Becoming the Leader Your Small Business Needs

Stepping into the role of “leader” isn’t something most independent retailers plan for. It usually happens because the business grows, you hire someone, and suddenly the way you show up matters in a new way. In this conversation, Krista Williamson joins me again to talk about the parts of leadership we rarely discuss—why it feels uncomfortable, the habits that hold us back, and the skills that actually make a difference.

We dig into the moments that trip business owners up: wanting to be liked, trying to avoid hard conversations, doing instead of leading, oversharing with the team, and hiring people but not really letting go. Krista also explains the difference between coaching a team member and realising you’ve simply hired the wrong fit, plus what “steady leadership” looks like on the tough days.

We finish by connecting it back to customer experience—because if expectations aren’t clear for your team, the customer feels it. This episode is practical, honest, and full of examples from two retailers who learned leadership the long way.

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