Podcast Ep. 23: Is Your Boss an Insecure Overachiever? A Woman Lawyer's Guide to Managing Up

Have you ever worked for someone who seemed impossible to please?

Perhaps they constantly changed their mind. Maybe they wanted to approve every email before it was sent. Or perhaps they gave feedback that felt unnecessarily harsh, even when your work was good.

If so, you may have been working for an insecure overachiever.

I was reminded of this recently while running a workshop for a large French company. The participants were not lawyers, but many of the conversations could just as easily have taken place in a law firm.

One participant told me he wanted to learn how to celebrate mistakes within his team.

It was an interesting way of putting it.

He explained that his team had told him his feedback was almost always right, but the way he delivered it felt brutal.

So I asked him a question.

"How hard are you on yourself?"

Without hesitation, he admitted that he expected an enormous amount from himself.

I knew exactly what he meant.

Throughout my life, people have often told me that I am too hard on myself. They have also told me that I can be intolerant of other people. Looking back, I do not think those two things are unrelated.

When we set impossibly high standards for ourselves, we often end up expecting the same from everyone around us.

Why law firms attract insecure overachievers

That conversation reminded me of a story Professor Laura Empson shares in her excellent book Leading Professionals.

In one interview, the head of HR at a professional services firm explained that they deliberately recruited insecure overachievers. They looked for candidates who described themselves as perfectionists or people who pushed themselves too hard.

Once they had hired them, they created an environment that amplified those insecurities, because the competition encouraged people to work even harder.

When Professor Empson suggested that the firm behaved almost like a drug dealer by finding vulnerable people and getting them hooked on the prestige the firm offered, the HR director replied that it was a symbiotic relationship.

The professionals wanted success.

The firm helped them achieve it.

Everyone became very successful, at least for the few who survived.

There is a great deal we could say about that story.

For today, though, I want to make just two observations.

The first is that law firms are often full of insecure overachievers.

The second is that there is a reasonable chance you are working for one.

What does an insecure overachiever look like?

We all experience self doubt from time to time. That is part of being human.

An insecure overachiever is different.

They often worry deeply about how they are perceived. They can find decision making difficult because they are afraid of getting it wrong. They may seek constant approval from those above them while being highly critical of those below them.

Many become micromanagers.

They want every conversation to go through them. Every decision needs their approval. Every piece of work has to be checked.

Ironically, the fear of being seen as an ineffective leader often creates the very leadership problems they are trying to avoid.

Before jumping to conclusions, though, it is worth asking whether something else might be happening.

Women in leadership, for example, are often scrutinised far more closely than men. Many of my clients tell me they are interrupted more often, challenged more frequently and made to feel they have something to prove.

Sometimes what appears to be insecurity is actually someone responding to constant pressure.

That does not excuse poor behaviour, but it does remind us to stay curious before we judge.

Before you decide your boss is the problem

Whenever I coach someone through a difficult working relationship, I encourage them to pause before taking action.

Ask yourself three questions.

What impact is this behaviour actually having?

Is it simply irritating, or is it affecting your work, your confidence or your reputation?

Could you be contributing to the dynamic without meaning to?

Relationships are complicated, and sometimes both people play a part.

Finally, what does your boss actually want?

One client told me about a partner who became increasingly tough with lawyers approaching partnership because he genuinely believed he was preparing them for life as a partner.

His intentions were good.

His behaviour had exactly the opposite effect.

Understanding someone's motivation does not mean accepting poor behaviour, but it often changes the way we respond.

How to manage an insecure overachiever

If you recognise your boss in this description, the first thing I would encourage you to do is create a little emotional distance.

This is not forever.

Try not to take every interaction personally.

When you do need to raise an issue, focus on the impact of the behaviour rather than criticising the person. It is much easier for someone to hear that a particular approach is making it harder for you to serve clients than it is to hear that they are controlling.

If your boss tends to micromanage, proactive communication can make an enormous difference.

Regular updates or weekly check ins often help people feel more comfortable letting go.

Where you can, become someone they trust.

Develop expertise they rely on.

Help them feel confident that things are under control.

And if you can genuinely do so, look for opportunities to acknowledge what they do well.

That is not about flattering someone.

It is about recognising that even senior people need appreciation.

The question worth asking

If someone at work is driving you mad, whether it is your boss, a colleague or even a client, pause before reacting.

Ask yourself these three questions.

What impact is their behaviour having on me?

Could I be contributing to the dynamic in ways I have not considered?

What are they really trying to achieve?

Those questions will not solve every difficult relationship.

But they often change the conversation.

And sometimes they change the relationship itself.

Success in a law firm is not only about developing technical expertise. It is also about learning how to navigate difficult people with wisdom, curiosity and compassion.

That is a skill that will serve you throughout your career.