From Monitoring Officer to Chief Executive: Learnings, Reflections and Advice from the AMO Conference

At the inaugural AMO & LLG Monitoring Officer Conference, Tom Hoult hosted fireside “Monitoring Officer to Chief Executive – Learnings, Reflections and Advice”, alongside Kim Sawyer and Kevin O’Keefe.

Tom opened with a striking statistic: just 4% of local government Chief Executives come from a legal background. The discussion explored why that figure remains so low and what Monitoring Officers can do to broaden their leadership influence.

Opportunity creates leaders

Neither Kim nor Kevin followed a traditional route to Chief Executive. Both described careers shaped by stepping into unfamiliar territory, particularly during periods of significant organisational change.

Their message was clear: leadership opportunities often emerge through change. Whether supporting devolution, establishing combined authorities or leading governance transformation, taking on complex challenges helped them build the experience, visibility and confidence needed to progress.

Be more than “the lawyer”

A key theme was the need for Monitoring Officers to move beyond being seen solely as legal advisers and become trusted strategic advisers.

Kevin argued that Chief Executives must focus on outcomes and organisational judgement, while Kim emphasised the importance of understanding the objective behind a question, not just providing the legal answer.

The strongest leaders, they suggested, combine legal expertise with strategic thinking and curiosity.

Think corporately

Kim and Kevin both stressed that Monitoring Officers should contribute to wider organisational discussions, not just legal matters.

Monitoring Officers sit at the centre of governance and decision-making, giving them a unique perspective across the organisation. Those who contribute confidently to strategic conversations are far more likely to be viewed as corporate leaders.

The advice was simple: don't wait to be invited into the conversation.

Relationships and judgement matter

According to Kevin, Chief Executives are appointed primarily for two reasons: good judgement and strong relationship management.

Relationships with elected members, senior officers and stakeholders are critical, while Kim highlighted the importance of surrounding yourself with people who are willing to challenge and provide honest feedback.

Both agreed that authenticity is essential to effective leadership.

Confidence remains a barrier

When asked why more Monitoring Officers do not become Chief Executives, both speakers pointed to confidence.

Kim observed that many talented professionals do not apply for senior roles because they do not feel ready. Her view was that nobody is ever completely ready; at some point, leaders need to step forward and take the opportunity.

She also noted that moving into a Chief Executive role requires accepting uncertainty and becoming comfortable making decisions without having all the answers.

Protecting the influence of the Monitoring Officer role

Kim raised concerns about the changing position of Monitoring Officers within some local authority structures, noting that many no longer sit at the top table.

The discussion highlighted the importance of ensuring Monitoring Officers continue to be recognised as strategic leaders rather than purely technical advisers. Kevin pointed to forums such as the Golden Triangle as opportunities to demonstrate wider organisational leadership and build trusted adviser status.

Key advice for aspiring Chief Executives

• Seek out major change and transformation programmes.

• Build a strong corporate voice.

• Look beyond the legal question to the strategic objective.

• Invest in relationships, mentoring and coaching.

• Ask for opportunities and broaden your experience.

• Be authentic and visible.

• Develop your profile beyond the legal profession.

• Use strategic forums to demonstrate leadership.

Final reflection

The session concluded with an encouraging challenge: don't underestimate the leadership potential of Monitoring Officers.

As Kevin put it, “just do it”. For those willing to think strategically, build influence and embrace opportunity, the path from Monitoring Officer to Chief Executive may be far more achievable than the 4% statistic suggests.

We share our heartfelt thanks to Kevin and Kim for being such brilliant guests.

Please contact Tom Hoult to discuss your career and aspirations.

Tom Hoult Senior Managing Consultant thoult@venngroup.com