Practical Diversity & Inclusion

Over my three years at Automattic, I’ve worked a great deal on diversity and inclusion. I recently decided to take a step back and, upon reflecting, I wanted to share one of the biggest lessons I learned: often folks will jump to help with seemingly insolvable problems but their minds go blank once the magic words “diversity” and “inclusion” are thrown into the mix. There’s load of research that shows when we feel our world view being attacked, we close up thanks to the good ol’ amygdala (funny comic on this). We also seem to have oversaturated the tech world with these two magic words that they can sometimes feel too big to hold in our minds. Combined together, getting large groups of people to move beyond talking about D&I to acting becomes quite difficult.

The same colleagues who always seem to have an idea, a fix, a hack to some of the most annoying or confusing issues slowly back away when it comes to diversity and inclusion. I’ve watched eloquent speakers nearly whisper the words or stumble over them. It reminds me of how I felt when I was first learning how to say LGBTQ. There is real fear in the tech world of messing it all up, saying the wrong thing, or misrepresenting others. It’s tough to watch and reminds me to always give folks the benefit of the doubt. I know personally I still have a ton to learn and am personally so thankful for those who were patient enough to walk with me when I was early in understanding diversity and inclusion more. Plus, just because I can speak with authority on some topics in D&I doesn’t mean I can on all – I have no what it’s like to be a person of color in tech or a parent in tech for example. Related: I truly do believe we have to see intersectionality in white men too to make progress (more here).

What follows is a a trick of sorts I played on Automattic, the company I work for. I recommend doing something similar in yours if you can 🙂 I personally love to point to it when folks say things about how insolvable it is or ask “where to start”. Ultimately, I think it’s a good way to get those folks who might stay quiet, to speak and to realize there are true actions they can take using the same framework they use to approach other problems. Boom – suddenly the light bulb has been turned on, the fear has been lessened, and the way forward doesn’t seem so dark and mysterious.

After I was showed this engagement graph [link removed] of user retention over 10 weeks, I wanted to dig into what this might look like for users in Jetpack.

I found some interesting stuff. For starters, those that signed up from VaultPress have higher views compared to those that signed up through the Jetpack sign up flow. The second graph shows the drop off by plan type as well. See the graphs below:



  • What’s enabling those that signed up through VaultPress to succeed more than those that came through the Jetpack Sign up flow?!
  • Why does this divide increase between the two right around the November mark?



  • Why does JP Premium see a bigger overall drop off?
  • Why are all of these plans dropping off regardless and none of them thriving?

What can we do to address this drop off? Where does your mind go when you see this graph? This doesn’t fare well for business if we are running in these problems.

Some ideas come to mind for me:

  • Let’s continue to track these users more and dig into those who are succeeding. Why are they succeeding? Are there any commonalities?
  • Let’s dig into what’s unique about the flow from the VP plans page vs the JP plans page listing out the differences as we go
  • Let’s run through our flow entirely to see what parts might be causing issues and run some experiments based on what we find (A/B tests for example)
  • Let’s create a task force to address these problems
  • Let’s do user interviews with folks who dropped off to help understand why they have
  • The list goes on…

WARNING: The above information is all fake 🙂 ^ Woops – sorry, growth team. These graphs below are real though:

This information comes from the 2008 “The Athena Factor: Reversing the Brain Drain in Science, Engineering, and Technology” (scroll to page 55):


Shows women across SET steadily dropping off over time with a large drop off in the 35-44 range on up.


Shows how there is a divide in this drop off in men vs women.

Now what do you see when you see these SAME graphs? What solutions can you think of? 

Some ideas come to mind for me:

  • Let’s continue to track the women who stay in the final cohort and dig into why they have. Why are they succeeding? Are there any commonalities? Let’s dig into why the men stay.
  • Let’s dig into what’s unique about the experience with men that’s helping them stay.
  • Let’s run through someone’s career cycle entirely in a case study format to see what parts might be causing problems and implement solutions (maternity leave is a big part of this!)
  • Let’s create a task force to address these problems
  • Let’s do follow up interviews with women who dropped off to help understand why they have
  • The list goes on…

Why did I post this?

D&I are more than just concepts and lofty ideas – they are guiding principles towards action. This was a thought exercise that I think we all need to do more of. When we see the stats about drop off or the lack of a certain group in the company, it can feel overwhelming to the point of inaction. Yet I see those same folks who feel overwhelmed thinking about these ideas around D&I put loads of hard work into essentially the same thought exercise around our products. The two are SO intertwined. The wild thing is that we could likely dig into stats and find that we’re reaching men and women differently with our own products. A solution to that marries this entire post together 🙂

We can apply the same thinking we bring to addressing broken parts of our products, flows, etc to addressing broken parts of D&I in tech. We need to apply the same thinking as the two sides of this get closer together. 

As Kat Holmes said

The physical, digital, and social spaces where we interact with each other are inclusive or exclusive by design. When we design diverse ways for people to participate, we just might be surprised by who shows up to play.

Who do we want to show up to play with

Who do we want to show up to play with Woo?

Who do we want to show up to play with JPOP?

Who do we want to show up to play with us at Automattic?

What kind of a playground is Automattic?

I think sometimes we get stuck on D&I just being conceptual when really there are very real actions we can take. When you feel this tug to be overwhelmed, take a step back and try to address it like you would any other problem. Change the way you view the graph. Address it like you would a technical problem. Start somewhere, experiment, bring in outside thoughts, return to the big picture as needed, track the results, on and on – rinse & repeat.

As I heard Kara Swisher say once at a conference, “I would say in Silicon Valley there’s a lot of big minds chasing small ideas. I’m really excited when they chase the big ideas like how to deal with poverty, cancer, illness and inequality.” Ditto. Enjoy:


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