When Good Brokers Make Mistakes

Some of the most troubling professional mistakes I've encountered over the course of my career have been made by people who were very good at their jobs.

Experienced brokers, capable account managers, conscientious professionals who understood their clients, knew their markets, and cared about the quality of their work.

People who would have been horrified to learn that something they'd done, or failed to do, had left a client exposed.

And yet, it happens.

A detail is overlooked, a conversation isn't documented, an assumption goes unchallenged, or an instruction is misunderstood. Something that should have been followed up on gets buried beneath the more immediate demands of the day.

Sometimes the oversight is caught in time and corrected. Sometimes it remains undiscovered for years, until a claim arrives and a seemingly insignificant decision takes on an entirely different meaning.

I've spent a great deal of my career examining these situations, and one thing has become increasingly clear to me.

The question of who made the mistake is often considerably easier to answer than the question of why it happened.

And if we're genuinely interested in preventing the next one, it's the second question that deserves more of our attention.

The comforting simplicity of blame.

When something goes wrong, our instinct is often to identify the person responsible.

Who handled the account? Who prepared the submission? Who was supposed to follow up? Who failed to notice the discrepancy?

These are legitimate questions, particularly in a profession where duties and responsibilities have real consequences. We cannot simply wave away individual accountability because someone was busy, distracted, or working under difficult circumstances.

But there is a danger in allowing the investigation to end there.

Finding the person who made the mistake gives us a name, an explanation, and perhaps the satisfaction of believing we've identified the problem. We can arrange additional training, issue a reminder, update a procedure, or have a difficult conversation about expectations.

Sometimes those are exactly the right things to do.

But what if the person who made the mistake was operating within a system that made the oversight more likely?

What if the workload had become unmanageable, the procedures were unclear, or the employee had been promoted into a role without the training and support needed to perform it confidently?

What if everyone knew there was a problem, but the organization had become so accustomed to working around it that nobody regarded it as unusual anymore?

Correcting the individual mistake without examining those conditions may leave the underlying problem untouched.

And then we wait for the next person to make it.

The things people learn to work around.

One of the more interesting aspects of organizational life is how adaptable people can be.

Give a capable person an inefficient system, and there's a good chance they'll find a way to make it work. Give them an unreasonable workload, and they'll develop shortcuts, informal processes, and personal routines that allow them to keep moving.

They may become remarkably good at compensating for the weaknesses around them, and because the work continues to get done, the organization can begin to mistake their adaptability for evidence that everything is functioning as it should.

I've seen experienced employees become the unofficial keepers of institutional knowledge, the people everyone turns to when a process doesn't make sense or an unusual situation arises.

They know which forms are outdated, which instructions need interpreting, and which colleagues can resolve a particular problem.

Their knowledge is valuable, but it can also conceal an uncomfortable truth.

The business may be relying on individual resourcefulness to compensate for organizational deficiencies.

And resourcefulness, however admirable, is not a substitute for sound operations.

Eventually, someone goes on holiday, changes roles, retires, or simply has a difficult week, and the arrangement that appeared to work so well begins to unravel.

The problem wasn't necessarily that somebody stopped caring. It may be that the organization had been depending on them to overcome problems that should have been addressed long ago.

The trouble with knowing what we know.

Not every professional mistake begins with an operational weakness. Sometimes it begins with confidence.

Experience is one of the most valuable things a broker can bring to a client relationship, but it comes with its own hazards. The more familiar we become with a type of risk, a particular market, or a longstanding account, the easier it can be to stop questioning what we believe we already understand.

We recognize the circumstances, remember how we've handled something similar before, and move forward on the strength of that knowledge.

Most of the time, this is precisely what expertise allows us to do. We make sound judgements efficiently because we've spent years developing the ability to distinguish what matters from what doesn't.

But occasionally, the familiar situation contains something unfamiliar.

A policy wording has changed, a client's operations have evolved, or a market has introduced a new exclusion. Perhaps a routine renewal conceals an exposure that wasn't there the year before.

The danger isn't necessarily ignorance. It's the possibility that our confidence may prevent us from recognizing what we don't know.

I've always been drawn to the more complicated corners of insurance, particularly questions that require us to examine policy language closely and consider how different pieces of coverage interact.

One of the things those experiences have taught me is the value of being willing to say, I'm not entirely sure. Let's look at that again.

Because good judgement isn't simply knowing the answer. It's recognizing when the answer deserves another question.

When the pace becomes the problem.

Insurance brokerages are busy places. Clients need answers, renewals have deadlines, markets have their own demands, and the work rarely arrives in manageable intervals.

But there's a difference between being busy and operating in a state of permanent urgency.

When everything is urgent, the activities that protect the quality of our work can begin to look like luxuries.

A careful review takes time. So does documenting a conversation properly, mentoring a junior colleague, checking a policy wording, or sitting with a client long enough to understand what's changed in their business.

These are not interruptions to the work. They are part of the work.

And yet, under sustained pressure, they're often among the first things to be compressed or postponed.

An employee may know perfectly well that a file deserves another look, but when there are fifteen other matters waiting and three people asking for an immediate response, the temptation to move on can be powerful.

Multiply that pressure across an organization, over months or years, and the cumulative effect can be significant.

We begin to normalize a pace that leaves little room for reflection, and then express surprise when something important is missed.

I don't think that's entirely fair to the people doing the work, or particularly useful to the people responsible for leading them.

Accountability belongs at more than one level.

None of this is an argument for lowering professional standards. Quite the opposite.

Our clients are entitled to expect competent advice, thoughtful attention, and the exercise of reasonable care. When we make commitments, we have an obligation to honour them, and when we make mistakes, we have a responsibility to address the consequences.

But that responsibility extends beyond the individual broker or account manager.

Leaders have responsibilities, too.

If we expect our people to exercise sound professional judgement, we must give them the knowledge, tools, time, and support necessary to do so.

If we want consistent service, we need clear standards that are understood across the organization. If we want employees to raise concerns before they become problems, we must create an environment in which asking questions is welcomed rather than regarded as a sign of weakness.

And if we want accountability, we have to be prepared to examine our own decisions about staffing, training, supervision, technology, and workload.

It's easy to tell people to be more careful.

It's considerably harder to ask whether we've created the conditions in which careful work is realistically possible.

But that's where meaningful leadership begins.

The stories we should be telling.

Over the years, I've studied many professional liability claims, and I'm continually struck by how much there is to learn from the ordinary circumstances surrounding them.

Not simply the coverage issue or the legal outcome, important though those may be, but the sequence of human decisions that led to the loss.

The assumptions, the missed opportunities to clarify something, the moments when an additional question might have changed the outcome, and the organizational conditions that allowed those moments to pass unnoticed.

There is a temptation to treat these stories as cautionary tales about what other people did wrong, but I think that misses much of their value.

The more useful question is whether we can recognize something of ourselves in them.

Have we ever assumed a longstanding client understood a limitation we hadn't discussed recently? Have we relied on an informal process because it was familiar, even though we knew it wasn't especially reliable?

Have we allowed a capable colleague to become so indispensable that nobody else fully understood what they were doing, or mistaken the absence of complaints for evidence that our systems were working?

These are uncomfortable questions, but they're worth asking.

The purpose of examining a professional mistake shouldn't be to establish how much wiser we are than the person who made it. It should be to understand how easily we might find ourselves in a similar position, and what we can do to make that less likely.

A little more humility, a little more care.

I have enormous respect for the people who work in this profession.

Insurance can be technically demanding, emotionally exhausting, and unforgiving of errors, particularly when the consequences of a decision may not become apparent until years later.

It asks us to make judgements in imperfect circumstances, often with incomplete information and competing demands on our attention.

And despite all of that, I see people doing excellent work every day, solving problems, advocating for clients, helping colleagues, and taking their responsibilities seriously.

They deserve organizations that take those responsibilities just as seriously.

Organizations willing to examine their weaknesses before a claim exposes them, invest in education before a mistake makes it necessary, and recognize that the quality of their service depends as much on the conditions they create as on the abilities of the people they employ.

There will always be mistakes. We're human, after all, and no amount of training, technology, or procedural discipline will make us infallible.

But we can become more thoughtful about how they happen, more honest about the pressures that contribute to them, and more willing to learn without immediately reaching for someone to blame.

We can hold people accountable while still treating them with dignity, and insist on high standards while acknowledging that even good professionals need support.

And perhaps most importantly, we can remember that preventing mistakes is not simply an exercise in protecting a brokerage from liability.

It's an expression of the care we owe to our clients, our colleagues, and the profession itself.

Good brokers will sometimes make mistakes.

Good organizations will work hard to understand why.

And the best ones will have the courage to do something about it.