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Is working with lawyers more likely than other fields to result with colleagues being impacted by scandals? I wouldn’t have thought so but now I’m not sure. The CEO of a former workplace—who hired me to go to Canada and who I had huge respect for—has just been let go (“is no longer employed by”) amid questions about how she was able to double her salary without the organization’s governance board knowing. This is not my first former boss to leave a job under a cloud.
I do not know any details beyond what has been reported in the Canadian media. And it’s a big story, as Ontario’s Law Society regulates the majority of lawyers in Canada, as well as paralegals. Sometimes these stories are just big in the legal press, but my wife told me about it, having seen it in mainstream Canadian publications. The whole thing is weird, though. Imagine a governance board taking these sorts of precautions around an independent reviewer’s report:
[Members of the governance board] were required to sign an undertaking and stay inside a room that had been designated for reviewing the report. Copies of the report were individually watermarked. [Board members] were permitted to take notes on the report, but all notes had to be placed in envelopes, which were then sealed. At the 5 p.m. meeting, [Board members] were given their notes back, which they had access to throughout the evening – but not the report.Diana Miles out as LSO CEO hours after benchers given access to report about her pay hike, Law Times, March 6, 2025
It’s really a baffling outcome. Diana Miles was a remarkable leader when I joined her team. I learned a lot of positive things and then, over time, a lot of negative things by watching her and other Law Society leaders. She could have been a brilliant leader outside the Law Society, where she was hamstrung by mediocrity within the staff but also a governance board that lacked the skills to perform its duties.
Frankly, a governance board full of lawyers is probably the worst governance board you could have. The Law Society, like many bar associations, has governors who think they represent the bar, when in fact the organization is supposed to be protecting the public. I’ve seen this on law library boards too, where the enacting legislation usually requires a fully bench-and-bar governance board. Huge mistake. The lack of expertise (in hiring and firing, in finance and purchasing, in technology, in marketing, in education, in managing and leadership) combined with the misalignment of goals means a lot of lawyer-centric boards are just time bombs waiting to go off.
It took me back to my time at the American Bar Association where, about 2 years after I arrived, my boss, the CFO, was fired. The ABA had an “over run” on a technology project involving outside contractors and big, internal complicated systems. The $12 million budget became a $19 million one before the governance board became aware of the overage. There was a lot of turmoil and also lots of lessons learned, including:
- someone will need to be blamed. This is a foolish waste of time but when the organization has a big issue, someone is going to have to go. It’s often not the person who should be going.
- money issues should always be transparent. If you are ever dealing with something with significant cost (salaries, licenses, purchases), do it it out in the open. Don’t assume people know what is going on. Highlight it in your board reports. Go out of your way to ensure people see it by using a bright highlighter color on your financial reports. Make sure your board is reading their financial reports (lots of lawyers do not know how to read financial reports or a budget document). The trouble may come because the governance board feels there has been a surprise—and perhaps realizes they’ve failed in their fiduciary duty—if you haven’t been clear about costs exceeding expectations.
I ended up as an acting CIO for that summer (the CIO was axed too) and I seem to recall some possibility of litigation with the consultants. I remember a deposition and, ever since that, I take no notes in meetings. I store things in my memory or I will make a note for a file but no random jottings.
The outcome is also usually easy to foresee. There is a new leader brought in, and the governance board now micro manages that person, to over-compensate for their own failing in the process. A new leader from inside will be hamstrung by the Board and may not have the right skills. The CEO prior to Diana was of that stripe, and never found his independence from the governing board. A new leader from outside may feel like they need to clean house. It could be a hard time for a lot of people.
Is It The Legal Profession?
This seems like a relatively high number of bosses to lose to scandal. The CFO was about ready to retire and so his departure was probably not as devastating to him as it could have been. He ended up on a sailboat near Baja California last I heard. I think it must be harder, especially in a very small market like Canada, to find a new role after experiencing such a public scandal.
It’s not always scandal, though. My first law school dean as a professional was a jerk and one of the reasons I looked for a new role despite having great immediate managers within the law library. He was eventually ousted as dean—and an anonymous student captured very much my experience of the dean—and arrested a few years later for soliciting a sex worker.
Even when I was interviewing on my most recent job search, I had some very off putting experiences. Interactions with leadership that made it clear that there was a fair chance that the culture was toxic and a person in a leadership role was not actually very well-suited to being a leader. When you interview with someone who isn’t like that and you have experienced it in the past, it is like night and day. Over time, you absolutely can tell who those people are.
But why so many in law? Is it because we ask lawyers to do a bunch of things they’re ill-suited for? That they’re not trained how to do in law school or in law practice, and then we’re surprised when they fail at it? Or because lawyers tend to think they know how to do everything, and so that hubris blinds them to the fact that they don’t understand a lot of what goes on in a governance setting?
My own experience suggests its not uncommon. I may have worked in more organizations than most people have in their career, but it still seems high to me to have people leaving organizations in a cloud like this. And I have seen and experienced this lack of specialized expertise, with people with legal backgrounds trying to “wing it“—in areas like human relations (HR), or law library operations management, or collection development, or financial operations—and making a shambles of it.
It makes me wonder how often an organization has dodged that bullet by sheer dumb luck. The person has moved on in time and the next person finds the problem and fixes it. Or someone joins the board who does have the right subject matter expertise (something other than a J.D.).
Disappointment
What I think doesn’t really matter. But I’m disappointed in her, because it seems like very poor judgment and she is too good a leader not to have seen the problem (I learned the word “optics” from her when I got to Canada), and I’m disappointed too in how her time at the Law Society ended. I have so many good memories about my own growth as a leader and manager thanks to Diana. There was one time where we were sitting listening to some user experience consultants (I had been given responsibility for the Law Society’s website after it had a horribly botched update by the IT team) and I must have looked like a goldfish. Diana was able to see my mouth open and then close. And I remember laughing about it afterwards, as I explained what she had intuited: if you have nothing nice to say, perhaps don’t say anything.
But I do also think about the world in which we all, law librarians, work. What are the circumstances that put us in the position of having leaders fall, or put ourselves in that position: law librarians embezzling money in Kern County (CA) or Knox County (KY) or racial profiling in Ontario?
One thing I have wondered is if the relatively limited number of opportunities in our professional world, especially as we become more senior, creates their own issues. There are clearly people who have spent 30 years in an organization who have not done anything that would result in this sort of outcome. But, at the same time, people in these roles often don’t have a lot of other options.
I have sometimes wondered about my own itinerant job path. I wonder if it is due at least in part to my own concern about ending up stuck in a role. I think that, on the whole, my lack of attachment to financial rewards (I like being paid for my work but I do not work to earn more money) probably means that I can make choices to jump from organization to organization more easily than someone who is tied to their lawyer persona or their pay cheque relative to other people.
A seasoned bar association executive or law library director or dean is not going to be able to jump into a new field easily (and no one is going to revere the law degree in the same way). If those senior people are not really very good at their job (you can become a dean or a law library director or a non-profit senior staff and still be a jerk or incompetent), there’s even less chance they’d find a home outside the legal profession or legal-adjacent organizations.
Our professional world seems so small that I guess each one of these events just stands out so starkly to me. Sure, each individual case may be an “exception”. But the outcome may just mean that other things are failing, allowing these other outcomes to happen. A common thread seems to be that lawyer-based governance boards aren’t very good at monitoring organizational finances. The Ohio law library I worked at had suffered something similar when the treasurer (a lawyer member of the Board) had embezzled from the law library.
I hope for the best for her because she really is one of the most remarkable people I’ve ever worked for. Even when it was politically unlikely, she attempted to improve law library and legal information delivery for the profession (ultimately a failure). She taught me how important it is to be a firewall against stupid for your people. She gave me space to stand up for my expertise—”Shouldn’t the CEO get to decide what’s on the home page,” she once asked, to which I responded, “No,” not when it isn’t the right thing to put there—and then backed me up.
I think, though, that, while we may hang on specific stories and the people involved, we may be ignoring a much larger problem. It’s a solvable problem but it’s not a problem that will be easy to solve. Legislation, egos, and money will hinder change that could benefit organizations that support the legal profession and the public’s access to justice.