The Room Where You Stop Proving Yourself

Lauren Bailey built three companies. Each one filled a gap she felt herself about five years before she had the language for it.

That is not a content strategy. That is what it looks like when someone pays close enough attention to her own experience to turn it into something useful for other people.

Lauren, known as LB to pretty much everyone who matters, is the Founder of Factor 8, an award-winning virtual sales training company; Girls Club, a program that has produced over 600 promotions for women in revenue roles; and Legacy Executive Club, a private community for purpose-driven senior leaders who are done climbing and ready to start choosing. When I sat down with her for this episode of Possibilities, I thought we would talk mostly about community and women in leadership.

We did. But first, she taught me something about sales that I wish I had heard twenty years ago.

Selling Is Helping. It Has Always Been Helping.

The ick factor in sales, Lauren says, is not a personality problem. It is a training problem.

Most sales reps enter the role knowing everything about the product and nothing about how to have a human conversation. They show up and throw up: the pitch, the marketing brochure read aloud to someone who has already mentally checked out, the speeds and feeds nobody asked for. They do this not because they are bad at their jobs but because nobody taught them anything else.

If you are providing value, it is not sales. That is how Monique put it to a CEO client she was working with that same morning. And Lauren’s one-sentence version is even cleaner: selling is helping.

The moment a rep leads with what is in it for the other person instead of what they are trying to prove, everything changes. The ick disappears. The resistance drops. And the person who spent their first weeks dreading every call starts to realize this profession is actually worth building a life around.

That is what Factor 8 sells. Not scripts. The understanding that great sales is a translation skill between what the product can do and what the customer actually needs, and you can learn it.

Why the Job Postings Are Advertising for the Wrong Person

Lauren hears a version of the same observation constantly from managers across industries: I only have two women on my team, but they are the top two.

From her experience training sales organizations across hundreds of companies, Lauren has seen that people who enter consultative sales roles often find their natural strengths genuinely rewarded there. The challenge she identifies is that most women encounter two barriers before they ever reach the role: the risk factor of commission-based pay, and the language of the job posting itself.

When you advertise for a hunter who crushes quotas and kills the competition, you are not attracting someone who wants to build long-term client relationships. You are advertising for a shark and then wondering why your culture and retention are struggling. Lauren’s advice is direct: if what you actually want is someone to take great care of your customers and build lasting relationships, say that. The language is the filter.

Girls Club: What Happens When 50 Women Realize They Are Not Alone

Girls Club was born from a specific, infuriating observation: the most qualified women Lauren knew were not raising their hands for promotions.

It was not about ability. Lauren has observed, across cohort after cohort, that many women consistently hold themselves to a higher standard of readiness before applying for a new role. She sees men often go for a position when they feel they can do most of it. Women, in her experience, frequently wait until they feel they can do it perfectly.

The program she built runs five months. It combines confidence-building, management competency training, and community. Fifty women in a cohort. Mentors who have been there. Role models who look like them.

At one point in every cohort, Lauren says, every woman cries. Because they had never been in a room full of people who felt exactly as they did. The ambition, the perfectionism, the sense of wanting more while feeling wrong for wanting it. They thought they were carrying it alone.

They come up together. And then they come back as mentors, as speakers, as the senior leader interviewing the junior Girls Club graduate for her first big role. It is now operating across 40 countries. Lauren still runs it part-time.

The Unintentional Boys Club

One of the most unexpectedly honest moments in this conversation came when Lauren described putting her former nemesis on stage.

The VP of Sales who had made her life miserable when she was the only woman in tech. The same man who, years later, became the first person to give her money for Girls Club. She invited him to do a fireside chat with the inaugural Girls Club cohort titled: The Unintentional Boys Club.

She introduced him as the man who made her life hell. Then she asked him how and why he had built one.

His answer, in front of that room: he was charged with building a team from ten to a hundred in under three months. His network was men. He called his network. He did not exclude women. That was simply who he knew.

And then he acknowledged something that landed differently than anyone expected: yes, he had treated women on his team differently. Because he worried about the impact of his management style in a way he never worried about with his male managers. So he pulled back. And the women in the room who heard that said something many of them had never said out loud: they recognized the dynamic, and they hated the position it put them in, too.

What Lauren took from that conversation, and what she now teaches: treat women on your team like your sister. Not your daughter, not your mother. Your sister. The one you would give grief to, invite along, and never use kid gloves with. The one who will also push back when you deserve it.

After that conversation, both sides left the room with something they had never had before: an honest explanation of the dynamic, from inside it.

And the line that has stayed with me from that section of the conversation was Lauren’s, delivered quietly: the question is not why am I crying. The question is why aren’t you?

Legacy: Finally Being in a Room That Gives Back

The idea for Legacy Executive Club arrived in a spa, in bathrobes, after too much wine, when two of the most accomplished women Lauren knew said the same thing to her independently: it is lonelier at the top than it was when I was coming up.

She had spent years watching women build Girls Club cohorts and graduate into senior leadership. And she had also watched what happened after. The loneliness of being the giver. The exhaustion of being the most connected, most generous person in every room, with no equivalent energy coming back.

Legacy was built for them. For the leaders who do not want to climb another ladder. Who want to make a difference and be around people doing the same. Who want a confidential room where they can take off the corporate mask and talk about what the next chapter actually looks like.

100 members a year by design. 80 percent nominated. Three golden rules, the first of which is simply: you show up. No ghosters. No exceptions.

What people get, Lauren says, is mostly joy. Business value, yes. Introductions, referrals, new ideas. But mostly the relief of finally being surrounded by their people.

The Five-Year Gap

Near the close of our conversation, Lauren described the through-line she had only recently recognized: each of my companies filled a gap I felt five years before I had the language for it.

Factor 8 was built by a woman who could not find the sales training she needed when she was leading inside sales teams. Girls Club was built by a woman who watched the most qualified people she knew hold themselves back from promotions. Legacy was built by a woman who felt the loneliness that comes with getting everything you worked for and discovering the top is quieter than expected.

She built for the person she once was. Every time.

That is a principle worth sitting with: the work you are most qualified to do is often the work that would have helped you most, years ago. Not the work you are credentialed for. The work you understand from the inside.

That is what this conversation kept returning to. The gap between where people are and where they could be is not primarily a skills gap. It is a confidence gap, a community gap, and occasionally a training gap. And all three are fixable, if someone who has been through it decides to build the thing.

Lauren Bailey has built it. Three times.

~ Monique

Listen to the full episode of Possibilities with Monique de Maio wherever you get your podcasts. Connect with Lauren Bailey at factor8.com, girlsclub.com, or legacy.vip.