Where Coaching Goes Wrong with Charlotte Jordan

What if the biggest barriers to coaching weren’t tools or talent — but clarity, trust, and courage? In this episode of Owlcast, David and William sit down with Charlotte Jordan, CEO of Coaching.com, to expose the biggest mistakes leaders and organizations make when building coaching cultures — and how to fix them fast. From misusing coaching to “fix” poor performers, to the wild‑west chaos of unstructured coaching programs, to the quiet power of manager‑as‑coach, Charlotte brings a rare 360° view of the coaching world. If you’re a leader, coach, or building a coaching culture, this conversation will change how you think about developing people.

Key Topics:

· Coaching fails inside organizations when there’s no clarity.
Coaching becomes ineffective when companies aren’t explicit about what coaching is, what it is not, and what it should be used for. When organizations treat coaching as a catch‑all solution, it turns into a solution for nothing.

· Using coaching to “fix underperformers” is a major pitfall.
Charlotte calls out that many organizations put poor performers into coaching long after the decision has already been made to exit them. This turns coaching into a checkbox exercise rather than genuine development — and destroys trust.

· Coaching cultures fail without aligned leadership.
A sustainable coaching culture must include manager skill‑building, executive sponsorship, and clear modeling of coaching‑like behaviors. Visibility + credibility = sustainability.

· Managers need coaching skills, not coach labels.
The false divide between “manager” and “coach” keeps organizations stuck. Coaching is not a title — it’s a set of behaviors. Great leaders ask: “What are you working on, and how can I help?”

· Decentralized, Wild‑West coaching creates chaos.
Charlotte warns that unorganized coaching efforts across departments dilute definitions, confuse employees, and prevent impact measurement. Without structure, teams can’t tell what’s working — or if coaching works at all.

· Measurement matters — even in early stages.