The Chicago Ventures Portfolio Discusses 1st Steps for Building Diverse + Inclusive Teams

Over the last 24 months we’ve brought together the teams leading People Ops efforts at our Chicago Ventures portfolio companies to cover topics like onboarding and orientation, culture, professional development, and comp planning. As we’ve engaged with this group closely over the years, we’ve explored how we, as investors, can best help our companies build diverse teams and inclusive environments.

With their feedback in mind, we’ve taken a few steps: we launched a data collection project to understand team makeup (particularly representation of females and underrepresented minorities) across the portfolio; we’re working to ensure that the talent we refer represents diverse backgrounds; we’re actively partnering with portfolio companies to place females on boards; and perhaps most importantly, we’ve created space for our companies to share strategies and learn from each other as they build out their own People Ops functions.

So the timing was right to host a workshop for our People Ops leaders covering “Best Practices for Building Diverse Teams.” From our conversations, we knew that most of our companies understand that diversity is important, but as one person put it in a pre-workshop survey: “I want to know the one thing I can start with to make a difference. Diversity, Inclusion, & Equity are SO IMPORTANT, but I feel like I have analysis paralysis and don’t know where to begin.”

Here are some other challenges these small teams (between 15-200 people) have when it comes to building diversity and inclusion initiatives. If you’re at a startup, they may sound familiar:

  • “Getting a program started with buy-in from everyone.”
  • “We try to be diverse, but our team so far has very much been built on the ‘referral’ basis.”
  • “We just don’t know how to talk about it, and so we don’t. But we believe in equity & inclusion, and want to talk more about it.”
  • “We have trouble finding a diverse candidate set within our market and experience level.”
  • “Buy in for investment and understanding on the value of DEI in an organization.”
  • “Finding and sourcing diverse candidates for open positions.”

And here are some takeaways this group wanted from a workshop:

  • “How to convince 1) top stakeholders and 2) peers that DEI initiatives are necessary”
  • “Small steps we can take/initiatives we can start to promote DEI”
  • “Hiring for diversity in a market that lacks diversity.”
  • “Learning what other initiatives other people are taking.”
  • “How to create the case for investment for DEI initiatives.”
  • “What are realistic goals and how to keep your leadership team focused on them.”

After getting leadership buy-in (by using data here and here to backup a pitch), just talking about diversity and knowing what first steps to take is a hurdle. To help kickstart those conversations, we recruited two community leaders, Michelle Y. Bess and Colin Espinales, to lead a conversation on how to tactically launch DEI initiatives within an early-stage startup. While creating harassment policies and signing decency pledges are important, we wanted to learn what one person can do to take a first step toward building meaningful and actionable initiatives.

Our guest speakers were perfectly poised to lead that conversation: Michelle, Diversity, Equity and Inclusion Lead + Operations Recruiter at Sprout Social, has built a program at her 500-person company from scratch, and leads a meetup group of dozens of folks leading these initiatives across the Chicago tech, academic and non-profit ecosystems. Colin, a Customer Success Manager at LinkedIn, advises his clients on how to use LinkedIn’s tools to source and connect with more diverse candidates.

While the highlights from the 2-hour workshops were different for everyone, a couple stuck out for me:

(1) Determine Your Why

Michelle taught us that before launching any initiatives, the entire team has to be on the same page about WHY building a diverse and inclusive culture is important. And it has to be written down. Reasons can be:

  • Your company (you want to build the best company, period)
  • Your customers (you want you company to mirror your customer base)
  • Your community (you want your company to mirror the community you live and work in)
  • Your competition (you know diverse teams yield better financial results)
  • Or Something else.

But most importantly, this why needs to be genuine. Companies and leaders shouldn’t talk about caring about diversity just because they think it’ll make them look good. People talk, and it’ll become known when promises aren’t backed up by action.

(2) Understand, and then Define, Diversity

Here are a couple ways to think about about Diversity, Equity (or Belonging, as LinkedIn calls it), and Inclusion, as Michelle and Colin describe them:

Diversity: A focus on numbers and representation of identities.

Inclusion: A feeling of belonging and identities are heard and integrated into the work at every level.

Equity/Belonging: A focus on a systemic level change. Having protocols and procedures to support a diverse and inclusive environment

Diversity: Being invited to the dance.

Inclusion: Being asked to dance.

Equity/Belonging: Dancing like no one is watching.

Diversity means something different in every organization. For some it means diversity of age, or of gender, or of background. Your own definition will stem from your why, and once you have this definition in place, you can plan initiatives and goals that correspond to it.

(Sprout, for instance, has a focus on the LGBTQIA+ community and has built all-gender restrooms. LinkedIn has created employee resource groups like Parents @ LinkedIn, Veterans @ LinkedIn, and Women @ LinkedIn.)

Our hope is that the startups in our portfolio and in central US ecosystems like Austin, Dallas, Denver, and Madison are being intentional about building diverse and inclusive teams while they’re still relatively young. I’m learning alongside our portfolio teams, and would love to hear more about what initiatives your startup is taking on this front. Feel free to email me at lindsay@chicagoventures.com.

Lindsay Knight


Posted On

March 2, 2018


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