CFO Mentoring
As the former CFO of Microsoft's Worldwide Operations, KenHickey has sat in the chair his clients sit in now. He brings that lived experience to help senior finance leaders strengthen judgement, influence, and leadership impact through the growth, transformation, and complexity they increasingly face.
CFO Mentoring
As a former CFO of Microsoft Worldwide Operations, Ken Hickey brings real-world C-suite executive experience to his client's leadership and business opportunities.
The CFO Mentoring Process
CFO Mentoring will accelerate your personal and professional development, offering expert level guidance on your goals and desired outcomes, and providing a confidential sounding board to test your ideas.
Schedule a confidential, no-obligation call by pressing the ‘Get Started’ button. We will spend 30 minutes discussing the pressures you’re facing, the leadership challenges ahead, and where you want to grow as a finance leader. If there is a good fit, you’ll receive a clear proposal.
We agree the foundation of the work; your objectives ,confidentiality, success measures, and the practical arrangements for the engagement. If your organisation is sponsoring the work, we'll agree how they're involved.
We begin with a deep dive into the opportunities, decisions, and challenges in front of you. Together, we identify the areas where experience-led perspective and practical guidance will add most value.
We then create a CFO Leadership Development Plan that becomes the roadmap for the engagement, tailored to your role, your business, and the outcomes you want to create. Engagements typically run for three, six, or twelve months, with sessions usually held every two weeks.
Our sessions are driven by what is happening in your role now. I bring direct perspective from leading Finance at scale: what I would look for, the questions I would ask, risks I would watch for, and approaches I have found effective in comparable situations.
We work through real decisions, stakeholder dynamics, and leadership challenges, translating insight into practical action between sessions. Typical themes include leading the Finance function, working with CEOs and boards, strategy, governance, AI and digital transformation, executive presence, career transition, and establishing credibility in a new CFO role.
What CFO Mentoring gives you
Learn from Someone Who Has Done the Job
Benefit from lessons earned by someone who has led global Finance through scale, transformation, complexity, and pressure. Draw on experience that can help you avoid learning every lesson the hard way.
See Around Corners
Spot risks, pitfalls, and likely wrong turns earlier. I help you anticipate what may be coming, ask better questions, and act before an issue becomes harder or more costly to address.
A Sounding Board You Can Trust
A confidential place to test your thinking before you commit. Bring the decision, stakeholder issue, or challenge you are wrestling with and talk it through with someone who has no agenda in the room and will give you a candid perspective.
Sharpen Strategy and the Big Decisions
Move beyond running the numbers to helping shape the direction of the business. Connect financial insight to strategy, weigh the choices that matter most, and bring greater clarity to high-consequence decisions.
Lead the Finance Function with Authority
Build a stronger leadership team and a more effective Finance function around you. Draw on practical experience of setting standards, developing people, creating accountability, and ensuring the function can deliver without every important decision routing through you.
Step Up to the Bigger Role
Whether you are moving into your first CFO role or taking on a broader mandate, build the credibility, executive presence, and judgement the role demands - grounded in what it takes in practice, not just in theory.
CFO Mentoring FAQs
Here are some of the most common questions when it comes to CFO mentoring. If you have any other questions, feel free to reach out.
What is CFO Mentoring?
A relationship in which you have the ear of someone who has done the job. Having spent decades in senior finance roles, including as CFO of Microsoft's Worldwide Operations, I share what I've learned - the guidance, perspective, and hard-won judgement that will help you lead with more confidence, avoid the avoidable mistakes, and step up to bigger challenges. It's practical, direct, and grounded in real experience of the role you're in.
Who can benefit from CFO Mentoring?
Sitting CFOs who want to sharpen their judgement, strategy, and influence. Newly appointed CFOs finding their feet in the role. Finance leaders stepping up to their first CFO seat. Experienced CFOs facing a new challenge - a transformation, a transaction, a bigger remit.
Is Mentoring confidential?
Yes. Mentoring is confidential, subject only to legal orprofessional obligations.
What we discuss stays between us. Nothing is shared with your CEO, board, HR team, or any other stakeholder without your explicit agreement. Where your organisation is sponsoring the work, we agree at the outset what will and will not be shared - typically broad themes and progress against objectives, never the substance of our conversations.
How does Mentoring differ from Coaching?
Mentoring allows you to draw on my experience. Coaching helps you develop and own the answer.
In mentoring, I am more direct. Drawing on decades in senior finance roles, including as CFO of Microsoft’s Worldwide Operations, I share what I would look for, risks I would consider, questions I would ask, and lessons I learned in comparable situations.
It is practical, experience-led support for the decisions, stakeholder dynamics, role transitions, and leadership challenges you are facing now.
In coaching, the emphasis is different. My primary role is to help you think more clearly, see your situation from new angles, and reach decisions that are genuinely yours. I use questions, challenge, reflection, and practical experimentation to strengthen your judgement, influence, and leadership effectiveness.
Mentoring is the core of this work. Where it will add value, we can also deliberately bring in a coaching approach - creating space to step back, challenge assumptions, and ensure that the decisions you make are right for your context rather than simply replicating someone else’s experience.
How often will we meet and for how long?
Most engagements run between three and twelve months - shorter for a focused goal, longer for sustained development - depending on what you want to achieve. We typically meet every two weeks, for an hour or ninety minutes, with real work applied between sessions.
Is CFO Mentoring in-person or online?
Most sessions take place online by video, providing flexibility around a demanding role and schedule. In-person is available where location allows. We'll do whatever works best for you.
I am an experienced CFO - why would I need a Mentor?
Because even the most accomplished CFOs encounter situations they have not faced before: a first major transformation, a difficult board dynamic, a transaction that reshapes the business, or a move into a materially bigger role.
You can work through those situations alone. But you do not have to.
Mentoring gives you access to relevant experience when it matters most: a confidential place to pressure-test your thinking, challenge assumptions, anticipate risks, and consider what may be coming next.
It is not a judgement on your ability. It is a way to add perspective when the stakes are high and the learning curve is steep. The objective is not to copy my approach, but to help you make the strongest call in your own context.
Experience takes time to build. Mentoring gives you the benefit of mine sooner.
Results that speaks for themselves
A significant impact on me, as a person and an executive
Energised, excited, and clearer about how I lead
Expert guidance through career transformation
Clarity, challenge, and lightbulb moments that stick
Genuinely transformative, with impact beyond the sessions
Clearer priorities, stronger leadership, more deliberate decisions
An outstanding coach
One of the best that I have worked with
An excellent executive coach
Provided a safe environment for us to push our boundaries
Guided me on a journey of self-discovery