What CEOs and senior leaders really talk about in executive coaching sessions

“I know I need you, Nicola but I’m not sure what I’d talk to you about.” 

I hear this sentence a lot. 

Senior leaders often assume executive coaching is about performance management or fixing problems. It isn’t. The work we do together is deeper than that. 

Executive coaching is about creating the thinking space that most CEOs, VPs and executive leaders rarely have. When you’re responsible for a business, board, strategy and hundreds or thousands of people, there are very few places where you can pause and explore the questions that really matter. 

So, when leaders tell me they’re not sure what they’d talk about, I usually smile. Because within a few minutes, the real questions start to appear. 

The questions leaders actually bring to executive coaching sessions

While every leader is different, many of the conversations in executive coaching sessions revolve around pivotal moments in leadership. 

So, whether we’re sitting in my coaching space or strolling together, here are some of the questions my clients bring to me.  

“I’m stepping into a deputy CEO role. How do I do that at my best?” 

Transitions into senior roles are some of the most complex moments in a leader’s career. 

The shift isn’t just about capability but about identity. 

Leaders are often navigating new expectations, power dynamics and a much bigger strategic lens.

Coaching helps them step back and ask themselves: 

• What kind of leader do I want to be in this role? 

• What strengths do I need to lean into? 

• How do I build respect from my new peers? 

• What habits or assumptions do I need to leave behind? 

These moments are less about learning new leadership techniques and more about leading self with greater intention. 

“I need to bring the board closer to the business. How do I work with them to do that?”

Boards and executive teams can sometimes operate at arm’s length from each other. 

Leaders often want to build stronger relationships with their board not just reporting to them but working with them as strategic partners. 

In coaching sessions, we explore questions such as: 

• How do I create transparency and togetherness – a feeling that we are on the same team? 

• How do I bring the board into the reality of the organisation? 

• How do I influence effectively inside and outside of our core meetings? 

  
  

Often, the answers lie in how the leader shows up, communicates and builds trust with their Chair and board members over time. The highest performing Exec / Board relationships I observe are ones of trust and understanding.  

"Her behaviour is inappropriate and it’s damaging the team. Help me have the conversation.”

Even the most experienced leaders can struggle with difficult conversations. 

Relationships matter and the consequences ripple across teams and cultures. 

Executive coaching creates a place to think through: 

• What outcome do I want from this conversation? 

• What assumptions might I be making? 

• How do I deliver the message clearly, so it is received as I intend it to be? 

• How do I do this while maintaining respect, our relationship and trust? 

Leaders usually know what needs to be said. Coaching helps them take time out to get to a point where they know what to say and feel capable to do so. 

“I don’t feel like I fit within the executive team. How do I build myself so that I do?”

This is more common than many people realise. There can be a sense of ‘imposter syndrome’ – a feeling they will be found out if they step into an exec role and a belief they will stumble. 

Highly capable leaders can step into executive teams and suddenly feel unheard or out of place. 

The work here is rarely about changing who they are. Instead, it’s about helping them understand:  

• What they uniquely bring to the team, owning this part of themselves and the value it brings. 

• Their leadership voice. How they engage with peers in a way that is congruent. 

• How they influence at an executive level. 

• How they show up as their confident, productive self and hold their own. 

When leaders connect with their own identity as a leader, they find they have all they need within themselves to pull up a seat and join the table. 

The real work of executive coaching

Many leaders arrive with practical challenges. But underneath those challenges are deeper leadership questions. 

My role as an executive coach isn’t to provide the answers. It’s to help leaders uncover the answers that already exist within themselves. 

Because the truth is, executive leaders aren’t necessarily lonely, but they can be alone. 

There are very few places where they can challenge their own thinking and step back from the relentless pace of leadership. There are very few places where they can develop resources from within. Executive coaching provides that space. A place where leaders can think more clearly, lead more intentionally, and become the leader they want to be. And when that happens, when they step into their space, their impact reaches far beyond the individual into the organisations and the people they lead. 

Find out more about my executive coaching and team coaching and drop me a line if you feel like you’re ready to lead as your best.