An Interview with Erika O'Leary

January 26, 2023

An interview with Erika O'Leary, Director of Investigations

Erika is a specialist investigator with a powerful fusion of law and intelligence. She runs contentious investigations spanning from fraud to sports corruption and wrongdoing. Below, she shares insights from her unique perspective.

What makes a good investigator and a good investigation?


There isn’t one ‘model’ person who will make a great investigator.  We come from an array of backgrounds which I think is a crucial factor. Personally, I come from a legal background, having practiced as a lawyer for several years but you find investigators naturally coming from law enforcement and military intelligence backgrounds and from interesting third level degrees such as politics and languages.  For me, an investigator needs to be like a Jack Russell, tenacious.  You need to have a yearning to get to the nub of an issue and trust your instincts when pursuing a line of enquiry.  Don’t take anything at face value and follow where the evidence takes you.  To be a really effective investigator I believe there is also a need for strong emotional intelligence.  I think it gives an investigator an added layer of capabilities.  Being able to build trust with human intelligence sources is a large part of gathering intel and being able to understand different personalities really goes a long way in developing that bond with sources.  


A good investigation requires planning.  In some circumstances a terms of reference will be applicable but not always.  In all cases though a thorough investigation plan is a must.  It isn’t always easy to outline an investigation plan at the outset of a case because of the unknown nature of where the information may take you so I would always look to plan an investigation in tranches, one leading on from the previous dependent on the intelligence and/or evidence obtainable.


What situations drive investigations?


The possibilities really are endless.  A large proportion of the investigations I have conducted emanate from frauds and breaches of regulatory codes or internal codes of conduct.  In essence it really is wrongdoing that drives the need for investigations.  Whether this is a theft, an attempt to hide assets illegally, a breach of rules and regulations or suspicions of any of the above.  Some of my investigations have been in the context of litigation support working closely with a client’s legal team but others have been standalone internal inquiries for corporations and organisations.  For instance, I have conducted several investigations within the sports industry, all emanating from suspicions of wrongdoing or evidence of wrongdoing.  These have included corruption investigations, regulatory breaches such as doping and match fixing investigations and more sensitive matters such as sexual harassment and bullying.  Most of these begin as standalone internal inquires and then dependent on the evidence unearthed are referred to the necessary law enforcement authorities or regulators.  


What kind of information do you look for, and how do you find it?


There actually isn’t one standard answer to this question because it all depends on what the investigation is looking into.  For argument’s sake, let’s take tranche 1 of an investigation which may entail enhanced due diligence on an individual/corporate. My aim would be to conduct 360-degree assessment by looking for a combination of open-source intelligence (OSINT) and human intelligence(HUMINT).  I would conduct a meticulous interrogation of all public record and non-public data in the relevant jurisdiction and our suite of specialist subscription-only databases. I would typically access resources such as global corporate aggregators, company filings, land registries, regulatory filings, local media records, cyber software, leaked data, and a host of other specialist investigative tools. This isn’t an exhaustive list and will adapt depending on the nature of the individual and/or corporate.  Married with this I would discreetly canvass suitably placed sources who have knowledge of our subject and/or industry etc. Each case is really approached in its own unique way, depending on the particular focus or requirements.


Can you share an interesting anecdote from one of your investigations?


So, it has less to do with an actual investigation and more to do with the environment I found myself in. Bearing in mind, I had up to the point in my career being a very traditional lawyer who had dipped my toe in more ‘exciting’ areas of the lawlike sports but nonetheless it was law and I never really had to leave my comfortable desk.    Then on one of my first overseas trips for the corporate intelligence company I was working with at the time, I found myself on a movie set (not literally mind!).  I had been tasked with passing intelligence to a law enforcement agency whom I had started building a relationship with. However, because of sensitivities this had to be done in person and not electronically.  So, I find myself in a city waiting nervously for a message from my intended contact to let me know where to meet.  The message arrives and simply says “Meet outside please I can’t find parking”.  So out I go and a black sedan with tinted windows swoops up.  In I get and we drive off.  


Traffic in this city is horrendous so we were getting nowhere fast.  I’m sitting next to my source armed with a glossy dossier of intel all prepped to fully debrief them in their office and that’s where I get ambushed, metaphorically. We pull over into a layby and the meeting is happening right here right now, what? How am I going to do this sitting in the passenger seat of a car.  First though my trusty iPhone which barely leaves my side ever is requested.  What?!I hesitantly hand it over.  The same request is made of my colleague sitting in the back of the car.  A faraday box appears and in go the phones.  Oh, right I’m not in Kansas anymore Toto!!  Next wired earphones are shoved into the earphone jack on my laptop. I’d no idea what was happening, but time would teach me the faraday box blocked any signals to and from our phones and the earphone trick was a technique used to prevent my laptop being hacked into.  However, in that moment I was like a rabbit caught in headlights.  Time to hand overthe intel I had collected.  For the previous months I have worked on a dossier containing open source and human intelligence on the corrupt activities of high-ranking executives at a global organisation.  Hours had been spent establishing trusted sources and creating detailed profiles and association charts on these people.  All the time my mind was whirling and wondering if I was just telling them information they already know, they were law enforcement after all!  The meeting was a whirlwind and I left without having any idea if my months of hard work were even relevant to them, let alone interesting.  A month later, on a Sunday afternoon I get an email from said people.  Included were court papers which had just been released and there was my intelligence in black and white.  It had meant something!  And thankfully, I’m glad to say to this day the relationship established on that faithful day is still strong.  It was nice to know the fruits of my investigation had formed the basis of charges brought.


Is it true that, like in the movies, investigators live and breathe their cases, operating from a dark room, without much sleep and with large amounts of caffeine?

It sounds so mysterious, doesn’t it?  I’m glad to report that in the 21stcentury I definitely don’t operate like that. First off small problem I don’t drink caffeine (no one wants to witness the heart palpitations!), secondly I don’t do well without a proper 8 hours sleep a night and thirdly who in their right mind wants to work in a dark room?  No, we operate like any other professional services operator, in a nice bright office thankfully with lots of light and if you'd believe it no clutter.  Whether we live and breathe our cases may be a different answer, it certainly isn’t always a traditional 9-5 job but then now what is? Our cases tend to be more on the interesting side of matters, so it never feels like an inconvenience if a little work creeps over into a weekend or an evening. Our work tends to flow in peaks and troughs so when you’re on an investigation it can be all go but then you'll reclaim balance when it ends and you get back to the bread and butter work.


As an investigator you see developments in the world from an interesting angle. What is something unfolding currently which you think more people ought to be aware of?


This is true.  Like in so many areas of our lives the long-term effects of the pandemic are slowly emerging.  As an investigator, I believe we will see an increase in frauds both internal and external as a result.


Many businesses had to scramble to ensure workers had the necessary equipment and access to systems to work remotely and with these changes came a significant rise in data security risk.  Secure office locations were empty, work data was accessed from a range of mobile devices and variations in encryption and security settings across devices has meant some businesses were wide open to attack.  With these weaknesses came a spike in the level of externally driven cyber-attacks.  I don’t believe though the management solution to this is to demand workers back into the office.  While it makes business data security easier to manage, the hybrid working model I believe is here to stay (and should be in my opinion personally).  It is up to businesses now to ensure they assess new and old fraud risks; update systems and procedures to reflect new or enhanced risks; conduct penetration testing across their new environments; focus on employee data access; and very importantly educate their workforce on fraud and how data is being shared.  


Internal threats also increased significantly during the pandemic, with many more employees provided access to sensitive data, sometimes with less physical or remote supervision. During this period and now in the 12months since there have been increases in potential incentives for employees to commit fraud including the soaring rise in inflation, fears of potential redundancy or a pressure to report positive financial results during a period of economic uncertainty. The reduction in the real value of wages have left some employees finding it easier to rationalise fraud, especially those feeling disengaged with their employers.  So, I think over the next 12 months we will start to see more businesses becoming aware of the need to investigate suspected frauds.


What advice would you give to people thinking about using investigations?

The world we operate in now is complex and more and more specialist services are required particularly in the context of litigation or contemplated litigation.  A client is specific with the type of legal team they choose dependent on their particular issue and I am a firm believer that investigations are an integral part of the development of any of these legal strategies. The forensic capabilities that an investigation brings ultimately can add that winning edge to a case.  Whether this is a pre litigation requirement of intelligence gathering to inform a legal strategy or during the course of active litigation which has more of a demand for evidence gathering, both I believe are invaluable.  So, if you’re apprehensive about reaching out directly to an investigator talk to your lawyers and discuss.  The strength comes when lawyers and investigators combine efforts and really work together to bolster a case.  This is also where it becomes important that your lawyers can trust investigators that they are professional and adhere to best practice and the highest levels of data protection compliance.