Lesson 6: When Things Go Wrong

Mistakes in legal practice are inevitable—deadlines are missed, instructions are misunderstood, assumptions are made, and work product falls short.

In high-pressure environments, these moments often create immediate frustration. The instinct is to identify what went wrong, who was responsible, and how quickly the issue can be corrected.

But in practice, another question matters just as much: How does leadership respond when something goes wrong?

A leader’s response does more than resolve the issue; it shapes how the team approaches the work moving forward.

The Immediate Reaction

When mistakes happen, the focus often narrows quickly to the individual involved.

The associate missed the issue.
The assignment was misunderstood.
The work required revision.

And in some instances, the opportunity itself is taken away as a consequence. The assignment is reassigned, the associate’s involvement is reduced, and the immediate problem is resolved. But the long-term cost is often less visible: the associate loses the opportunity to develop through the mistake, and the firm loses the benefit of that future growth.

And while accountability matters, focusing exclusively on the outcome often overlooks the process that produced it.

What instructions were given?
Was context provided?
Was there an opportunity to check alignment before the work progressed too far?

Most mistakes are not created in isolation. They develop through gaps in communication, unclear expectations, or assumptions left unaddressed.

And in many cases, they are also a natural part of the learning process itself. Associates develop judgment through experience, and experience inevitably includes moments where something is missed, misunderstood, or imperfectly executed.

Immediate frustration often fails to account for that reality.

That does not remove responsibility from the associate, but it does broaden it.

Correction or Hesitation

By the time a mistake reaches a partner’s attention, the associate is usually already aware that something went wrong. They are replaying the assignment, reviewing the work mentally, and anticipating the conversation that follows.

In those moments, associates are not only looking for correction; they are evaluating something else entirely.

Whether questions are safe to ask.
Whether uncertainty can be communicated early.
Whether support exists when pressure increases.

Because over time, people adjust not only to expectations—but to reactions.

How leaders respond to mistakes has a direct impact on how teams communicate afterward. A response focused solely on frustration often creates hesitation—not necessarily in how work is produced, but in how uncertainty is communicated. Associates become more cautious in approaching leadership, less communicative, and more likely to avoid raising questions until issues have already expanded.

This is not a matter of disengagement. Instead—and unfortunately—associates often become focused on avoiding a repeat of the experience rather than a repeat of the mistake itself.

In contrast, responses grounded in clarity, accountability, and development create a different outcome.

Questions surface earlier.
Issues are raised sooner.
Alignment happens before deadlines tighten.

The mistake still gets addressed, but so does the process that allowed it to happen.

In many cases, the timing of when mistakes surface is itself revealing.

Associates who raise concerns early—while uncertainty still exists, before issues have compounded—often do so because they trust the response they will receive. They believe questions can be asked without immediate frustration or judgment.

Where mistakes consistently surface later in the process, however, there is often something else at play: hesitation, fear of overstepping, and concern that uncertainty will be interpreted as incompetence rather than part of development.

In practice, the timing of communication is often a reflection of the environment leadership has created around it.

Leadership Under Pressure

Legal practice is, and likely always will be, a profession shaped by pressure—deadlines tighten, expectations escalate, and mistakes carry consequences. But while pressure is inevitable, disorganization does not have to be.

In practice, many moments that become unnecessarily reactive are often the result of insufficient structure earlier in the process: clear instructions, periodic check-ins, examples of prior similar work, and assigning peers or mentors associates can rely on when leadership is unavailable. These measures do not eliminate mistakes, but they often reduce the pressure surrounding them—and create environments where communication happens earlier and more openly.

Leadership under pressure is often what people remember most. For many partners, leadership is modeled after the environments they themselves experienced. But the goal should not simply be to become the partners they once had. It should be to build stronger, more developed, and more sustainable teams than the ones they inherited.

In many ways, how mistakes are handled is where that distinction becomes most visible. Associates remember those moments. They discuss them with peers. They share them with classmates, colleagues, and future applicants considering where they want to build their careers.

Reputations within the profession are often shaped long before formal interviews ever occur. And increasingly, the firms that stand out are not simply those producing strong work—but those developing strong people.

From a management perspective, this matters beyond any individual assignment or mistake. People rarely leave organizations because work is difficult. More often, they leave because of how leadership responds when pressure increases.

How mistakes are handled shapes retention, communication, trust, and ultimately the long-term strength of the team itself.

The Bottom Line

Mistakes are inevitable. The response is not.

Over time, a leader’s reaction to mistakes shapes not only how teams perform—but whether people choose to remain part of them.

While correction resolves the immediate issue, development determines whether the team improves from it.

Weekly Reflection: When mistakes happen on your team, do people become more comfortable communicating uncertainty—or more careful about hiding it?