A Guide to Diversity & Inclusion for Lost and Confused Startups

Last week, a founder in our portfolio reached out in search of guidance around how to attract diverse candidates to his company. He’d just locked in a Series A and was getting ready to hit the gas on hiring. The team was actively sourcing candidates for several new roles, but they had one problem — they all had the same profile: white, male, engineer.

I didn’t need to tell them why building a diverse and inclusive company benefit is good business and leads to better financial performance––they already knew. They initiated the conversation. They wanted a game plan. They just weren’t quite sure where to start.

They’re not alone. I’ve talked to dozens of founders with genuine intent who want to create diverse and inclusive companies. Folks who are well-intentioned, who want to back up their words with action…but who are lost and confused about where to begin. It’s not just founders —as we grow our team, we want to be purposeful about fostering diversity, inclusion and belonging at Pillar.

We reached out to some of the people we know who are leading the charge on this front, to pull together a guide with concrete suggestions about how you and your company can be purposeful about diversity and inclusion.


TL;DR — here’s a quick summary of the entire guide:

  1. Broaden your perspective to encompass diversity, inclusion and belonging (DI&B)
  2. As CEO, own responsibility for making sure DI&B are company priorities
  3. Initiate a conversation with your team about why this matters to you, and how you hope your company will evolve over time
  4. Clearly articulate your mission & values
  5. Set goals and measure your progress
  6. Consider whether your environment fosters belonging
  7. Construct a diverse Board of Directors and Advisory Board
  8. Now focus on your pipeline––remove bias from your job descriptions, expand your sourcing channels, and design an inclusive interview process

This guide is clearly incomplete––scroll to the bottom if you have insight to share around how your company is thinking about diversity, inclusion and belonging.


Think Bigger — Diversity & Inclusion Doesn’t Start or End with Building Your Candidate Pipeline

The first mistake we often see early-stage founders make is thinking they only have a pipeline problem. You don’t just want to find candidates––you also want them to choose your company. Most importantly, after they join, you want them to feel accepted, welcomed, and heard.

Christina Luconi, Chief People Officer at Rapid7, urges founders to broaden your perception of what diversity really means.

“For me, diversity and inclusion isn’t just about race and gender. A diversity of mindset is a key ingredient in driving innovation and growth. It’s imperative that this isn’t thought of as an initiative, but rather a way of life within the company. Every single person you bring on should feel like they are set up to have an excellent career — no matter who they are. When you curate an inclusive culture, that will drive recruiting efforts, positive glass door ratings, etc. organically…as long as it’s authentic.”

Beyond diversity and inclusion, Katie Burke, Chief People Officer at HubSpot emphasizes why it’s also critical to create a sense of belonging.

“Belonging is the third piece of the D&I trifecta. And, candidly, it may be the most important factor. It’s no longer enough to just focus on creating teams that are diverse and an environment that is inclusive. When people feel as though they belong and are heard, they’re more motivated to do their best work because they can be the best version of themselves.

If you’re simply focused on building a pipeline of underrepresented candidates, you’re missing the big picture.

It’s Your Job (Not Someone Else’s)

Overwhelmed? Take a deep breath and take a cue from Amy Knapp, Head of Talent at Redpoint.

“You can’t boil the ocean. Start with one thing and build a plan. Do you want to work to increase female engineering candidates in your pipeline? Well, then make a plan to do just that. Next quarter, create new goal.” Start small, start somewhere. Start with a conversation with your team.

As CEO, you have to own it. Your approach to creating a diverse and inclusive company starts with you. Plenty of people in your company will influence your culture, but you set the tone for everyone else.

Your company will scale and your team will expand, and you may even find yourself hiring a Director of Diversity, Inclusion & Belonging; that doesn’t mean you’re off the hook. You have to continue to show up, signaling why this is important to your team, and what you’re doing about it. That means throwing your own time, energy and voice behind diversity and inclusion at your company.

Use Your Words

Don’t be afraid to have the conversation.

  • Create a safe environment for discussion by making it clear that no one has all the answers — rather, you’re trying to create a forum to share what you value and how you want to the team to improve together over time.
  • Ask people what diversity means to them. What are all the different forms of diversity and why do they matter to your company?
  • Talk with your team and with candidates about what you want the company to become in 1, 5, 10 years.
  • Share some of the companies you admire and reasons why.
  • Ask your team to add their perspectives. Make it clear that this is something that everyone in the company will shape and encompass.

A conversation about why this is important creates a clear north star.

For David Salinger, CEO of EyeLevel, as an underrepresented founder and CEO, diversity and inclusion are top priorities for his team.

“When it comes to inclusivity, we talk openly within our team and with prospective new team members about how to ensure our interactions and dynamics are empowering and that we celebrate the backgrounds, experiences, and perspectives that everyone brings to the table.”

Some of these conversations are aspirational, laying the groundwork for how the company will progress in the future.

David notes, “As a small team with limited resources, our benefits package is quite limited as you’d probably expect. But that doesn’t mean benefits aren’t top of mind — we have candid discussions in a #benefits channel in Slack about benefits we intend to offer in the future that ensure our workplace is welcoming, safe, and supportive of the wide spectrum of people we hope to attract to the team.”

It’s ok to talk about where you want to be in the future, even if it isn’t reflective of where you are today. Don’t be so hard on yourself. You’ve got to start somewhere. Just be sure to back it up with meaningful action.

Articulate Your Mission & Values

Many startups often wait way too long to articulate their mission and values. Big mistake. Huge mistake.

A clear crystallization of your beliefs is a powerful tool to to attract employees, advisors, and even customers to your business.

When our team at Smarterer was in early discussions with Pluralsight about a potential acquisition, we were introduced to the company’s Culture Guide. Within the pages, we discovered three core values and two rules. Short and simple. Every single employee knew what they were and what they meant, how they guided everyday decisions and how they shaped the way people were expected to treat each other. It was powerful message––if you join our company, this is what you’re signing up for. We were all in.

Taking the time to convey your mission and values (and keeping them simple and easy to grasp) is a critical exercise that helps people understand what you stand for. If you’re lost about where to start, connect with a firm like Gray Scalable or Catlin & Cookman (we’ve had great experience with both).

Even better, extend this to an employee code of conduct for every team member to embrace and embody. If diversity and inclusion are important to you, sharing this with candidates is an incredibly compelling way to attract the right people to your team.

Set Goals and Measure

I’ve long admired The Help Scout Team for the transparency they’ve shared around the path they’ve traveled to creating a diverse and inclusive startup. It wasn’t always a straight line. In 2017, Leah Knobler noted that a look under the hood revealed that the team was falling short of their goal of building a truly diverse team; so they committed to measuring themselves, identifying benchmarks, setting goals for how to improve, and tracking their progress.

There’s truth in the adage “if you don’t measure it you can’t manage it”. Celebrate your wins as a company, but openly discuss your failures and where you’re lagging behind. You’ll never improve if you don’t.

(Check out Help Scout’s 2018 results here.)

Create a Environment That Fosters Belonging

Metrics are an important piece of the equation, but they’re also not a silver bullet. Everything from your personalized benefits (check out Compt) to the way you construct your physical space paints a picture for candidates about what you value and whether you’re creating an environment that promotes belonging.

Beyond messaging and the way your team treats each other every day, consider the signals your physical environment sends to candidates.

When we were building our new office at Pluralsight, our CMO, Brett Barlow, and Director of Operations, Steve Woolley, scoped in a beautiful mother’s room with a fridge for milk, a comfy chair, and plenty of privacy. Think about how it would feel to stumble on that room as a new mother interviewing for a role at at the company––without a word, it signaled “we understand what you need, and want to be sure you’re comfortable here.”

Start At the Top — Your Board & Executive Team

Before you even begin to think about sourcing candidates, start with your independent directors on your Board of Directors and with your Advisory Board. You have the freedom to construct your advisory board however you choose––start at the top by making sure this group represents the ambitions you have for the composition of your company overall.

Does your board include individuals from underrepresented groups?

If you’re struggling to identify a pool of qualified candidates, there are plenty of people and organizations who can help. Tap the networks of executives you admire at companies that have been thoughtful about diversity. Connect with organizations like The Boardlist that are dedicated to promoting board diversity and have access to a group of talented candidates. Partner on a search with a firm like Parity Partners that has experience helping companies build diverse boards. Who you select to influence your company at the highest levels speaks volumes about whether you really truly value diversity.

Just as important, be purposeful from the very beginning about the construction of your management team. Set a goal to make sure you’re interviewing candidates from underrepresented groups for each of these roles.

When I joined the executive team at Pluralsight, I was surprised to receive notes from women across the company who were relieved, encouraged and inspired by the addition of a woman to the senior leadership team. I’d honestly never considered the impact my joining the team would have on women in the company (perhaps a bit dense on my part). Now at Pillar, our early-stage venture firm, I often meet women making career moves who are actively looking to join companies that have women in senior leadership roles.

When people are considering joining your company, they’re looking to see whether you’ve demonstrated that you appreciate diverse perspectives at all levels of the company.

…Now It’s Time to Focus on Your Pipeline

Once you’ve broadened your thinking in all these ways to consider diversity and inclusion as more than just a pipeline problem, you’re ready to turn your focus to sourcing and interviewing.

Remove Bias from Your Job Descriptions

Every word you use in your job posts sends a signal to candidates about the qualities you value in potential new team members; perhaps unbeknownst to you, bias is often lurking within your descriptions. Tools like the Gender Decoder for Job Ads will do the heavy lifting for you, helping you understand whether you’ve unknowingly loaded your job descriptions with gender-specific language.

Don’t Wait for Candidates to Come to You

If you’re lucky, word may have gotten around that you and your team have been purposeful about building an environment that is attractive to people from underrepresented groups. More likely, you’re going to need to roll up your sleeves and hustle to find candidates. Part of developing the right outbound sourcing strategy is moving beyond your first tier relationships and standard recruiting channels. For technical roles, tap into groups like Hack Diversity, Resilient Coders, Thinkful and Lamba School. Move beyond recruiting from the same old top tier schools; make your way to some of the colleges and universities that are off the beaten path.

Get out of your comfort zone and commit to this approach––it will take time to build your brand on campus, but if you keep showing up and you stay engaged, you’ll attract new candidates.

Structure Your Interview Process

While they’re still just a handful of people, Khaled Kteily, CEO of Legacy, and his team are already being deliberate about trying to take the bias out of the hiring process. They follow a highly structured interview process to rule out subjectivity. (Skillist is a Boston company that provides software and tools to make this seamless.)

They’ve taken a cue from Iris Bohnet, who shares tips in her HBR Article, How to Take the Bias Out of Interviews, around how to build an interview workflow and an evaluation process that are free from bias.

  1. First, be thoughtful in choosing the group of people who will be leading the interviews. The group should be diverse, representing different perspectives inside your company. If you’re a small team, pull in members of your Board of Directors or outside advisors to help.
  2. The interview experience itself should be driven by individuals––avoid group interviews where there is potential for individuals to influence and bias each other.
  3. Consider leaning on project-based work samples and problem-solving challenges that demonstrate whether a candidate has the specific skills needed to thrive in the role.
  4. When using interview questions, make sure they are structured. Use the same set of questions, presented in the same order, across candidates. Create an interview guide that ensures you’ve been thoughtful about choosing questions that will help you gauge the specific skills required for the job.
  5. Score each answer immediately after it is provided, when a candidate’s response is fresh in your mind, giving you a quantified measure of your impression.
  6. Compare answers horizontally, across each individual question, rather than comparing candidates holistically to each other. Top scoring candidates should move on to the final review.
  7. Only then, reconvene the group together to review, discuss and decide which offer to extend.

Learn Something New Everyday

My favorite takeaway from Katie Burke’s article is the personal commitment she shares to learn something new every day related to diversity, inclusion and belonging. We meet a lot of founders who are paralyzed by fear when it comes to this stuff. Start small. Take steps in the right direction. Stay the course and keep learning and evolving.

What are you doing at your early-stage company to promote diversity, inclusion and belonging? I’d love to hear from you in the comments.