive’s calendar” is a responsibility. “Own scheduling for a leader with 35 external meetings a month across four time zones, including rescheduling under pressure” is a task, and it tells you something about who you need.
Two things happen when you do this. First, you find out whether you’re describing one job or two, which is more common than you’d think. Second, you give your recruiter something to work with beyond a title.
We ask clients for this every time. The conversations where someone has genuinely thought it through move roughly twice as fast as the ones where they haven’t.
Executive assistant vs. chief of staff: get this settled early
This is the single most common source of confusion in the roles we recruit for, so it’s worth being direct about it.
An executive assistant makes an individual leader more effective. The work is proximate to that person — their time, their inbox, their travel, their preparation, their follow-through. The best ones develop an almost uncanny read on their executive and start making decisions on their behalf.
A chief of staff makes an organization more effective through the leader. The work extends outward — running the operating cadence, driving initiatives that cross departments, sitting in rooms as the executive’s proxy, and generally holding the strategic threads that nobody else owns.
There’s overlap. Plenty of people do both. But the hiring bar, the compensation, the candidate pool, and the interview process are meaningfully different, and pretending otherwise wastes everyone’s time. If you’re not sure which one you need, that’s a signal worth taking seriously — it usually means the role hasn’t been defined yet.
Interview for judgment, not for tools
Software proficiency is table stakes and easy to teach. A strong candidate will learn your project management platform in a week.
What you want to test is how they think. Some questions that consistently surface something real:
“Walk me through a time you disagreed with your executive. What did you do?” — You’re listening for whether they have a spine and whether they know how to use it diplomatically.
“Your executive has three conflicting priorities and time for one. How do you help?” — The weak answer escalates everything back up. The strong answer shows a framework for triage.
“Tell me about something that fell through the cracks on your watch.” — Anyone who says nothing ever has is either inexperienced or not being candid.
We also push clients toward a paid work sample where it’s appropriate. A short scheduling puzzle, a real (anonymized) email thread to triage, a one-page briefing document. Thirty minutes of actual work reveals more than a third interview.
Move faster than you think you need to
The strongest candidates in this space are rarely on the market for long. They’re usually employed, quietly looking, and talking to two or three organizations at once.
If your process involves five rounds spread across six weeks, you’re going to lose your top choice with some regularity. Not because the process was bad, but because someone else finished first.
Compress it. Two or three well-designed conversations, decision-makers involved early, references done in parallel rather than at the end. A tight process also signals something to the candidate about how your company operates, which matters more than most hiring managers realize.
Where a recruiting partner earns its keep
Not every role need outside help. If you’re hiring an office administrator in a market where you have a strong employer brand and a decent applicant flow, you may be fine on your own.
Where a specialist partner makes a real difference is when the role is senior, confidential, or unusually specific. Chief of staff searches almost always fall into that category. So do executive support roles for founders and C-suite leaders, where fit is idiosyncratic and a bad hire is expensive in ways that go well beyond salary.
The value isn’t a database of résumés. It’s the ability to have a real conversation with a candidate who isn’t looking, to assess judgment rather than keywords, and to tell a client honestly when the role they’ve described isn’t the role they need.
Local knowledge matters more here than people expect, too. The Baltimore market has its own shape — a heavy concentration of hospital systems, universities, and nonprofits, each with hiring norms that look nothing like the private sector’s; clearance requirements that quietly narrow a pool for anything near Fort Meade; and commute realities that make a downtown Baltimore office a hard sell for someone in Columbia or Bel Air. After 100+ searches across these counties, we’ve learned where the real candidates are and what moves them.
The short version
These roles are leverage. A great executive assistant gives a leader back ten hours a week. A great chief of staff makes an entire leadership team run better. A great project coordinator is the reason things ship on time.
Hire for them like it matters, because it does.
Career Image Solutions has helped over 100 businesses in Baltimore and the surrounding counties hire for executive support, office administration, project coordination, and chief of staff roles. If you’re working through a search right now, we’re happy to talk it through—even if you’re not ready to engage anyone yet. Contact Us
