What CEOs learn Behind Closed Doors: Real Coaching Cases on Hiring, Engagement and Difficult Conversations
Real coaching cases: How CEOs turn complexity into confident action. Hire right, lead with clarity, and streamline strategic execution.

Simona Spilak, MSc 02 June. 2025

Occasionally, I provide findings from my executive coaching work—real cases from real leaders, dealing with pressure, uncertainty, and the weight of high-stakes decision-making.
What brings them to coaching? It's rarely because something is broken. It's because they've reached a point where doing more is no longer working—and something needs to shift.
Around 90% of the CEOs and senior managers I work with want to lead their teams more effectively, manage key relationships with less friction, and grow without carrying everything themselves.
Others come with broader strategic concerns—how to restructure leadership, manage complexity, or adapt their role to fit the business's needs.
What connects them all is a shared impulse:
To move forward with clarity, relevance, and strength.
Findings from the Coaching Room
The short cases that follow are drawn directly from these moments.
Each one offers a specific context, a challenge we worked through, and a few coaching questions that might shift how you see your own.
- Hiring Right: Why Values Alignment is the Real Dealbreaker
- Developing Talent from Within: Why Performance is About More Than Numbers
- Creating Proactive Teams: Why Leadership Begins With How You Listen
- From Helpful to Harmful: Rethinking Supportive Leadership
I use a structured methodology that starts with an Assessment to understand your personality profile and challenges. In Inquiry, we explore the patterns, beliefs, and dynamics that shape how you lead. Based on that, you define focused Actions as concrete steps tailored to your position and situation. Finally, through Measurement, we track the impact to ensure the results are sustainable and aligned with your goals.
These cases are here to open your perspective. They show what happens when you pause, reflect, and act with direction.
And they offer a sense of what working 1:1 with me feels like—focused, personal, and always confidential.
1. Hiring Right: Why Values Alignment is the Real Dealbreaker
Context
Few decisions influence the direction of your organisation, like a leadership hire. It’s not just about finding someone competent—it’s about finding someone who will grow your culture and results, not dilute it.
In my work as an executive coach and executive search consultant, I’ve seen it too often: a hire looks perfect on paper, delivers strong results, and doesn’t last. The reason?
A silent misalignment in values that no one named—until it was too late.
Challenge
Many hiring processes focus on skills, experience, and potential. These matter, but they’re not enough.
The real risk isn’t a lack of competence—it’s a lack of shared direction.
What happens when the new leader doesn’t see success as you do? When they lead in a way that clashes with what your team needs?
That’s where disengagement starts. And where high turnover begins.
Actions
When I support clients through critical hiring and succession decisions, we work on three non-negotiables:
- Encouraging values alignment. We explore how your culture is lived—not just stated—and what kind of leadership will strengthen it, not stretch it.
- Humanity goes first. Leadership is relational. If there’s no trust, there’s no long-term performance. Values alignment isn’t soft or accessory; it is the glue that holds your leadership team together.
- Sustainability over sacrifice. Top performers won’t stay in a system where delivering results means losing balance. It’s not about making it easier—it’s about making it coherent.
I make use of tools like the Saville Wave, Hogan Assessment and Process Communication Model (PCM) to bring objectivity into the process and see how candidates handle pressure, relate to others, and operate in your leadership ecosystem. This goes far beyond the CV and surface impressions.
It’s not about removing risk but making intelligent decisions with long-term traction.
Results
When you don’t, even your strongest hire becomes a costly short-term fix.
When you hire with values alignment, you don't just reduce turnover—you gain a leader who adds energy to your system.
You build trust, strengthen culture, and create continuity at the top.
Even your strongest hire becomes a costly short-term fix when you don't.
Coaching Questions
- How are you assessing value alignment in your executive hiring process?
- What unspoken expectations might clash with how your new hires lead?
- What signals are you sending candidates about what really counts in your organisation?
2. Developing Talent from Within: Why Performance is About More Than Numbers
Context
A country sales manager came to coaching ahead of a performance evaluation with one of his team members—a reliable, consistent salesperson who always delivered on target.
Nothing more. Nothing less.
The issue? This individual expected a promotion and a bonus but showed no interest in supporting colleagues, strengthening team culture, or contributing beyond their numbers.
Challenge
How do you help someone who sees performance only as hitting targets understand that leadership requires more?
That success isn’t just about the what—but also about the how:
- How they collaborate
- How they contribute to the bigger picture
- How they shape the environment around them
The sales manager needed a structured, thoughtful way to challenge this expectation—and open a new perspective.
Actions
In our coaching session, we built a clear two-part message for the evaluation:
- Promotion is for overachievers—not just for meeting expectations. Growth means stepping beyond your current scope.
- Performance includes impact. That means you support others, drive culture, and help the whole team succeed—not just how you deliver your results.
To bring this to life, we used the 9-box grid—a tool that helps visualise the relationship between performance (what) and potential (how).
This gave the manager a structure to lead the conversation with clarity and confidence. It also allowed the salesperson to see where the gap really was and take ownership of it.
Together, they co-created an action plan: ways to engage more actively across the team, take initiative outside of personal targets, and begin contributing at the level expected of someone preparing for leadership.
Results
The shift was immediate.
The salesperson understood that numbers alone wouldn’t carry him forward and that if he wanted to grow, he had to evolve.
The manager, in turn, felt better equipped to lead future evaluations, not just as performance reviews but as development conversations.
Reflection Questions
- Are you using evaluations to reinforce status, or to open growth?
- Are your high performers increasing their impact, or just results?
- What are you rewarding in your team—and what message does that send about leadership potential?
3. Creating Proactive Teams: Why Leadership Begins With How You Listen
Most leaders are comfortable talking strategy, but things shift when the conversation turns personal or emotionally charged. Emotional intelligence becomes your most effective asset, whether you're letting someone go, giving difficult feedback, or reframing organisational relationships.
I've worked with CEOs preparing for sensitive conversations where trust, clarity, and confidence had to be present in every word. Even the toughest messages can create alignment and leave the door open for future respect. And yes—this too can be coached, practised, and refined until it becomes part of how you lead naturally.
Context
A CEO approached coaching with a goal that many senior leaders recognise immediately:
“I want my team to take the initiative and bring solutions, not wait for instructions.”
He and his team had weekly meetings. The team discussed goals, made agreements, and then ignored them altogether.
Nothing seemed to stick. Deadlines slipped. Ownership was low.
At first, he thought the team was disengaged.
But in the coaching session, we explored a more uncomfortable truth:
“I think I come across as too strict. I want to be less harsh—and more confident.”
Challenge
The problem wasn’t the lack of process. It was the tone of leadership.
The CEO:
- Dominated the meetings
- Rarely invited reflection or encouraged conversation
- Reacted strongly when the team didn't deliver on time
The team didn’t speak up. It didn’t challenge. It didn’t lean in. There was no space for psychological safety.
Actions
We worked through the gap between how he wanted to be perceived and what he was projecting.
He made a strategic change:
- Started biweekly one-on-one conversations with direct reports
- Asked open-ended questions instead of offering help:
“Where do you see a challenge coming up?”
“What’s not working as expected?” - Shifted from delivering content to facilitating conversation
Result
Trust increased. Engagement followed.
People spoke up earlier, raised flags, and proposed improvements instead of avoiding risk.
The CEO learned that presence isn’t just about being available—it’s about creating space for others to think, speak, and act.
Coaching Questions
- Do your meetings invite input—or just share expectations?
- How do people feel when they bring up a problem with you?
- What would shift if you spoke less and listened more?
4. From Helpful to Harmful: Rethinking Supportive Leadership
Context
In a coaching session, a senior executive shared her frustration: She invested time and energy to support her team, but nothing changed. Engagement was low. Sales weren’t improving.
She managed a large, highly technical business unit, drawing on her strengths in both technical expertise and commercial experience.
Her approach to leadership was to be present and helpful. She made time for her team every day.
Always asking:
- “What do you need?”
- “How can I help you?”
But it wasn’t working.
Challenge
The issue wasn’t goodwill—it was effectiveness. Her supportive style wasn’t building trust or driving performance in a male-dominated, highly technical environment.
Her team saw her as available—but not as an authority. She wasn’t leading by example. She was hovering.
Actions
In coaching, we reframed her presence from supportive to strategic.
She made three key changes:
- Moved into the same office space, increasing visibility and natural interaction
- Shifted to a peer-level leadership tone, showing—not just saying—what good performance looked like
- Focused on relevant communication, connecting team goals with day-to-day priorities
Results
She stopped “mumming” the team and started leading with a grounded presence. People became more responsive and more confident—and performance began to lift.
She didn’t have to push harder. She had to show up differently.
Coaching Questions
- Is your leadership presence building authority—or blurring roles?
- Do you show trust in your team by guiding them—or by protecting them?
- Where might your support be disempowering rather than enabling?
- How does my presence and communication style affect how others take ownership and contribute?
Clarity isn’t about knowing everything. It’s about seeing what matters most.
If you're facing hiring decisions, feedback conversations, or wondering how to grow your team without carrying it all on your back—you're not alone. These are the conversations I have with CEOs and top managers every week.
In moments of uncertainty, the question isn't what will happen next, but how will you respond?
What we do together isn't complicated. It's focused. Strategic. Sometimes challenging. And always personal.
It's about helping you lead better—with less friction, more confidence, and the kind of presence that moves things forward.
If that's something you'd like to explore, let's talk.
Book a 1:1 consultation. We'll see where you are and whether what I do is what you need. If it isn't—I'll tell you. We'll find the fastest, most straightforward way forward if it is.
To your success,
Simona

I'm the founder of BOC Institute, one of the renowned consulting agencies for international companies operating in Slovenia and South-East Europe.
I coach CEOs and top managers 1:1 worldwide. I'm here to save you time, energy, and money through your objectives, decision-making, and leadership development. I understand we can change the world one coaching session at a time!
Do you feel like having a call? You can reach out here and let me guide you from there.
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Simona Špilak www.simonaspilak.com