What got you here won’t get you there – key insights from my recent webinar with the Keysearch team on scaling leadership and overcoming common founder pitfalls.
From Founder to CEO: Strategic Insights for a Smooth Transition
Last week, I sat down with Keysearch to tackle a challenge I see over and over again in my work coaching CEOs: how to transition from a visionary founder to a truly effective CEO.
If you’re a founder or a leader on this journey, this is for you.
It starts with one big realization:
The skills that make you brilliant at starting a company – vision, energy, raising funds – are not the same ones you need to scale and manage it.
I call this the point where you stop “laying the tracks” and start “running the trains.”
Here are three big ideas we covered:
1. Your Role as CEO = Seeding, Feeding, and Weeding
Think of yourself as the gardener of your organization:
Seeding: Plant the vision, the ideas, and the “what ifs.” Inspire your team with the why and leave the how to them.
Feeding: Support projects that are already in motion. Don’t just check on progress – help teams overcome roadblocks and move in the right direction.
Weeding: Cut out what’s not working. Whether it’s a struggling initiative, misaligned priorities, or the wrong fit for a role, it’s your job to prune and refocus.
Ask yourself: Am I seeding, feeding, and weeding my business, or am I getting stuck in the weeds?
2. Subject Matter Experts vs. Real Leaders
Once your company grows past 100 employees, the leadership challenge becomes clear: the team of subject matter experts who got you here may not be the leaders who’ll take you further.
Scaling to the next level requires leaders – “mini-CEOs” – in key roles. These are people who can not only think strategically but also manage larger teams and push forward the vision on your behalf.
If you’re feeling stuck, ask yourself: Who on my team is a brilliant expert but not a leader? And where do I need to bring in new leadership?
3. Don’t Skip the Celebrations
Here’s the truth: Founders are terrible at celebrating wins. You hit $5 million ARR and immediately say, “Great, now let’s get to $10 million.” Sound familiar?
Your team, however, needs to pause and celebrate those milestones. Skipping this step can leave your people drained, demotivated, and wondering, “Does any of this matter?”
Balancing short-term wins with long-term goals is a muscle you need to build. Take a moment to look back, recognize progress, and then move forward with renewed energy.
Want to Dive Deeper?
There’s so much more in this conversation, from the traps visionary founders fall into to tactics for building an efficient, thriving team. If this resonated, you’ll get even more from the full webinar.
Watch the full session here.