Seeking Professional Help: Why Every Startup CEO Needs an Assistant

This post originally appeared on Matt’s Medium in July, 2013. You can read the original post here.

As a first-time CEO, I made a mistake that many other CEOs have also told me they’ve made: I waited way too long to hire an assistant. Early in the company’s life, the topic feels taboo: if you bring it up with your cofounders or board members (“I think I should hire an assistant”), you fear you’ll be judged. But delaying the hire is a shortsighted and even disrespectful move, since in reality most people think you need one anyway.

I know, I know. You’re a lean startup! You need to keep expenses low. Eat food out of boxes, sit on hard wooden stools, use a Pentium II laptop until you’ve raised your next round. You’re such a martyr! Eric Ries would be so proud. (1)

In reality, delaying the hire is usually driven by false humility and overreaching frugality. There are no rewards for being an inefficient CEO. As my friend and fellow CEO Clara Shih put it,

I worried about creating a sense of entitlement and didn’t want anyone internally or externally to think I was “too important” to do my own scheduling. We ultimately hired one around employee number 10, which was too late. By then I was near my breaking point with scheduling, cleaning, ordering lunch and dinner for the company in addition to sales, marketing, business development, customer support, and coding.

The common wisdom in an early-stage startup is to hire only engineers and designers for as long as you can. You’ll rationalize this in a few ways.

First, you’ll feel like any expenditure on staff not directly involved in building the product is slavish or wasteful. This oversimplifies the “lean startup” into blind frugality. The point of keeping your engineer-to-overhead ratio high is to maximize efficiency, and that’s precisely what hiring an assistant will help you do. However he or she helps, your assistant will probably help everyone at the company spend their time more wisely, not just you.

Second, you’ll cling to the quaint notion that you’re just another member of the team, and you’ll avoid the trappings of the CEO role to “prove” it to everyone around you. Doing your fair share of the dishes, lunch-buying and the like is ostensibly good, at least culturally, but remember that every minute you spend managing your calendar and doing dishes is a minute you’re not providing significantly more value by recruiting or finding customers. So get over it.

Third, you’ll argue that the assistant’s role is not yet a full time job. This argument is illogical. If it were already a full time job, you’d be a full time assistant to yourself. It cannot possibly be a full time job before you hire someone.

All of this, of course, despite the voice in your head that you’re ignoring: “I really need an assistant.”

Remember: Time is your scarcest resource, so the CEO should only be spending time on things that only the CEO can do.

Quoting Clara again,

Early on, the admin stuff is easier to delegate than coding or sales, which you’ll want to do yourself until you figure out the minimum viable product and go-to-market formula.

When you look at it that way, delegating these tasks should be the first thing you get off your plate, not the last. If you’ll have more time to spend doing things that are actually company-building activities, why on earth would you delay this hire?

Don’t worry! You’re still a penny-pinching, self-effacing, deeply humble and eminently egalitarian CEO. You just need to hire an assistant.

For what it’s worth, having an assistant who is also the office manager, receptionist, or other pinch hitter is fine for a while. It worked well for us initially, although it’s not ideal. If possible, it’s better instead to have your assistant double up as an assistant to others on your team. The only way he or she can keep your calendar smooth and your time focused on what’s important is when everyone knows that the job title is “executive assistant.” It provides the sense of clarity and accountability that anyone needs in their work.

As founder and CEO, it’s critical to get as much out of your time as you can. A good assistant will quickly learn to see the patterns in your life and help you do it. He or she will ensure you’re scheduled not just efficiently, but also clearly, and will anticipate the things that make your days run smoothly. When you build mutual trust, you can toss things over your shoulder without looking, knowing that your assistant will catch and process whatever you’ve tossed. There is a mild professional euphoria that ensues when you hire the right person (2).

As missteps go, waiting too long to hire a full-time assistant is a big but easy one to avoid. I was too afraid of the optics and the politics to acknowledge the need, and it reached the point that others had begun to complain. If I had had this little blog post back then, I’d have forwarded it to my cofounders and said, “What do you think?”

I know what they would have said: “Duh.”

Thanks to Clara Shih for her views, and Josh Forman, Bryan Schreier, and Dan Gill for their thoughtful revisions to the post.

Notes

1. I’m being facetious; he wouldn’t be. The concept of the lean startup has much more nuance and value than “don’t spend money.”
2. Hiring the wrong person can be a nightmare, noted one of my post reviewers. You really have to establish trust with the person you hire. I’ll have to do a separate post on what makes a good EA golden, and how to find him or her; like any other hire, it’s quite difficult to find the right person.