
By Tina Kamel (24-25)
I’ve worked in both worlds: the scrappy pace of startups and the structured reality of big companies. Watching leaders in each made one thing clear: the behaviours that make you a brilliant leader at 20 or 40 people don’t sustain a 300-person organisation, and vice versa. So I asked: what happens when founders must cross that gap? How do they shift from doing everything to designing systems others can run? And how do those shifts affect employees’ belonging, alignment, and decision to stay? To answer, I interviewed eight founders who scaled from ≤50 to ≥250 people, analysing what they stopped, started, and reweighted. Three leadership shifts emerged with practical lessons.
Why this is important
People often join startups for the buzz: fast decisions, incredible innovation, everyone knows everyone. As headcount grows, the company changes, new managers join, processes multiply, and the founder can’t be everywhere anymore. Handled well, this phase can unlock performance and keep people proud to be there. Handled poorly, it can drain energy, create confusion, and push good people out. The difference often comes down to how the founder evolves.
What I did
I conducted in-depth, confidential interviews with eight founders/leaders who personally led growth from ≤50 to ≥250 employees, across a mix of industries. I looked for patterns in what they actually did, what they stopped doing, and how they believed those moves shaped culture and people outcomes. Three big leadership shifts emerged, each with very practical implications.
What we found: Three shifts that help companies scale
1) Architecting for scale
Early on, every founder described being “in everything”. As teams expanded, seven of the eight leaders deliberately installed leadership layers, clarified who decides what, and formalised decision routines (think: regular leadership discussions, a simple set of metrics reviewed regularly, and clear owners for key goals). Crucially, their own role changed: from operator to strategist and communicator. They spent more time setting direction, aligning leaders, and reinforcing the “why”, and less time solving today’s tactical problem.
Why organisations should care: Clear ownership and predictable decision routines reduce bottlenecks and cross-team friction. When the founder shows up as a strategist-communicator (for example, through monthly all-hands and site visits), people hear a consistent story about where the company is going and how their work fits. That builds alignment and speeds execution.
2) People-centred leadership and culture
Five founders talked about becoming “last to speak, first to listen”. Seven described delegating more, but not blindly. The rule was autonomy when ready: give people room to run when capability and support are in place, and pair it with mentoring and time-boxed trials that can be reversed without consequences. Leaders also made culture visible in action, not just words. Several leaders spoke of backing staff when disrespected or addressing toxic behaviour quickly, which makes values real across layers and locations.
Why organisations should care: Matched autonomy plus psychological safety fuels belonging and better decisions. When leaders enforce values in visible ways, employees trust that “what we say we believe” is not just a poster on a wall. That keeps culture coherent when the founder isn’t in every room.
3) A talent and development engine
Six founders raised the hiring bar for senior roles and surrounded themselves with strong specialists, often saying, in plain terms, “hire people better than you and trust them”. Four built repeatable development mechanisms (mentoring programs, funded education, structured training) and made careers visible (clear role levels, promotion criteria, and succession). The combination mattered: structure without skill-building frustrated people; training without visible paths encouraged them to take their new skills elsewhere. Retention improved when both worked hand-in-hand.
Why organisations should care: People stay when they can see where they can go and feel supported to get there. A credible internal pipeline reduces costly external hiring and protects hard-won culture.
How these shifts affect employees
Founders linked the three shifts to three human outcomes:
- Belonging: People felt trusted when autonomy matched readiness, they had a voice in healthy debates, and roles were clear. Belonging showed up as confidence, pride, and stronger team identity.
- Alignment: Purpose and values were codified in simple language, then reinforced by behaviour. Regular, founder-led communication kept the mission and priorities front-of-mind as layers grew.
- Commitment: Employees were more likely to stay when they saw investment in their growth, fair and transparent rewards, and visible care during tough moments (for example, practical support in crises).
These aren’t “soft” wins. They translate into lower friction, faster decisions, better execution, and reduced turnover; the foundations of sustainable growth.
What organisations can do next
- Write down the founder’s role shift: What decisions will they stop and keep? Then, schedule a steady communication rhythm (monthly all-hands, quarterly roadshows).
- Grant autonomy when employees are ready: Define readiness (skills, track record, support) and pair it with mentoring and reversible, time-boxed trials.
- Make values visible: Set non-negotiables and act consistently when they’re tested.
- Hire leaders who raise the standard: People better than you in their domain, and trust them.
- Build structure and capability together by publishing career paths and funding mentoring, stretch roles, and targeted learning.
- Reward fairly and transparently, including team targets where suitable.
What makes this different from generic “leadership tips”?
Three things. First, it’s grounded in the lived experience of founders who have already navigated the transition from small team to large company. Second, it translates ideas into observable behaviours (e.g., who decides what; how often you communicate; what you do when values are tested). Third, it clarifies conditions: autonomy works when people are ready; culture sticks when leaders act; retention is strongest when structure and capability move together.
A final word to founders (and those who support them)
If you’re in that messy middle, too big to run on hustle and not yet built for scale, your job is changing! You don’t have to become someone else, but you do have to evaluate how you lead. Do these things, and you’ll do more than grow a company. You’ll build a place where people belong, pull in the same direction, and choose to stay, exactly the conditions that turn early promise into lasting performance.