My Approach

Customized Strategic Results-Oriented

I work with CEOs who want to accelerate their performance. Programs are tailored to suit individual needs and the leader’s specific circumstances

In 2007, I had an opportunity to coach a leader who was “the CEO in waiting.” That engagement was unlike any of my other coaching engagements. That experience would help shape my view that coaching at the CEO and c-suite level requires a unique approach. Over the years, I’ve learned that c-suite coaching requires the following three areas of focus.

Every leader is unique and leads in unique circumstances. I approach customization in two ways. First, it honors the fact that we humans are complex; a cookie-cutter approach to individual leaders is unhelpful. Second, leadership is situational—what a leader needs to do depends on what’s happening at the company: the unique business context.

With these two considerations in mind, I quickly focus on:

  • What is the business context? (e.g. growth, turnaround, new strategy)
  • What is expected of the leader in this business context?
  • How is the leader uniquely qualified to deliver what is expected of her/him?

At the c-suite level, coaching needs to be heavily customized to the specific leader who is working in a particular business context.

Senior leaders often have a handful of development opportunities. An effective coaching engagement should prioritize those development opportunities so that the work has a significant, strategic impact.

Further, in my fifteen years of coaching c-suite leaders, I’ve learned it’s not uncommon for a leader to have some blind spots about what is required to be successful in their new role. Quite often it’s a case of “what got you here, won’t keep you here.” When new in a senior role, a leader’s development needs fall into one or more of three categories: issues with leadership style, underdeveloped management skills, and/or business-experience gaps. I take pride in supporting a leader in minimizing learning through trial and error.

I do this by creating clarity for the leader about how they might (a) need to adjust their leadership style and (b) address some of the standard challenges of leading from the c-suite (e.g. how to effectively work with a board or create strategic clarity).

In conversation with my clients, we create a plan that focuses on:

  • What are two or three development areas for the leader that will have the biggest impact on the leader’s effectiveness?
  • What is there about leading from the c-suite that they might need to learn?

This strategic calibration is required to ensure that the coaching/advisory work has maximum impact.

Coaching goals can’t be vague or aspirational. Translating what the leader needs to do into practical plans is critical, so I focus on helping my clients identify specific actions to take and habits to build. This ensures that results are observable. The work the leader wants to do should be crystal clear, as should the value and impact of that work.

In terms of results, the leader should notice changes in their leadership style, and those around the leader (stakeholders) should report that they are noticing the changes.

This approach to producing results honors the reality that c-suite leaders don’t have unlimited time to devote to coaching, so the coaching work needs to translate into clear results. It also assures the engagement sponsor that the investment has produced an expected return.

Finally, any leader who chooses to work with me must be willing to invest in a full-day meeting with me at the start of the engagement to ensure that we get a “fast start” to the work. To learn about what this day entails, please click here.

While these are unique aspects to my coaching approach, I also adhere to a common set of Best Practices and Principles for leadership coaching.

These include the following steps:

  • First: Build self-awareness. This step helps the leader understand both their strengths and their gaps or development areas.
  • Second: Build other-awareness. This step helps the leader understand what they are expected to do in their role (what success looks like) and how colleagues view them. Typically, this involves securing 360 Feedback. I speak with the leader’s colleagues to understand more about the leader’s style, the business context, and what is expected of the leader.
  • Third: Develop a set of coaching/development goals. These allow the leader to leverage strengths and address gaps. This creates clarity and focus for the coaching work.
  • Fourth: Build a feedback loop. A leader should not have to wait for a 360 process to hear what they need to do differently. I engage stakeholders (e.g. board, CEO, directs, peers) in providing “real-time” feedback to the leader. This serves a number of purposes:
    • It creates transparency about the coaching,
    • It creates accountability, and
    • It creates an even more positive view of the leader.
  • Fifth: Deepen leadership impact. Ongoing coaching work focuses on creating insight, awareness, self-belief, and the courage to try some atypical approaches. We meet once every 4–6 weeks in person and speak by phone between in-person visits (every 2–3 weeks). This ongoing work should noticeably improve the leader’s impact.
  • Finally: Focus on results. I conduct a midpoint and end-point engagement review to gauge progress and course-correct as appropriate.

Given that this is a highly customized offering, my coaching approach is heavily focused on providing support and guidance. The goal is to ensure that the leader is executing on the development plan while ensuring that key stakeholders provide quarterly feedback to the leader about their progress.

Engagements range from 6–12 months in duration and I have a long and strong track record of accomplishing results. Sometimes, I’m proud to say, those results are life-changing.



I’ve found executive coaching to be very empowering and transformative at different times in my career. Shout out to my coach Damien Faughnan.

General Manager

Matt Donovan, General Manager, Microsoft 365 Studio.

Contact Damien

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