The CEO guide I wish I had

As I said this very logistical sentence, I felt my throat choked up and tears welled up in my eyes.

I was standing in front of 100+ Ampushers at our annual Miami offsite, weeks before COVID-19, formally announcing the end of my CEO term.  It had been 10 years. It took me 2+ years to make that decision and then a year to actually do the transition.

I was going through a mixture of emotions: sadness, relief, and fear for the future.

Fast forward 2.5 years, and I see 8 figures hitting my bank account.

We sold Ampush to Tinuiti.  But, my life didn't change.  I was old news, no longer tied to the day-to-day operations of the company I had built and ran for 10 years.

All my founder friends gazed at me in awe… "you did it, you built it, sold it, and then didn't have to go with it, HOW did you do that Jesse?"

I can break the WHOLE story down over a series of emails. Revisionist history is beautiful because it wasn't SO intentional that it played out that way.  And much of the story is about one Jon Oberlander, a unique and talented guy!

But for today's email, I'll show you one of the most important building blocks behind this successful outcome.  One that I think YOU can use immediately.

It's a document I wrote for Jon called "CEO Advice" - as he took on the role, he had worked with me for almost a decade. He had done every position in the company except CEO, he knew the people, he knew the clients but he had never been "the guy." This is the advice I shared with him (more or less verbatim).

(Disclaimer to newsletter readers: It’s crucial to tailor your approach to what works best for you and your strengths. For example, processing large amounts of information is one of my unique "Zones of Genius," so some of what I share may not align with others like Jon’s expertise in systems thinking. Also, I’ve had the advantage of being the "frog in the water," gradually adapting to the role over time, which is very different from stepping in as CEO while the company is already in motion.)

This real-time prioritization helps keep things moving. Without it, you risk letting tasks pile up, becoming the bottleneck yourself.

When:

Usually in the morning, once during the day, and at night

Even when it’s not perfect:

Sometimes, I push things forward even if they aren’t quite ready, like asking for more info or raising the bar on a task. This keeps momentum going, even for lower-priority items.

Why it matters:

It helps me be intentional about how I spend my time and decide what truly matters. It also gives me control over how others use my time, ensuring my and the company’s priorities are met.

Related to this:

I realized I often don’t tell people to empathize with my workload, but when I do, things improve—people naturally raise the quality of their deliverables. For example, I’ll say: “Please don’t just Slack me a document and expect a quick review. I get 5-10 similar requests daily. I need your help—send it to Evelyn and help me prioritize.”

When:

Mostly nights and on weekends. Sometimes I ask Evelyn to block off large chunks of time if there’s a heavy load of requests and deadlines.

Hire a top-notch Executive Assistant:
This might be even more valuable than a Chief of Staff, especially if you find a young, smart candidate. Ideally, they’d be local, able to assist in person, join meetings, and pull you out of meetings when necessary

Daily check-ins:
Meet with your assistant daily to align priorities and ways they can support you.

Weekly meetings:
Have a longer meeting weekly to review the upcoming week, travel plans, and any specific asks from key people. (Bill Gates uses the same approach.)

Read the "Managing Self" chapter from The Great CEO Within:
It’s packed with practical tips, especially the concept of a "Waiting For" list. I started using it, and it brought a ton of mental freedom.

Create a "Waiting For" tracker:
Set up a spreadsheet to track every partner, direct report, and stakeholder. Your assistant can manage it. Anytime you need to follow up with someone, they add it to the list, including next steps, waiting items, and reminders for when to ping again. This will help ensure clear promises, requests, and a running list of topics. (You might have someone own this.)

Ask for help more:
Lean on your senior leadership team and others. Explain your situation, build empathy, and delegate effectively.

Set a higher bar for review readiness:
Create strict standards for how fully developed something needs to be before it gets to you. Early on, I was hesitant to implement this, but it’s crucial for your productivity. For example, have Martha (Jon’s Chief Of Staff) draft a one-pager outlining what should be ready before meeting with Jon. It’ll be painful for a month or so, but it will lead to greater efficiency in the long run. If something isn’t ready, end the meeting. Managers should use their teams to QA and protect their time.

Aggressive prioritization:
Focus on the most important tasks and be willing to leave other things aside week to week. It truly does work even though it feels uncomfortable. For example, “this week, I'll prioritize closing a key partner deal, reorganizing a team, and delivering feedback to this person.”

Leverage Partners and the Board:
Use key stakeholders to maintain a strict operating cadence. For upcoming meetings with partners or critical stakeholders, ensure the team is prepared well in advance, giving you time to review. Hold your direct reports accountable for helping you stay ahead.

Run a tight staff meeting:
Though I’ve never been great at this, running a structured staff meeting can help keep things moving. The more things progress WITHOUT YOU, the more time you have for high-impact work.

Address bottlenecks in coaching:
Use your next month of coaching with Dave to explore what unconscious commitments are making you a bottleneck (assuming you are). What behaviors or beliefs need to change? Set clear goals and have him hold you accountable for improvement.

Get ahead on big/obvious tasks:
Book all board meetings, offsites, major internal reviews, business reviews, and partner QBRs NOW. It’ll free you from last-minute scrambling and allow better preparation.

So there you have it - the CEO productivity guide I made for my replacement, which I continue to give other CEOs.

Have a great week!

-jesse