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The Gaps Inbetween: What Actually Matters When Hiring Executive Assistants or Chiefs of Staff

By James Ketteringham · Founder

2 September 2026

Any strong EA or Chief of Staff interviews well. That is the job. The real signal in a search sits between the interviews: how a candidate communicates, flexes, negotiates, and treats every person in the process. Here is what the gaps inbetween reveal, and how a rigorous search captures it.

What matters most in an interview process for roles that sit in close proximity to a leader?

The interviews themselves matter, clearly. But any strong Executive Assistant or Chief of Staff should hold their own in a high-stakes conversation with a senior leader. That is the job. If they cannot, the process ends there anyway.

The interview alone therefore tells you less than most hiring processes assume. The stronger signal sits in the gaps inbetween.

Why conventional hiring misses it

Most hiring processes are built around scheduled contact: a screening call, two or three interviews, perhaps a final panel. Everything between those fixtures is treated as administration. Someone books the slots, chases the confirmations, and reports upward only whether the candidate showed up.

That design has two flaws for principal-adjacent roles.

First, it measures candidates exclusively in the environment they have spent their careers mastering. EAs and Chiefs of Staff perform in rooms with senior people for a living. Assessing them only in that setting is assessing them at their most rehearsed.

Second, the unscheduled contact is usually handled by the people least empowered to report on it. The coordinator who received a terse reply, the receptionist who was ignored, the recruiter who chased three times for availability: their observations rarely reach the hiring principal, because nobody asked for them and no mechanism exists to carry them.

So the richest data in the process is generated constantly and captured almost never.

What the gaps reveal

Between the first call and the final offer, a candidate shows you how they operate when no formal assessment is taking place.

  • How quickly do they respond, and in what form?
  • Do they write long emails, send short texts, or pick up the phone when a conversation would be faster?
  • How do they handle a last-minute reschedule?
  • How far will they flex to make the process work around a busy principal's calendar?
  • How do they treat the receptionist, the security guard, the coordinator booking their slot?
  • Is their appetite for this role genuine, or is it one of several options they are keeping warm?

For roles built on operating under pressure, at pace, and with people at every level of an organization, these moments carry more predictive weight than a polished hour in a boardroom.

What bad looks like

We have seen every version of this. A few that end processes quickly:

The ghost. A strong first interview, then two days of silence on next steps. A principal who waits 48 hours for a reply does not have an EA. Responsiveness in the process is a preview of responsiveness in the role.

The receptionist test. Warm and impressive with the hiring principal, curt with the receptionist. These roles demand influence without authority, up and down an organization. A candidate who adjusts their courtesy to seniority will do the same in the role.

The nuclear negotiator. Negotiating well is a positive signal. Treating a reasonable offer as an insult is a different matter. Chiefs of Staff negotiate on behalf of their principal daily. How a candidate negotiates for themselves is the audition.

The inflexible. Genuine constraints exist. But a candidate who makes no effort to flex for a principal whose calendar runs in seven-minute increments has misunderstood the role. The work is making things happen. The process is the first test of it.

The avoider. A gap on the CV, a short tenure, a reference they would rather we did not call. Candidates who address these directly fare better than those who deflect. Principals need someone who delivers uncomfortable truths quickly.

No single instance is fatal. A slow reply can be a family emergency. Patterns are what matter, and the gaps inbetween are where patterns show.

How good search firms capture this

Capturing this signal requires deliberate design. A rigorous search assesses three areas, in parallel, from first contact to signed offer.

1. Interviews. Interest, experience, capability, soft skills, and chemistry with the principal or team. Chemistry carries real weight at this level. A technically perfect candidate who does not gel with the principal will not last.

2. Assessments. Interviews measure how well someone talks about the work. Assessments measure whether they can do it. Interviewing well and performing well are separate claims, and a rigorous process proves the second through structured, role-relevant assessment rather than inferring it from the first.

3. The gaps inbetween. Communication, responsiveness, flexibility, appetite, and conduct toward every person in the process. This area only works if every touchpoint reports in: the coordinator, the researcher, the consultant chasing availability all contribute observations to a single picture, and behavior toward the most junior person is weighted as heavily as behavior toward the most senior.

Assessing all three is one thing. Reporting honestly on them is another, and this is where fee structure stops being a commercial detail and becomes a quality issue. A contingent recruiter is paid only on placement, so every awkward observation about a frontrunner is a threat to the fee. A retained firm has the majority of the fee already committed, sits on the employer's side of the table, and can afford to report what it sees.

This is how Blackbook Associates runs every retained search: all three areas assessed throughout, feeding an open feedback loop with the client. Sometimes that means reporting that a preferred candidate went quiet for three days, or was short with our coordinator, or negotiated in a way that should give pause. Our clients retain us as a strategic partner in these appointments, and a partner reports what a salesperson will not.

What this means for clients and candidates

For clients: ask your search partner what they are seeing between the interviews. If the answer is nothing, they are assessing a third of the picture. And ask whether their fee structure allows them to tell you something inconvenient about their own frontrunner.

For candidates: the process starts the moment you reply to the first message and does not pause until you sign. Every interaction is signal, in both directions. Responsiveness, warmth, and flexibility in the gaps inbetween have decided plenty of close calls in a candidate's favor.

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