The CEO’s Do-Not-Delegate List

Welcome to Peaceful Growth, where you will find actionable tips to grow your agency to $10M (without working overtime).

As a CEO, there’s one question I keep coming back to:

What should I do myself—and what’s okay to delegate?

I found one of the clearest answers in Chapter 9 of The Road Less Stupid by Keith Cunningham (a book I’ve recommended more than once in this newsletter).

The chapter is titled:

“A CEO Should Never Delegate…”

And it changed the way I think about my role.

Here are those 7 jobs from the book, plus a few more I’ve learned from experience.

1. Clarity on Point A and Point B: Only you can zoom out and see the full picture—where the business truly stands today and where it needs to go. No one else has the vantage point or responsibility to align dreams with reality.

2. Identify the Gap and the Obstacle: Your team sees symptoms, but only you can connect the dots and uncover the real obstacle that's holding the business back. This kind of strategic thinking sits at the top—it can't be crowdsourced.

3. Design the Plan and Machine: The CEO must design the right plan and build the right system to overcome the obstacle and move from A to B.

4. Allocate Resources: You control the levers—budget, time, people. If someone else is making resource calls without owning the vision, priorities will drift and the business will stall. Only the CEO can balance short-term survival with long-term goals.

5. Top Grade for A Players: Nobody else will care about the quality of your team as much as you do. Others might settle—only you will fight to raise the bar and protect the culture and momentum of your company.

6. Build the Organization Chart: Structure determines speed and clarity. If you don’t shape how your team is organized, you’ll end up with overlapping roles, power struggles, and confusion—and you’ll be the one cleaning up the mess.

7. Create the Culture: Your daily actions, decisions, and conversations set the tone for how your company operates. You can’t outsource leadership by example—culture flows from the top, and that means it flows from you.

A Few More Tasks I’ve Learned a CEO Should Never Delegate

8. Firing Toxic or Underperforming People: Delegating performance management is okay, but you must pull the trigger on major exits. Few—especially if it affects morale.

9. Fixing Broken Loops: What’s that one issue that keeps coming back? You don’t need to solve every problem, but if something is broken across departments (like bad handoffs or unclear scopes), you must lead the redesign.

10. Testing Big Growth Bets: A new service, geography, or client segment? When it’s unproven, it’s yours. Once it works, you can hand it off. But innovation always starts with the founder.

11. Approving Big Financial Decisions: Should we hire 3 engineers or spend that on marketing? CFOs can model, but CEOs choose. Especially in a small company, money is strategy.

12. Thinking Time + Strategic Decisions: Are we still solving the right problem? Nobody else will sit and do the “thinking work” for you. Strategy isn’t just a deck—it’s quiet reflection and bold decisions.

13. Hiring Your Direct Reports: COO, CTO, Head of Delivery, etc. You can delegate interviews, but final decision-making and cultural fit judgment for key leadership roles must be yours.

14. Negotiating high-value Contracts: Some CEOs think contract negotiation is a “small task”—but it’s anything but. A founder’s involvement in key deals can make a massive difference. Say you secure just 5% more on a $15K/month retainer. Over 10 years, that’s an extra $90,000 from one client. These moments may seem minor, but they compound. And no one is better positioned to close, upsell, or protect margins than you.

15. Reviewing the Balance Sheet and P&L Regularly: Are you reading the story behind the numbers? Cash hides mistakes. Only the CEO can connect financial data to strategic decisions. You can’t delegate financial vigilance.

16. Defining (Updating) Rates for Your Products and Services: Only the CEO can truly weigh market trends, brand value, team capacity, and long-term vision when setting or adjusting rates. If you undercharge, the business bleeds. If you overcharge without value, you lose trust. This decision sits at the intersection of growth, brand, and survival—too important to outsource.

17. Solving High-Impact Business Problems: Will this decision impact revenue by 20% or more? When a problem or opportunity could significantly change your top line, it's not someone else’s call—it’s yours.

18. Leading the Company Through Winter Seasons: Who leads when growth stalls or storms hit? Slow quarters, tough markets, or internal chaos—this is when your team looks to you the most. You can delegate wins, but not the hard seasons. Leadership in winter is a CEO’s job.

📎 Bookmarked, Highlighted, and Worth Sharing

#1. The “Remove the Logo” Test: How Brand Differentiation Drives SEO Success

My friend Alex Denning—founder of a digital marketing agency and writer of a great newsletter on modern marketing—recently shared a fresh take on how to win at SEO.

You’ll need a subscription to read the full article, but I’ve saved a version with my highlights—worth your time if you care about SEO that actually works.

#2. A Masterclass on Business Valuation—and Knowing When to Hire a CEO

My founder friend Manish recently made a big move: he hired a CEO to run his agency.

When I asked what inspired the decision, he pointed me to this tweet (and the video linked in it).

It’s a sharp take on business valuation, founder self-awareness, and knowing when it’s time to step back from day-to-day operations.

Did you enjoy this newsletter? Check out my other stuffs too:

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One More Thing...

A lot of you have asked about the tools I use to stay productive and grow my agency.

So, I put them all in one place—organized by category:

• Writing Tools ✍️
• Productivity Apps ⏳
• Skills and Courses for Founders 🎓

And more.

You can check them out here.

Hope it helps! 🚀