“An entrepreneur can help you grow, pivot, and innovate…if the environment truly supports it.”
When people ask whether they should hire an entrepreneur, I tend to say that it depends. Not every role requires someone who thinks like a business owner, but some roles absolutely demand it. I’ve seen organizations struggle because they hired someone reliable and skilled, yet the role quietly required a builder. They needed someone who sees opportunity, takes initiative, and embraces accountability.
This topic makes me think of a small community pharmacy that needed more than a pharmacist who could open the doors each morning. They needed someone who could run the business, build trust in the community, and generate ideas that actually moved revenue. Hiring a “good employee” wasn’t going to be good enough. They needed an entrepreneur who just happened to be a pharmacist. When they hired for that mindset, the business took off.
Hiring an entrepreneur only works though if you’re ready to give them real authority. You can’t ask someone to act like an owner and then handcuff them with rigid processes or keep decision-making for yourself. Guardrails? Absolutely. Micromanagement? That’s how you lose the very spark you hired them for.
On the flip side, not every entrepreneur wants to return to organizational life. Some have no interest in leading people again. Others are running from something rather than to something. Motivation matters as much as skill.
There is no blanket answer. But if you have a role that genuinely requires innovation, autonomy, and business-building instincts, hiring an entrepreneur may be exactly what unlocks your next level of growth. If you build the right environment where authority matches responsibility, you might be surprised at how quickly momentum follows.
Connect with Tim and his team:
Website: https://bestculturesolutions.ca/
LinkedIn: Best Culture Solutions, Inc
Instagram: @best.culture.solutions
Email: tim@bestculturesolutions.ca
Notable Moments
[00:02] Why hiring an entrepreneur “depends”
[00:04] Pharmacy story illustrates entrepreneurial fit
[00:06] How autonomy drives performance
[00:07] Red flags when evaluating entrepreneurs
[00:08] Accountability and guardrails for supervision
[00:09] When a role truly requires an entrepreneur
[00:11] Why entrepreneurs may return to organizations
[00:13] Leadership considerations when hiring entrepreneurs
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