Grace Hopper 2016: Should I Stay or Should I Go?

Ever felt stuck in your career? In this panel, executives from a variety of tech companies — from tiny startups to giants — will share their experiences navigating career ups & downs. They will discuss how to tell the difference between “weathering the storm” vs. “enduring a toxic situation,” and when “staying” makes more sense than “going.” Join us for a lively and candid conversation.

The panel included

Gail started by sharing why she left Microsoft and why she chose GoDaddy. After 15 years at Microsoft, she felt like she needed a career change. In terms of a new company, she wanted a senior leadership team with leaders who would support her and help her grow. She want the opportunity to have a big impact. She wanted a company with a mission she could believe in. And finally she was looking for a culture where she could do her best work — an inclusive culture where diverse view points are appreciated and where there is transparency around decisions. I think the key message here is to be clear about what YOU want and then go after it.

There was a lot of discussions about pivots — sometimes you pivot within the same company, sometimes you pivot out. Alex pointed out that sometimes it was her attitude that needed a pivot and that she participated in hackathons and Startup Weekend events in order to refresh her perspective. Rebecca noted that sometimes you get to choose when you pivot and sometimes they are a “gift” (noting that sometimes gifts are unwelcome).

The panel then moved into discussing the five reasons women generally leave the workforce:

  1. Unconscious bias

Unconscious bias

Sumit shared that right out of college, she faked it and wasn’t herself for the first 3 years because she was trying to conform to expected stereotypes. She later wished she hadn’t done that. Alex was pregnant when there was a specific job she wanted. She couldn’t convince people it would work, so she walked away. Believes she should have pursued a 3rd option — rather than fight or flight, she could have found a solution that benefitted both her and the company.


Rebecca shared stories of training for and competing in ironman and triathlon events. At some point, you end up feeling isolated. Friend taught her to ask what does she want and what does she need. It applies to training and to work. It’s OK to admit you can’t do everything and ask for help.

Supervisory relationships

Gail started with a quick anecdote from early in her career and she had a manager who was new to managing. Their one-on-ones tended to focus on what she could be doing better. She finally made the ask and said for all the tough feedback you’re sharing, can you please tell me one thing I’m doing well. It really opened up his eyes and they are still good friends to this day.

Rebecca shared a story titled “the time that I worked for Satan.” Rebecca has a great sense of humor and all I could think about in her telling of the story was Dana Carvey, The Church Lady, and the way “she” talked about Satan. That aside, her message was key — if the voices in your head are telling you to get out, get out. Make sure your boss shares your core values and values you. You don’t need to tolerate jerks and/or abuse.

Promotion processes

Gail was suddenly promoted to manager one day, given a brand new hire as a new report, but was then told they didn’t think they’d give her the same title “Lead xxxx” as everyone else. She pushed back, got the title change, and was suddenly invited to key meetings. Push for what you feel is right and what you feel you deserve.

Liz shared important advice for would-be entrepreneurs in the room. Do the job you want before it is identified. Don’t wait. That was how she had gotten most of her roles (including her current CEO role).

Conflicting life responsibilities

Rebecca noted that women are often caretakers, and not just for children. At one point early on, she needed to suddenly care for her mom. She didn’t want to stop working and put together a plan of how she would manage caring for (and being across the country with) her mom and still get work done. Rather than apologize and ask, she told her boss that she had a plan, what it was, and then said *I need your support*. When you have a solid plan, people won’t say they don’t support you.

The panel then opened up to the audience for Q&A. There was a question about changing jobs when you might not hit every checkbox in the job description. Liz shared her mother’s advice (her mom is a career coach). You have 3 things — your company, your job function, and your industry. Don’t change all of them at once.

Someone asked if the panel had ever struggled with a good boss or mentor that suddenly left the company. Sumit noted that two of her closest advocates recently left Microsoft. She realized she hadn’t done enough work to build networks outside her current group and that she needed to invest in that going forward.

The overall message of the session was that you have to be you. Listen to your heart (or the voices in your head) but be creative — there may be more paths to achieving your goals that were immediately obvious.



Posts and thoughts from #womenintech who want #diversity in #technology and to share their expertise and experiences

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Lori Fraleigh

Developer tools gEEk; Product Lead for @AzureSDK at @Microsoft; Queen of Corner Cases; Purdue & Stanford grad; Space Nerd & Virgin Galactic Future Astronaut