Coaching case studies
From People-Pleasing to Confident Leadership
The Challenge
A senior leader struggled with being assertive in her role. She wanted to be an encouraging leader but feared coming across as too harsh or dismissive. As a result, she often softened her communication too much, leading to misalignment and inefficiency in decision-making.
The Coaching Approach
We worked on balancing validation and assertion—acknowledging perspectives while standing firm on decisions. Through structured conversations and confidence-building exercises, she learned to articulate expectations clearly and reduce the optionality in her communication.
The Transformation
She developed an internal leadership strategy that reinforced clear, confident communication. Instead of “asking” for input on settled decisions, she asserted ownership with statements like:
“This is the direction we’re moving in. Please share your suggestions or concerns by X date.”
Her executive presence strengthened, and productivity among her team and with stakeholders noticeably improved.
Key Takeaway
Confidence and kindness aren’t mutually exclusive. Clear, firm communication fosters respect and efficiency.
Struggling to balance confidence with approachability in leadership? Let’s talk.
How a Simple Framework Transformed Difficult Conversations
The Challenge
A mid-level leader faced constant friction with a colleague who took every conversation personally. The emotional tension made collaboration difficult and stalled progress on critical projects.
The Coaching Approach
We introduced a conversation framework to help her depersonalize discussions:
✅ My intent is to… (clarify purpose)
✅ I’m trying to accomplish this by… (explain the approach)
✅ So that… (state the intended outcome)
✅ Can you help me… (invite collaboration)
By shifting the focus to shared goals, she could defuse defensiveness and keep conversations solution-oriented.
The Transformation
Using this framework, she led a 1:1 discussion on a high-stakes issue. The conversation, which previously would have spiraled into blame, instead led to a collaborative resolution. She now uses this approach regularly to keep discussions productive.
Key Takeaway
Difficult conversations become easier when you shift from blame to shared problem-solving.
Want to handle tough workplace conversations with confidence? Let’s explore how.
Winning the CEO’s Confidence
The Challenge
A high-potential leader wanted to anticipate the CEO’s needs better. She often found herself reacting to last-minute requests instead of proactively addressing issues ahead of time. The CEO’s feedback was clear: “If only you could have anticipated this.”
The Coaching Approach
We developed a tiered urgency matrix to help her categorize scenarios based on response time and risk level. By mapping out different situations and preparing responses in advance, she positioned herself to act preemptively rather than reactively.
The Transformation
Within weeks, the CEO stopped demanding revisions to her finished products and began asking for her recommendations. Though she is a skip-level leader to him, he now more frequently reaches out to her directly for critical requests, a clear sign of increased trust and respect for her expertise.
Key Takeaway
Anticipation is a leadership superpower. Systems and frameworks can help shift from reactive to proactive leadership.
Struggling to get ahead of leadership requests? Let’s build a strategy that works for you.