Leading by Example on Diversity, Equity, and Inclusion: How and Where to Start Tough (but Necessary) Conversations

Threshold Ventures
Threshold Ventures
Published in
4 min readJul 2, 2020

By Carol Wentworth, Marketing Partner, and Jen Kodner, Talent Partner

In recent years, all of us, from founders to advisors to top executives, have given serious thought to building diverse and inclusive businesses. But if the past several weeks taught us anything, it’s that whatever we’ve been doing is simply not enough. It’s time for action, and fast. Fortunately, we have that action plan from some of the very best diversity, equity, and inclusion (DEI) leaders around, who shared their DEI vision and lessons learned with us in our leadership webinar series. We’ve distilled their advice below.

Many, if not all, of the ideas proposed by Traunza Adams (Chief People Officer, OODA Health), Michael Kyle (Head of Talent and Belonging, Planet), and Megan Dalessio (DEI Leader) are easy to spin up. Many are interactive, giving workers space to share their concerns, voice their pain, and commit to doing better. All require unwavering support from leadership: founders and other leaders need to model the values they want to see in their companies if they expect DEI initiatives to take hold.

Line up your champions

You have to start with executive buy-in. “I like to say that HR initiatives are bound for failure unless you have everyone aligned,” says Adams. In her case, OODA Health’s DEI strategy loops in not just the CEO but the head of operations and other leaders. “They need to feel ownership of the strategy.”

At Planet’s monthly “Belonging” meetings, to move the company’s DEI programs forward, Kyle also seeks out leadership buy-in. “We have executive sponsorship,” he says. “We also established core beliefs and operating principles and presented those at the executive level.” When new employees are given those core beliefs during orientation, “we let them know that everyone plays a role,” Kyle says.

Establish DEI OKRs

Just as you set up OKRs for sales and deliverables, you need measurable milestones for DEI. Dalessio sees the OKRs as less about numbers and more about people with power doing some deep thinking about how they can change their views and behaviors to move their companies forward — a critical step if you’re intent on changing the company.

“So many people start at the organization level, and ask, how do I fix my company?” Dalessio says. “The first OKR is going to be about that personal inventory. Change needs to come from within. If you don’t do this, none of this work will stick.”

It also helps to establish DEI goals as OKRs, which Kyle has helped do at Planet. In 2020, one of the company’s OKRs is improving the percentage of total leadership from underrepresented groups.

Help people take action

Faced with the enormity of racial injustice, many people feel helpless. Giving them a well-defined activity can jump-start change once people see that their first steps may make a difference. At OODA Health, CEO Seth Cohen, along with Adams, initiated an employee letter-writing campaign to the Kentucky state attorney general, asking that the police officers involved in the shooting death of Breonna Taylor be held accountable. “People felt good that there was an action they could take right now,” Adams says.

Tap DEI experts

There’s a wealth of talent out there ready to guide your DEI initiatives if you don’t yet have a deep bench in-house. Dalessio likes using outsiders: “Sometimes the messages are better when they don’t come from your own team.” She has seen success at multiple organizations working with external DEI consultants to deliver company-wide content that encourages employees to adjust to uncomfortable conversations so they can focus on their personal learning journeys.

Invite conversation

People are nervous about talking about diversity and race; they’re scared to offend their colleagues or appear unknowledgeable about diversity and inclusion. The solution is to create spaces where people can push past these barriers and ask for guidance. At Planet earlier this year, Kyle brought in Karen Fleshman to present one of her “Racy Conversations” workshops on creating fair workplaces. “It was important to let our folks know, how do we begin to have conversations around race, and how do we understand the historical context in which we’re operating?” Kyle says.

Even when those conversations are uncomfortable — well, especially when they are uncomfortable — companies need to encourage the discussion. OODA Health recently introduced Ideawake, an idea management platform for soliciting ideas from a community. It can help with product or sales decisions, but the OODA team is using it now to gather ideas about racial justice. People are posing questions such as, “What’s something about the Black experience you’ve always wanted to ask?” Some of the submissions: “If you’re mixed race, which side do you align with?” and “Is it appropriate to say Black or African-American?”

“You’re not going to walk up to your friend and ask them that,” says Adams. “But we want to get those things out there.”