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Bootstrapping Inclusion

In a prior life, I worked for a popular e-commerce site for seven years. I joined when the company was about 100 employees and was fortunate to stay long enough to see it grow to over 1,000. During that time, I managed and led a subset of the engineering organization—overseeing its growth from 8 engineers to 80—and witnessed our transformation into a more diverse and inclusive organization. I worked with my staff to effect equitable pay practices, fight against bias in promotions, adjust our interview process, diversify our hiring funnel, and sponsor under represented minorities (URMs). My management staff and I diverted six figures worth of dollars toward pay equalization, grew women/nb engineers to represent about 30% of the team, achieved a 50% male/female hiring ratio, and our group was the only one to have successfully promoted a woman into a senior engineering management leadership position. While this all sounds great, there was still a lot of work remaining when I left the company.

I know what went well and what didn’t go well. I saw where we really struggled, and have ideas on how to do better. I now find myself at a new company starting over.

In my new, current life, I’ve talked with enough leaders of small companies to know that there are a lot of questions on how to get started on this work. There’s a lot of focus on where to find and how to hire underrepresented minorities. There’s also a lack of understanding of what this truly means and how much effort it requires.

Who is this for?

If you are a tech leader of a 5 to 30 person engineering organization sitting around a table with your all-male leadership team wondering how you can hire more under represented minorities, this is for you.

Over a series of posts, I’ll detail how I’ve approached D&I in my new life. To set expectations: I have not achieved D&I nirvana in the course of four months. I don’t have much to show for my efforts. I do think sharing what I’ve done can help others get started. I am more than certainly doing many things wrong.

So let’s get started.

Inclusion First (like Cate Huston says)

First, congratulations for thinking about this now. Now is literally the easiest time to fix your problem. It will never get easier. And the good news is that finding diverse candidates is literally the easiest problem to solve. The bad news, is that you’re thinking about the wrong problem.

Having been through this transition before, I can tell you that our engineering organizations are meat grinders. By default, they are wildly unsafe places for underrepresented minorities. Our companies are overflowing with sexism, racism, and anti-LGBTQ sentiment. If you’re lucky, it comes in the form of casual jokes or comments. If you’re like most, there’s already some degree of sexual harassment or racial discrimination being committed. If you care about people not being put through some of the most traumatic experiences of their lives, you’re going to need to fix your inclusion problem first.


Whenever I embark on a work thing, I find it useful to start with a VMSO. So, here’s my V, M, and S:

Vision (h/t to American University)

A workplace where people of all identities and experiences are understood, appreciated, and fully included in the community and where equitable treatment and outcomes prevail.


Create a company of allies.


  • Awareness. Increase exposure to differing viewpoints and perspectives for the purposes of recognizing the systemic inequities affecting underrepresented minorities (URMs).
  • Education. Acquire foundational knowledge in order to operate from a shared understanding. Understand the current state of the art, terms and language—which are rapidly changing—as well as basic concepts and etiquette.
  • Effecting Behavioral Change. Address and remove exclusionary behaviors and establish inclusive ones.

You’ll know it’s working if you find yourselves moving through three inflection points:

  • Not complicit/complicit. We all like to think of ourselves as good people. For many of us, coming face-to-face with the idea that we have been complicit in perpetuating sexism and discrimination is a real stumbling point. You’ll know you’re in the middle of this when you start cursing “political correctness.” When you feel like no matter what you’re doing, you’re doing it wrong. A lot of people quit at this point. In truth, we are all complicit. Even the woke ones. The difference is whether we opt for changing our complicit behaviors.
  • Believing in the lived experiences of others. Once we open ourselves up to hearing from different voices, the next phase is understanding and acknowledging that experiences can differ greatly for different populations given a similar set of challenges. You’re going to need to get to a point where you believe the stories you’re hearing despite them being completely counter to life as you have experienced it.
  • Spending Time and Money. Talk is cheap. What does putting time and money behind our efforts look like? Should we pay URMs for second shift work and emotional labor? Should we be providing doxxing defense, anti-harassment and anti-discrimination services as benefits? There are a lot of questions here. We don’t need to answer them right away, but answering them is an eventuality.

You will find yourself and your organization moving through these inflection points over and over again. You will accept one aspect of your complicitness, then come across another. You will begin to believe one set of lived experiences while still being incredulous of someone else’s. You will hear how your words and actions (or inactions!) are contributing to the problem and not the solution. You will not believe people when they tell you this. You will need to accept that they are probably right. This is normal. This is difficult. This is frustrating and tiring. Welcome to the struggle.

Published inD&I
Copyright 2017 Jason Wong