Steps the Python community and Dropbox are taking to increase diversity

At the Red Hat Summit in San Francisco last month, DeLisa Alexander, executive vice president and chief people officer at Red Hat, announced the winners of the company's second annual Women in Open Source Award. Jessica McKellar, director of engineering and chief of staff to the vice president of engineering at Dropbox, and Preeti Murthy, a graduate student at Carnegie Mellon University, won the 2016 Women in Open Source Award.

I first met Jessica McKellar, who was recognized in the community category, back in 2012 when she was a project lead on Ksplice, a startup she helped found and that was later sold to Oracle. She was on a panel I moderated at the 2012 USENIX Women in Advanced Computing Summit, Strategies for a Successful Career in Computing.

In this recent interview, McKellar explains the achievements she's most proud of, and the steps the Python community and Dropbox are taking to create diverse, inclusive environments.

Your concise Twitter bio sums up an impressive career in eight words: Startup founder, open source developer, Engineering Director @Dropbox. Which achievements are you most proud of so far in your career?

Something I didn't consciously anticipate when I was starting out in my professional career was how intertwined my corporate and open source lives would end up being.

The technical and leadership skills that I've developed and the experiences that I've had have been highly transferable across these contexts. It has been deeply inspiring to participate in the overlap and positive feedback loop between work on diversity and inclusive culture in open source communities and companies over the past couple of years. The work ends up being very similar.

Rather than pointing out any particular achievement, I'd say that I'm proud of being consistent in using the opportunities and the visibility I have in a variety of contexts for social change, and for creating sustainable programs that outlive my involvement, which is what true success often means.

Wearing your PyCon Diversity Chair hat, in May you released statistics on PyCon talks by women. At the recent PyCon, 40% of the talks were by women—up from 1% in 2011. What works for getting more women to submit proposals and speak at events? What do you see event organizers doing that does not work?

A commonly attempted strategy that usually doesn't work is issuing a call for proposals, saying "it's really important for us that diverse speakers submit talks. Please, diverse people, submit talks," and then seeing what happens.

No matter how earnest and heartfelt that call to action is, it usually doesn't work because conference organizers haven't tackled prerequisite steps for diverse conferences, and they don't put in enough work to bootstrap a diverse speaker pool.

Here's a generic framework for building up a program for diverse conference speakers:

• Step 0: Inclusive culture
• Step 1: Equitable evaluation process
• Step 2: Proactive outreach
• Step 3: Sustainable program

Let's talk about each of these briefly.

Step 0: Inclusive culture

Before we worry about having a diverse speaker line-up, we need our conference to be one that people from diverse backgrounds want to and are able to attend. What a successful inclusive culture means varies from community to community and conference to conference, and you don't know if you are doing a good job of this if you aren't asking, and getting quantitative and qualitative data.

Common questions for conference organizers to ask themselves around building an inclusive culture include:

• Do diverse participants feel welcome? Do we need a code of conduct? What does our branding convey about our culture?
• Can diverse participants afford to attend this conference? Do we need a financial aid program or childcare?
• What is considered on-topic for conference talks, and are those topics interesting to people of diverse backgrounds?
• Is the conference accessible?

Step 1: Equitable evaluation process

The next thing to tackle is how the conference talk selection committee pick talks. There are many ways to do this that create high-quality, diverse lineups, but some things to consider:

• Do new speakers (diverse speakers in a historically un-diverse conference are likely to be new speakers) have the context, tools, and support to write proposals competitive with experienced speakers?
• Do the selection process and committee training minimize conscious and unconscious bias?
• Does the conference have a framework for getting to a diverse portfolio of talks across dimensions like topic category and audience experience level?

Step 2: Proactive outreach

Once you have a conference that people from diverse backgrounds want to and are able to attend, and you have a talk evaluation process that encourages a diverse portfolio of talks, you need a diverse top of the funnel to your application process.

If your speaker lineup is historically un-diverse, you probably need to do a lot of work to bootstrap that diverse top of the funnel. This usually looks like getting a set of conference organizers together, generating a list of candidate speakers, and emailing them encouraging them to submit talks. For a conference of PyCon's size—around 100 talk slots and historically around 500-700 talk submissions—this means reaching out to 200 or 300 people directly, in addition to partnering with other organizations working on inclusive communities to promote the talk submission process and deadlines (e.g., PyLadies).

Is that a lot of work? Yes. Is it the only way that I am aware of to successfully bootstrap a diverse to of the funnel? Yes.

Some tips to help fill the funnel:

• Think broadly about sources of potential speakers. Regional conferences, user group talks, blog writers, university societies, and social media communities are a good start.
• Invest in speakers for the long term. A common multi-year progression is
  1. attendee
  2. poster presenter or lightning talk speaker
  3. full talk or tutorial presenter.
• Partner with user groups and other community organizations to run proposal ideation, writing, and feedback workshops.

Step 3: Sustainable program

Measure the results, double down on what worked well, iterate on what didn't, and do it again next year. The program should be durable to turnover in conference staff.

What steps do you and/or Dropbox take to create an inclusive, diverse organization?

As I mentioned earlier in the conversation, one of the things that has been gratifying about working on inclusive culture and diversity at Dropbox and in the Python community is how similar the work is.

At Dropbox, as an employer with additional responsibilities around career growth and recognition, we need to expand the steps from inclusive culture to successful diversity recruiting:

• Step 0: Definitions and focus. What does "diversity" mean to the company, and what demographics are we going to focus on right now?
• Step 1: Inclusive culture and employee engagement. Making our company a place where people from diverse backgrounds want to be.
• Step 2: Recognition and retention. Making our company an equitable place to grow.
• Step 3: Evaluation. Making our candidate evaluation process equitable and unbiased.
• Step 4: Recruiting. By this step, using hiring to increase diversity is mostly a question of prioritization plus some basic top-of-the-funnel math.

You only know how you are doing on each of these fronts if you measure it, and I am consistently impressed with Dropbox's commitment to the data. We have recurring Pulse surveys that measure, across demographic cuts, if employees:

• feel like they belong
• feel equitably valued and recognized
• feel that the company's values are aligned with their own

and other measures of employee engagement. We track and monitor equality in promotion rates, compensation, and retention rates. We do funnel analyses on our evaluation process, to ensure that candidates applying to work at the company are evaluated equitably across demographic cuts.

Once you are measuring everything you need to measure, to drive improvements you need to set clear targets and a clear accountability model for achieving those targets.

If I were leading an open source community project and wanted to increase the diversity in my community, what are three bits of advice you'd offer?

I'd first call back to our steps from before:

• Step 0: Inclusive culture
• Step 1: Equitable evaluation process
• Step 2: Proactive outreach
• Step 3: Sustainable program

and then say:

1. There is no shortcut to avoid putting in the work of direct outreach.
2. You can't fix what you don't measure.
3. Focus on creating sustainable systems.

What's next for you?

In the Python community, we've clearly established a sustainable model for bringing women into PyCon as speakers and attendees, and I'm excited for us to broaden our scope for diversity outreach to other demographics. Not many conferences have gotten to this point, so we have some new ground to walk in terms of partnerships for successful outreach and how we measure success. I'm excited to publish our methodology for the broader community to critique and remix, like we've done with our existing outreach.

Beyond that, in general I want to keep my sleeves rolled up and stay scrappy and discontented with the status quo and attentive to the fact that a lot of my job is giving opportunities and the megaphone to other people.

Also read Jen Wike Huger's interview with Preeti Murthy, who won in the academic category, and our interviews with 2015 award winners Sarah Sharp and Kesha Shah.