#111: I’d like to tell you about one of my biggest failures as a leader.

I got my first big break to move from individual contributor to sales manager in 2013 while working for Prudential.

The job was intimidating and exhilarating:

At the fresh-faced age of 34, my responsibility was to lead 7 men to knock down a collective $1.4 billion sales goal.

All 7 of these salespeople were men (which is an important factor to this story).

One of my strategies was to transform the individualistic sales team dynamic from “7 guys on 7 separate islands…”

…to a cohesive, powerful unit.

I wanted to lead a group of brothers who supported one another, called each other forward and genuinely reveled in the other man’s success.

In the first few years of leading this group, that’s exactly how they developed.

These guys let their guards down.

Showed vulnerability.

Shared their winning formulas that they’d previously kept close to the vest.

This group genuinely cared for each other.

Some of the men closed the biggest deals of their 2- or 3-decade careers.

Others had their best sales years ever.

The seasoned sales guys were actively mentoring the greener sales guys.

It was a thing to behold.

And then one of the men left to go to a competitor.

I had a vacancy to fill.

By far, the most qualified person to fill his role, was a woman.

We hired her immediately.

But now I had a problem.

The culture she was stepping into was built on 2 years of men exclusively working with other men.

During those two years, we’d grown to love having that bond of brothers.

Some of these guys had never experienced being part of a group of other men where they felt they could let the guard down, be supported and talk about men’s issues that typically weren’t welcome in the workplace.

We weren’t the locker room talk guys.

Sure, we were more casual in our language, talked a lot about sports and had open conversations about life’s ups and downs with respect to marriages and dating.

But even though we weren’t crossing any lines, these same dynamics wouldn’t always be appropriate in a mixed setting.

And that’s where I could see my failing:

I had not prepared our team for evolution.

As an immature leader, I did not have the awareness, nor did I set the expectation that one day our team would evolve to a place of greater diversity.

I had not spoken to the team about the fact that we should be excited for and welcome that evolution because that would give us an opportunity to grow together.

Instead, it felt like that day of evolution kicked the door down without warning, and I hadn’t prepared myself or the team for it.

I feared the men would experience this evolution as a loss.

A loss of their freedom, a loss of their bond and a need to go back to being “buttoned up.”

I feared that the men would unconsciously resent our new female team member through no fault of her own, but simply because she represented a need to change.

I feared that the 6 remaining men would maintain their own “club” of separate text message chains and inside jokes that would create a barrier between them and a fully inclusive team experience for our new female member.

I had not sown the seeds for an environment of inclusion where anyone – like the best candidate – could quickly step in, feel welcomed and thrive.

I had not built a culture of the future.

This all could’ve gone terribly wrong because of my failings and immaturity as a leader.

But I got off easy.

Our new team member happened to be a 20-year veteran of Prudential. She already carried a tremendous amount of respect from the men on our sales team.

The men on our team were excited to have her, and they welcomed her aboard quickly.

After a few hiccups and bumps in the road that accompany most evolving team dynamics, we found our new rhythm and established a new culture and team identity.

But looking back, I know on some level she must’ve felt “different.”

Not just the type of “different” that comes from being the one outlier in terms of gender, but because of her stepping into a pre-existing culture and intangible energy that hadn’t been built with consideration of her.

I wonder how that must’ve felt for her – already trying to sell in a man’s game, and maybe also feeling like she wasn’t fully at home, even in her own home.

I wonder if she ever truly felt 100% supported by me or the rest of the team.

These are questions to which I may never know the answers.

I know on some level that I failed her.

In turn, I failed other women who aspired to be salespeople.

Could they look up at me and the culture I was creating and say, “I want to be part of that team…because I know I’d thrive there.”

I doubt it.

And that’s one of my greatest failings as a leader.

A Great Leader creates environments where you and those you care about can thrive.

Especially for men leading in male-dominated environments, it’s our duty to raise our awareness.

We must be aware that our advantage in numbers alone creates an imbalance in power dynamics, opportunities for growth and chances to create meaningful bonds.

We must be committed to leading beyond what is just comfortable, easy and natural for us…

…and seek to set a higher standard of inclusion where the best talent feels welcome, supported and set up to thrive.

Unlike how I did in my first role as a leader.

I can tell you one thing for certain:

I have not, nor will I ever, allow that to happen again under my watch as a leader.

A Great Leader creates environments where you and those that you lead can thrive.

The lynchpin to creating such environments, is inclusion.

Beyond Salary: The Real Secret to Employee Happiness with Howard Watson