ISSUE #44

Welcome to the Forward Obsessed Founder, my newsletter with insights, awesome tools, and real-world advice to grow your business and career.

GO FORWARD THOUGHT OF THE WEEK ➡️

How to Hire an EA to Buy Back Your Greatest Asset: Time ⏰

Your time is your most finite asset. And it's one that you share with countless others who’ll gladly eat it up if you’re not careful.

I used to seriously suck at time management. And sure, I would try to delegate things to team members or assistants. But that didn't stop me from pushing myself to squeeze as much productivity as possible out of every moment. Finding shortcuts, tools, and just putting in the grind.

And then I ran out of hours.

Years ago, while in the thick of running one of my companies, a lack of smart delegation and buying back my time caused a pretty severe health breakdown, which I wrote about.

So, let me start by paraphrasing one of my favorite quotes from serial entrepreneur Dan Martell:

In other words, stop wearing all the hats. Insist on prioritizing working in what I call your “Green Zone” — that sweet spot where you’re absorbed and inspired, working in a flow state, and producing innovative, unique, and next-level work.

The best way to do that? Delegating.

That sounds simple, but it’s nearly impossible if you don’t have the proper criteria to hire people who can not only truly assist you but actually know how to take the initiative and work to support your best interests.

This is what today’s Go Forward thought is all about: how to become masterful at delegation and hiring the best possible executive assistant (EA).

It’s Not the Assistant, It’s the Assistance

In my career, I’ve had all kinds of assistants — in-person executive assistants (EA), virtual assistants (VAs), junior assistants, and interns. (Seriously, even motivated interns have been game-changers.)

The worst-case scenario is investing hours and hours training someone who sits and waits for your next request.

But the best-case scenario? That’s when you find someone genuinely interested in being of assistance — proactive and enthusiastically engaged in your collective mission.

An executive assistant (EA) done right can be a force multiplier, reclaiming hours of your week and allowing you to focus on what truly matters. The right EA can transform your productivity — as long as you've done the work to ensure they're trustworthy and consistent.

The GOAT of Delegation

So, how do you find this unicorn of an assistant? For the best advice, I turn to a GOAT in leadership best practices: Michael Hyatt.

Hyatt's “Five Levels of Delegation” is an invaluable framework to help you delegate tasks effectively, maintain control where necessary, and empower your team members.

Here’s a quick summary of Hyatt’s five levels:

1. Level 1: Do exactly what I say.
2. Level 2: Research and report back.
3. Level 3: Research and recommend.
4. Level 4: Decide and inform.
5. Level 5: Decide and act.

Most of my delegation with EAs falls between levels 2 and 4, reserving level 5 for more experienced team members.

If you already have an awesome chief of staff, stop reading here 🛑 and give yourself back a few minutes in your day.

Still here? Well then, you are curious about how to not suck at delegating and working with executive assistants. Let’s keep going.

5 Tools I Can’t Live Without

I’m not kidding when I say this: these tools save me easily 20+ hours each week. They put all I need at my finger tips to funnel action items and requests from various places (i.e., meetings, one-on-one conversations, my head) and clearly communicate with my people.

Here are my go-to’s that I use every single day:

• ​Loom - I use this messaging tool to make quick videos and eliminate tons of meetings. Async is a time-saving cheat code.
• ​ChatGPT Plus - ChatGPT is used constantly for almost everything in my work and personal life.
• ​Fathom - Invaluable for Zoom meeting AI note-taking. Ask me how this also helps me create 90% of my content marketing ideas.
• ​Notion - What I use to store content about content — it’s my second brain.
• ​Superhuman - Eliminates the email time suck by being the fastest and best tool out there. (Yes, it works with Gmail & Office365). Their new AI features allow me to reply and find info better than I can.

The trick with these tools is figuring out how to get them working together. For example, I’ll download a transcript from Loom, upload it to a custom GPT I created to generate Standard Operating Procedures (SOPs) and playbooks, and voilà! It takes me minutes instead of endless hours to make.
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​Pro tip: If you do something more than once, you should document it. Be sure to clearly describe what “done” looks like to ensure the tasks you delegate are done to your standards.

Finding the Right EA

In my career, I’ve tried countless approaches and resources to find the best possible assistants. I’m about to share with you a free, detailed resource that has all of what we’ve already discussed, including an in-depth guide to use in the interviewing process, but first, here are a few core pointers:

• Group your interviewing questions into categories.
  We interview candidates across four key behavioral areas: Drive & Motivation, Adaptability, Leadership Skills, and Teamwork. The first two categories are the most critical, but all four make a candidate exceptional.
• Ask specific, illustrative questions and listen carefully to their answers. ​
  For example: “Can you provide an example of a time when you identified an opportunity and took the initiative to seize it?” Once the person shares specifics, be sure to drill down with more questions so you can extract detailed answers that will lend insight into critical areas of competence, including proactivity, autonomy, problem-solving, learning, and adaptability.
• Go deeper.
  ​If someone appears to be a behavioral fit, we may also ask a tactical question to understand their hard skills on the job.

My #1 cheat code for finding awesome EAs and for getting excellent advice on delegating is a platform called Athena. Click here for my Athena referral code so you can get some free perks. (And it helps me out, too, since I’m a big fan of theirs.)

If this short article on delegation and hiring excellent assistants got you fired up, you’ll love this Notion document I've created to help my friends and clients scale themselves more efficiently with the right support.

Check it out, and if you have questions, just give me a shout.

Always here to help 🙌
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​Pete Sena​

Podcast 🎙: A Curious Path to a 7+-Figure Exit

“Scrappy” is probably the most trite word you can use to describe an entrepreneur. But Ben Lamson, exited co-founder of the crowdfunding platform WeDidIt and tech company Paperspace, embodies that spirit.

Early on, Ben and his WeDidIt partner took divergent paths to make their business successful, from entering business plan competitions to even taking on odd jobs, like participating in game shows and writing fake reviews, to extend their runway and keep the business afloat.

So, if being scrappy AF means you raise multi-millions as Ben did before a successful exit, that’s exactly what you want to be. Just remember that scrappy isn’t a synonym for sloppy — it means leading with curiosity, a hunger for knowledge, and a willingness to take risks to continuously serve your audience.

Listen: ​Hacking a Startup from Idea to Exit with Ben Lamson​

Creative Caffeine ☕️🍵

To complement the Go Forward thought on delegating and hiring the best possible assistants, here are a few articles I highly recommend reading.

​Unlock Your Business Potential With the 10-80-10 Formula: The Secret to Scaling Your Creative Empire​

About a decade ago, I first learned about a principle for maximizing time and effort pioneered by a legendary leader of leaders, John Maxwell, called the “10–80–10 Principle.” It was my first step to stop getting caught up in the little day-to-day tasks and becoming a leader who builds sustainable businesses.

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

Sam Corcos, the co-founder and CEO of Levels, is a master delegator who’s obsessive about optimizing his time. He delegates 400 tasks a month! So, if you find it hard to delegate even one or two tasks, stop everything and read how he does it right now. (You can also listen to Sam talk about 10X delegation on Tim Ferriss’ podcast.)

​Clear is Kind. Unclear is Unkind.​

Years ago, I saw vulnerability expert Brené Brown speak at a conference, and her words on vulnerability and courage literally changed my life. This article is also a game-changer, and it’s all about the crux of why we find delegating so hard — we avoid tough conversations, including giving honest, productive feedback. This will help you get over that and become a better leader.

My Obsession of the Week 🖤:

Answer Engines and the Quest for Knowledge

I haven't used Google in almost six months. Goodbye search engines, hello answer engines. I turn to Perplexity, which fetches real-time search results and uses LLMs to bundle and give you the data as needed without being flooded with sponsored ads.

Bottom line: Remember what I said at the top of this newsletter? Trade money for time, not time for money. I happily pay Perplexity's monthly fee for a better search experience optimized for information retrieval.

Thanks so much for reading this edition of The Forward Obsessed Founder — you can also check out this issue on the web [Link].
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