1289 words – 12 minute read
What does it take to protect what you’re building, not just your business, but your purpose?
In a world moving at exponential speed, where AI can write your emails, clone your voice, and scale your company overnight, one truth remains: innovation without intention is risk. And leadership without community is fragile.
To celebrate International Women’s Month 2026, Naomi Haile of the Power of Why Podcast has partnered with Invest Ottawa to spotlight five extraordinary women shaping Ottawa’s innovation ecosystem.
These featured leaders represent more than titles. They represent influence, resilience, and the courage to step into rooms that weren’t always designed with them in mind. In this episode, we begin with Diane Watson, a global technology leader whose journey spans continents, industries, and technological revolutions.
From mainframes to AI, from job loss to community builder, from hesitation to influence, Diane embodies what it means to protect both your business and your purpose in the age of AI.
The Power of Why: A Conversation with Diane Watson
In this powerful conversation, Diane Watson shares her journey from growing up in Jamaica to becoming a global technology leader in Canada, with a career spanning telecommunications, cloud technologies, and cybersecurity.
What began as an accidental choice to study computer science evolved into a mission rooted in purpose, shaped by the Japanese concept of ikigai and fueled by a deep commitment to representation, mentorship, and community building.
Diane breaks down cybersecurity in clear, practical terms for founders and entrepreneurs, outlining the three critical areas every business must protect: identity, data, and backup. She speaks candidly about the accelerating risks introduced by AI, from deep fakes to AI-generated phishing, and emphasizes that security is not overhead but insurance.
At its core, she reminds us that it all comes down to risk. What are you protecting, and how much are you willing to tolerate?
Beyond technology, Diane reflects on job loss, reinvention, and how community became medicine during moments of uncertainty. She shares how Tech2Step Ottawa was born, the importance of adaptability as a power skill, and why success has shifted for her from climbing to contributing.
The episode closes with a glimpse into her long-awaited children’s book, a cybersecurity adventure story designed to introduce young girls to STEM through imagination and storytelling.
This conversation is both a practical guide for protecting your business in the age of AI and a deeply human reflection on purpose, resilience, and widening the doorway for others to lead.
“In an abundance of water, only a fool is thirsty. And here it is that we’re living in this great abundance, especially with technology. Everybody’s connected. If you want to learn anything, it’s right there. Now, how do you determine what is relevant to what you need to do?” – Diane Watson
Listen to How to Protect Your Business and Your Purpose in the Age of AI with Diane Watson Now.
- Listen to the episode on Spotify and Apple Podcasts.
- For a full transcript and more, visit the Naomi Haile Consulting website.
This episode is for you if:
- You’re a founder or entrepreneur who has been putting cybersecurity off – and you’re ready to change that.
- You’re curious about what it looks like to build a career spanning multiple continents, industries, and technological eras.
- You’re in a transition (job loss, a pivot, a reinvention) and need a framework to find your footing
- You’re scaling with AI and want to know how to move fast without leaving yourself exposed
- You’re building community and want to learn from someone who’s turned networks into ecosystems
What Do You Have to Lose? The Question That Changed My Leadership Journey
A personal story of leadership growth by Diane Watson.
When I was Chair of WCT-NCR, my Vice-Chair and I were having an honest conversation about influence.
We were reflecting on the reality that there are still not many women of colour sitting on boards, especially in influential ecosystem spaces. Around that same time, there was a call for board members at Invest Ottawa.
She looked at me and said, “You should apply.”
My first reaction wasn’t excitement.
It was hesitation.
I remember thinking, That’s a prestigious board. Do I really have what it takes to sit at that table? The doubt was immediate and quiet, the kind many women carry internally.
She didn’t let me sit in it.
“What do you have to lose?” she asked.
It was such a simple question. But it disrupted my hesitation.
Research tells us that women often wait until they feel 100% qualified before stepping forward, while men apply when they meet far fewer of the criteria. At that moment, I recognized myself in that pattern.
So I decided: Why not? What do I have to lose?
I applied.
I didn’t get the board seat.
But what happened next changed my leadership trajectory.
Instead, I was invited to serve on the Women Founders and Funders Subcommittee, an opportunity championed by Sonya Shorey, President of Invest Ottawa, who saw value in my voice and perspective.
That invitation mattered.
It allowed me to see what happens behind the scenes. How capital conversations unfold, how ecosystem strategy is shaped, how decisions influence access and opportunity. More importantly, it allowed me to bring the community voice into those conversations.
That act of inclusion built my confidence in a different way.
It showed me that influence isn’t only about titles, it’s about contribution. It reminded me that being invited into the room is powerful, but being encouraged to use your voice is transformative.
And I carried that lesson back to WCT-NCR.
When it came time to revitalize the board last year, we had more women interested in serving than there were formal positions available. Instead of limiting opportunity, I expanded it. We created subcommittees so more women could participate, lead initiatives, and build governance experience.
Because someone once told me, “What do you have to lose?”
And someone else chose to believe in me enough to open a door.
Now, I make it a point to widen the doorway so others don’t have to hesitate as long as I did.
About Diane
Diane Watson is an illustrious technology leader with over two decades of experience in telecommunications, cloud technologies, and cybersecurity, having held senior roles at global firms such as Nokia and Fujitsu. With a proven track record in program management, innovation delivery, and stakeholder engagement, Diane is currently leading product security initiatives as a Product Security Program Manager at Ribbon Communications.
Beyond her professional work, Diane has been a driving force behind inclusive leadership in Canada’s tech ecosystem. She served on the Women in Communications and Technology National Capital Region (WCT-NCR) board for seven years, including two transformative years as Chair.
In 2025, she revived the WCT-NCR board after a period of dormancy, rebuilding its leadership team and reestablishing community partnerships. During her years of service, she spearheaded the launching of impactful programming focused on equity, mentorship, and career development for women in tech and communications.
Diane now serves in an advisory capacity as Past Chair, while also holding the role of Vice President of Advocacy and Partnerships at Tech2Step Canada, a national nonprofit creating mentorship and networking opportunities. She also contributes her expertise as a member of Invest Ottawa’s Women Founders and Funders Subcommittee, supporting the advancement of women entrepreneurs.
Known for blending technical excellence with purpose-driven leadership, Diane is deeply committed to mentorship, community building, and creating pathways for underrepresented voices to thrive in Canada’s innovation economy.
Connect with Diane
- LinkedIn: Diane Watson
- March 31, 2026 Tech2Step Event (Ottawa) Give to Gain – Restore, Reflect, Reconnect
- Tech2Step Ottawa
- Tech2Step Canada
- Women in Communications and Technology NCR
Connect with Naomi Haile
- Website: www.naomihaile.com
- LinkedIn: Naomi Haile
- Instagram: @naomiahaile
- Twitter: @naomiathaile
- YouTube: Naomi Haile
Explore IWM 2026
- Get involved! Visit the IWM 2026 event calendar here.
The Power of Why: A Conversation with Diane Watson







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