Unpainted pawns stand in strict rows facing colorful, dispersed pawns on a table, representing a workforce failing to integrate true DEI

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“Discrimination is a form of gaslighting. No one’s actually going to come out and tell you, ‘I’m not going to give you a check because you’re Black or you’re a woman.’”

This sentiment, shared by TechCrunch senior editor Walter Thompson at this year’s TechCrunch Disrupt conference, is all too true. Though companies have made huge advancements in diversity over the last few decades, there are still many mountains to conquer. Mangers know their businesses need diversity—now the challenge is implementing diversity, equity, and inclusion (DEI) initiatives effectively.

And too often, business leaders with the best of intentions end up working counterproductively.

What do you do if you want to leverage DEI as a business leader, if you feel like you’re doing everything you can, but you still have nothing to show for it?

Start by asking yourself these three questions:

  • Is my company buying into the myth of meritocracy?
  • Am I expecting all of my leaders to behave the same way?
  • Am I alienating valuable, diverse talent before they event apply?

Address these honestly, and you should get an idea of where the wedge lies between you and a healthy, thriving culture populated by diverse talent.

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Is your company buying into the myth of meritocracy?

Every business leader wants to believe their organization is a meritocracy—a perfectly objective, well-oiled machine in which everyone is hired, promoted, and rewarded for their abilities and achievements alone. But the reality faced by underrepresented groups is a minefield of conscious and unconscious biases.

Leslie Feinzaig, founder and CEO of the Female Founders Alliance, felt that reality come crashing down around her in Silicon Valley. Her attempts to raise capital for her startup were going nowhere, despite years of preparation and established sales potential. “I bought into the whole meritocracy thing,” she says. “I expected that it would be hard, but I also expected that it would be fair. And in reality, it was just kind of a gaslit experience. I felt like I was in this really dark room, and nobody would tell me how to turn on the lights.”

I felt like I was in this really dark room, and nobody would tell me how to turn on the lights.

Leslie Feinzaig, Founder & CEO, Female Founders Alliance

Soon after, in 2017, she discovered that only 2.19% of venture capital funding from the previous year had gone to companies founded by women. Seeing that data, Feinzaig remembers thinking, “Oh. That wasn’t personal. That was systemic.”

Underrepresented employees at your company might very well be experiencing the same thing: a system forcing them to stumble around in the dark.

How to Start Seeing Your Corporate Culture for What It Really Is

Hana Mohan, cofounder and CEO of MagicBell, admits that meritocracy “is an idea that we all want to believe in . . . So I think it takes a certain amount of courage and maturity to reject that idea.”

Once you’ve accepted that your corporate culture has its flaws, take a close look at your practices. Here are a few places to scrutinize:

  • Meeting behavior: Are there equal opportunities for everyone to speak? When underrepresented members of a team do speak up, are their ideas met with the same active listening, discussion time, and questions for clarification?
  • Promotions: Are most of your managers (including those being groomed for promotion) men or white or cis gender? Do you even know? Is it possible your work environment is lacking the psychological safety needed for underrepresented groups to be their authentic selves and move up in their careers?
  • Expectations: Do certain ideas or arguments get dismissed because they don’t use favored jargon or adhere to a particular presentation style? How important is it that your employees reframe their words or behavior just for their bosses to give them the time of day?

To leverage diverse talent at your organization, let go of the idea that you’re living the dream of meritocracy. Until you do, you’ll remain blind to the problems that are killing your company’s DEI initiatives.

People of different heights standing on equal stacks of books reaching for fruit (equality, a perceived DEI value) vs. people standing on stacks adjusted for their height so they can all reach the fruit (equity, a true DEI value)
Pro tip: Don’t confuse equality for equity if you want actual value from DEI. | iStock/Author

Are you expecting all of your leaders to behave the same way?

“The hardest area to diversify is leadership,” says Stephen Bailey, cofounder and CEO of ExecOnline. Despite the difficulty, getting underrepresented groups to excel as leaders is a must for lasting DEI value. And that comes down to two big things:

  1. Changing your mindset of how leaders should behave
  2. Rethinking what your existing leaders can offer

“If I’m a white male,” says Bailey, “and I am mentoring a Black female, I might be giving really best-intended advice around how I advanced and succeeded in the organization and encourage them to do the same thing. But if you try to model those same behaviors . . . it can often be disastrous.”

Feinzaig recalls how following conventional wisdom and modeling the behavior of her predecessors simply didn’t work—in fact, it made people not want to work with her. Why? Because most top-selling career advice resources are written for a business world dominated by men. “When women exhibit traditional masculine ambition traits,” she says, “we come off as unlikeable . . . which, for a woman, is also kind of a kiss of death. You’re a little bit damned if you do, damned if you don’t.”

The hardest area to diversify is leadership.

Stephen Bailey, Cofounder & CEO, ExecOnline

How to Find Opportunity in Underrepresented Leaders

Attempting to squeeze a diverse workforce into a single mold won’t only cause stress and confusion—it’ll quickly erode the value of DEI. Instead, try to see unconventional leadership as an opportunity.

Focus on the leadership goal. If your organization identifies a leader as someone who inspires people, it shouldn’t matter how they do that. Does every team in your organization really perform better with daily check-ins? Or weekly reports? Or all after-work social outings? Some teams might thrive on that—others, not so much.

Underrepresented individuals are uniquely positioned to model new leadership styles and inspire change from within. To claim a competitive edge through DEI, don’t just let these voices blend into your ecosystem—empower them to transform it.

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A businessman on a blue background braces himself to pull a sword from a stone, as in the Excalibur myth

Are you alienating valuable, diverse talent before they even apply?

If your efforts and intentions are true, be brave enough to share them with the world. Put yourself in the shoes of prospective applicants. In a world where Google sways many of our decisions, a job hunter seeking a diverse workplace can easily validate (or eliminate) you as a choice based on two things:



“If you want to recruit the best people,” says Bailey, “if you want to win the biggest customers, if you want to attract the smartest capital over time, there’s an increasing desire to see a commitment to DEI and to see organizations that look like society.”

People seeking a diverse workforce, whether they’re part of an underrepresented group or not, also want to see proof of accountability—on multiple tiers, from appointments to the board to the day-to-day experiences of new hires.

While that can be a scary prospect for organizations that prefer to keep internal practices to themselves, there’s a bonus to bravery: going public with your DEI strategy will actually help force change within your organization.

“Even as a woman,” says Mohan, “when I invest, I have to consciously make sure that at least half of my investments are in women because there are just so many men who are pitching—and pitching loudly.”

In short, making your DEI progress public will attract valuable talent and keep you on track.

How to Be Transparent and Authentic about DEI

Your company needs DEI, so build your initiatives with authenticity, not tokens and lip service.

If you promise a no-tolerance policy toward sexual harassment, prove it in your mission statements, contract clauses, and responses to employee complaints. If you say you’re committed to supporting BIPOC diversity in management, publicly announce an initiative to reach a certain numerical goal within a specified timeline.

As you reach or adjust your goals, publicize that, too—let people know you’re serious by being open about the changes you’re making.

Are you ready for the DEI long haul?

To stay motivated while building meaningful DEI initiatives for your company, keep your eye on the prize—otherwise, it can be a truly overwhelming task.

Feinzaig emphasizes that creating equality for underrepresented groups in business isn’t simple. “This is a gigantic gap,” she says. “This is a huge problem, and it doesn’t have a single solution.”

But every company, including yours, can be part of catalyzing the solution. Identify your existing DEI weak points and approach them from multiple perspectives. Ask yourself self-reflective questions, make adjustments, and then ask those questions again.

More than anything, be sure to talk to the members of underrepresented groups you do have in your organization. After all, their voices represent the future trajectory of your business.


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