• Imposter syndrome. I’ve seen leaders that have a mentality of, “Who am I to give this task to someone else who’s probably smarter than me?”
• Timesuck. It can be hard to justify spending the time to hand a task off to someone (especially if that task only takes a few minutes to complete). But what most people fail to realize is that it might only take five minutes — but that’s five minutes every day (or every week). It also adds cognitive load, along with the cost of context switching — which is way more than five minutes.
• Lack of proof points. But the biggest reason in my experience that most founders shy away from adding support staff is simply because they’ve never done it successfully before. The majority of founders I’ve talked to who have hired EAs have had a bad experience, and almost all of these mistakes were preventable.
  
  

And when folks do get over these three common hurdles and bring onboard an EA, there are two oft-repeated mistakes to avoid.

• Creating more work. The most common mistake I’ve seen is that people feel a compulsion to ensure that their EA is using 100% of their time all the time. This is wrong. Remember that your EA is on the team to help you be more effective. If you’re going out of your way to find things for your EA to do in order to keep them occupied, you’re doing it wrong. If they don’t have any immediate tasks, you’re better off instructing them to read a book or take a vacation than create unnecessary work for them (or consider expanding EA access to a larger group).
• Sticking to the basics. Another common mistake is to approach working with an EA by starting with the question: “How do most people use an EA?” which almost always ends with people using their EAs for scheduling and travel planning.