A Tactical Guide to Working with EAs: How to Make Delegation Your Superpower

Sam Corcos, co-founder & CEO of Levels, admits he's obsessive about optimizing his time. He shares the ins and outs of how he delegates 400 tasks a month with this ultra-specific guide to working with executive assistants.

Outline

Delegation is a superpower. It also takes practice.

I know dozens of founders who have worked with an Executive Assistant (EA) and stopped after a few months because they couldn’t figure out how to make effective use of the resource — often writing off EAs altogether. Another common pitfall I see is early-stage, scrappy founding teams that think it’s too premature to bring on board someone with this skill set.

When leveraged correctly, an EA can be one of the most important tools in a startup team’s arsenal — freeing up space to focus on the thorniest challenges facing the business. But there isn’t all that much tactical information out there on how to specifically work with EAs — often, it’s just something leaders are expected to know how to do.

As a four-time founder and now CEO at Levels, I’ve worked with all sorts of EAs in the past and I’ve learned a lot of lessons the hard way. I’m also obsessive about tracking my time and optimizing how I’m spending each day as an early-stage startup CEO.

When it came to adding EAs to Levels, we took a different approach. Currently, Levels is a team of 47 people, and we have 12 outsourced EAs. Notably, our EA pool is available to everyone on the team, regardless of seniority — and we encourage everyone to make use of them.

I think support staff is one of the most under-utilized resources available to every startup. Fundamentally, you want your best people working on the highest value projects for your company. Any time your highest-leverage people are spending time on routine tasks that could be performed by someone else, it’s not only a loss for the company, but it’s limiting that person’s ability to reach their full potential.

Learning how to delegate effectively is perhaps the single most important skill that folks need to develop in order to transition into a leadership role, and yet, many are reluctant to embrace it.

In this article, I’ll outline specific tips for working with EAs — whether it’s your first time bringing one on board, or you’re looking to better leverage the EAs you already work with. Along the way, I’ll share tons of specific examples, documents and templates that illustrate exactly how we do this at Levels. I’ll also unpack the process for expanding the EA pool across the entire team at Levels, and why I think it’s a practice more early-stage startups should adopt.

Delegating mishaps to avoid

As a multi-time founder, I’ve helped many leaders develop better delegation skills. I’ve seen a few primary reasons that cause folks to avoid delegating to an EA:

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?” It’s important to recognize this as a source of inner conflict that prevents people from delegating effectively.
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. It isn’t strictly wrong to use an EA for these things, but there are better tools available. For example, I use Calendly for scheduling and I book my own flights because I’ve found that travel usually involves prioritization tradeoffs that an EA doesn’t have the proper context to be able to make.

Why you should consider an EA Pool

If you’re finding that you don’t have enough tasks to occupy 100% of an EA’s time, rather than writing off EAs altogether, I encourage you to consider making your EAs available to everyone at the company in what we call an “EA Pool.” Most of our executives at Levels still have a primary EA, but when they have downtime, the EAs contribute to other parts of the business that need support.

One of the reasons many startups don’t hire an EA is because each individual doesn’t have enough tasks to occupy someone full-time. But if you make that EA time fungible, you can spread that time across many people on your team.

The key here is to make sure communication is crisp between your team and the EAs — otherwise, they can end up overworked and spread across too many responsibilities.

My Delegated Tasks

To set the context here and for some added visibility, here’s a link to the Notion doc where we keep track of all the delegations I’ve handed off to our EA team. This is about a third of my actual list of delegations — I redacted anything that includes confidential information.

This should give you a feel for just how much leverage you can get by working with EAs and learning how to delegate effectively. In total, our EAs handle about 400 tasks per month for me, split between 5 EAs. If you’re looking for ideas on all the different types of tasks you can delegate to your EA, I recommend exploring the Notion doc. As you’ll notice, some of these are small tasks, like updating my Goodreads list or reminding folks on the engineering team to update their priorities tracker sheet. Others are much larger, more time-consuming tasks — like working on our monthly investor update email.

What to Delegate, Automate, or Eliminate.

In “The 4-Hour Workweek,” one line from author Tim Ferriss stuck out to me: “Never automate something that can be eliminated, and never delegate something that can be automated or streamlined. Otherwise, you waste someone else’s time instead of your own, which now wastes your hard-earned cash.”

Eliminate

Before you consider delegating or automating a task, it’s always worth interrogating whether that task is worth doing in the first place. There’s nothing worse than spending time improving something that should never have existed to begin with.

An interesting tactic you can implement here is the “anti-pilot.” When you run a pilot program, you test something with a group of users to get feedback. With an anti-pilot, you remove the feature and see if anyone notices. If you don’t get a lot of complaints, it’s a strong indicator that the feature wasn’t adding as much value as you may have thought.

Automate

The best way to Automate a task is with computers. But sometimes, it’s either not worth the investment of engineering time or the integrations are too cumbersome to solve the specific problem you have. This is where you can delegate some of your tasks to EAs in order to automate them.

Delegate

A useful way to think about the difference between an automation and a delegation is that automations are imperative while delegations are declarative. Automations are also generally recurring tasks, while delegations are usually one-time or short-lived tasks.

8 Tactics for Better Delegation

By assigning the right kinds of tasks to your EA, you’re well on your way to becoming a more effective delegator. But there are plenty of other tips I’ve picked up along the way that can help your EA pick up altitude as they take on new tasks.

1. Use Async Video and Audio

This is going to feel unnatural for most people, but you should try to lean into recorded, asynchronous video and voice memos for delegation. It’s way more time-efficient for you and your EA, and it allows that video recording to be used as an asset in the future when new people need to be onboarded to the task.

2. Define the Output Format

It’s almost always better to make it clear to your EA what the format of the output should look like. For example, should the deliverable be a spreadsheet? If so, what are the columns you’re expecting?

3. Ask for Playback

This might feel awkward at first, but it’s super important that you do this every time. It often means delaying the start of the task by a few hours, but it’s worth it.

4. Try Partial Implementation

If a task requires meaningful time (e.g. more than a couple of hours), it’s almost always a good idea to ask your EA to do a partial implementation of a task before spending significant time on it.

5. Give Feedback

Don’t expect things to be right the first time, especially for big tasks. This is another common failure mode that people experience when working with EAs.

6. Test the Waters with Parallel Tasking

If you’re not totally confident that a task you’re currently doing can be handed off effectively, one strategy is to have your EA do the task in parallel in a sandbox.

7. Close the Loop

It’s extremely important to figure out a process for accountability and transparency on what your EAs are spending their time on to ensure things are being done consistently and correctly.

8. Use Task Recording

You need confidence that the tasks are being done consistently, on time, and correctly. But sometimes, errors happen, and it’s not always clear why.

Wrapping Up: Play the delegation long game.

The most important thing to keep in mind is that this is going to take time. It took me years to get to the point where I’m able to confidently delegate all of these recurring tasks to our EA pool. Like anything in startups, whether it’s talking to customers or running an executive meeting, you’re not going to nail it the first time. That doesn’t mean you throw in the towel.