Olive & OakExecutive Coaching
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Executive coaching & leadership advisory

Better decisions, made by leaders who are not doing this alone.

We coach executives and leadership teams through the work that has no clean answer — the reorganisation, the underperforming peer, the strategy nobody can repeat back to you. Practical, confidential, and grounded in how your organisation actually runs.

18 yrsAverage partner experience
240+Executives coached
92%Engagements extended or renewed

What we do

Three ways to work with us, all built around real decisions.

Every engagement starts with the same question: what is actually limiting results here? Sometimes the answer is an individual's judgement. More often it is how a team decides, or a structure nobody has revisited in three years.

01

One-to-one executive coaching

Six or twelve months with a senior coach for CEOs, functional leaders, and newly promoted executives. Assessment, a written development focus, and fortnightly sessions built around live decisions rather than theory.

02

Leadership team development

Work with the team as a unit: decision rights, meeting design, conflict that stays productive, and a shared operating rhythm. Usually a diagnostic, two offsites, and a quarter of follow-through.

03

Manager and emerging-leader programmes

Cohort programmes for the layer that determines most of your employee experience. Four modules on the conversations that matter, with practice, peer groups, and manager involvement.

Our approach

We are not here to be your most agreeable adviser.

Senior leaders have no shortage of people who agree with them. What is scarce is someone with no stake in the outcome who has read the room, talked to your colleagues, and will tell you plainly what they heard.

  • Evidence before advice — we interview the people around you before we form a view.
  • Work on live situations, not case studies or generic frameworks.
  • Written focus areas your sponsor can see, so the engagement is accountable.
  • Complete confidentiality on content; transparency on progress.
Talk to a partner
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How an engagement runs

Four phases over six months, with progress measured by the people around you.

Phase 1

Diagnose

Interviews with the people around you, a review of how decisions actually get made, and one clear picture of what is limiting your results.

Phase 2

Focus

Two or three development priorities, written down, with the behaviours and the business outcome each one is meant to change.

Phase 3

Practise

Fortnightly sessions built on real situations in your week — the board paper, the difficult peer, the reorganisation you are considering.

Phase 4

Embed

Progress checked with the same people we interviewed at the start, so change is measured by what others notice, not by how the sessions felt.

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Who we work with

Companies between forty and four thousand people, where the leader's judgement still shows up in the results.

Founders holding a company that has outgrown informal coordination. Functional executives newly responsible for people they used to sit beside. Leadership teams that are individually strong and collectively slow. Managers promoted for excellent individual work and never taught the rest.

I arrived expecting to be coached on communication. Six weeks in, we had established that the real problem was three unresolved decisions I had been avoiding for a year. Chief Operating Officer, healthcare services group

From the coaching journal

Recent writing

All 36 articles
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Organizational Management

How to Reorganize Without Losing a Year

Structure changes fail on sequencing and silence, not on the design. A calmer approach to the announcement and the ninety days after.

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Leadership

The First 90 Days Are Not About Proving Yourself

New senior leaders lose credibility by moving too fast on the wrong things. A better sequence: learn the system, secure one early win, then commit publicly.

Start with a conversation, not a proposal.

Forty-five minutes with a partner. We will tell you honestly whether coaching is the right instrument for what you are facing.

Book an introductory call