my ceo productivity system

Good morning Predictable Revenue community,

First up, thank you to everyone that voted in the poll and replied back with suggestions and ideas. The team and I worked through all of them and settled on our final title / subtitle combination:

The Terrifying Art of Finding Customers
A Sleep-Deprived Founder’s Guide to Revenue

I especially want to thank everyone that sent me their ideas that we didn’t use, your contributions helped us explore all the different angles to make sure that we were super happy with where we ended up. So even if we didn’t go your direction, know that your feedback was helpful. My favourite comment from the poll was:

“That's me. I am too tired to even be afraid.”

I’m currently waiting on my last round of substantive edits and should get those back in the next two weeks. Then I’ll have my final chance to add new content to the book before it goes to the copy editors (grammar and spelling). I hope to have some initial cover designs to show off next week but I haven’t seen anything yet.

Okay, enough book business, here’s the email:

tl;dr

• Send a weekly email every Friday that outlines what you accomplished this week and your top priorities for next week

• I expanded the PS of this email to include some bonus content from a chat I had with another founder this week on outbound

Stepping into the CEO role for the first time was weird. I had the title, but I didn’t feel like I deserved it - and I definitely wasn’t acting like one. It took years to accept the burden that comes with the job. In the early days, it was easier. With a small team and mostly individual contributor (IC) responsibilities, I knew what I needed to do each day and could see tangible results, whether it was closing a deal or updating a marketing page.

But as the team grew and I transitioned into managerial and executive roles, I got lost. The work became less visible and harder to measure. How do you quantify the impact of a good one-on-one or a day spent on strategy? It didn’t feel as satisfying as shipping something or landing a customer.

I always felt like I had three full-time jobs competing for my attention: admin (finances, forecasts, legal), IC work I hadn’t hired for yet (sales, customer success, product), and leadership (strategy, planning, culture). Any one of those could easily fill a day, and trying to juggle them all led to 12-14 hour workdays where only the last two hours felt productive because I’d finally get to something tangible.

In the early days, my inbox was my main productivity tool. Every email felt urgent, and clearing my inbox gave me a fleeting sense of accomplishment. But once it was empty, I didn’t know what to do next. I’d refresh it or check Slack, staying reactive instead of proactive. What I lacked was an executive-level productivity system.

When I was in sales, I had my system nailed down: active deals, prospecting accounts, nurture opps - each managed with a clear process. As a CEO, I needed a new system but didn’t build one. Instead, I stayed stuck in my inbox.

Over the years, I’ve tried every productivity app and tactic, but what works best for me is paper. At the end of each week, I write the top 3-6 priorities for the next week on a post-it note. It’s simple, visible, and helps me focus, especially after back-to-back meetings. Checking things off feels great, and it orients me when I need direction.

Paper works for me now because I’ve simplified my workload to focus on writing. But there was a time, during VoltageCRM, when my cofounders were remote and nervous about our progress. My post-it system didn’t give them visibility, so I started emailing the team every Friday with what I’d accomplished and my plans for the next week.

That small act of public accountability did wonders. It forced me to reflect, gave me a greater sense of accomplishment, and reassured the team that I was moving the ball forward. This habit brought clarity to my work and better alignment with the team.

If you’re in a similar spot, here’s how to start:

This afternoon, open your inbox and create a new email addressed to your team. Let them know:

• What you accomplished from this week’s top 3 priorities

• Your top 3 priorities for next week

That’s it. It’s simple, visible, and creates accountability. Over time, this habit will help you clarify your focus, track progress, and keep your team aligned. It worked for me, and I hope it works for you too.

Thanks for reading,

Collin

The PS (space for extra content that didn’t fit the above theme)

PS1: I’m looking to add a few stories on early growth to the book, ping me back here if you’re interested. Format would be a short podcast on the topic → 30-45 mins total time commitment.

PS2: Here’s a nugget from a conversation I had this week with another founder:

We were talking about outbound sales and how most founders approach planning for it the wrong way. They’ll try it for a few months, look at the results, and think, “This isn’t working.” The problem is, they’re measuring results too early and not accounting for how outbound actually works. It’s not a quick win - it’s a long game.

When we hired our first SDR, Pete, I almost made the same mistake. For the first six months, we closed nothing. It was slow the next 6 months too, Pete booked meetings, but we were closing maybe one deal every other month. By month 12, something changed: we started closing deals at twice the rate. When we looked closer, we realized it wasn’t because Pete had suddenly gotten better at cold outreach - it was because he’d been playing the long game all along.

Pete had spent his first year working his "nurture opportunities." These were leads who weren’t ready to buy right away but hadn’t said no either. Most founders forget about those people, but Pete didn’t. He had a system for staying in touch, following up consistently, and keeping himself top of mind. By month 12, those nurtured prospects started coming back - ready to buy. His persistence turned one deal every other month into multiple deals every month.

That’s the real secret of outbound: it’s like a flywheel. It takes a ton of effort to get it moving, and most people give up before it starts to turn. But once it does, it builds momentum. Every follow-up adds to the future pipeline. Every nurtured lead turns into a deal you wouldn’t have had otherwise. The trick is sticking with it long enough to see that momentum kick in.

The biggest mistake I see is founders who focus only on the “cream off the top” of outbound - the leads ready to buy in the next 90 days - and give up before they’ve worked the milk underneath. Outbound isn’t just about landing the easy wins; it’s about creating a system to stay in front of prospects until they’re ready.

So here’s my advice: don’t measure outbound results too early. Track your nurture opportunities. Build a process to stay in touch. And most importantly, don’t stop before the wheel has a chance to turn. Outbound works - if you give it time.