Transitioning from Founder to Leader

At 10 employees, I led every meeting. At 30, I started removing myself more. At 60, I had to completely hand them over. Here are the 3 leadership transitions every CEO of a scaling solar company faces: 1/ The Manager Phase (0-10 employees). You do everything: sales meetings, crew check-ins, brainstorming installs. This works when everyone knows each other and you can track every job in your head. The transition begins when you hire people to take specific functions off your plate. Let them own those areas completely. You'll be successful if you stop doing the work and start managing the people doing the work. 2/ The System Building Phase (10-30 employees). You're managing managers but still making every decision. You start building processes and systems: Writing policies. Buying software. Creating departments with clear ownership. During this phase: → We became a B-Corp → Hired an HR professional → Bought HubSpot instead of using free tools → Made our head of Operations the highest-paid person You'll be successful if decisions get made without you. Systems run the business, not your memory. 3/ The True Trust Phase (30+ employees) You've built systems, but you're still the final decision-maker on everything. Here, your goal is to step out of daily operations entirely. Let your management team run their departments. What this looked like for me: → Stopped leading sales meetings → Stopped giving warehouse speeches → Let the Director of Sales run the show → Managed through dashboards and KPIs, not daily check-ins You'll be successful if the business runs for weeks without your input. You work on strategy, culture, not operations. — My biggest lesson was that each transition meant letting go of control to gain leverage. Most solar CEOs get stuck at transition 2. They build systems but won't step aside. The company hits a ceiling because the CEO becomes the bottleneck. But if you want to scale beyond 50+ installs per month, you need systems and managers, not a heroic founder. — Which transition is your solar company stuck on? Photo from the recent RE+ event.

Many founders struggle with identity shifts as their startups scale. And that's the hardest transition I've seen founders face. You're no longer the hands-on entrepreneur wearing every hat. You're evolving, and so is your role. But with that evolution comes fear, grief, and a sense of losing control. What makes it harder? It's not just you feeling this way—your team feels it too. When a founder's role shifts, the entire organization feels the ripple effects. It's not just about hiring more people or delegating tasks; It's about managing the emotional and strategic transitions that come with growth. The founder journey isn't just a job—it's an identity. And when that identity morphs, it can feel like an existential crisis wrapped in a business challenge. Ready to navigate this shift smoothly? Here's a 5-step framework designed to help you lead this shift for both yourself and your team: 1/ From Control to Systems →  Build scalable systems, empower your team 2/ From Impostor Syndrome to Leadership Clarity →  Embrace your role as a leader 3/ From Isolation to Alignment →  Build a trusted circle, align your team 4/ From Hands-On to Hands-Off →  Guide strategically, not operationally 5/ From Grief to Celebration →  Celebrate growth, honor your roots 👉 Swipe to discover: →  How each step affects you and your team →  Actionable steps to implement each transition — What's been the hardest part of scaling your role as a founder? Share 👇 — ♻️Share with a fellow entrepreneur who needs this 📌 Follow me for more actionable insights from the startup trenches

This past week it seemed like everyone I know was talking about Paul Graham’s Founder Mode essay. I recently transitioned from CTO → CEO and had assumed the strange feeling I had was just ‘being a CEO.’ After reading the blog post, I suspect the feeling is closer to ‘being a founder-CEO.’ Some thoughts on that transition: 🔎 Increasing your breadth but maintaining focus As CTO of Metronome, I was really close to the means of production - reading PRDs, writing PRDs, watching demos, reading code. As I’ve transitioned to CEO, I still want to be deep in the weeds, but I’ve had to let go of R&D a bit, to focus on other parts of the business. At Metronome, this means that I’m really focused on Marketing right now. Constantly assessing and adjusting your focus is a key part of the job. 🚀 Nature abhors a vacuum If you’re doing your job as CTO at an early stage company you’re likely a load bearing beam. You’re shipping code, writing specs, doing design, your job doesn’t change that much so things get built around you. As CEO, your job can shift day-to-day, week-to-week and this can leave little eddies and vacuums as you move around the org. My only advice here is to try to stagger your transition by first transferring out of CTO and then transition in to CEO. 🤑 The buck stops with you CTO is kind of a sweet gig. You get to make lots of fun decisions and steer the product toward the outcome you’ve been dreaming of. Billing is a fractal puzzle, I’m never bored. AND, you get to do all this stuff without needing to run a board. Ultimately, if you mess up bad enough someone else has to help you clean it up. As CEO, you’re literally the last line of defense. Even though I am an equal co-founder, I really under-appreciated the psychological burden of knowing that there is no one there to help pick up your mess. 👁️ All eyes on you CTO is a pretty behind-the-scenes gig. Sure, you might be the life of the party or the star of the back-end show, but almost by definition you’re not the face of the company in public or internally. There’s an old adage that goes like ‘If your boss is smiling, you’re happy.’ Keeping that smile is the CEO’s job. The problem is that things go wrong all the time. Maintaining the cheery disposition and optimism is not always an easy task. Perhaps the power posers were on to something. 💚 1 is the loneliest number Before you become CEO, you have some notion of ‘peers’. They may report to you, but you can still kvetch about the boss. When you become the boss, all those former peers now report to you and the community disappears. The best advice I’ve gotten is to develop relationships with other CEOs (perhaps more specifically Founder-CEOs, per Paul Graham) to make sure that you have someone you can confide in.

The statistics are sobering: 70% of startups fail due to premature scaling, and 40% fail from missing market needs. Having walked this path myself, I've learned that the transition from technical founder to strategic leader is perhaps the most critical evolution in a startup's journey. Three key challenges emerge during this transition: Strategic Vision Paralysis - Moving from technical specifications to market-driven strategy requires a fundamental mindset shift. Your product brilliance must now translate into business acumen. Operational Chaos - As teams grow, the informal processes that worked for 5 people crumble under the weight of 15, 25, or 50. Suddenly, your role becomes more about systems than solutions. Leadership Identity Crisis - The hands-on technical contributor must evolve into a delegator, coach, and strategic thinker. This identity shift challenges even the most self-aware founders. The solution isn't mysterious, but it requires intentionality: * Regular vision alignment sessions with your team * Documented operational systems that scale with growth * Personalized leadership coaching * Data-driven decision frameworks (which McKinsey reports can increase profitability by 19x) The most successful founders recognize that scaling isn't just about hiring more people or raising more capital—it's about transforming yourself from the technical expert who built the product into the leader who builds the company. What's been your biggest challenge in making this transition? Has anyone found particularly effective leadership development resources for technical founders? #StartupLeadership #ScalingStrategies #TechFounders From Tech Whiz to People Pro: Scaling Your Startup with Heart and Smarts 🚀 – Expertise Guides

One of the biggest transitions in any career is going from manager to leader. It sounds simple—but it’s a powerful shift, and it doesn’t happen overnight. When you’re managing, your focus is execution: making sure the work gets done, hitting deadlines, solving the immediate problems. But leading? Leadership is about vision. It’s about stepping back to see the big picture—and helping others see it, too. Here are a few shifts I’ve seen (and lived) over the years: ✔️ From taskmaster to culture shaper: Leaders connect the work to something bigger. They help people understand why their work matters—and how it ladders up to a shared mission. It’s not just about getting things done. It’s about creating an environment where people feel energized and encouraged. Where they can grow, feel heard, and want to show up and contribute. Culture doesn’t just happen—it’s shaped every day by what leaders choose to emphasize and how they show up. ✔️ From solving problems to asking better questions. You don’t need to have all the answers. In fact, you shouldn’t. Leaders create space for new ideas and unexpected solutions. That means asking better questions, being curious, and letting new information shift your thinking. When you lead with curiosity instead of certainty, you get better outcomes—and better relationships. ✔️ From managing outcomes to investing in people. The best leaders I know care about performance—and they care just as much about potential. They give people opportunities to build on their strengths. They invest in development. They make space for mistakes, because they know that’s how learning happens. Leadership isn’t about perfection—it’s about helping others grow into their own leadership, too. So if you’re in the middle of this shift, here’s what I’ll say: trust the process. Let go of control. Listen more than you speak. Support more than you direct. Because at the end of the day, people don’t follow job titles—they follow clarity, trust, and purpose. Anyone who has made this transition, what are other shifts and advice you would give?

When I started my entrepreneurial journey, I believed a founder’s role was to set vision and targets. But over time, I learned that the real role of a leader is far deeper—it’s about creating an ecosystem where people feel safe to experiment, fail, and rise stronger. I remember one instance clearly. A young team member once pitched a campaign idea that didn’t perform as expected. The easy way out? Blame and move on. But instead, we reviewed it together, identified what went wrong, and gave her the lead on the next campaign. The result? She delivered one of our most successful campaigns to date—and today, she leads an entire vertical. That day taught me: ⚡ Leaders don’t create followers. They create more leaders. ⚡People thrive where mistakes are seen as lessons, not verdicts. ⚡Vision matters, but empowering people to own it matters even more. True leadership is not about controlling outcomes—it’s about inspiring ownership, building confidence, and celebrating growth both personal and professional. Because at the end of the day, leadership is never about me. It’s always about we. #leaders #founder #company

Learnings from a 7-time founder who's built multiple successful companies: "if you're a second stage business or you're getting there... I promise you, you have inefficiencies that are costing you money" Ray Orsini, CEO of OIT, LLC | OITVOIP and serial entrepreneur, shared a crucial insight about scaling past the founder stage. Even with recent promotions and strong processes, "when you get bigger, there's so much leakage...so many little things that cause big impacts on your company, both in terms of your bottom line, in terms of how they operate and employee happiness." The root cause? Vision locked in the founder's head. "I knew the vision because it's all I think about 24/7/365. If there were more hours, I'd think about it more. But the rest of the company didn't have the full picture." Even after building a profitable, process-driven company over 14 years, Ray recognized four key elements for next-level growth: 1. Getting crystal clear vision out of his head and documented in a way that is easy for his team to lean into 2. Building operating rhythms that go beyond accountability to a sense of ownership  3. Transforming doers into architects and directors 4. Creating an operating system for the business that runs without founder input The result? Ray positioned his leadership team to architect solutions independently, turn on a dime, and drive the company forward. The key was creating clarity and alignment across the organization. Ray's goal isn't just building another successful company - it's creating freedom for his entire team. "That's one of our core tenets: work is in service of personal life, like the whole point of this. So you feel satisfied and then you have the resources needed to go live a wonderful life and that starts with me, but that continues down through every employee..." Let's GO. #leadership #servantleaders PS If you are a founder or CEO and want a free preview of the same vision builder that was part of the ResultMaps solution for Ray and OIT, comment VISION below.

There is one thing more difficult than letting go - watching someone else take over what you built. I have worked with multiple founders who struggled to step back. Not because they didn’t trust the next generation. But because so much of their identity was tied to the business that it affected their self-worth. They were not handing over tasks. They were handing over a legacy. What helped was not just a formal succession plan. It was consistent, respectful communication. Asking questions like: - Where would you like to see this business five years from now? - What core values are non-negotiable? - What role would you like to take up in helping the organisation scale-up? When these conversations happen with openness, the transition becomes less about control and more about continuity. The next generation does not need freedom handed to them. They need space to earn it and the older generation needs the grace to be seen, not sidelined. When both are honoured, something powerful happens. #Entrepreneurship #Culture #Business #Familybusiness #Coaching

𝗦𝘁𝗲𝗽𝗽𝗶𝗻𝗴 𝗶𝗻𝘁𝗼 𝗮 𝗻𝗲𝘄 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗿𝗼𝗹𝗲 𝗶𝘀𝗻’𝘁 𝗷𝘂𝘀𝘁 𝗮 𝗽𝗿𝗼𝗳𝗲𝘀𝘀𝗶𝗼𝗻𝗮𝗹 𝘀𝗵𝗶𝗳𝘁. It’s an identity shift that most senior leaders underestimate. Whether it’s a promotion, a cross-functional switch, or stepping into a CXO seat, the external responsibilities are clear, but the inner alignment? That’s where the real challenge lies. You’re now managing former peers. You’re expected to lead with more vision, not just execution. The unspoken expectations suddenly feel heavier than the job description. One of my clients, recently promoted to a regional leadership role, shared: “Everyone around me assumes I’ve ‘arrived’. But inside, I’m still figuring out how to show up in this new skin.” This is more common than you think. In my coaching experience, here’s what shows up most often during such transitions: 1/ Identity Lag: You’ve earned the title, but haven’t yet embodied the role. This creates hesitation in decision-making leading to second-guessing. 2/ Peer-to-Leader Shift: Suddenly, you're the one giving feedback to the person who used to be your lunch buddy. That emotional shift needs space and support. 3/ Pressure to Perform Instantly: Many feel they need to “prove” their worth early on. This often leads to overcommitment and burnout within the first few months of the new role. So what’s the most important shift to make? Instead of asking: “How do I prove I belong here?” Start by asking: “Who do I need to become to lead from this space?” Most transitions don’t just require a strategy. They require support, self-awareness, and inner leadership. Remember: Your first 90 days aren’t just about results; they’re about embracing your new leadership identity. So, make space for reflection, not just action.

Making the leap from founder to CEO is a big transition. It’s about learning how to lead and manage a team effectively. After working with 100+ early-stage founders who’ve made this shift, I’ve noticed a few key approaches that help build and motivate great teams: Communicate your vision and mission clearly. Your team needs to understand the bigger picture and how their work contributes to it. This alignment drives focus and purpose. Set clear expectations and goals. When everyone knows what’s expected, they stay on track and accountable. Foster a positive work environment. Open communication, recognition of great work, and genuine support go a long way in boosting morale and productivity. Invest in your team’s growth. Training and development keep their skills sharp and show you care about their progress. Encourage collaboration. Building trust and fostering a sense of community strengthens the team and leads to better results. Show appreciation and give constructive feedback regularly. People thrive when they know their efforts are valued and when they’re given space to improve. What strategies have worked for you in leading and motivating your team? Let’s share insights in the comments.