Microsoft Canada chief Janet Kennedy talks career, leadership and innovation

I recently got the unique opportunity to gain some insights from a very successful leader who tripled the MS enterprise business to $3 billion, led the transformation to the cloud with Office 365 and prior to that enjoyed a series of wins for IBM before being tapped to be Microsoft Canada president. Quite a journey for this Toronto resident and self-proclaimed “device geek” who enjoys playing with apps, trying the latest exercise trend, and enjoying movies – both box office and obscure!

She is a global star and model in the need for diversity at the highest levels.

I had a chance to talk with Janet Kennedy in an engaging chat. To listen to the full podcast (a dynamic exchange based upon and adding to the Q & A below), click on this MP3 file link.

Here is an excerpt from our conversation:

Q: Janet, your outstanding contributions in innovation and executive leadership have a significant global impact. Thank you for sharing your considerable expertise, deep accumulated insights, and wisdom with our audience.

A:  “Thank you so much, it’s a pleasure to chat with you today.”

Q: Janet, can you profile your extensive education and corporate background from Purdue University to IBM and Microsoft? How is your prior work still impacting today and into the future?

A:  “I’ve been in the tech industry for almost 30 years and it’s been a wild ride – particularly for a woman that came out of engineering school. I graduated from Purdue University in Industrial Management and Industrial Engineering. As you might imagine, at that time there weren’t a ton of women doing what I’m doing today. I’ve been really fortunate because tech is an industry that’s always changing. There’s always something new and exciting to learn. In my early career at IBM I actually started as a Job Control Language (JCL) Programmer but quickly decided I preferred the customer and the client side, learning about how technology can help solve business needs for our customers. I later came to Microsoft and I just finished my 13th year here with the company.”

Q: As a top notable leader, what are five or more tips for strong leadership?

A:  “I’ve learned a lot along the way – sometimes by making mistakes and sometimes by getting lucky. I would probably say that first of all, make sure that you step outside of your comfort zone. There were times along the way when perhaps I was very comfortable with the customer-facing side and was challenged to take a strategy role. For example, in the early 2000s, I moved out of a customer-facing role and helped work on the retail and hospitality strategy for Microsoft at our headquarters. Then I was challenged again to take a full P&L role so I could understand the end-to-end operations. Each time that I did that it gave me a new experience that I could gain, allowing me to be ready for my dream job – which is being the president of Microsoft Canada.

I would also add that you don’t always move with a promotion. People often agree to take a move and try something different if they get promoted. But I like to use the phrase ‘your career is a jungle gym’. You often have to go lateral to get to where you want to be. That’s true in my case. I’ve had six different jobs at Microsoft and people might be surprised hearing the different moves I took. Only one was a promotion, the other ones I had to earn my way by getting different experiences. I would really challenge people to look at their career that way.”

Q: Are there specifics you can share about new upcoming Microsoft innovations that will be transformational?

A:  “Absolutely. This is a very exciting time in the tech industry. In my career, I often talk about how I’ve been able to see three big tech innovations. I got to see Bill Gates talk about a-PC-in-every-desk and every home – of course, that clearly happened. The second in my career has been the Internet, and ‘what always-on, always-connected’ meant for consumers.

The third one is happening now and that’s the transformation to the cloud. That’s part of the reason I was brought to Canada – I did have some deep expertise in my past role when I was working with Fortune-100 customers, helping them move to cloud-based solutions and transform their businesses. Canada was actually a little bit late to the market in this area, but the last two years, it’s exploded. It’s fun to be leading a team at the very early part of the transformation in this country and there are lots of things happening that are exciting.

I love to work with the tech start-up community, because just a few years ago if you were in Communitech, MaRS, Notman House or Launch Academy, the big incubators across our country, these entrepreneurs would start a company, need some funding that then they would leave for Silicon Valley. Today with cloud-based solutions, with companies like Microsoft offering them free compute power to get their company started, we’re seeing new start-ups all over the country on cloud-based solutions. You can literally set up, go through the development cycle, get storage and a network without having to go get a multi-million dollar investment.

I’m really excited about some of the new capabilities that we’re seeing that are using the cloud, things like machine learning, business intelligence, disaster backup; there were many things you couldn’t do just a few years ago.

Finally, the thing that’s just fun for me in this role running Microsoft Canada is that every single person in Canada is a customer in some way. We’ve talked a lot about cloud computing for start-ups and commercial customers, but I also get to spend time with those passionate about gaming, Xbox Live, and Minecraft – there’s just a lot going on in this country that Microsoft is excited about.”

Q: I was just speaking at a recent conference here in Vancouver and there was so much excitement about the Hololens, are you able to talk a bit about that?

A:  “We saw Hololens at an announcement about two months ago. While I don’t have anything more to share at this time in terms of a launch date or when it would be in-market in Canada, it is a great vision of what’s coming and what’s possible. The potential of playing Xbox or Minecraft on the Hololens is really amazing, but another breakthrough in that area will be what commercial businesses can do to bring innovation to market using that technology.”

Q: How can corporations and non-profits such as CIPS and the ACM work together?

A:  “We do a ton with non-profits – I think the number last year was we did almost 46 million dollars of software grants and cash grants. We offer our software to the non-profits, particularly Office 365, for their use. We’ve been offering Office 365 for universities and colleges but we just announced for kindergarten to grade 12 that we’ll be doing the same. We’re trying to help people understand that we want to help our students and the non-profits to become more productive.

Something that was surprising to me is that I recently saw a presentation at a CEO dinner down at Communitech in which it was discussed that Canada’s productivity is not strong compared to the rest of the world – I think we’re 22nd in the latest World Economic Development Forum. It’s really an opportunity for us to use the benefits of productivity and software not only for companies and government but most importantly for our students and their future. Big announcements in the education area, I think you’re going to see a bunch more coming up later this year.”

Q: You choose the topic area. What do you see as the three top challenges facing us today and how do you propose they be solved?

A:  “Considering what I think about in my role, I would probably say firstly, innovation. Our CEO likes to talk about growth-hacking – which is that anything you do in whatever role you have, there’s always ways you can get together as a team and find new ways to stream productivity, grow top line revenue and bring innovation to the marketplace. Innovation is big in our company and in our industry.

From my personal perspective it’s about leading through transformation. We’re a hundred billion dollar company and are about six-to-seven years into this transformation to the cloud, yet only about seven billion of that hundred is from the cloud. I would tell you we’re at the very beginning of a journey. There’s almost 2,000 people that work for Microsoft Canada, so how do you lead a culture so that people understand what we’re going through, which is shifting to an entirely different business model than we were in the past.

The third one for me is the chase for talent, and how do we find the right people with the right energy and the right mindset to make sure that we can best serve our customers here in the country?”

Q: Do you have any advice to give to encourage diversity and increase participation across the board in STEM?

A:  “There are actually multiple ways to increase diversity and participation in STEM fields. I think about how our company is working hard to do so. I know you got to participate in our recent YouthSpark Live event in Vancouver, but we’re trying to get students to understand the opportunity they have if they invest in STEM – science, technology, engineering and math. In particular, I have a passion for showing these possibilities to young women – many of them have the technical and math aptitudes but they hit middle school and high school and then suddenly it’s not cool anymore for them to invest in those areas that they’d need to get a good job in this industry.

We have programs like YouthSpark, we also do DigiGirlz camps and we’ve done Hour of Code. There are many areas we support in order to help show youth the path to these careers, such as taking the right classes in university to come out with a strong job in the Canadian marketplace.

It doesn’t stop there, though, the next piece of it is BizSpark, which is the piece where we help start-ups and Independent Software Vendors to start their businesses. It’s very exciting to me to be part of a company that really is giving back, both to our students and the entrepreneurs that start here in the country. There’s so much opportunity if they can get their arms around what the potential is.”

Q: Janet, with your demanding schedule, we are indeed fortunate to have you come in to do this interview. Thank you for sharing your substantial wisdom with our audience.

A:  “Thanks for chatting with me – it’s been a wonderful conversation!”

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Jim Love, Chief Content Officer, IT World Canada
Stephen Ibaraki
Stephen Ibaraki
Stephen Ibaraki Chairman and Managing General Partner REDDS Capital, Founder chair outreach UN ITU AI for good Global Summit. Globally unique with Chairman, Founder, Board roles in: Business/finance, successful Entrepreneurship / startups / investments / VC, no.1 global Science orgs, UN innovation progs, top CEO Industry-orgs/think tanks, no.1 Summits (acronym BE-SUNIS). 300+ global engagements impacting $100+ Trillion in sustainable investments. For more information see Ibaraki's official CIPS Fellows profile: --- For Microsoft Awards profile: ----- For a personal profile see Ibaraki's LinkedIn profile:

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