How to Hire an Epic Executive Assistant

Each week I get asked if I have any great EA or Chief of Staff candidates on standby by a startup founder or VC. Short answer, I don’t. But, all is not lost, it’s easy to hire an incredible Executive Assistant IF you are willing to put in the time and follow this time-tested system.

I’ve been hiring assistants, both virtual and in-person, for over a decade. Below you’ll find my personal system for hiring great EAs that I’ve used at my own companies, and others’ to help them hire a truly great assistant who is right for *your* specific role and your unique culture. 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 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

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 with the client to get a basic understanding of what it is now and where they want it to be. Understand the personality of the direct supervisor for [new role] and also the personalities and team culture of the group they’d be working within.

Step 2: Start with Why

Clarify the high-level mission for a particular role and develop no more than a paragraph that 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. Developing 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 the client and stakeholders who work with the hire to gut-check what has been created thus far. Then adjusting and formalizing the finished product.

What are the written objectives of the job?

  • 3 months
  • 6 months
  • 12 months

What are the qualities required?

  • Personal
  • Professional

Step 5: Creating a Compelling Job Description

  • About the company: selling them on the big vision
  • About the role: describe what the day-to-day, week-to-week and month-to-month look like.
  • About the application: (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.
  • Please submit a cover letter that includes what drew you to this specific role, why you are a fit, and how you personally keep organized? (this can be as an attachment, or in-flow if you use an ATS).

I tend to like to create separate written screen questions, beyond a generic cover letter I feel that they (a) filter a lot of people who don’t want to put in the leg work and (b) they help bubble up good candidates. Plus, when you are hiring an executive assistant it is critical to get a good sense of their written communication style early on.

Filling the Funnel

  • Post the job to ZipRecruiter for largest reach.
  • Post to AngeList.
  • Use the “Everyone’s a Recruiter” method with current employees to tap their networks.

Filtering the Funnel

We suggest using an ATS, or Trello or Google Spreadsheets, whichever the person designated to fill this position is most familiar with. The levels are:

  1. Written Submission
  2. Interview Process
  3. Phone Screen
  4. In-person Story Interview
  5. Outcomes + Competency Deep Dive
  6. Reference Check
  7. Decision

The Interview Process

[Make Copy> title: Full Name, Position, YYYY-MM-DD by Interviewer’s Name]

Part 1: Phone Screen

*Remember to pepper your interview with “what, how, why” and “tell me more” to make sure we 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, foremost of which is 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.

Could you 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 EA interviews will begin and kickstarts understanding how the candidate thinks under pressure. This 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 their passion/energy around arenas that may relate to the role. This method might disqualify the candidate for X position, but reveal that they are perfect for Y position — pass on or store in 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, 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 if we see gaps between what the role/company needs and what the interviewee can offer.

What are you not good at professionally?

If you get cookie cutter responses or “I work too hard” push them for more honest answers: “that seems like a strength to me, what are you actually not good or not interested in”. Talented people will be able to self-assess accurately, sometimes if someone is having a hard time ask them to guess 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 strength and weakness list. We will want 8, 9s, and 10s. Similar to NPS rating, 7s are neutral — 6 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 candidate.

Do you have any questions for us?

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

Part 2: The Story

*this is a separate interview, usually in person

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 most proud 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 references 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 name to them…

— 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.

4.B) Only for managers

— How would you rate the team you inherited?

— When we speak to members of your team, what will they say your biggest strengths and weaknesses were?”

5) Why did you leave that job?

Were they promoted, recruited or fired from each job along their career progression? Were they taking the next step in their career or running from something? How did they feel about it? How did their boss react?

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


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 a ‘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: How we can evaluate the accomplishment a candidate is telling us about.

  1. How did your performance compare to the previous year’s?
  2. How did your performance compare to the plan?
  3. 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:

  1. 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”
  2. 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:

Part 3: 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 for this specific role. Interviewers should be experienced in the Outcome or Competency they are interviewing for.

Time: 45 minutes to an hour.

Cultural Fit: This is important to create a cultural fit scorecard that is unique to each company/client we work with — then add to this section as has a vastly different cultural DNA than Bridgewater Associates.

Part 4: 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.

PART 5: The Decision

Skill: Are we 90% or more confident that the candidate can get the job 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 role, as well as the culture of the company.

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


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 below system (it does take discipline and rigor to be done correctly) feel free to connect with us directly.