Kevin O'Leary

Mental health & wellbeing in the hardened world of undercover operations.

There is, without doubt, a romantic Hollywood view of the undercover officer and the list of movies and TV shows where the role is portrayed is endless.  Many observers imagine the danger in undercover work comes from the potential for being unmasked and the consequences of confrontation with hardened criminals. There’s certainly a risk in that.  However, the most common and dangerous hazard comes not from the bad guys, but the corrosive effects on mental health that come with living with a covert identity.

Exposure to criminal environments, blurring of social identity and boundaries from having to move in and out of role were among the underlying causes leading to symptoms of work-related stress, increased anxiety, loneliness, depression, paranoia, and identity strain arising from long-term role playing.

No one could doubt that undercover officers were psychologically at risk, but it was tricky to address. They were often emotionally invested and committed to the task, sometimes resisting efforts from management to intervene and rarely self-disclosing when they were experiencing stress. They are able to think several Chess moves ahead.

From his unique perspective as the former head of Scotland Yard’s undercover unit, O’Leary uses case studies to describe how certain behavioural red flags signalled the need for leadership intervention.  In a complex and highly specialised world, the expectation is that technical know-how prevails.  However, leading heroes and protecting their mental health and well-being is relational, not transactional.  It’s about knowing where trouble lurks and when to intervene, using more grounded leadership and management skills to reduce complexity and make it human centred.

Getting Change to Stick with Frontline People

Keeping up with changes in society, technology, legislation and multiple generations in the workforce affects policing as it does any organisation.  The more specialist the function, the harder it can be to convince those on the frontline that change is necessary.

That’s because, to the highly action oriented, change is the language of management consultants and can be viewed as a far cry from the operational sharp end they inhabit.   And the sharp end doesn’t get more challenging than undercover police work.  Going toe to toe with hardened criminals couldn’t be further from the image of the change management project, with structured meetings, conversations and milestones plotted on a Gantt chart.   Though they’re unlike many challenges, undercover operations require the same innovative mindset, in a different and unique context.  Adapting to novel situations, dealing with rapidly changing circumstances and seeking new answers to tackle offenders who think they’re untouchable is where undercover officers excel.

Yet, when it came to managing change, O’Leary was faced with the same challenges and resistance commonplace in many transformation projects.  These challenges can be much harder when stakeholders come from the 43 autonomous police forces of the UK, and other agencies, such as the National Crime Agency, Customs and Border Agencies that use the same techniques and training.  In a national context, this is about influence rather than rank and authority.   Getting front line operatives onside was key to achieving outcomes.

How did he get buy-in from a highly specialised and experienced cohort of undercover detectives?   In a specialised operational context, it’s about clarity of purpose and making the complex simpler.    When they came, the results were astounding and helped remove barriers to recruitment, changing the national profile of undercover officers and better reflecting the communities served.

Key takeaways from this presentation include, clarity of purpose, leading people who know more than you, managing multiple generations in the workforce, outside-in vs. inside-out thinking.  Influencing without authority. Diversity and inclusion.

Weak signals

Incubating within the daily noise of long ‘to do’ lists and heavy workloads are the sleepers; the cases that don’t stand out above the routine; victims that might go unnoticed and serious offenders that slip through the net. But for the detective instinct, these time bombs lie dormant in the noise, time silently ticking away.  They may run down the clock and never be revealed or explode in a way that suggests it should always have been an obvious priority.

All professions suffer from this.  We prioritise and decide, using metrics that make it seem linear, when the reality of an uncertain and volatile world requires leaders to find ways to pick up on those weak signals that create highly perishable opportunities to advance or to avoid career limiting disasters.  In this case study, O’Leary discusses curiosity as a foundational trait of the detective and of leaders.

One routine case in a pile of other cases triggered his detective instinct to pull on a small thread, which led to another and then another.  Before long, the discovery of a body led to a serial killer, eventually jailed for a rare whole life term, following other grim discoveries.  A compelling and harrowing case study, told from his own experience, which began as a busy, routine day in the office.

Key takeaways from this presentation include insights into judgment, leveraging experience, distinguishing weak signals from noise, navigating decision-making in uncertainty, and recognising curiosity as a foundational trait of effective leadership.