What To Look for When Hiring An Executive Assistant for a Start-Up

Hiring an EA for a start-up is an important decision. The start-up environment is different from the culture at a larger, more established company. So how do you determine the responsibilities and hire the right person for this critical Executive Assistant role for the CEO or C-Suite of a start-up? 

How Do You Begin When You Are Ready to Hire an EA for Your Start-Up?

The best way to start is to determine the tasks and responsibilities you want your Executive Assistant to take off your plate. Be rigorous and idealistic about this. Think about it this way: according to Tobi Lutke in his podcast with The Knowledge Project, every time you say “Yes” to something (like booking your own travel), you are actually saying “No” to every other thing you could have done during that period of time.

Finding an executive assistant who can take on all the responsibilities and tasks you want to shed is going to be hard. Finding the right EA who can successfully work with a CEO is difficult enough, but finding an EA with the skills and attributes necessary for working in a start-up environment is even harder. Start-ups operate differently from more established companies. So, while it’s good to be realistic, start by being idealistic and look for someone with the following traits to ensure your Executive Assistant will add the most value for you.

Must-Have Attributes When Hiring an EA for a Start-Up, Founder, or CEO

• Tolerance for Ambiguity– Making your expectations and requests clear will go a long way to ensuring your EA performs well, but this is not always possible in any job much less a start-up environment. So if ambiguous situations are too stressful for your Executive Assistant, they may not last long. 
• Flexibility and Adaptability– In a start-up, a lot can change quickly. Roles, responsibilities, organizational structure, client or prospect requests, markets, technology, and processes can change quickly. Priorities can shift all the time. Make sure you hire someone who can pivot when needed and thrives on change rather than finding it stressful. 
• A Team Player– Look for someone who can communicate, shares knowledge, and understands the start-up organization. 
• A Juggler– Start-ups can be chaotic and very fast-paced. The Executive Assistant to a Founder will often find themselves being pointed in a million directions. They need to be able to sort through the priorities as well as help their executive stay focused by blocking out the noise and taking on some of the incoming traffic. 
• Efficiency Expert– Without being focused on efficiency, your Juggler EA will eventually become overwhelmed. Keeping everything organized and always looking for ways to speed up and simplify workflow will allow them to prioritize and focus on what absolutely needs to get done while still keeping their eye on all other balls in the air.
• Solution Oriented– When obstacles arise, it’s important that your EA focuses on finding solutions rather than looking at reasons something can’t be done or blaming someone else.
• Openness and Ability to Learn – The desire and the ability to quickly grasp the players and their personalities, the industry, and also new tech skills are critical.
• Ability to Anticipate, Be Proactive and Work Independently – Nothing is worse than an EA who constantly needs to be told what to do, but you also want an EA who asks for direction and advice when necessary.
• Ability to See the Big Picture– Without the ability to see the big picture an EA to a Founder cannot consistently anticipate and be proactive.
• Curious- The key to being open to learning new things is curiosity and a love of learning. These traits can be an indicator that your EA can consistently up their game. But watch out! Sometimes too much curiosity can keep an EA from focusing on the humdrum of regular but critical activities.
• Detail Oriented, but not necessarily a Perfectionist– You need someone who recognizes when “Perfect is the Enemy of the Good”. There’s a time for perfection and a time when good enough is good enough
• Ability to Manage Conflict– By nature, successful start-ups attract passionate, outspoken, and determined people. Fundraising stress can also exasperate conflict. Be sure your Executive Assistant can tolerate conflict, work with strong personalities, and doesn’t just shut down when conflict happens. 
• Emotional Intelligence– An overused term but important.  Having an Executive Assistant who can read a room quickly and knows when to back off, recalibrate and circle around later is so important. 
• Perseverance and Grit– These traits are always important in a start-up, but there are important caveats. It doesn’t help if your EA perseveres but keeps doing things that aren’t working. Insanity is doing the same thing over and over and expecting different results (a definition attributed to Albert Einstein). You need an executive assistant who believes in your company’s mission and product, but when it comes to their specific responsibilities knows when to try a different approach when something isn’t working. 

Do You Hire an Experienced Career EA For a Start-Up or Someone with Less Experience but a Lot of Runway?

Hiring an EA for a start-up who has experience is usually best; less training is involved so the ramp-up time is shorter. But, you want to hire an EA who already has start-up experience or experience at a smaller company where responsibilities and culture more closely mirror your company. Generally speaking, an EA who has only worked at large organizations will not be a good fit, unless something in their background shows they have some of the characteristics we have listed.

An important issue to also sort out in your own mind and to screen for is whether or not you want your EA to be a career EA who wants to stay in that role or whether you are open to someone who will be ready to move into another role in a couple of years. If you are willing to consider someone who views the EA role as a foundational learning experience for eventually moving up in your company into some other function, you will widen the talent pool to candidates with much less experience but who have a lot of runway. There are perils and pitfalls with this approach and we can help you think through them,  but it can work.

Hiring an Experienced Expert Executive Assistant Recruiter Has Advantages

We specialize in hiring Executive Assistants and Executive/Personal Assistants anywhere in the USA. Much of our experience is with start-ups, smaller companies, or larger companies with an entrepreneurial culture. We are happy to advise you on what the market looks like, and what is reasonable to expect in terms of talent and market compensation benchmarks. Read our success stories about recent hires to see how we’ve helped clients hire the right executive assistant. We have nearly 60,000 executive assistants in our network, so we can help you quickly find your perfect executive assistant.