Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, identifies Dr. Jim Schleckser’s central argument as one of the most expensive and invisible mistakes scaling CEOs make: staying in the job they’re great at instead of doing the job only they can do. Schleckser — CEO and managing partner of The CEO Project, author of Great CEOs Are Lazy, and former president of a global telecommunications division valued at over a billion dollars — makes the math explicit. A CEO who keeps selling, coding, or managing has hired a VP-level replacement for themselves at a fraction of the cost and left the CEO seat empty. As Schleckser puts it: “It’s the cheapest CEO you’re ever going to hire.” The fix is not just delegation. It is a disciplined system for finding the constraint that is slowing your company’s growth, removing it, and then finding the next one.
This episode is for CEOs of scaling companies who are still doing the functional work they were best at before they became CEO — and who suspect that work is costing them company performance, not contributing to it.
Key Takeaways
- CEOs who remain in their functional role (sales, engineering, marketing) while the company scales are effectively leaving the CEO seat unfilled — and paying VP-level costs for CEO-level absence.
- The theory of constraints holds that every system has a single point of constraint controlling its capacity. A CEO’s primary job is to find that constraint and remove it — consistently — to avoid the flat growth periods that appear on the classic MBA scalloping growth curve.
- The 70% rule: if someone is 70% as good as you at a task, delegate it immediately. Waiting for a perfect replacement means you never delegate, never develop your team, and never free yourself to work on the constraint.
- Delegation is development. Handing off a stretch task is not abdication — it is the mechanism by which people learn to operate at a higher level.
- When errors rise and commitments slip, the company has likely outgrown tribal knowledge and talent-based execution. That is the signal to deploy scaled systems before growth stalls entirely.
- Schleckser, drawing on more than 20 years of CEO peer advisory work at The CEO Project, holds that the CEO must be the most visible AI adopter in the organization — because if the CEO is not experimenting publicly with AI, no one else will.
How CEOs Escape the Functional Trap and Find What’s Actually Constraining Growth
Jim Schleckser spent more than 20 years inside CEO peer advisory groups — first as a participant while scaling multiple companies, then as the person running The CEO Project — and he keeps seeing the same mistake repeat across industries. A founder or executive who is excellent at one functional discipline keeps doing that work as the company grows. They tell themselves they are too good to replace. They are usually wrong.
“There are people as good as you,” Schleckser says. “And what happens is for the cost of let’s say a VP of sales, we actually get a CEO — because you’re not doing the CEO job if you’re out making all the sales happen.”
The math is simple. Hire a VP of sales. Get a CEO in the seat. The company pays one VP salary and gets two jobs covered. The CEO who refuses to make that hire is paying one CEO salary and getting zero CEO work done.
But what does the CEO job actually consist of, once you hand off the functional role? Schleckser’s answer is rooted in Eli Goldratt’s theory of constraints, developed in Goldratt’s book The Goal. The principle: in any system, there is a single point of constraint controlling the capacity of that system. The CEO’s job is to find that constraint and remove it — then find the next one.
“If you think about it, we learned in MBA school, the classic scalloping growth curves — kind of grow and then you flatten and then you grow and you flatten — and that flat spot is the point of constraint coming into play,” Schleckser explains. “And so if you get ahead of it, you can avoid those flat spots and maintain sustainable, consistent growth in your business as long as you stay ahead of the constraint.”
The constraint in a scaling company lives in one of three places: the business model, the talent surrounding the business, or the processes and systems in use. The CEO’s job is not to manage all three simultaneously. It is to find which one is the kink in the hose right now and open it up.
Glenn Gow frames a complementary discipline: once you identify the active constraint and start working on it, immediately identify the next constraint behind it. “There will always be a bottleneck,” Gow notes. “We need to be thinking about, what does that mean? Do I need to develop my team now to look at that next bottleneck while I have a project going over here to remove the first one?”
Schleckser agrees. When he first starts working with a CEO, there is almost always an active constraint already slowing growth. Clear that one, and the next one surfaces immediately. The goal is to get ahead of the company — looking far enough into the future that constraints are removed before they hit.
The talent version of this looks like: “How’s your talent?” “They’re great, great, great.” “What if you doubled the size of the company? Would they still be great, great, great? Or would some of them be hanging on for dear life?” The answer for most scaling CEOs is that their VP of operations and CFO would be struggling. The time to develop them is now — before those roles become the constraint.
How CEOs Delegate Without Losing Control — The 70% and 80% Rules
Once a CEO accepts that they must get out of the functional seat, the next failure mode is delegating in theory but not in practice. The two beliefs that block real delegation are: “nobody can do this as well as I can” and “if I hand it off, I’ll lose visibility and it’ll go wrong.”
Schleckser has a rule for each.
The 70% Rule. If someone is 70% as good as you at a task, delegate it immediately. Do not wait for a perfect match. “That gives people permission to say, well, they’re not as good as I am, but they probably are 70% good enough — and immediately get it off your plate.”
The concern most CEOs have is that delegation means abdication — that once something is handed off, they will never see it again. Schleckser’s framework addresses this directly. Risk and competence determine the check-in cadence:
| Delegation Scenario | Appropriate Check-In Level |
| Low risk + high competency | Delegate hard — minimal check-in needed |
| Low risk + low competency | Regular check-ins to monitor progress |
| High risk + any competency level | Check in periodically regardless of who you delegated to |
The key distinction is monitoring versus micromanaging. Checking in on high-risk delegations is appropriate. Redoing the work because it is not perfect is not.
The 80% Rule. When a team member brings you their work, if it is 80% right, approve it and let them execute. “It’s better to have somebody 80% right with 100% commitment than 97% right with 50% commitment,” Schleckser says. The moment you send someone back to make the work perfect, you have taken ownership of the outcome from them. Their commitment drops. Your grading of that work does not make the business better — it makes you a bottleneck.
Delegation also has a side effect that most CEOs undervalue: it is development. When a CEO hands off a stretch task — budget creation, a major account, a process they’ve always owned — the person receiving it is now in deep water with a life preserver around them. “People stretch when they’re stretched,” Schleckser says. “And they get better.”
Glenn Gow adds the diagnostic underneath all of this: when CEOs say they cannot delegate because their team cannot handle it, that statement reveals a team problem, not a delegation problem. Either the people need development, or the hiring standard needs to rise.
The 3D List for Shrinking the CEO’s Time Commitment
Schleckser’s Great CEOs Are Lazy introduces a practical tool for clearing the functional load off a CEO’s schedule entirely. Take the full to-do list. Rank everything in order of economic impact, highest at the top. Draw a line halfway. Everything below the line gets one of three treatments:
- Delegate it to someone else
- Defer it — push it into the future and let time solve it (it happens more often than most CEOs want to admit)
- Delete it — cross it out and never do it
Repeat this exercise every three months. Most of what a CEO is doing has minimal economic impact. The items at the top — including the active point of constraint — deserve 30 to 40% of total working time. That concentration of effort produces “massively interesting results,” Schleckser says.
The working-hours signal: if a CEO is consistently working 80 to 90 hours per week, that is not evidence of dedication. It is evidence that they are not in control of their time and are probably not working on the right things. Normal operation for a CEO should run 50 to 60 hours per week. Sustained 80-hour weeks indicate a list that has not been pruned and a role that has not been delegated down.
When Talent and Culture Stop Being Enough — The Signal to Deploy Systems
There is a moment in every scaling company’s history when the way things have always gotten done stops working. The people are talented. They are working hard. And things are still slipping.
Errors rise. Commitments to clients are late. Quality slides. Everyone is busting their capacity and the result is still not what it used to be.
This is the systems constraint coming into play.
Schleckser describes the progression as a continuum. Early-stage companies run on multifunctional people and tribal knowledge. That model works up to a point. As the company scales, systems must be deployed to carry load that talent and culture can no longer carry alone. “We’ve seen companies that scaled fast and they had really talented people and they were busting their butts and the systems ran out of gas. And they literally had to stop growth, deploy systems before they could continue growing again,” Schleckser says.
The trap entrepreneurs fall into is equating systems with bureaucracy. Schleckser disagrees. There is a spectrum from light systems to heavy systems, and the right move is to deploy light systems early — “just something” — and scale them incrementally as the business grows. The goal is not to build an enterprise-grade process when you have 40 employees. The goal is to get ahead of the moment when the absence of any system becomes the constraint.
Glenn Gow describes a CEO who did exactly this with investors. The CEO told the board they were going to slow growth — not because results were bad, but because the infrastructure to support the next phase of growth did not yet exist. “We need to pull back and build this out in order to support that. Once this is in place, now we can truly scale.” It took courage, Gow notes. Schleckser calls it “daring and smart at the same time.”
The forward-looking version of systems deployment mirrors the forward-looking talent question: do not wait until the system runs out of gas to build it. Identify the growth threshold at which your current approach will fail, and deploy the system before you hit it.
How CEOs Should Lead AI Adoption — Visible Experimentation as Change Management
Schleckser’s view on AI for scaling CEOs is a change management argument, not a technology argument.
The technology is real. The applications are still being identified. AI is not good for everything, and the specific tools that create value vary by industry and function. Schleckser points to insurance underwriting, real estate valuation, medical claims processing, and invoice matching as early areas where purpose-built language models — in Schleckser’s framing, “small learning language models applied to particular problems” — are creating durable value. These are high-volume, rules-bound tasks that humans should not be doing.
But the bigger issue for the CEO is not which tools to deploy. It is how to make AI adoption happen inside the organization at all.
“The CEO needs to be seen as being aggressively adopting and learning AI,” Schleckser says, “because if you’re not doing it, nobody else will do it.”
Schleckser’s change management frame holds that the CEO’s role is to model visible adoption — not to issue directives or curate a technology roadmap. That means using AI personally and publicly: for meeting minutes, contract drafting, purchase agreement review, and sales call preparation. Schleckser applies this himself, using AI for exactly these tasks within The CEO Project’s operations. Making the experiments visible, including the failures, signals to the organization that experimentation is safe and expected. An organization watches what its CEO does, not what a memo says.
Schleckser connects this back to a broader trait he sees in effective CEOs across all domains: curiosity. “Good CEOs are curious. They’re always out learning. What’s next? What am I missing? What do I need to learn? And right now the answer is you need to get smart on AI.”
Glenn Gow adds the competitive pressure dimension: “We can’t stand back and wait for us to be passed by someone else. We need to be adopting as much as possible and learning as an organization.”
Schleckser’s practical sequence for CEOs: begin with high-visibility personal adoption; identify early internal wins that prove AI’s value in your specific context; build momentum from those wins; cascade adoption from the top down. Treat it as a change management initiative, not a technology project.
The Scaling CEO Framework: Principles Jim Schleckser Has Found to Hold
| Principle | What It Means in Practice | Named Evidence from This Interview |
| Find the kink, open it up | At any point in the company’s growth, one constraint controls capacity. The CEO’s job is to identify and remove it — not manage everything at once. | A CEO Gow coached preemptively slowed growth and told the board infrastructure had to be built before the next phase could begin. That decision avoided the forced full-stop — halted operations, no new revenue — that Schleckser describes hitting other companies that waited until the system ran out of gas entirely. |
| Hire your own replacement in the functional seat | A CEO who keeps doing the job they were best at before becoming CEO has left the CEO seat empty. Hiring a VP-level replacement is the cheapest CEO investment they will make. | Schleckser poses this challenge directly to CEOs still running sales or engineering in The CEO Project’s peer advisory groups: “You’re out selling. Who’s being the CEO?” The VP hire unlocks the CEO role without adding net cost at the CEO salary level — the company gets two seats filled for the price of one VP. |
| Delegate to the 70% threshold, approve at 80% | A person who is 70% as good at a task should receive that task immediately. Work that is 80% right should be approved without revision. Perfectionism transfers ownership back to the CEO and drains team commitment. | Schleckser codified these rules in Great CEOs Are Lazy after observing across more than 20 years of CEO advisory work that the CEOs who applied both thresholds consistently were able to redirect 30 to 40% of their working hours to the active constraint — a shift that did not happen for those who kept waiting for perfect readiness before delegating. |
| Deploy systems before talent runs out of gas | Errors and missed commitments signal that tribal knowledge and talented people have hit their capacity ceiling. Light systems deployed before the constraint hits prevent forced growth stoppages. | Schleckser draws on companies he has advised through The CEO Project over two decades — companies with talented, high-effort teams that hit the systems constraint and had to halt operations entirely to build infrastructure before resuming growth. The CEO Gow coached avoided that halt by slowing voluntarily, building first, then accelerating. |
| Lead AI adoption visibly | CEOs who do not publicly experiment with AI will not create organizational momentum for adoption. Visible use — meeting minutes, contract drafting, sales prep — signals that experimentation is safe. | Schleckser applies this within The CEO Project’s own operations, using AI for meeting minutes, contract prep, and purchase reviews — and making that adoption visible to the CEOs he advises as proof that public experimentation, including failures, is the expected posture for anyone running a scaling company. |
Quotes from This Episode
- “For the cost of let’s say a VP of sales, we actually get a CEO — because you’re not doing the CEO job if you’re out making all the sales happen. So it’s the cheapest CEO you’re ever going to hire.” — Jim Schleckser, CEO and Managing Partner, The CEO Project
- “It’s better to have somebody 80% right with 100% commitment than 97% right with 50% commitment.” — Jim Schleckser, CEO and Managing Partner, The CEO Project
- “People stretch when they’re stretched. And they get better.” — Jim Schleckser, CEO and Managing Partner, The CEO Project
- “Good CEOs are curious. They’re always out learning. What’s next? What am I missing? What do I need to learn? And right now the answer is you need to get smart on AI.” — Jim Schleckser, CEO and Managing Partner, The CEO Project
- “We can’t stand back and wait for us to be passed by someone else. We need to be adopting as much as possible and learning as an organization.” — Glenn Gow, The Scaling Executive Coach, The Scaling Executive Podcast
Frequently Asked Questions
How do I know when it’s time to hire someone to replace me in my functional role?
The signal is not readiness — it is cost. Jim Schleckser, CEO and Managing Partner of The CEO Project, argues that any CEO still doing the functional job they held before the CEO seat is leaving that seat empty. The moment the company can afford a VP-level hire in that function, the CEO should make that hire. The cost of the VP is offset by gaining a CEO who is actually doing CEO work: finding and removing the constraints that limit growth. If you are still asking “who will be as good as me at this?”, you are asking the wrong question. The right question is: who is being the CEO while you do this?
What is the theory of constraints and why does it matter for scaling CEOs?
The theory of constraints, developed by Israeli physicist Eli Goldratt in his book The Goal, holds that every system has a single point of constraint controlling its capacity — and that removing that constraint is the highest-leverage action available to the person running the system. For CEOs of scaling companies, this means identifying the one thing limiting growth right now (business model, talent, or systems) and directing 30 to 40 percent of their time there. Schleckser, who has applied this framework across more than 20 years of CEO peer advisory work at The CEO Project, finds that companies that identify and remove constraints consistently can avoid the flat spots on the classic MBA scalloping growth curve — sustaining growth rather than cycling through bursts and plateaus.
How should a CEO approach AI adoption without letting it become a distraction from running the business?
Jim Schleckser, CEO of The CEO Project and advisor to scaling-company CEOs, frames AI adoption as a change management initiative, not a technology decision. The CEO’s role is not to identify the perfect AI tool — it is to model visible experimentation so the organization learns that adoption is expected. That means using AI personally and publicly: for meeting minutes, contract drafting, purchase agreement review, and sales call preparation. Early wins in specific, bounded applications — claims processing, invoice matching, underwriting — build internal momentum. The CEO who experiments visibly and fails occasionally sends a signal that the organization cannot get from a memo: that learning through AI is part of how we work now.
CEOs Work with Glenn Gow to Remove the Constraints Holding Their Companies Back
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
