Paying it Forward

When the mentee becomes the mentor.

Kay Bolden
Good News Daily
5 min readOct 1, 2019

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Image credit: mixkit.co

My first real job out of college was for a state social service agency. I’d moved to San Diego on a whim, with no job or prospects. Just two suitcases, four hundred bucks, and that ridiculous sense of invincibility you have when you’re 23.

My job search was a joke. For months, I worked 4 nights a week as a cocktail waitress, wearing the shortest skirts and the highest heels I could get away with, because I needed the tips from the geriatric (40-year-old) guys. When I saw the ad for the social services job, I rushed down the list of qualifications.

College degree, check. Experience in social services, check. Fast learner, self-starter, plays well with others. Check, check, mostly check.

Some Spanish preferred. Well, thanks to all the time I spent partying in Tijuana, I could order a beer in Spanish, and find the loo after. That counts, right?

I got the job.

My boss, a towering, 6’4", Mexican immigrant named Tomás, took one look at me and said, “You fooled those white folks into thinking you speak Spanish, eh? Well, you better learn it fast.”

This was the 1980’s; people of color in management were rare, and not always welcome. Tomás was surrounded by politically-connected managers with expensive briefcases and advanced degrees; he’d gotten his GED while serving in the U.S. Marines. He was brash and outspoken and big-hearted, and he taught me everything I know about being a manager — not by lecturing or instructing, but by doing his job, and letting me watch.

He’d take me with him to policy meetings and regional conferences. We’d be the only people of color in the room, and I’d be one of very few women. Tomás would lobby hard for our clients, who were mostly low-income Latinx who’d lost their jobs in the tuna factory. They needed English as Second Language classes, basic reading skills, as well as retraining in a new field.

“Why aren’t we contracting with local Latino vendors?” he’d ask. “Why aren’t we teaching in both English and Spanish? Why aren’t there any women on the policy team? Why don’t we have child care in place?”

Sometimes, he’d be ignored. Sometimes he’d get a convoluted version of “Well, we can’t.”

Of all the questions he asked, “Why not?” was his hands-down favorite.

He fought hard to make our work culture more inclusive, and to make sure marginalized communities had a voice. He didn’t always win these battles — in fact, he lost most of the time — but he always spoke up.

Within a few years, I was promoted, and running my own team. We would get together for lunch, so I could rant about my staff or my coworkers or my new boss. He’d never tell me what to do about my problems. He’d just ask me questions.

What is your desired outcome?

What do you want to happen? How do you want this to unfold? He reminded me, always, to begin with the end in mind.

What are you willing to sacrifice to achieve it?

If I wasn’t willing to put in the time and energy, why should I expect it from my staff? I had to be willing to accept criticism, to learn the new steps, to slog through the boring stuff. To persist. If I didn’t, nobody else would either.

Are you demanding submission to your authority, or are you offering to share responsibility?

When it came to hiring, supervising and managing staff, asking myself this invariably cut though the drama. If it was all about me, it would shortly be all about nothing. But if it was all about us, all about the team and the clients, we could work miracles.

Are you building a system, or building relationships?

You can’t be besties with everyone, and it’s pointless to try. But to make real progress, you do need allies, collaborators and friends. If you’re not building relationships, your system — no matter how shiny — will fail.

Why not? Why the hell not?

This was his standard response to me — or anyone — who said a project couldn’t be done in this fiscal year, or in this election cycle, or with this client group. I learned early not to say “We can’t” unless my rationale was rock solid.

The lesson here was twofold. He insisted that I consider ideas outside my comfort zone, that I think through the reasons. And if I had to say no, to do so only after examining it from every angle, and salvaging every shred of usefulness.

And sometimes he’d just say:

Stop whining, Kid. Do your job.

Tomás radically shifted my way of thinking, not just about our profession, but about my own role in a changing workplace. So often, he let me take the lead. He trusted my judgment, and because he did, I learned to trust it, too. He always had my back in public; any scolding was done in private.

Over the years, I gradually shifted from mentee to mentor; I was sounding board and cheerleader for countless interns and fresh-out-of-college staff. I tried to be like Tomás: to ask questions instead of demanding obedience.

During a mid-1990’s hiring phase, I recommended a smart, outspoken young woman for a promotion. Nikki was full of energy and passion and I thought she’d be great for our college recruitment team, so I was irritated when our CEO passed her over. “Not a good fit,” he’d written. “Doesn’t comply with dress code/appearance standards. Doesn’t accept criticism well.”

Translation: Nikki was way too gay, and not bothering to hide it.

I scheduled an appointment with the CEO, and then I called Tomás, who had retired but was now on the executive board. I admit — I was nervous about bringing up the reason I suspected she’d been declined. Tomás had grown up in the 1930’s; he was old-school and deeply Catholic.

“Is she good at her job?” he asked me.

“She’s great,” I said.

“Then why the hell not?” he barked. He went and barked at the CEO, too, and Nikki was promoted.

When she was offered a job in Philadelphia the next year, she got busy training her replacement team, explaining the new funding deadlines and the upcoming work schedule. They stared at her with open mouths.

“We can’t do all of that in 8 weeks,” one of them said.

We could all hear her answer reverberating through the halls.

“Why not? Why the hell not?”

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Kay Bolden
Good News Daily

Author of Breakfast with Alligators: Tales of Traveling After 50, available now on Amazon | Tweet @KayBolden | Contact: kaybolden.xyz