West: Excited to be speaking with you all today. This topic is one that all of us are committed to, so let’s just get right to it. Why is it taking this long to make what feels like such a small dent getting more women on boards?

Jocelyn: Well there are a few factors—and this is specific to boards of private companies. First, the investor community, CEOs, and limited partners (LPs) are not diverse. There’s a big tendency for those in our industry to pick people they already know and like. The excuse sounds like, “It’s easier to have trust and candor with who you know.” Moreover, adding a board member who is independent––meaning they didn’t get that board seat because of an investment in the company––is not usually urgent and/or no one at the table is asking for it. So, unfortunately, when no one speaks up about it or the leadership team is really not committed to making it happen or the investors are not prioritizing it, this just gets deprioritized.

West: What do you think should be done to try and change that, or is it even possible for a company that is series A or seed funded?

Brad: First, I think it’s not just about “what’s possible”; this is truly imperative. A board is a team and a lot of CEOs miss the opportunity to use their board as such. You’d think that you would want more diversity in a board to extend the reach of your network––whether it’s people, companies, or actual organizational structure and characteristics. Furthermore, if as a leader you believe in DE&I, you believe in the value of diverse teams, creating inclusion, value, and belonging in your company, then this has to be inclusive of the board. The feeling that somehow it’s not your problem and you don’t focus on what’s going on at the board level immediately undermines your credibility and statements as a CEO.

West: So then what are the consequences of not having a diverse board?

Jocelyn: Well, the consequence is that the company is not being guided to be the most impactful way it can be. If a board is all investors, then the conversation goes to financial performance. You are missing the lived experience of the society you are hoping to serve. How do you understand the hearts and minds of your customer base? By not gathering multiple perspectives, you end up with groupthink and narrow conversation. That ultimately means you’re not maximizing potential. In that situation, the board is underserving the CEO because they’re providing only one lens.

West: But if we know all this––that diverse boards truly lead to better outcomes––then why is it so difficult to prioritize building a diverse board?

Brad: It would be a powerful thing if all of the founders, the CEOs, and the investors actively engaged to impact change. For some context here, when George Floyd was murdered, I realized a few things. One of those realizations was that my activity and engagements up to that day were passive. I was not fundamentally or actively engaging in ending racism in America. So as I dug in and did the work, my business and board story changed. I reviewed every board I was on. None of them had a person of color and only a few had one or maybe two women. So I went to all the CEOs and said, “I do not want to sit on a board that does not have a single person of color on it and I’m willing to give up my board seat to get this done.”

And I share this anecdote because it gets to the heart of show vs. tell. How can we systematically change the composition of boards? By actively supporting the CEOs and leaders to get the work done. It’s all about deciding it’s important and then prioritizing the work. And as board members, it is imperative that we support and facilitate this work.

Jocelyn: I think there’s a lack of urgency because CEOs––especially startup CEOs––are always focused on putting out the immediate fires. Or, having a diverse board may be a stated priority but there’s no clear path to execution. For example, board seats are often filled via word of mouth. HimForHer was developed to make it much easier to prioritize diversity and find the right people for your board. We really find that people want to get there, but they just don’t know how because their immediate networks just aren’t diverse enough.

West: Another factor is that in venture, so much comes down to the terms of the Term Sheet … who has invested and how much.

Brad: Exactly. We need more investors who are taking that thought process and asking, “What is the best configuration for the company?” Not, “I own 20% of this company and I want a board seat.”

You’re really getting at the issues of the dynamics of power here. If we really want to see change, the first thing is to be a good advocate for others on the board. Let’s say you have that board seat because you are the company’s largest investor. That’s a massive power dynamic at play that you need to be aware of and work to balance. Which means you’re going to need to be comfortable feeling uncomfortable. It is important for anyone who is in a position of power to allow themselves to be uncomfortable in situations. When a person is in a position of power, it’s typically never uncomfortable. The person who is typically one to two seats down is the uncomfortable one.

West: So switching gears now to the dynamics in the boardroom. As a board member, how do you trust the CEO’s vision with the reality of where the company is at present day? How can board members get to the truth of the companies they serve?

Jocelyn: Well, it needs to be constantly questioned. The business landscape is too dynamic for it not to be. Board members also need to ask thoughtful questions. This two-way dialogue helps to gain trust. You can’t be given the vision and then not talk about it for three years. How does a board stay in touch with what is really going on? The board is an oversight role and not inside the company, so how the board communicates with the CEO and the rest of the company is critical. Does the board understand mental health? Does the board empathize with the leadership team? People make up companies, not the other way around.

West: This leads us to our next question about how board members can speak their own truths … especially when it might be in contrast to the majority opinion?

Brad: It goes back to being aware of power dynamics. If you are in a position of power, then it is also your responsibility to be a good advocate for others, and there are very simple ways of bringing others into the conversation when they might not feel as comfortable as you. I also remind the boards I am on that our goal as a board is to get to the good answers. And that does not require everyone agreeing with one another all the time.

Jocelyn: The #1 thing is to listen to your gut. Pause when everyone else is agreeing and, if you have a different opinion, state it in a thoughtful way. It’s about finding and using your voice in a productive way. Remember that you earned your seat, they chose you, and so it is your job to speak up. That’s also why we started Illumyn—to help accelerate people’s comfort level on boards.

West: But when is blatant truth-telling not the best path as a board member?

Jocelyn: I don’t think there is ever a downside to truth-telling. Some truths are harder than others to tell. There are also always different ways to get toward truth––vulnerability, impartiality, empathy, and wonder. If you are sharing your truth out of a spirit of humanity, not meanness, then it is always the right path.

Brad: We all need to be able to own it. Be uncomfortable owning your own learning process and doing that in all contexts––especially in a board situation where you are learning from each other and there are so many power dynamics at play.