Diane had a way of making even a casual coffee meeting feel like a battlefield strategy session.
The espresso machine hissed behind us as she dissected my latest career mistake. I’d shown empathy to a struggling team member, offered flexibility when she was going through a divorce.
“Never expose yourself like that,” Diane said, stirring her coffee. “Compassion makes you vulnerable. Vulnerability makes you weak.”
I curled my fingers around my latte, still too hot to drink, and tried not to wince. The ceramic burned against my skin, but I kept my grip firm. Diane noticed everything. Any sign of discomfort would become another lesson in weakness.
She was the only female VP when I met her, back when I still believed hard work alone could crack the glass ceiling. She moved with the sharp efficiency of someone who’d spent decades navigating hostile territory, from Silicon Valley in the ’90s to boardrooms still run like boys’ clubs.
“You’re too nice,” she told me once, barely glancing up from her BlackBerry. “It’ll cost you.”
At the time, I thought she was wrong.
I was also desperate enough to listen.
Weapons of survival
Diane had survived an era where sexual harassment was called banter and discrimination handled with a wink. Each battle left its mark — visible in the way she scanned rooms before speaking, in how she positioned herself with clear sight lines to every door.
“Document everything,” she taught me. “Forward important emails to your personal account. Save meeting recordings. Build a paper trail.”
She shared her war stories during lunch meetings and coffee breaks, her voice flat and factual, as if recounting data points rather than wounds. The VP who propositioned her during a performance review. The colleague who claimed credit for her project. The manager who denied her promotion because she was “too emotional.”
Her lessons worked. When male peers talked over me in meetings, I had strategies ready. When my ideas were dismissed then repeated by others, I had documentation proving origin. When workplace politics threatened my position, I deployed the protective tactics she’d drilled into me.
But each victory felt hollow. Each time I outmaneuvered someone, another piece of my original self fell away.
Mothers and daughters at war
The painful truth about Diane? She cared.
“Think of me as your corporate mother,” she said during a particularly brutal feedback session. “I’m hard on you because the world is harder.”
Our dynamic mirrored countless mother-daughter relationships — women trying to protect their daughters by teaching them to be ruthless, to trust no one. Love expressed through lessons in warfare. Protection through preemptive strikes.
I wanted to believe I was different. That I could succeed without becoming that woman — the one who hoarded power, who saw every interaction as a calculated move. Who measured relationships in terms of strategic value rather than human connection.
But last year, when my company assigned me five mentees — women new to tech leadership — I heard Diane’s voice rise from my own lips.
“Never show weakness. Never admit doubt. Never trust without verification.”
The words caught in my throat as I watched their faces. Eager. Hopeful. Not yet hardened by corporate battle strategies. Not yet transformed by protective armor into something unrecognizable.
I saw myself in them. The person I was before Diane’s lessons stripped away my softness.
The price of protection
Diane’s guidance worked exactly as intended. I climbed the corporate ladder. Built strategic alliances. Maintained perfect political awareness. Avoided the pitfalls that claimed less savvy women.
I also lost pieces of myself along the way.
My natural empathy became calculated relationship management. My collaborative instincts transformed into strategic coalition-building. My desire to help others got filtered through complex risk assessment.
Success came at the cost of authenticity. Protection required constant vigilance.
And now, as I prepare to retire in a few months, I keep asking myself: Did I win? Or did I just survive long enough to perpetuate the same system that wounded us both?
Breaking the inheritance
A junior developer approached me after a recent mentoring session, anxiety written all over her face. She was preparing for a big presentation.
My trained response formed immediately: Never show fear. Never admit uncertainty. Never let them see you sweat.
Instead, I told her about my own ongoing battle with perfectionism. My exhaustion from decades of corporate politics. My growing belief that success shouldn’t require becoming what hurt us.
She twisted a pen between her fingers, her nails bitten to the quick. “But will that help me advance?” she asked, voice low, like she already knew the answer and didn’t want to hear it out loud.
The answer felt complicated in ways Diane’s guidance never was. Her black-and-white strategies offered clarity. The path forward I imagined was messier, less certain, but possibly more transformative.
Questioning the armor
Last week, as I cleaned out my inbox in preparation for retirement, I found one of Diane’s first emails to me.
“Trust is a liability. Don’t forget it.”
I stared at it for a long time before picking up my phone.
It took me three tries to dial her number.
When she finally picked up, her voice was the same — sharp, efficient.
“You’re calling me?” she asked, a mix of amusement and suspicion.
“Yeah,” I said. “I retire in a few months. Thought you should know.”
A pause.
“You made it.”
“I did.”
Another pause, longer this time.
“You still keeping a paper trail?”
I laughed. For the first time in years, I wasn’t sure if she was joking.
“You tell me, Diane,” I said. “Was it worth it?”
She didn’t answer right away. When she finally spoke, her voice was quieter than I’d ever heard it.
“I don’t know.”
Passing it forward
My mentees receive a different inheritance now. Yes, I teach them to document important interactions. Yes, I explain political awareness.
But I also encourage them to question the systems that demand armor. To view vulnerability as connection rather than weakness. To measure success by more than just survival.
This feels harder than passing down battle tactics. Messier than teaching pure protection.
But perhaps the greatest gift a mentor can offer is permission to imagine something different than what wounded them.
