Microsoft VP Gretchen O’Hara on helping launch Women in Cloud, the work-life continuum, and more


Gretchen O’Hara (right) at the United Nation General Assembly’s Ideagen in September 2018, sharing information about Women in Cloud. (Women in Cloud Photo)

Gretchen O’Hara is a diehard Microsoft fan.

You might have guessed as much given that she’s worked for the Redmond, Wash.-based cloud and tech giant for more than two decades, with a short break early in her career. In her current job as vice president of Go-to-Market Strategy for Microsoft’s One Commercial Partner Organization, O’Hara is working on initiatives directed at the company’s 100,000 U.S. business partners.

“The passion at the company and mission are really near and dear to my heart,” she said. “From a personal perspective, I get excited about the people. I get challenged every day.”

As part of the One Commercial Partner Organization, which launched two years ago to create an umbrella organization of the partners, she’s leading areas including market strategy, product revenue growth, and community development.

O’Hara’s adoration for her employer is fueled in part by its engagement in her life outside of work as well.

In 2017, she helped launch Women in Cloud, an initiative to help female tech entrepreneurs. The venture is led by Ignite WA with collaboration from corporations including Microsoft, Hewlett Packard Enterprise and Meylah.

O’Hara, who had worked on STEM education issues, was increasingly concerned about the underrepresentation of women in the tech sector. She cited troubling statistics: while women own 36 percent of U.S. businesses, they run only 6 percent of tech startups.

When it comes to this disparity, O’Hara asked herself, “how do I really give back in a bigger way, beyond volunteering? How do I work deeper, at the root cause?”

Gretchen O'Hara - GeekWire Cloud Summit 2019
Microsoft’s Gretchen O’Hara, vice president of Go-to-Market Strategy in the One Commercial Partner group, announces the expansion of its Women in Cloud startup accelerator at the 2019 GeekWire Cloud Summit. (GeekWire Photo / Kevin Lisota)

Women in Cloud supports networking and mentoring, hosts an annual summit, and runs a six-month-long Microsoft-supported cloud accelerator to help startups build and grow a cloud-enabled business. This month the organization launched its inaugural #CloudInnovateHER Pitch Challenge, which will culminate in a startup pitch competition at its January summit with a top prize of $10,000.

O’Hara said Women in Cloud, which has a global reach, is growing rapidly and has an equal number of women and men in the organization.

She encourages others to get involved in these important issues of inequality and underrepresentation.

“It doesn’t have to be huge, it’s just one little step — mentoring someone who needs help, picking up the phone when someone needs answers,” she said. “All of these little things lead to really big changes.”

We caught up with O’Hara for this Working Geek, a regular GeekWire feature. Continue reading for her answers to our questionnaire.

Current location: Bellevue, Wash.

Computer types: Microsoft Surface Pro, and lots of fun with the new Microsoft Surface Go

Mobile devices: iPhone, using Microsoft productivity

Favorite apps, cloud services and software tools: My favorite apps are about saving time and being productive. Microsoft Office Mobile, Outlook with Microsoft Teams and OneNote are a must! I am addicted to LinkedIn and shop on the go. I love the AI in Stitch Fix, Rue La La, Thumbtack for fast fixes and can’t live without the Starbucks app — a complete time saver as a coffee lover.

Describe your workspace. Why does it work for you? When I’m not traveling to meet with customers partners or employees, I enjoy being in our Bellevue office, which overlooks our beautiful city. I never get tired of the views here in the Northwest. At Microsoft, we have an open workspace and an open-door policy that allows us to have more of an open dialogue and real-time huddles. My workspace includes extra comfy chairs, some fun decorations depending on the month and opportunity for a place to pause and have a resting space.

O’Hara attended the United Nation General Assembly’s Ideagen in September 2018 with other members of Women in Cloud. (Women in Cloud Photo)

My Surface Hub (an interactive whiteboard) is front and center to stay connected via video in every conversation I hold. While I prefer face-to-face meetings when possible, in a dispersed world feeling connected across the globe is incredibly important to develop an inclusive environment. Microsoft Teams is set as a standard for all customers and partners to ensure they have an opportunity to connect remotely or even in person using the latest tools.

Your best advice for managing everyday work and life? As a mother of three, I certainly understand the need to balance a fulfilling career with a fulfilling home life. But I’ve never liked the term “work/life balance” because it suggests that if you’re focused on one then you’re by necessity neglecting the other. I think about work and life as part of a continuum and, yes, there will be tradeoffs along the way, but overall one enriches the other and I would not be complete without both.

We’re lucky at Microsoft. We have generous benefits that allow us to keep ourselves and families healthy and we also have a commitment to an inclusive environment, where we are encouraged to bring our whole selves to work each day. My best advice for your readers is to know your non-negotiables and feel empowered to communicate those to your management. If you haven’t yet figured that out, spend some time thinking about what your own philosophy and values are. This is personal, unique and needs to reflect what is deeply important to you.

Your preferred social network? How do you use it for business/work? My favorite social network is LinkedIn. I use it to stay connected to present and former colleagues and partners. I love reading the articles and take away something every day. Sales Navigator, which is a great tool that’s part of LinkedIn, also helps me make new connections and build lists of people I want to stay connected with on particular issues, recruiting or just thought leadership.

I like Twitter for the fast pace and I try to mix personal and business to be my authentic self. I tweet mostly when I am learning something or have something to say in the moment.

O’Hara with her family, celebrating the University of California, Berkeley, which one of her kids attends. (Photo courtesy of the O’Hara family)

I try to stay current with Instagram, SnapChat and VISCO but more to keep the pulse on the social scene. I place a value on trying to help others who reach out to me. I can’t always be the one to help, but that’s what your network is for!

Current number of unanswered emails in your inbox? I try to respond to my email within at least a day, which can be challenging when I’m on the road or in a series of meetings that are email-free as I can get almost 500 or more per day. To avoid getting lost in my inbox, we are trying to be more productive with Microsoft Teams, but externally it’s best to catch me on LinkedIn and never give up on the importance of your message. People think that one mail should be all it takes, but I appreciate the persistence and any unanswered mail is just by pure accident.

I get hundreds of emails a day and use Microsoft MyAnalytics to help me triage and focus on the most important or time sensitive ones to make sure I’m following up on action items and optimizing my productivity. But if you have something important to say, I want to hear it!

Number of appointments/meetings on your calendar this week? I have about eight hours of meetings every day. This doesn’t include dinners, evening events, etc. Due to the heaviness of meetings, I have developed meeting-free zones on a weekly basis to give people time to think, be creative and have space to work.

How do you run meetings? My perfect meeting is 45 minutes. It allows for deep discussion, but gets you to the point. I ask for a clear agenda, a meeting owner and accountabilities for who is driving actions and follow-up. If these are not defined, I prefer to wait to optimize the time. For bigger meetings that require decision making, investments, alignment across organizations, I always ask for a pre-read to support cross stakeholders.

Everyday work uniform? Microsoft is a unique place where there is really no dress code and no judgement. So my work uniform is highly dependent on the meetings and audiences I have during my work week. But regardless of the audience, my staple is a great pair of shoes and jewelry to dress up or down my work uniform. Be professional, but have fun and bring your authentic self.

How do you make time for family? As one of my nonnegotiables, I’ve always prioritized family and make my best efforts to always attend the events that matter most to my children. When my kids were younger, I committed to making them breakfast every morning as a way to set up the day, and leave with energy and connection because evenings can be quite chaotic. To ground and regroup, my mandatory Sunday dinners required no phones or devices and featured hot topics to share as family.

O’Hara outside of the Nasdaq building in New York City. (Photo courtesy of O’Hara)

Now that they are older and two of them are off to college — Berkeley (go Bears!) and Alabama (roll Tide!) — I try to visit them as much as possible and to stay present when they need me.

Best stress reliever? How do you unplug? People give me energy and a great stress reliever is just talking to my team or friends on a personal level, extremely unplugged. Laughing is the best medicine and laughing at yourself and finding humor gives you incredible relief.

I also get energy from the water, and I spend much of my time boating, kayaking, paddle boarding — regardless of the season. In the winter, I enjoy skiing and bring my family on at least one ski vacation, which is a fun bonding experience.

And if I don’t have those in my near future, my last resort is picking my next crazy TV binge series. I don’t often have time to watch day to day, but will catch up on ancient must-see series for some mindless downtime. Thank you Netflix!

What are you listening to? I love that song by Cage the Elephant, “Ain’t No Rest for the Wicked” — I think it must speak to my work ethic! I love Ed Sheeran for his creativity, think Lady Gaga is brilliant, can listen to Shallow a thousand times and I am a throwback to all the rock classics: Rolling Stones, Eagles, Aerosmith, Led Zeppelin, Journey, Queen, Elton John….the list goes on and on.

Daily reads? Favorite sites and newsletters? My favorite place to get caught up on both industry news as well as updates from colleagues and partners are LinkedIn, a combination of Apple News sources (CNN, New York Times, C-SPAN, MSNBC, Fox News, Bloomberg, Wall Street Journal, Forbes, etc.), and I subscribe to TechCrunch, GeekWire, Wired, CRN, CNET, Sirius Decisions, Harvard Business Review, PitchBook and CMO Weekly.

O’Hara speaking at the U.S. Area General Session at Microsoft Inspire 2019. (Microsoft Photo)

Book on your nightstand (or e-reader)? I’ve been reading and listening to Brené Brown and just finished, “Dare to Lead.” I’m also reading Brad Smith and Carol Ann Browne’s new book “Tools and Weapons” about the promise and peril of the Digital Age. I’m a fan of Margaret Atwood and just about to start “The Testaments,” a sequel to “The Handmaid’s Tale.”

Night owl or early riser? I am definitely a night owl. I do my best work and get into creative mode in the evenings. But the reality — with a family and work commitments — I am an early riser!

Where do you get your best ideas? Funny enough, I think I get my best ideas driving to or from home or in the shower. I write notes, diagrams and ideas by my nightstand. However, at this point they are only my ideas.

I firmly believe that the best ideas come from diverse teams that can have the room and space to ideate with different perspectives. That’s why diversity and inclusion are such keys to everything we do at Microsoft and I live this every day. Diverse teams create better ideas collectively and give unique perspective to drive and improve on innovation.

Whose work style would you want to learn more about or emulate? As one of the most influential business women of our time and someone who has helped to transform both Microsoft and the industry, I’m always interested in learning more about Microsoft’s Chief Financial Officer Amy Hood. I’ve had some opportunity to interact with her and I love the way she thinks, innovates and has the courage to face the street in an authentic and convicted way. She will continue to change the industry.

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