How to Hire an Epic Executive Assistant

How to Hire an Epic Executive Assistant

A week doesn’t go by without someone asking me if I have a great Executive Assistant or Chief of Staff candidate on standby from an eager would-be employer. The short answer is I do not. Great people go fast, and though I have personally interviewed hundreds of epic executive assistants in my day. Most of them are happily employed somewhere.

However, all is not lost. Luckily you can hire an epic EA that will fit your specific culture and requirements IF you are willing to put in the time and follow this time-tested system.

I’ve been hiring assistants, and executive assistants, both virtual and in-person, for over a decade. Below you’ll find my personal system for hiring great executive assistants that I’ve used at my own companies, and others’ to help hire a truly great assistant who is right for your specific role and your unique culture. As a result, this system has been compiled based on patterns from the 500+ hires I’ve made or been involved in recruiting. Several amazing books I love: Who and How Google Works, and learnings from some truly stellar acquirers of talent over the years. 

If you don’t have the time, or the desire, to implement the below system (it does take discipline and rigor to be done correctly) feel free to drop us a line, because we do a bang-up job of it IMHO 😉

Part 1: Defining the Role (aka “What is your Executive Assistant actually going to do?)

Step 1: Culture first

What is the company’s culture? Is it clarified into stated core values? What does a great culture fit look like, why? If the culture is not already defined, work hard to develop a basic understanding of what it is now and more importantly, where it needs to be. Understand the personality of the direct supervisor and also the personalities and team culture of the group the Executive Assistant will be working with.

Step 2: Start with Why

Clarify the high-level mission for the particular role and develop no more than a paragraph that therefore describes WHY that role exists. 

Step 3: Outcomes, Competency-Zones

  • Outcomes: Develop 3–7 objective outcomes that a potential team member must accomplish to be considered a successful (A player) hire. Establishing outcomes that are objective and quantifiable is essential.
  • Core-competencies: These are role-based, culture-based competencies that each candidate must have to be successful.

Step 4: Gut check

This involves working with all stakeholders who will work with your new hire to gut-check what has been created thus far, then adjusting and formalizing before you post. Some things to consider are:

  • Written objectives of the job. What do you want to be accomplished by 3 months? 6 months? 12 months?
  • Qualities required to be successful in both this role and at your company. Some of these will be professional but others will be personal. 
  • What is our environment? Are you a remote-first company? Are you a hard-charging sales organization where coffee is only for closers?  To clarify, the aspects of your business and culture will impact the type of person who will flourish and they’re important to outline before you start your recruiting process.

Step 5: Creating a Compelling Job Description

You can check out our blog post on writing a compelling job description for a deeper dive into the art of making your JD pop. But below is a quick version, keeping in mind that this will be drafted specifically for an Executive Assistant role.

  • Company: selling them on the big vision and why they want to work here
  • Role: describe what the day-to-day, week-to-week, and month-to-month looks like for this open Executive Assistant role.
  • Application: how to apply, what to include, etc. (and if instructions are not followed to the letter, screen out)
  • Normal stuff: CV, professional links, phone, name, etc.
  • Work eligibility within the country of the job.

Step 6: Create Vetting Questions

We like to ask candidates for an assistant type role to submit a cover letter that includes what drew them to this specific role, why they think they are a fit, and how they personally keep organized. This can be as an attachment, or in-flow if you use an ATS. When you are hiring an executive assistant it is critical to get a good sense of their written communication style early on.

Part 2: Running the Process

Now that you have defined what your ideal Executive Assistant will do and are tying it all together into a  neat little package with a compelling job description on top as a pretty red bow, you’ll need a few filtering questions to include in the application. You can then start filling the top of your recruiting funnel. A few tips if you’re doing this yourself:

As applicants start coming in we suggest using an ATS, Trello or Google Spreadsheets, to track them.  Here’s our guide on using an ATS. You’ll want to set up a few stages that you move applicants through, including but not limited to:

  • Application Stage
  • Written Submission
  • Phone Screen
  • In-person Interview (or Zoom if you are remote)
  • Outcomes + Competency Deep Dive
  • Reference Check

Step 1: The Phone Screen

Some questions to help you build out your phone screen document are below. Also, remember to pepper your interview with “what, how, why” and “tell me more” to make sure you are really understanding what the candidate is saying.

  • Explain what [X CO] does as if you’re speaking to an 8-year-old child?

This serves several purposes, firstly to make sure the candidate actually KNOWS what the company does. A surprising amount of people will blanket apply to jobs without doing the research. Secondly, this is a great window into (a) their communication style and (b) their ability to understand and follow instructions.

  • Teach me something that you recently learned, that I probably wouldn’t know?

Assimilated from one of Google’s favorite questions, this is different from the way most Executive Assistant interviews will begin and kickstarts understanding how the candidate thinks under pressure. This also certainly gives a glimpse into their knowledge base and if they’re a lifelong learner or not.

  • What are your career goals?

Candidates that lack goals, or sound like they are just regurgitating the company’s website or job posting should be screened out. This question allows us to see if they are aligned with the company’s goal and vibe. In addition, it reveals their passion/energy around arenas that may relate to the role. Using this method might disqualify the candidate for the Executive Assistant position, but reveal that they are perfect for another — pass on or store in a recruiting Rolodex if that is the case.

  • What are you really good at professionally?

Try to get the candidate to list 5 to 7 strengths while asking for examples to help understand strengths in context. This is the first step in getting a holistic view of strengths and weaknesses. Screen out candidates with gaps between what the role/company needs and likewise, what the interviewee can offer.

  • What are you not good at/not interested in doing professionally?

If you get a cookie-cutter response or something like “I work too hard,” push them for more honest answers. For example, “That seems like a strength to me, what are you actually not good at or not interested in?” Talented people will be able to self-assess accurately. Sometimes, if someone is having a hard time, ask them to infer what past colleagues or bosses would say.

  • Who were your last three bosses and how would they each rate your performance on a scale of 0 to 10 when we talk to them during the reference check part of this process?

Saying “when” pushes for honesty. After each response ask “Why do you think they would rate you X?” This should allow strong candidates to reinforce and expand on their strengths and weaknesses list. Look out for scores of eight, nine and ten. Similar to the NPS rating, seven is neutral. Six and below could be a flag for screening out based on the circumstances. Honesty and understanding of what went wrong and why is critical in a good Executive Assistant candidate.

  • Do you have any questions for us?

Regardless of the outcome,  show the interviewees respect through this last step… Take notes, good questions can tell a lot about a candidate.

Step 2: The In-person or Zoom Deep Dive

Everyone has a story, it’s our job to get the real one and truly understand the candidate to assess for the role and culture. Think of a person’s career “story” in the framework of chapters… each chapter represents a single job or a group of jobs that span a few years, etc.

IMPORTANT: Ask for each job in the past 10 years. Start with the earliest role and go through it chronologically.

Setting the tone: “Thanks for coming in, we’re excited to talk to you. This is going to be a chronological interview that helps us better understand your work history and strengths by verbally ‘walking through’ each job you have held. For each job, I am going to ask you five core questions: What were you hired to do? What accomplishments are you the proudest of? What were some low points during that job? Who were the people you worked with? Why did you leave that job?

At the end of the interview, we will discuss your career goals and aspirations and you will have a chance to ask questions.

80% of the process is going to happen now but if we mutually decide to move forward we will conduct reference calls to complete the process.

Finally, while this sounds like a lengthy interview, it will go remarkably fast. I want to make sure you have the opportunity to share your full story; so, it is my job to guide the pace of the discussion. Sometimes, we’ll go into more depth. Other times, I will ask us to move on to the next topic. I will try and make sure we leave plenty of time to cover your most recent and most relevant jobs.”

1) At [Earliest chronological company] what were you hired to do?

If they have a hard time answering this, ask “How do you think your success was measured in the role, what was your mission and what were your key outcomes? What competencies mattered in achieving those goals — if goals existed?” The aim is to get a clear window into the candidate’s goals and targets for a specific job and understand what their scorecard might have been had they been assessed.

2) What accomplishments are you most proud of in that role?

This is where we listen for the stories behind the buzzwords in their resume. Most candidates will focus on what really mattered to them in their career rather than regurgitating what they put on their resume. Be wary of accomplishments that don’t seem to correlate with the expectations of said job. ‘A’ players will talk about outcomes that were linked to expectations. ‘B’ and ‘C’ players will talk about events, people they met, or aspects of the job they liked without getting into results.

3) What were some low points during that job?

Continue to reframe and push until they give you something. Everyone had lows, get responses by asking: “What was your biggest mistake, what would you have done differently, what part of the job did you not like, how was the culture?”

4) Who were the people you worked with?

  • Who was your direct supervisor, can you spell that, repeat the name to them…
  • Tell me what was it like working with John Doe?
  • What would John Doe say your biggest strengths and areas of improvement are?”

Keep pushing until you get something. If they say “I don’t know”, ask “what do you guess they’d say” etc.

5) Why did you leave that job?

Were they promoted, recruited or fired from each job along their career path? Did they take the next step in their career or run from something? How did they feel about it? How did their boss react?

‘A’ players are usually highly valued by their bosses, ‘B and C’ players not so much. If you hear a simple “my boss and I didn’t connect” ask why until you get something meatier.

Interviewing tools and tactics

Interrupting: Smile broadly, match their enthusiasm level, use reflective listening to parrot what they just said (so they don’t feel ashamed or shut down on you) and then redirect to get back on track. There is a stop-and-shut up way of interrupting and an ‘I’m-super-excited-to-hear-more-about-such-and-such’ rapport.

What/Why/How/Tell me more: Get curious after every answer that doesn’t CLEARLY paint a picture in your head.

3Ps of Performance: Evaluate the accomplishment a candidate is telling us about.

  • How did your performance compare to the previous year?
  • In what way(s) did your performance compare to the plan?
  • How did your performance compare to that of your peers?

Push vs. Pull: Was the candidate pushed out of their role or pulled into a greater opportunity. If they were pushed out of more than 20% of their roles, this could be a sign of a ‘B/C’ player. This is important when asking “Why did you leave that role?”. Here are some examples:

  • Push: “it was mutual”, “it was time for me to leave”, “I don’t get along with my boss”, “X got promoted and I didn’t”
  • Pull: “My former boss hired me to a new role at Y Co”, “My biggest client hired me”, “I decided I wanted a different path for my life.” You’d follow that up by finding out if XYZ proactively then moved to LA for new opportunities.

Reading body language: During the Story interview, it’s important to pay attention to physical cues. Shifts in body language and other inconsistencies can be more telling than the words coming out of a candidate’s mouth. Read more about the science of body language here.

Outcomes + Competency Deep Dive

Outcomes: X, Y, and Z

Competencies: 1,2,3,4

Assign up to three interviewers individually or separately to deep dive into how the candidate’s experience and strengths align with the Outcomes + Competencies within the scope of the Executive Assistant role.

Time: 45 minutes to an hour.

Cultural Fit: It is important to create a cultural fit scorecard that is unique to your company.

Reference checking, also known as NEVER SKIP THE REFERENCES!

The goal is 5 reference calls depending on the level of hire: past bosses, peers or customers.

Pick the right references, review the previous steps and pick out the people you think would be most enlightening.

Reference questions:

Don’t forget to use What/Why/How/Tell me more framework

  1. In what context did you work with [candidate]?
  2. What were their biggest strengths?
  3. What were their biggest areas for improvement back then?
  4. How would you rate his/her overall permanence in that job on a scale of 0–10? What about their performance causes you to give that rating?
  5. The person mentioned that he/struggled with __________ in that job. Can you tell me more about that?

What to look for:

How do the references rate the person on 0–10 versus how they rated themselves? Wide discrepancies should be a red flag. A 6 isn’t a deal-breaker — just get curious about why that discrepancy exists.

We are looking for candidates that consistently get 8,9,10 ratings across reference calls.

The best way to learn about a leader or manager is to talk to their subordinates, more than their managers.

Remember human psychology — people don’t want to give negative references outright, even if the person was a poor performer. In general, we don’t want to hurt other people’s chances, even if they were subpar. Pay attention to WHAT people say and HOW they say it.

Lukewarm or qualified praise is likely to signal ambivalence or worse about the candidate.

The Decision

Ratings: A, B, C

Skill: Are we 90% or more confident that the candidate can get the job of Executive Assistant done because of his/her skills match the desired outcomes from our scorecard?

Alignment: Are we 90% or more confident that the candidate will be a good fit because what they want matches the mission and competencies of the Executive Assistant role, as well as the culture of the company?

Go back through the process — rate each candidate based on their scorecard, updating for reference checks — then give an A, B or C.

Create a compelling offer letter for your new Executive Assistant!

That’s it, folks! Granted this is my particular method, feel free to edit and make it your own. And again if you don’t have the time, or desire, to implement the system (it does take discipline and rigor to be done correctly) feel free to connect with us directly.



Interested in working remotely? Check out our open roles. 

Interested in hiring remote workers? We can help with that too, just give us a shout!

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