Gratitude Endures: 10 Acquisition and Cultural Learnings as Flipgrid Celebrates 5 Years at Microsoft

In 2015 the Flipgrid team raised our Series A investment in Minneapolis and established our mission to empower every learner on the planet to share their voice and respect the diverse voices of others. At the time, those three inspiring words “on the planet” were purely a dream for me and my team.?

Three years later, on the morning of June 8, 2018, we had the extraordinary privilege of joining Microsoft through an acquisition to realize these three words, accelerate our mission, and grow Flipgrid into a global community of learners, educators, families, and schools. That day, Satya Nadella articulated the magnitude of the moment as he shared, “together with Flipgrid we aim to democratize these tools to empower every educator and student to create the world of tomorrow.” Satya’s words reflected the passion of our team, reinforced that we’d found a proud new home, and left each of us with a lasting memory of our first day at Microsoft.?

Today, I’m honored to share that Flipgrid is celebrating 5 years at Microsoft. In these 5 years, Flipgrid has been used by learners of every age (PreK through PhD), in every domain of education (from math to world languages to nursing and beyond), across 190 countries. Learners have shared their beautiful voices more than 8.3 billion times on Flipgrid representing more than 14,000 years of short videos highlighting learners’ beliefs, a-ha moments, challenges, wonders, creativity, and passions.?

We believe community is the point where our stories intersect. The Flipgrid community has grown exponentially thanks to inspiring educators worldwide that not only believe in empowering student voice, but also share the experiences learners love with their peers. We are proud of the unique community-led product-building this growth flywheel has created for Flipgrid.?

In celebrating five years, I’d like to share my deepest gratitude to Eran Megiddo , michele freed , Rajesh Jha , Amy Hood , and Satya Nadella for embracing the power of community, believing in a small Minnesota team, and providing us with both the pathway and the jet fuel to realize our mission at Microsoft. I’d also like to thank every member of the Flipgrid team and every educator, learner, and family member in the Flipgrid community. You are my why.

10 Acquisition, Integration and Cultural Learnings

1. Build the Bridge of Culture and Community

I love this image as I’ve lived every moment of it. Every founder, product leader, designer, engineer, author, artist, and creator has experienced The Emotional Journey of Creating Anything Great.

While imprecise in its curvature, and often not complete, this is the arc of most startups and creative endeavors. From passion and excitement, to trials and tribulations, to #%@}!!! and the dark swamp of despair, the journey is often most turbulent in the early phases. Sadly, many teams and ideas fail to locate or build a bridge, sinking endlessly into the swamp. And what most of your friends, family, and peers see is the top 99% of the arc. This is the journey of a startup, and for our team the bridge of persistence was built upon foundations of enduring culture and authentic love for the community we served.

Satya once shared, “Ultimately, what any company does when it is successful is merely a lagging indicator of its existing culture”. I’ve had a similar sentiment throughout the years, but I certainly didn’t know it as eloquently at the time. And shortly after we celebrated our acquisition by Microsoft, I realized integration only levels up and resets the Journey.?

As the integration experience challenged our team in new ways while we continued to serve our growing community, we were armed with knowledge from the previous bridge. We purposefully chose to fuse the best parts of the Flipgrid culture with the best parts of the Microsoft culture, while doubling down on our community-first strategy. I’m thrilled to say we built a far stronger bridge in our second journey, and this has created global impact opportunities beyond our original mission. We also made some extraordinary friends along the path.

2. Echo the “We” and “Us”

Every company should have a Book of Acronyms printed and leather bound for acquired teammates. Seriously. The onboarding of an acquisition team isn’t simply a firehose of information, the firehose itself is often thrown into their hands with no instructions.

While acronyms were their own challenge, early on I heard the word “they” quite often from my team, and I definitely used this word many times in moments of frustration. “Why do they want this?” “Why do they do it this way?” “Why did they even acquire us?” It’s relatively natural, but ultimately harmful. As a leader I realized we needed to welcome an intentional shift of language. Languages across companies will certainly differ but should never divide.?

As my leadership team and I decisively began using and echoing the words “we” and “us” in All Hands meetings and internal communications, I noticed an abrupt shift in our collective team language. These simple words turned the Flipgrid ship a few degrees in making us, and me, feel more a part of Microsoft, ultimately working alongside each other on a larger shared mission. Small investment, big ROI.

Embracing “we” also created additional team value. At this same time, we were able to accelerate internal Microsoft partnerships and avoid territorial roadblocks through a shared focus on serving our collective Microsoft customers.

3. Air Grievances with Recommendations

The acquisition process is exhausting, due diligence is draining, and unfortunately this level of fatigue often carries into the integration phase for leaders. While integration and compliance needs are always challenging in the first year, it often feels like your team is going through a uniquely difficult situation, custom-designed to put the press on you as a leader, possibly the first acquisition in history to experience this level of frustration. Well… as it turns out… you’re not. You’re experiencing the collision of processes, rhythms, language, and cultures. It’s also natural for your frustrations to become aired grievances (cue Frank Costanza volume) in meetings with leadership. I was certainly guilty of this on several occasions.

I’m grateful to Rajesh Jha who pushed me to pair specific frustrations with clear ideas for action, even if the proposed solution may not be immediately actionable. Further, I built additional context into my proposals, specifically highlighting our previous experience operating independently. I clearly identified what we had learned and how we would – or would not – want to resolve. In doing so I learned that most requests often come from a sense of purpose, an individual doing what is expected in their critical role for the broader organization. And more importantly, I found that most of these leaders wanted to engage in a discussion and learn, not simply impose a requirement.

Don’t get me wrong, I still air grievances – but they’re always paired with forward-looking recommendations.?

4. Ask “Is this Recommended or Required?”…often!

Similarly, Deb (Johnson) McFadden (who helped integrate our team into Microsoft Education, joined our team shortly after, and I’m proud to say now leads Flipgrid at Microsoft) suggested I start asking, “Is this recommended or required?” in integration discussions. Note, this approach is significantly more successful when the question is raised from a spirit of curiosity and growth, not defensiveness.?

What I found is many integration requirements were actually recommendations to help with existing rhythms, and many of these rhythms, in the end, benefited from some fresh perspectives. My heart rate lowered, and I met colleagues across the company that were vital to our successful integration over time. They became valuable partners to our integration through these conversations, as opposed to my early flawed perspective as obstacles.

5. Schedule Time to Reflect and Share

This one is surprisingly simple, but remarkably difficult to accomplish. I’m thankful to my startup co-founder, friend, and mentor Jim Leslie who taught me if you don’t intentionally block time to reflect, reflection rarely happens. As a founder or leader every journey is filled with successes, challenges, excitement, discouragement, and conviction. There are highs, lows, and everything in between throughout product-building, creating a team, growing your customer community, and shaping organizational culture. Far too often these monumental learnings are only fleeting moments in the velocity of a startup.

Over the last few years, I’ve talked with many founders and the regret I hear most often is that they didn’t stop to reflect. Schedule time to reflect on the journey for your customers and communities, your team, your culture, your family, and for you. And more importantly, schedule some time to share and discuss these reflections with a few peers. It compounds beyond expectation.

6. Embrace a Learner Mindset

As a professor I often used the phrase “Fail fast, fail often, and fail gracefully” with my students to spark a culture of curiosity and instill the value of failure in learning forward. While this led to passionate conversations, and as a startup founder and Microsoft leader I’ve certainly embraced these words, I realized it’s time for a shift in verbiage. Failure is often perceived as an endpoint, whereas learning is a continuum.

At Microsoft there is a strong culture of Growth Mindset that Satya and his Senior Leadership Team have modeled and shepherded impressively. As the landscape evolves and learning is embraced within a culture, the foundation of a Learner Mindset is created. I’m pretty sure I got it wrong as a professor. Today I’d rephrase as, “Learn fast and share proudly.”

This Learner Mindset has also become the keystone of our monthly team Sharefest, a tradition we’ve embraced for more than 10 years. All teammates are encouraged to share their learnings, demos, a-ha moments, life moments (we’ve had more than a dozen pregnancies and engagements announced!), and customer stories in a celebratory All Hands forum. These are my favorite meetings of every month highlighting beautiful moments of a collective Learner Mindset.

7. Enjoy Seeing your Teammates Grow

My co-founder and friend Phil Soran , a successful entrepreneur of several startups, shared with me that there are often three Celebratory Team Moments during an acquisition. The moment of the acquisition, the moment of expanded opportunities, and the moment of new paths. As a leader, I had no idea how important and inspiring these moments would be for my team.

The moment of the acquisition is a time to reflect on the past as we prepare for the future. The moment of expanded opportunities is a time when team members discover they are valued for broader impacts across the larger organization, potentially at a scale and depth they had previously never imagined. And the moment of new paths is when individual contributors become managers of broader teams, and former managers become team leaders in larger or possibly different organizations.?

I’m exceptionally proud that the majority of teammates from Flipgrid’s start-up days are still present at Microsoft today, several of whom were my former MA and PhD students. Seeing these teammates grow as exceptional Microsoft managers and extraordinary team leaders has been the most rewarding moment of my career.

I’m honored to continue working alongside you on this larger mission Jornea Armant , Sherene Azar , Paul C. , Sindy Gebhard , Adam Parker Goldberg , Martin Gostisha , Patrick Johnson , Liz Maddy , George Melookaran , Bryce Schmidt , Christine Shoup , Joey Taralson , and Shaomeng Zhang .

8. Realize Starters and Scalers are Important

When I joined Microsoft, I often asked new colleagues how long they worked at the company. I was genuinely intrigued and often heard 10, 15, 25+ years from executives. Inspiring… and intimidating – my imposter syndrome overdrive kicked in.

While many executives have decades at the company and are exceptional leaders, several shared that they admired how our team started a company, grew a product, and built a community from the ground up. I was surprised and I realized we had more to share than initially expected. Both Scalers and Starters are critical to large companies, not only in operating large organizations or launching innovations, but also in growing the collective culture.

To every leader and member of an acquired team, I can’t stress this enough. Keep building the launchpad and sharing your unique experiences, whether in product-led growth, technical expertise, unique go-to-market strategies, customer-centric values, or culture building. Raise your hand to help with acquisitions, investments, strategic partnerships, and corporate development opportunities. But please avoid stating, “Here’s the way we always did it” (see item 2 above). Try sharing, “Here’s a few of our learnings, how can we help?” Language matters!

9. Help Welcome the Next

One of the most rewarding investments I’ve made in the last few years is in welcoming new acquisition teams and leaders to Microsoft. While our Flipgrid team was welcomed warmly by the Microsoft Education team when we joined Microsoft, I personally wanted to meet other leaders that had been through the startup, acquisition, and integration journey. Ultimately, I didn’t find this group and felt isolated as there was much I wanted to ask and share with full candor.

Then, about 18 months after joining, a new founder reached out to have a safe channel for some needed venting. I was excited to connect and grow my network with another Microsoft founder. Unfortunately, this leader’s integration was not as they hoped, and they simply needed someone to listen. I listened. And I learned a lot. Without a goal in hand, I invited this leader to join me in meeting the CEO of a new company that was about to join Microsoft.

This meeting represented a pivotal shift for me. For the first time I felt I was representing the culture, the opportunity, and the mission of Microsoft. And, to my surprise, it was also an important shift for the other leader I invited. Other members of our Flipgrid team also reached out to welcome this new team to Microsoft, and this became the foundation of a larger internal acquisition community we continue to grow.

Integration of cultures is hard, and it should be, as there’s likely something more valuable as a result. Many leaders have experienced this journey, are on this journey, and are about to start this journey. Here’s my challenge to any leader of an acquisition team… to become a stronger member of the current community, help welcome the next!?

10. Show Gratitude

Since Day 1, the Flipgrid community was built on two powerful words that every educator, everywhere in the world, should hear every day: “Thank you.” This simple expression of gratitude to the customers we serve and the teammates we serve alongside became the foundation of our team culture that persists to this day. I’m immensely proud of this. Again, small investment, big ROI.

It’s funny writing this, as it’s so fundamentally simple, yet it took me a decade to understand. The most profound and rewarding thing I’ve learned as a father, a husband, a professor, an entrepreneur, and now a Microsoft executive, is this… Invest your energy to help those around you (regardless of hierarchy or recency or geography or even familiarity) feel proud of their impacts, echo their perspectives, share their learnings, and show gratitude.?

To this, “Thank You” to my Microsoft mentors and friends that have helped shape my perspectives, welcome our team, and accelerate our Microsoft culture over these last 5 years. Phil Spencer , Mikhail Parakhin , Lila Tretikov , Rajesh Jha , Deb (Johnson) McFadden , Krystle Murphy , Joe Belfiore , Amy Hood , Jeff Teper , Panos Panay , Eran Megiddo , michele freed , Deirdre Quarnstrom , David Washington , Jordi Ribas , Dave McCarthy , Jessica Ostrow , Jim Federico , Ryan Roslansky , Jeff Weiner , Ale? Hole?ek , Sumit Chauhan , Omar Shahine , Gail Giacobbe , Manik Gupta , Chris Pratley , Justin Chando , Kevin Wiggen , Randy Wallingford , Mike Tholfsen , Liat Ben-Zur , and Shalima D. .