“I feel successful when I am loving what I do, loving who I work with, and I am able to do this while managing my time, taking care of my health, and being with family and friends.” – Candina Weston
Leaving behind the safety net of corporate prestige for the uncertainty of independence is never easy, but Candina Weston made that leap. Today, she is an international technology executive and is known for her decisiveness and willingness to take risks—a confidence that she readily admits was hard-won.
Early in her career, Weston faced her insecurities head-on when she left a secure role at Microsoft, where she had played a pivotal part in launching the company’s first major global digital event at the outset of the pandemic. She understands the comfort of working within the structure of a global corporation: guaranteed income, benefits, the prestige of a renowned brand and title, abundant resources, a supportive
infrastructure, clear priorities, and the discipline of business fundamentals.
“I realised I was a bit naive about how the world operates outside this bubble,” she says. “Having always excelled in roles that centred on incubation and business transformation, entrepreneurship felt instinctive. Yet, experiencing firsthand how things truly get done—and uncovering the many gaps in standard business practices when no one is there to bridge them—has been eye-opening.”
What experience or moment most clearly set you on your current path?
When I first started working, I tried multiple different industries and decided that technology sounded like the most interesting to me. At the time, Microsoft was the most interesting player in tech and jobs at the company were really hard to come by, so I took a 50 per cent pay cut to start again and do an internship. It turned out to be a great decision.
Who do you turn to for advice?
I am fortunate to have an amazing circle of friends and mentors who have always been generous with their time. The best advice I have received was early in my career. We were working long days that almost always ended in some event that finished late, it wasn’t sustainable. My manager at the time said to me, ‘You can work 24 hours a day in this company but it won’t matter. Work out what the big rocks are and focus on those, they will matter’.
How has your definition of success evolved?
Previously my definition of success was based on my level. It evolved to being given the opportunity and autonomy to do interesting things that change the norm. I feel successful when I am loving what I do, loving who I work with, and I am able to do this while managing my time, taking care of my health, and being with family and friends.
How do you balance ambition with well-being?
I ran competitively for about 20 years. What that teaches is that, in order to perform at your best, you have to take care of yourself. It also teaches you how far you can push yourself. I haven’t always got this right and at times I have pushed too far. Some fundamental things I follow are prioritising sleep and downtime.
What is an important lesson you had to learn the hard way?
A trait that the best and most senior leaders I have worked with share is that they want the truth so that they have the best information available to move the business forward. I learnt this the hard way. Now, I can manage conversations better according to necessity, with an understanding of where the decision-maker is at and what they need to build trust. This is different to withholding information and it is a critical skill in order to move businesses forward.
What do you hope people say about you when you’re not in the room?
I hope they feel comfortable saying the same as they do when I am in the room.
