Ollie Smedley
& Associates
Helping senior leaders think clearly, lead confidently and make better decisions
Executive coaching, team coaching and thinking partnership for leaders carrying real accountability

Ollie Smedley
Leadership can be immensely rewarding. It can also be demanding, complicated and, at times, surprisingly lonely.
The higher you go, the fewer places there are to think out loud, test ideas, admit uncertainty or work through difficult decisions with someone who understands the realities of leadership.
I work with finance leaders and senior executives to help them think more clearly, lead more confidently and make better decisions about the things that matter to them, their teams and their organisations.
As a former CFO and Managing Director, I understand the accountability, pressure and personal compromises that can come with senior leadership. I've made some of those compromises myself and, at times, without even realising I was making them.
Coaching and mentoring helped me become a more effective and confident business leader. It didn't give me the answers - it helped me ask better questions, make better decisions and lead in a way that was more sustainable for both me and the people around me.
Today, that's what I provide for others.
I now act as a confidential sounding board and thinking partner for leaders who want to:
- Step back from the day-to-day and see the bigger picture
- Make better decisions when the stakes are high
- Build stronger relationships with colleagues, boards and stakeholders
- Increase their impact and confidence around the leadership table
- Become more trusted, commercial and influential advisers
- Get more from their teams without carrying everything themselves
- Stay effective without losing yourself in the role
I combine business experience, coaching skill and practical challenge to create a high-trust, high-challenge environment where leaders can talk honestly, think clearly and leave with something useful.
Alongside my coaching and mentoring work, I am Chair of Transform Housing & Support, giving me an additional perspective on governance, board dynamics and organisational leadership.
Clients
Associate Work
Finding the right coach or thinking partner matters.
Our first conversation is simply an opportunity to explore what's going on, what you're hoping to achieve and whether we're the right fit.
If it doesn’t feel right, that’s fine too.
No hard sales. No head-shrinking. Just a common sense conversation.
It's all about context
No two leadership roles are the same.
Every organisation has its own culture, politics, pressures and pace. Every leader faces different expectations from colleagues, customers, boards and stakeholders.
That's why I don't start with a model or a formula.
Instead, we work with your context - helping you make sense of the challenges you're facing and the opportunities in front of you.
Whether you're leading growth, navigating change, developing your team or simply trying to become a better leader, context matters.
Leadership is never just about strategy.
It's about people. Boards. Bosses. Peers. Customers. Regulators. Investors. Your team.
Every relationship brings different expectations, different pressures and different conversations.
Helping leaders navigate those relationships is often where the biggest shifts happen.
And then there's you. The person everyone relies on. How's your work-life balance? How's your health? When was the last time you invested properly in your own development?
Is work something you do, or is it what you have become?
How I help
No two coaching relationships look exactly the same. Some people need a confidential sounding board. Some want support as they step into a bigger role. Others want someone who will challenge their thinking, help them navigate difficult relationships or get more from their teams.
Whatever brings us together, we'll focus on what matters most to you.
Focus areas can include:
- Thinking through difficult decisions
- Leading with greater confidence
- Building stronger stakeholder relationships
- Getting more from your team
- Navigating change
- Managing pressure more effectively
- Preparing for promotion or a bigger role
- Leading in a way that's authentic and sustainable



