Hiring and Managing your EA

The “promise” of an Executive Assistant can be so alluring -- a single person who could provide so much leverage, someone to help you focus, someone who can 4x your productivity, someone who supports you to get the impossible done day after day, week after week. And yet -- I see so many clients struggle with hiring and managing an EA. 

I set out in search of answers through phone chats with PeopleOps leaders, CEOs, VC operating partners who specialize in People/Talent, and with a few EAs who work successfully with startup founders. Here is what I found: 

Where might you, as a startup leader, go wrong with hiring or managing an EA? 

1 - You don't truly understand what the EA role can do and more broadly, what the various overlapping options are across a spectrum of executive support. So, then - you plunge ahead and hire blindly for an EA without really matching the job description to your needs and/or thinking creatively about how to get more of your needs met.And then, when you make a hire, you’ve set them up to get frustrated by being underutilized or overwhelmed -- and yourself up to get disappointed when you realize how they can’t or won’t fulfill the expectations you only just clarified for yourself. 

2 - You assume, on some level, that being an EA is an "easy" job. It’s all the “admin” work you don’t want to do or that others tell you that you shouldn’t be spending time on, so you treat the EA hire as more of a service transaction vendor relationship and/or are unwilling to pay the salary or hourly rate to get someone with the skill, experience, and motivation to deliver on what you truly need.  

3 - You don't invest enough in the human relationship. The EAs who will have the biggest impact for you are those who seek out these roles because they love helping and supporting executives like you. They are deeply relational people and, as such, are turned off and demotivated when they sense they are being treated more like a transaction or a tool. Sometimes this arises simply as a blind spot (“I didn’t realize that I needed to invest in this way”) or as resistance (“Can’t I just have an EA without having to “manage” them?”) or you impatiently want the benefits without being willing to invest the time (“They’ve been here for over a month and I still am having to spend so much time giving them context and feedback!”)

4 - You resist letting the EA in. You don’t train them fully on the tools your team uses. You don’t have them attend certain team meetings to get exposed to the context and people they need to know to do their job well. You give them partial or no access to the office systems they need to help you. This can also happen in the more psychological sense when you don’t let them into your fears or what’s keeping you up at night. As a result of all these barriers you’ve (unintentionally) created for the EA, you have undermined your own ability to delegate—artificially capping both the range of tasks and the amount of “cognitive load” they could be taking on to support you.

5 - You worry too much about optics. These fears can block you from even exploring this hire in the first place: “We’re so early”, or “The team is so small. What would people think of me hiring an EA?” Sometimes startup leaders make the hire, but because they fear negative judgment from investors or teammates -- they keep the EA “hidden” by not introducing them to people; not having the EA attend important meetings, or not involving the EA in certain projects that would expose them more broadly to the company or external contacts. These worries, when left unchecked to guide your decisions and behaviors, all limit the EA’s effectiveness and may even hurt the working relationship (see #3 above). 

Given all these opportunities to get it wrong, how can you start hiring and managing an EA more effectively? 

1 - Deepen and broaden your understanding of the EA role: When you first start to explore your options for hiring an EA, start first with you: your needs and your pain points. Do NOT start with the anchoring of "I need to hire an EA", or "We need an office manager." Write the body of the job description first based on the needs you identify and then let that clarify and inform the title second. There is a high likelihood that your support needs are more than what any one person can provide, so it’s time to get creative and selective.  

2 - Challenge any assumptions about how “easy” the job is and how that might be limiting your perception of value. Cash constraints at startups are real and always feel pressing. But if you have defined needs for an EA and are convinced of the value they could generate, make sure you pay what you need to get that person. This is not a role where you can skimp a bit on pay and just “hope for the best.” If you're not sure about salary or hourly rates, ask around. You could even ask the candidates themselves.

3 - Spend time and attention investing in the relationship with your EA both upfront and in ongoing ways. The two key things that an EA needs to succeed in their unique support role are: Context and Trust---and both of those require intention and time to build. It doesn’t matter if your EA is a full-time employee or works for an hourly rate as a contractor--you can’t skip these steps if you want to experience the support of a fully empowered EA. 

Upfront: A lot of context transfer can happen in the early stages of the relationship so make sure to set aside a few (if not several) hours to transfer context to your EA. Depending on the scope of their role, here are some things you might do with them early on: 

• A guided tour through your calendar with live dialogue about your scheduling preferences; any scheduling habits you want to break; what sort of calendar gatekeeping support you’d like; rules of thumb you’d like them to follow when scheduling for you; context for current meetings on your calendar; etc.  

• An orientation to the key people in your life. This could be narrated by you, and you might even have them schedule short “get to know you” meetings with really key people with whom they will be interacting often. Remember that EAs are deeply relational people so for them: human names, faces, backstories are important context for them to have. Don’t be shy about telling them your family member’s names, sharing photos; telling them who your physical therapist is and what injury you’ve been rehabbing for a few months now; giving them some back story on members of your leadership team; how they joined the company; where you feel strong connections and where you want stronger connections with teammates, etc.

• An info-sharing exchange or data dump of all the passwords, contact info, key dates, key numbers, and other bits of logistical information they will need so there is less friction in the future when they don’t say, know your passport number when booking an international business trip or don’t have your LinkedIn password if they need to go post something for you,, etc.

• Inviting them to attend meetings where company context you would like them to know is shared (e.g., All-hands, Exec Team Weekly Meetings) and depending on their specific scope you might even have them sit in on certain retros, offsites, or board meetings.

• Creating a “social contract” together to define mutual expectations for how you want to work together, including communication, feedback, boundaries, systems of tracking work that is being delegated/accomplished. If this is your first time working with an EA but not their first time working with an executive, you can also look to the EA for their ideas & suggestions about what to dialogue about in this social contract and how to align on expectations. 

• If you’ve hired an experienced EA, ask them to generate a list of EA tasks and responsibilities they’ve done before and could imagine fitting into their role with you as well -- read through it together and see if you may have missed areas where you could, over time, delegate more to them. 

• Walk through your current Job Description or set of responsibilities and priorities and ideate on areas where they could help you operate more effectively or more efficiently. (Note: If you don’t have a current JD for yourself, seize this moment as an opportunity to make one -- if your EA doesn’t know what your job is, they can’t provide maximal support and leverage.)

• Introduce them with thought and intention to your team and other key players in your executive life so that they are treated with the status you want them to have. For example, if your EA is going to be setting up meetings for you or gathering input from teammates on your behalf, and you want to influence people to be as responsive as possible to the EA you might say something like, “Please treat any request from them, whether it’s to schedule a meeting or to gather updates for our board deck/dashboard as if it is a direct request from me.” 

Ongoing: In addition to the upfront work, there are a few activities you’ll want to engage in on an ongoing basis to continue to transfer context and build trust over time:

• Continuous feedback and expectations reset - Pro tip: using voice memos or Loom videos to provide asynchronous feedback adds a relational element that otherwise can get lost in written feedback that lacks vocal tone or body language.

• Calibration on under-use or over-use of the EA’s time - EAs might be working more hours than they report. People with a “helper” psychology will sometimes struggle with their boundaries especially when supporting someone in power. So, it will help if you’re the one to initiate the calibration conversation.

• Delegation levels - Are you delegating both tasks and cognitive load at the desired level you both want to be working at? (Read more about Delegation Levels here)

• Building trust - How are the two of you building trust? Is there one underlying component of a trust equation where either of you needs to focus to rebuild or build more trust? 

• Resisting your human tendency to over anchor to negatives and mistakes - they may do 20 things well that are invisible to you precisely because they were done well/flawlessly, and then make one mistake that is visible to you. Be careful in these moments to not over-anchor to the one visible mistake and, when evaluating performance make sure you are balancing all the data, especially if much of it is invisible to you.  

Last two thoughts on trust-building:

Give an EA hire slightly longer to work up to high performance than you'd give a functional expert hire because it's such a high-context and high-trust relationship. Keep this in mind when you’re setting up the cadence for your performance reviews at a 30/60/90-day review. 

Finally, if you expect an EA to “hit the ground running” make sure you understand that entails more about knowing shortcuts (knowing what context questions to ask you) or being proactive (asserting what context they need vs. waiting for it) -- but it’s no substitute for time. Even an experienced EA who can hit the ground running needs TIME to build shared context and trust. It’s not fair to expect overnight impact in this role. 

4 - You can take it slow but do let your EA in -- so you can delegate more effectively to them. 

Make a list of all the ways you could “let your EA in” and start inviting them in/providing access and passwords as soon as you feel ready. Start with both physical and digital systems and work up to more sensitive or private information over time, and have an intended timeline that you’re working towards.

When it comes to letting them into more of your internal mind/psychological system, a good EA will naturally inquire about what’s important to you and what’s stressing you out. You can also initiate this type of disclosure. Even if you are not talking about stressors that your EA can help with directly---them having that context on what you’re dealing with/focused on will help them to help you indirectly. For example: by how they optimize your calendar on a given week to triage other issues as a way to free you up to deal with the major stressor that week.

5 - Explore any reflexes you have around optics and make sure your decisions and actions reflect your deliberate intentions to minimize risk, not your uncalibrated fears. For example, if you find yourself resisting hiring an EA or keeping your EA “low-profile” because of your fears of how it will be perceived, stop and take a step back. Those risk calculations are usually biased towards personal risk, “what will people think of me?” and fail to account for company risk; “What will happen to the company if I continue to operate so fragmented and unproductively? What ‘return’ is the company missing out on with this hire if I don’t elevate and empower my EA fully?” Even though your socially wired brain might protest, it’s your job as a leader to overcome your own “emotional reasoning trap” biases and make decisions based on what’s truly risky (or rewarding) for the company. 

A few closing thoughts about the EA hiring process based on common questions I hear: 

Will an Executive Assistant (EA) do Personal Assistant (PA) work? 

Sometimes I encounter leaders who are craving support with more personal tasks (e.g., ordering lunch, planning a date night, buying a birthday gift, booking a moving van or a medical appt, etc.) but they are reluctant to ask their EAs for this type of support. My sense is there is not a clearly defined border between PA and EA so each situation and individual is going to be different. All the EAs I spoke with about this question also offered a nuanced answer. In general, they are open to taking a “whole life perspective” in terms of what it means to truly support an executive. If the PA tasks are an integrated part of the overall role, most EAs are usually quite amenable to doing that work. It may help upfront to align on expectations around what % of time/tasks will fall more into the PA category so the EA knows what to expect and feels comfortable with that ratio. 

Can I hire an EA too early?  

In general, it seems like hiring a FTE who is 100% dedicated to being the EA to a founder/C-level leader is something that tends to hire around a Series B/C stage. However, many companies who are earlier than that hire remote EAs to support key leaders. One EA I spoke with said she was hired as a part-time EA for a small team that was still in stealth mode! So, no, I don’t think you can hire an EA too early--it just depends on what your needs are and what’s the most effective way to fulfill those needs.  

What’s the best way to find an EA for a startup? 

Historically, startup leaders and founders have tried online marketplaces for remote contractor EA talent. (I myself have successfully hired a previous Business Manager and Operations Assistant through Upwork.) But hiring for any role you haven’t hired for before is time-consuming and it’s hard to know how to screen the wide range of options out there. 

Over the last year, I’ve been hearing positive reviews of Double which is itself a tech startup that is cleverly addressing many of the pain points of hiring and managing an EA. What I particularly like about Double’s approach: 

(1) Double simplifies and expedites the hiring/screening process by running their own vetting process and then “matching” you with one of their EAs based on a short intake interview with you.

(2) Double enables you to delegate more effectively through a task assignment and tracking app including various delegation templates to help you and your EA “double” identify more ways for them to support you. This is particularly useful when you’ve never worked with an EA before and need more guidance on how to partner with them more effectively.  

(3) Double fosters a “community” among their EAs and invests in them with training --- so in a way you have just one EA but you also have access to much larger collective EA brain trust.

My only concern about Double long-term is what happens when you are working with an EA you love and your company has reached a point where you want to scale and hire that EA full-time. My understanding is you are contractually prohibited from doing so -- I could imagine feeling frustrated in the future if the EA you’ve invested context & built trust in for a year+ is not a person you can ever hire full-time. 

But that’s a future problem to work out in the future, not a barrier to checking out this innovative new service if you are early-stage and not ready to hire a FTE. Note I don’t know anyone on the Double team so these aren’t affiliate or sponsored links -- I’m just a coach who has been impressed so far with a much-needed service for the startup leader community. 

My sincere thanks to: Amy, Fiona, Liz, Madeline, Marissa, Michelle, Rajiv, Ray & Tracy
for their input and influence on my exploration of this topic.