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Women’s Enterprise Playbook: Navigating the Gray Zones

These notes are from our Enterprise Forum: Playbooks from 6 Women event we hosted at Work-Bench on July 25, 2017.

The evening was an intimate, powerful, and real evening of stories from 6 women, across a diverse range of experiences and backgrounds at enterprise tech startups.

Each speaker shared a “A Page from My Playbook”: getting granular and tactical about the *exact* steps they have taken when looking for a male sponsor, pitching/selling a deal, responding in uncomfortable situations, and in scaling their careers.

Here at Work-Bench, we are a venture fund that invests in enterprise technology startups throughout the country.

In addition, for the past 4 years, we have also been building this home and this hub for enterprise tech here in NYC.

In our 4 years, we’ve hosted almost 1000 events to date. And of those 1000 events I can say with almost absolute certainty, they have been attended by 80% men, 20% women.

And I used to think that this number would get better over time on its own, and that we would see more and more women come out.

But quite frankly,…we haven’t.

That, coupled with all the news that has come out over the last few months has made it clear that not only do we have a women in tech problem…but we also have a women in enterprise tech problem.

And there may be unique challenges in enterprise tech that make it uniquely hard for women.

And this is why rather than the usual panel, we’re going to change it up a bit and do it a bit differently, with 6 monologues from our 6 speakers.

What I admire about these women is that each bring a unique perspective to the table, not only in their roles and functions, but also frankly, where they each are in their careers. And I think that perspective is so needed as well.

So tonight’s theme I’ve asked our speakers to think about is this idea of a gray zone.

When things are black and white, it’s pretty clear usually what needs to be done.

But it’s the gray zone where I think many of us — and where I know I personally struggle (editor’s note: even Hillary).

When it’s not maybe sexual harassment, but it’s still rude or patronizing or hard. And it adds up, right?

There are days when we think, this is hard! And it takes up emotional and mental bandwidth.

On the flip side, I’ve asked to hear the good stories too. I think we’ve all had our share of truly terrible ones these past few months. But I know many of us if not all of us would not have gotten to where we are today without the mentorship and support of both men and women. So would love to hear more on that too.

Our big vision really is — can we ultimately create an open source playbook of navigating these gray zones, out of these conversations? Because as we all know, there is no one right route to take…but it can be *so* helpful to hear how others have traversed these paths ahead of us.

6 Actionable Takeaways from the Forum

1. Build Diversity into Actionable OKRs

To encourage your team to embrace diversity, dedicate one team OKR (Objectives and Key Results) to a diversity initiative. The OKR can be to merely have a diversity metric, attend a diverse event, or volunteer time to an organization like “Girls Who Code”.

2. Build Your Social Currency

The best way to get a sponsor is by showing up and standing out so that people are gravitated to make an investment in you. At the end of the day you don’t select a sponsor they select you.

3. Deliver your message using a powerful non-emotional data driven approach.

If you want to change something within your company assemble the facts, develop a solution, and then meet with the key decision makers. Always leave emotions out of it.

4. Before accepting a role determine how the company measures success.

To truly understand how you will be measured at a company you need to have a thorough understanding of what they see as success and how they measure success within your role. Without understanding these two things you can’t fully determine whether a position is the best fit for you.

5. When giving feedback to colleagues about a time they made you uncomfortable frame it in a non-confrontational way.

When discussing uncomfortable situations strive to take an educational approach. A great template to start with is: When you did “insert action here” I don’t think your intent was to “insert feeling here”.

6. List of 10 microaggressions.

The first step in addressing microaggressions is to recognize when a microaggression has occurred and what message it may be sending. Find the list of 10 microaggressions in the workplace linked here.

What other takeaways do you have, or contributions to be made to a greater playbook? We’d always love to hear.

Many thanks to our speakers from our Enterprise Forum event: Lisa Skeete Tatum, Cristina Dolan, Emily Disston, Natalie Fratto, Francesca Krihely, and Teresa Dietrich, and to Allie Felix.