Executive coaching for small business leaders.
Rethinkery's executive coaching is built for the realities of leading in small business — where stakes are real, change is slow, and the leadership patterns that need to shift are rarely the ones being talked about openly.
What we work on
Coaching engagements for small business leaders are scoped to the pattern that's actually slowing the leader down — not the symptom that prompted the call.
Owner as bottleneck
Decisions still flow through you because that's what worked at year one.
Founder identity entanglement
The business's growth is gated on a personal shift you haven't named yet.
No mirror in the building
Nobody on the team can — or will — give you the feedback you actually need.
What changes
- Sharper decisions that don't all route through you
- A clear next move on the role you've outgrown
- Honest sounding-board work that compounds week over week
- A team that starts taking the calls you've been carrying
Our approach
Small business coaching at Rethinkery is built for owner-operators and founders who are growing past the version of themselves the business was originally built around. The work is direct, fast, and honest — and tailored to the realities of running something where you carry both the strategy and the laundry.
Engagements typically run 4 to 6 months on our accordion approach — intensive periods of work followed by integration windows where new behaviours actually take root.
Coaching for other industries
Construction & Trades
Where safety, schedule, and culture all live in the same conversation.
Defence & Military
Mission-critical leadership, civilian conversations.
Government
All levels, all complexity.
Finance & Investment
Performance under pressure — and the patterns that erode it.
Energy
Long horizons. Hard decisions. High consequence.
Ready to surface what's hiding in your culture's blind spots?
Book a free Hidden Threats Assessment. We'll show you the language to name what others avoid, whether or not we end up working together.