Leadership Skills Start with Conversations: Insights from Celeste Cleary

Leadership Skills Start with Conversations: Insights from Celeste Cleary

At our July coffee catch-up, proudly sponsored by Flourishing Wellness, we were joined by Chamber member Celeste Cleary to discuss a challenge many businesses face—staff being promoted to leadership roles without receiving any training in how to lead.

In this short video chat, Celeste shares a story from a recent workshop she facilitated with a group of supervisors. While technically skilled and respected by their teams, many struggled with giving feedback effectively—especially in a way that encouraged accountability without damaging rapport.

Key takeaways from the conversation:

  • Many leaders are promoted for technical skill, not people skills.
  • Feedback can easily be misinterpreted as personal criticism.
  • A simple shift—like stating your intention and leading with shared goals—can make difficult conversations more productive.
  • Empathy is a leadership tool, not a weakness. Used strategically, it helps build trust and accountability.
  • Old-school “teeth out” leadership might get results short-term, but often at the cost of long-term engagement and retention.

If you’re finding leadership a challenge, Celeste offers workshops and one-on-one sessions tailored to help managers grow the skills they need.

👉 Watch the full video for the full story.

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