Do you pass the CEO test?

25 Oct 2026 · 2 min

Watch on YouTube

1:44

In this short YouTube video, Ryan Deiss presents three CEO-style decision scenarios and provides practical leadership advice. The first scenario addresses a growing team (from 8 to 25) where the flat "everyone talks to everyone" culture is breaking down; the recommended solution is to formalize communication through structured meetings and cascading communications, ensuring consistent messaging from leadership down to teams. The second scenario tackles hiring for a role the leader has never held; the advice is to bring in a fractional external expert to help define the role, write the job description, and assist with the interview process before committing to a full‑time hire. The third scenario concerns revenue concentration, where a single customer makes up a large share of income; the suggested approach is to actively diversify the customer base rather than deepening the existing relationship or imposing hard caps. Throughout, the tone is conversational and supportive, offering clear, actionable guidance for CEOs facing scaling, hiring, and risk‑management challenges.

Questions this video answers

A – Implement structured meetings and cascading communications to ensure consistent messaging across the organization.

C – Bring in an outside fractional expert to help define the role, write the description, and assist with interviewing.

A – Actively diversify your customer base to reduce concentration risk.

Chapters

Your team has grown from 8 to 25, and the everyone talks to everyone culture is breaking down. Do you A, formalize communication with structured meetings and reporting lines, B, hire a COO to own this problem, C, protect the flat culture as long as possible and delay the structure?
Yeah, you can't just keep it flat forever. No, it's gotta be A, and what we wanna do is practice what's known as cascading communications. And so we want to be clear at the leadership level. This is what we're saying. Now managers go say the exact same thing to If you're gonna do that, you gotta make sure that everybody agrees. If somebody disagrees, they need to make it clear at the start they're not allowed to disagree in front of their team.
You're hiring for a role you've never had before, and you don't really know what good looks like. Do you A, hire the most experienced person that you can afford and trust them to define it? B, write the job description yourself first, even imperfectly, before hiring? Or C, bring in a fractional expert to help you define the role before hiring full-time?
C. Bring in an outside expert, let them help you write the role, define the role, and ideally help with the interviewing process.
One customer now makes up a large share of your revenue, and it makes you nervous. Do you A, actively diversify, even if it means turning down more of their business? B, deepen the relationship? Concentration is fine if it's sticky. Or C, set a hard cap on what percentage any one customer can represent?
I gotta go with option D. Let's just go get more customers. You know, the problem really is a sales and marketing problem. But if we can solve for the sales and marketing, if we can get more customers, congratulations, customer concentration is solved and we didn't have to get rid of the ones that we had. Yeah, deepen the relationship, but don't deepen it at the expense of going and getting new customers. So none of the above, D.