Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, identifies Damon Lembi’s approach as the clearest evidence that scaling yourself and scaling your company are the same problem. Lembi is CEO of Learn It, a corporate learning company that has upskilled over two million people across three decades. His core claim: great leaders aren’t born and they aren’t made — they’re in the making. Every CEO who believes they’ve arrived has already started falling behind.
When Lembi stepped into the CEO role, he faced what every CEO faces — the question of whether he belonged there. He didn’t wait for the feeling to pass. He built a system to move through it. That same system now shapes how Learn It trains thousands of leaders inside companies across the country.
This episode is for CEOs who feel the gap between the leader they are today and the leader their company needs — and want a repeatable process to close it.
Key Takeaways
- Modeling learning publicly — not just endorsing it — is the single variable that determines whether a corporate learning investment produces results or collects dust. CEOs who open training programs by sharing their own learning journey change what the organization believes is expected of them.
- Imposter syndrome affects leaders at every level. CEOs who say otherwise are, in Lembi’s words, “either a sociopath or just lying to yourself.” The fix is a five-element framework: label the fear, go all in, practice deliberately, let go at game time, and validate yourself rather than waiting for external confirmation.
- Recognizing when a founding operator has hit their ceiling saves significant time, money, and culture damage. The director of operations who built the early operation may not be the COO the next stage requires — and acting on that distinction early is a structural decision, not a personal one.
- Defaulting to “how do we do this differently or better, leveraging AI” before defaulting to the old process is what separates teams building future capability from teams managing present tasks. CEOs who haven’t moved on AI are already a year behind.
- The workforce entering companies in the next few years is the last generation CEOs will lead using only human management skills. The next cohort will require skills for managing human-agent hybrid teams that most companies are not building yet.
The Five-Element Framework CEOs Use to Beat Imposter Syndrome
Damon Lembi built his framework for overcoming imposter syndrome during his years as a Division I baseball player at Arizona State — and has applied it in every leadership transition since.
Step one is labeling. Lembi calls it “purposeful awfulizing.” Before moving into a new role, ask: if this doesn’t work out, what is the absolute worst thing that could happen? “Maybe I get fired. Maybe I get demoted. But is it something you can overcome? Because if it’s something that you can overcome where you’re not gonna bankrupt yourself or your company, you could see what the fear is.”
Step two is going all in. “There’s no shortcuts to hard work. There’s no hacks.” Lembi’s argument is direct: maximum effort crowds out limiting beliefs. When you are genuinely putting in the work, the mental space for self-doubt shrinks. He applied this to keynote speaking — logging reps in practice until confidence followed competence, not the other way around.
Step three is deliberate practice on weak spots, not comfortable ones. “It’s easy to get out there and just practice things and work hard on areas that you’re comfortable with.” The discipline is to target the gap. For Lembi, that meant isolating one specific speaking transition — bridging from topic to topic — and drilling it repeatedly. For a CEO, it might be the difficult conversation they keep postponing or the board presentation they keep softening.
Step four is letting go at game time. Once the preparation is done, stop thinking about technique. “Whether you’re stepping into the batter’s box or you’re stepping on stage, it’s time to learn and let go.” Win or lose, the rep is a learning opportunity.
Step five is self-validation. Lembi credits author Steven Pressfield with this one. “We don’t do enough of it. We’re always looking for other people to give us kudos. Take some time, in your inner self, to say, hey, pat on the back — because you tried something where a lot of people just pass up those opportunities.”
Glenn Gow reinforced this directly from his coaching experience: CEOs rarely receive positive feedback from boards or from their teams. The CEO has to supply their own perspective calibration. “You often don’t get positive feedback from the board or from anyone else. So it’s up to the CEO to actually acknowledge themselves from time to time.” One of Gow’s clients called in distress over missing quarterly numbers — until Gow pointed out that the client had just posted the best quarter in company history. The CEO had no external signal to correct his self-assessment. He had to learn to supply one himself.
How CEOs Model Learning to Scale Organizational Culture
Damon Lembi has worked with thousands of companies through Learn It. He has a clear answer on what separates organizations that build genuine learning cultures from those that buy training programs and get nothing back.
“Leadership, starting with the CEO, models it themselves.”
When a CEO opens a company-wide training kickoff — whether in person or virtually — and shares their own learning journey, the message lands differently than any internal communication can. “If the CEO comes in and just says, ‘this is so important for us, this is why I believe in learning and development,’ or they even share some of the learning that they’ve done — I think that makes a world of difference.”
Lembi is explicit about the opposite case. He has walked away from contracts with CEOs who described their training investment as a checkbox exercise. “I’ve had conversations with CEOs who will basically tell me, ‘we’re just doing this for checkbox reasons. We’re just doing this because it looks good publicly, but they don’t really believe in it.'” His position: if leadership doesn’t buy in, the program won’t work. He doesn’t want his team put in a position to fail.
The modeling requirement extends beyond formal programs. A learning culture requires psychological safety to make mistakes. “You have to have the type of organization where if you make a mistake, you’re not ridiculed for making that mistake — that’s used as a learning opportunity.” If the CEO punishes visible failure, no training curriculum can counteract it.
Lembi also reframes the coaching relationship through the lens of his athletic experience. Athletes receive feedback constantly, publicly, and immediately. A strikeout delivers instant information. The CEO who has never played a competitive sport often lacks the muscle memory for receiving feedback — which means they also lack the model for giving it. As Lembi puts it: “Feedback is a fuel for learning.”
How CEOs Adjust Their Talent Strategy as Companies Scale
Damon Lembi built Learn It as a bootstrapped company in the San Francisco Bay Area, competing for talent against Salesforce, Stripe, and the full weight of well-funded tech. His early talent strategy was deliberate: find people with the right attitude and aptitude early in their careers, give them a sandbox to try and fail and learn, and accept that many of them would stay three to four years before moving on.
The alumni of that approach now run their own companies. One became a CTO at Autodesk. “They all started here at Learn It, which really helped us grow early on, and they’re part of the Learn It alumni.”
But Lembi is direct about where that strategy hits a ceiling. “What got you to five million isn’t going to get you to ten million. And so your director of operations may not be the person you need as a COO.” The question is not whether to make the change. The question is how. Can you find another role in the organization for that person? If not, help them find the next chapter in their career.
The two-path talent model — develop rookies early, bring in experienced operators at inflection points — reflects a scaling reality that catches many CEOs off guard. The people who built the early version of the company earned that position through effort and loyalty. The next stage of the company may need a different profile. Lembi treats that as a structural reality to navigate, not a betrayal to avoid.
How Learn It CEO Damon Lembi Applies AI to Scale Learning Without Replacing It
The workforce leaders are managing today is likely the last one composed only of humans — and Damon Lembi argues most companies are not building the skills they will need to manage what comes next.
Lembi does not hold an ambivalent position on AI. He uses it constantly — to challenge his own assumptions, generate feedback on his performance as a podcast host, build compensation plans, and stress-test decisions. His instruction to every team member at Learn It: “When you be curious and say to yourself, ‘how do we do this different or better, leveraging AI’ — I want that to be like the default.”
His view on AI and corporate learning is not defensive. He sees opportunity. “I don’t think there’s ever going to be a replacement for live learning.” The human element — the real-time conversation, the coaching relationship, the moment of genuine connection — is not something AI replicates. “Speaking to an AI CEO coach bot is one thing, but having a real life conversation with somebody is not gonna go away, at least in our lifetime.”
What AI changes is personalization. Learn It is developing an AI habit coach that allows employees to role-play difficult conversations between formal training sessions. The example Lembi gives: you learned a feedback model in a Learn It class, then forgot it under pressure. Your AI coach is available to practice with before the actual conversation.
Glenn Gow added the ground-level reality from his coaching practice: roughly half of CEOs he works with have not yet moved on AI. His approach is to sit down, identify the business context — manufacturing, services, professional services — and surface ten specific use cases in five minutes. “Their eyes pop open and they say, okay, let’s learn more about this.”
The delay has a cost. Lembi puts it plainly: “If you think AI isn’t ready for your business, you’re already a year behind.” The pace of change removes the buffer that earlier technology shifts allowed. “It used to be you have two years to catch up to the internet or whatever. Now you have no time.”
The Learn-It-All Framework: Principles Damon Lembi Applies to Scale CEOs and Companies
| Principle | What It Means in Practice | Named Evidence |
| Label the fear, then move | Purposeful awfulizing — identify the worst realistic outcome before committing to a new role. If you can survive it, the fear loses its hold. | Lembi moved into the CEO role at Learn It without a business background, applied this process, and has led the company through upskilling two million people over 30 years. |
| Modeling beats mandating | A CEO who publicly demonstrates their own learning investment produces organizational learning culture. A CEO who endorses it without modeling produces a checkbox program that fails regardless of curriculum quality. | Lembi declined a contract with a CEO who confirmed the training spend was a checkbox exercise — the decision protected Learn It’s program outcomes and the client’s employees from a setup where success was impossible without leadership buy-in. |
| Talent strategy must shift at revenue inflection points | The director who got you to $5M may not be the COO you need at $10M. The decision is structural, not personal. | Learn It alumni now hold senior roles at Autodesk and multiple companies — built through the rookie development model — while Lembi adds experienced operators as the company scales past each inflection point. |
| AI adoption requires modeling, not just endorsement | CEOs who use AI daily — for feedback, planning, and assumption-testing — set the default for their teams. | Lembi’s daily AI use across compensation planning and podcast self-coaching produced a team operating instruction: default to “how do we do this better, leveraging AI” before reverting to existing processes — a shift that Lembi describes as the difference between building future capability and managing present tasks. |
| The next workforce requires new leadership skills | CEOs are managing the last all-human workforce. Managing human-agent hybrid teams will require learning investments companies are not currently making. | Lembi has positioned Learn It’s product development — including the AI habit coach for between-session practice — ahead of a skills gap he identifies as the defining leadership challenge of the next decade, with the first cohort of agent-managing CEOs entering that transition within the current hiring cycle. |
Quotes from This Episode
- “Great leaders aren’t born, they’re not made either — they’re in the making.” — Damon Lembi, CEO, Learn It
- “If you say you don’t have imposter syndrome, you’re either a sociopath or just lying to yourself.” — Damon Lembi, CEO, Learn It
- “What got you to five million isn’t going to get you to ten million.” — Damon Lembi, CEO, Learn It
- “The next generation — you’re going to be leading agents and humans.” — Damon Lembi, CEO, Learn It
- “I don’t think there’s ever going to be a replacement for live learning.” — Damon Lembi, CEO, Learn It
Frequently Asked Questions
How do CEOs beat imposter syndrome without waiting for confidence to arrive on its own?
Damon Lembi, CEO of Learn It and author of The Learn It All Leader, developed a five-element framework from his years as a Division I baseball player at Arizona State: label the fear by identifying the worst realistic outcome; go all in without shortcuts; practice deliberately on weak spots rather than comfortable ones; let go at game time to perform rather than analyze; and validate yourself internally rather than waiting for external confirmation. The self-validation step is essential because CEOs rarely receive positive feedback from boards or teams — a reality Glenn Gow confirms from his coaching practice. One of Gow’s clients called in distress over missing quarterly numbers, until Gow identified that the client had just posted the best quarter in company history. No external signal had corrected his self-assessment. Lembi credits author Steven Pressfield with making self-validation a discipline rather than an afterthought.
How do CEOs build a learning culture that actually changes behavior instead of just purchasing training programs?
According to Damon Lembi, who has worked with thousands of companies through Learn It since 1995, the single deciding variable is whether the CEO models learning behavior publicly — not just endorses it. When a CEO opens a training program by sharing their own learning journey, or visibly uses tools and feedback to get better at their own craft, the signal reaches the organization in ways that internal communications cannot. Lembi has declined contracts with CEOs who described their training investment as a checkbox exercise, because his evidence shows that without genuine leadership buy-in at the top, organizational learning programs fail regardless of curriculum quality.
How should CEOs approach AI adoption without falling behind competitors who are already using it?
Damon Lembi argues that CEOs who have not yet moved on AI are already approximately one year behind, and that the pace of AI change allows no buffer period comparable to earlier technology shifts. His approach is to make AI use the team default — instructing every employee to ask “how do we do this differently or better, leveraging AI” before defaulting to existing processes. For his own company, Learn It, Lembi uses AI daily for assumption-challenging, compensation planning, and self-coaching as a podcast host, while investing in AI-integrated learning products including a habit coach for between-session practice. His broader argument: the workforce leaders are managing today is likely the last one composed only of humans — the next generation will require skills for managing both agents and people simultaneously.
CEOs Work with Glenn Gow to Scale Their Companies and Careers
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.
