Building Leaders, Not Bottlenecks
A Practical Guide for Business Leaders Navigating Scale
1. The Hidden Growth Ceiling
What got your company to 100 people won’t get you to 1,000.
As scaleups grow, the pressure on business leaders rises fast. Founders, heads of ops, and general managers suddenly find themselves managing managers, putting out fires, and wondering why the team feels slower even as it grows bigger.
Often, the problem isn’t strategy. It’s leadership bandwidth. New layers of managers emerge, many of them brilliant individual contributors now struggling in leadership roles. Meanwhile, senior leaders face an identity shift: from hands-on execution to building systems and enabling others.
One tech veteran put it best: “After around 100 people, your job isn’t managing individuals. It’s creating systems so others can manage independently.”
If you don’t intentionally grow your leadership capacity, you risk becoming the ceiling on your company’s growth.
2. Why Leadership Breaks at Scale
When leadership doesn’t evolve, teams stall. You start noticing:
In one scaleup we worked with, over 40% of new managers were promoted from individual contributor roles without any structured support. Within six months, feedback scores dropped and turnover in key teams increased—until group coaching was introduced to course-correct.
Without the right support, even your best people can falter. Poor management habits spread. Teams lose momentum. And your top talent starts looking elsewhere.
3. Five Moves to Build Leadership Capacity Fast
This section offers tactical guidance for business leaders who want to stay ahead of the chaos.
a. Train New Managers Before They Break Things
Most managers start leading without training. In scaleups, the pace is too fast for trial and error.
Get ahead of it:
Claire Hughes Johnson (ex-Stripe) recommends codifying decision-making principles early. It saves time and protects culture.
Action step: Build a lightweight onboarding track for new managers. Keep it practical.
b. Build a Support System for Managers
New leaders need support, not just pressure. Pairing them with experienced mentors or running peer forums can prevent burnout and build confidence.
Stripe and other top tech firms invested in peer learning as a force multiplier for leadership development.
Action step: Create monthly manager meetups to share challenges, tools, and tactics.
c. Bring in Senior Talent with Intent
You can’t promote everyone from within. But bringing in experienced leaders without breaking your culture takes care.
Use structured hiring, value-based interviews, and intentional onboarding to make it work.
Sheryl Sandberg’s playbook? “Hire for roles that never existed before”—but onboard them like you would a co-founder.
Action step: Design a 30-60-90 onboarding plan for every senior hire.
d. Let Go to Grow
Keith Rabois puts it simply: “Delegate completely. Let people make mistakes and learn.”
Business leaders often hold on too long. Delegation feels risky. But without it, you become the bottleneck.
Use clear goals and weekly reviews. Focus on outcomes, not inputs. Let managers own their space.
Action step: List the top 5 things you should stop doing. Delegate one this week.
e. Use Group Coaching to Build Leadership Muscle
You don’t have time to personally coach every manager. But you do need them aligned, skilled, and growing fast.
Oliva’s Group Coaching helps leaders across functions:
Facilitated coaching groups build shared language, reduce silos, and help managers feel less alone.
At companies like Leapsome, group coaching became the lever that turned scattered leadership efforts into a cohesive, confident management layer. One leader shared that it “gave managers a shared language and a support system we didn’t even know we needed.”
Action step: Enrol your managers in a quarterly coaching cohort. Start with your most stretched teams.
4. Leadership Scalability Self-Check
Use this as a quick pulse-check:
✅ New managers have access to training and playbooks
✅ Peer learning or mentoring exists for leadership roles
✅ Senior hires are onboarded with cultural alignment
✅ You’ve delegated high-leverage tasks in the past 30 days
✅ Your managers are part of structured coaching or development
5. From Advice to Action
If this guide hit close to home, here’s where to go next:
Companies that invested in structured leadership development saw measurable ROI: stronger engagement, reduced attrition, and faster time-to-performance for new managers. It’s not a ‘nice-to-have’, it’s a scale enabler.
Leadership is your limiting factor or your multiplier. Build it with care.
6. Why We’re Sharing This
We’ve felt the pain of scale ourselves, leading teams at hypergrowth companies like Box, Hotjar, Typeform, and TravelPerk. We know what it’s like when your calendar’s full of one-to-ones, your best ICs are suddenly managing people, and decisions start slowing down.
Now, we partner with founders, ops leaders, and managers navigating that same chaos every day. We’ve seen what works, what breaks, and what turns well-meaning managers into bottlenecks.
That’s why we’re sharing this, no forms, no friction. Just the kind of tools we wish we had when we were in your shoes.
Explore more at [oliva.health]