In the book that our late CEO Fawn Annan and I co-authored, Digital Transformation in the First Person, I wrote a piece about my first meeting at IT World Canada’s offices, where I met Fawn for the first time.
One of the things that impressed me about coming to these offices is that the IT World brands – Canadian CIO, IT World, IT Business, Channel Daily News – these publications were iconic – they were a window into the IT industry. I used to joke that being on the cover of Canadian CIO was the industry equivalent of being on the
So I was more than a little nervous when I came to the offices for the first time. It wasn’t quite a “fanboy” thing, but I was — impressed.

The story gives my first impressions – the place, the office, resembled IT as it was when I “grew up.” The corner office for the man in charge. Other offices arranged in terms of pecking order. The cubicles for the peons.
Two impressions that I had – one was in terms of office location. Fawn, then the president of IT World Canada didn’t have a corner office. She had a table and chairs, a sign of status in those days but not a corner office.
The other impression was how much “the boys” got away with. It was still a “rough and tumble” culture – it had, what I would reflect on later as — a little too much testosterone even for me – and at the time, that was saying something.
Fawn had plans of where to take the organization. She knew the power structure with a male owner. I’d only find out later the struggles that she had to get to where she was.
I came in as consultant. Fawn, after a few meetings set about recruiting me to be her CIO and her second in command. I had left corporate life as a global vice president reporting to the CEO of a billion dollar company. I was not interested in a “job..”
But as it turns out, Fawn wasn’t interested in offering me a job. She wanted a partner – an ally.
And in case you think that she saw the ultimate ally in me, don’t. The truth is, I grew up in an old boy culture in IT and was quite comfortable with it. A woman friend once described me as a “guy’s guy” – not as a complement.
But I did come to this meeting having had at least one or two women mentors who put up with me, and who tried to open my eyes, to make me a better leader. So I had some of this going for me.
Fawn saw that potential, I guess, and she set about helping me become an ally. She had the patience, she knew how to manage a patriarchal culture and it’s attitudes. And she taught me some very valuable lessons.
Am I perfect? Far from it. But I have realized one thing. Fawn spent far too much time managing what I can now see was a culture that didn’t enable growth for far too many people. It didn’t give the opportunities to develop.
More than a decade later, I think I can say our culture has changed. I think I can say that we have some incredible women – and men who are able to be the best they can be.
But I can tell you without exception that we would not have this team if Fawn had not recruited me as her “ally” and if we hadn’t together, changed the culture of our organization. That’s her legacy.
So as we look out at other areas in IT where we need to find great talent – like cybersecurity – I wonder if we can learn some of these same lessons. So I’ve invited …to join me in a discussion of how we can all learn to be ally’s.
My guests are Helen Oakley, co-founder of “Leading Cyber Ladies,” and Ali Afshari, General Manager of Security at Cisco
We talk about the problems in cybersecurity, starting with the shortage of talent. We talk about burnout and other things that are exacerbating the issues of recruiting and holding onto cybersecurity talent.
We also talk about efforts to get more women involved in cybersecurity, why more women are not interested, how we can offer more support and be “allies” of women who want to enter the field.The post Diversity and the Cybersecurity resourcing crisis – Hashtag Trending, the Weekend Edition with Helen Oakley, co-founder of “Leading Cyber Ladies,” and Ali Afshari, General Manager of Security at Cisco first appeared on IT World Canada.