What’s one highlight and one lowlight of your career so far?

Question

Answer

The highlight of my career was when I was made redundant a few years ago with a very good severance package. I was able to go out and self-fund the business that I'm running now. That was probably my highlight because that doesn't happen every day. The lowlight of my career was some of the incidents that I used to get involved in as a major incident manager. I'd be woken up at 3:00AM to deal with interbank payment issues.

Answer

I don't think I necessarily have a career highlight, but it’s probably the job I'm in at the moment and the role I'm in because it really gives me a great chance to make a difference to society through tech enablement. I'm in a healthcare organization, which is part of a larger group that does aged care community services, and a whole range of different things. It’s a large organization with lots of diversity, so there are lots of applications for different types of technology in healthcare. It's a slow-moving industry, but there’s lots of potential ahead in terms of transformation. A career lowlight is probably just being previously stuck in a job which didn't align to my personal values and moving out of that.

Answer

I'd say the low point was getting burned out early in my career. I was getting completely overwhelmed and just enjoying technology too much, it was like a drug. And it got to a point that it was taking literally a physical toll to the point that I ended up in the doctor's office. It was a reality check, which ironically sent me to another organization where I got knocked down for being too out there in terms of what I wanted to do. And that was also a reality check of what you have to learn and how you work.

A high point is where I am now. I've had a great successful career and I'm incredibly grateful to technology for that, having served as CIO and IT leader for a number of prominent organizations over the course of my career. But where I am now, I get to help a lot of different people and take that expertise and share it with others. It's incredibly satisfying and fulfilling to build something that others can benefit from. And I'm grateful for that.

Answer

The low point in my career was probably when I had left HP for the glamor of a startup CIO-ish job in the middle of the year 2000. The job didn't even last 10 months before the company went bust. I'd worked at HP and a company that was acquired by HP continuously for 17 years before that and I never networked. I thought just doing my job and getting promoted at HP was all I needed to worry about.

When I was released along with the rest of the team at that startup, I was in the worst technology hiring period in two-decades and I didn't know anybody. All the people I knew were at HP and HP was laying off people left and right. I hadn't been unemployed for any period of time since I was about 12, so it was hard. It took about three months before I landed a gig. So that was a real low point for me. But since then, it's been all good.

And there are a few points in my career that I could pick as highlights. But realistically, finally starting my own business at Edgevana has been a real highlight for me. Building a team again, making a product-market fit, and working on the technologies and solutions that I've been familiar with throughout my career, and with global partners doing the same has been a lot of work, but it's also been a lot of fun.

Answer

I think I might be living the highlight of my career. I'm excited to be starting a new IT organization from scratch—we call it corporate engineering here. It's super exciting to be solving problems, and there are so many opportunities to make an impact from growing revenue to optimizing cost, synergies, automation, you name it. I'm loving it.

The lowlight was when Symantec got bought by Broadcom, because it came as a shock to me. I was really enjoying my career and thought, "Okay, Symantec is it." It was like a family, and I built great relationships there. All of a sudden, things changed on me. When Broadcom does acquisitions, they don't take the IT organizations with them. They have their own consulting agency. So all of the 600 folks in IT had to find another job, over time.

But that's where I built my strongest network. In that situation, you find out who is a true supporter and who's not. And now I'm so empathetic to people who reach out to me. I always carve out a certain amount of time to respond to my LinkedIn reach-outs or people who are looking for opportunities. I want to give back. When I connect the dots and look back, it all makes sense now. It helped me to eventually get to the next level and be where I am now. But those three months were really hard on me.

Answer

I would say my career highlight was definitely the scale and growth, etc., that went along with Uber. That was a super interesting part of my career, having full-time employees that doubled in number every quarter. And then we had 2-3X that of contractors, which aren't drivers. So I always felt like that was really cool for that kind of scale. Growing the team from zero to 60—which is not a whole lot, but it's the most in my career—over 2.5 years was a cool experience and I wouldn't trade it in. And I'm sure there will be some case studies on what we did right and what we did wrong.

As far as lowlights, whenever I get into a new role, I tend to go super deep into it and it almost consumes me. It's a part of my personality. And people know me because of my job and not necessarily because of me. So with this all-consuming drive to ramp up, make an impact and do all the things I can as a new leader, the one piece that my wife gets used to is that I'll be away more from the family, traveling, etc., and that it's for the greater good. So I would say those are the lowlights, but they’re part of the role. Sometimes you just have to make Sophie's choice when you do these kinds of things.

Answer

I guess the highlight of my career is that when a role is starting to approach a lowlight, I've had the flexibility to take some time off and enjoy it, usually. It's often been coincident with some transitions either in my personal life. And because of what we do, I can take a break, I can do some consulting in-between, and come fresh back to a new role.

I can share horror stories, but those things usually turned out to be opportunities that ultimately made me more successful. They led to bigger and better things, so I don't typically think of them as lowlights even though they might've been stressful, emotional, physical, or mental challenges. Maybe the biggest disappointment was mid-career, when I went to a startup that didn't turn out to be Uber. But I still got a lot out of that role, and it set me up to do other interesting things later on. I still don't look back at it and think, "Well, that was a lowlight of my career."

Answer

I’ve had a lot of career highlights, but if I were to peg a couple, the first one is when I became CIO at Palm, back in 1999. It was a very exciting time to be on the forefront of mobile technology. We were spinning off Palm into an independent public company. The company was a billion-dollar startup and was growing incredibly fast. So it was a great highlight of my career because we had to move very quickly, and build everything from scratch because Palm was a small piece of a larger company, 3Com, and received all their infrastructure support from the mothership.

Highlight number two was 10 years ago, when I made a change in my career. I stopped being an operator after 30 years in the industry, and started my own technology advisory business. I became a partner in a VC firm, and in 2014, I joined my first public board. I’d wanted that for a long time and when I was able to achieve that it was a very significant milestone.

In terms of lowlights, Palm went through ups and downs—a lot of downs. I had to go through seven rounds of layoffs. And the scariest part for me was, by the sixth time it was almost like business as usual. The first time, you have a lot of emotions. But then you get used to this terrible thing called layoff and at the end, it's like, "Well, yet another layoff. Let's go do it."That was my lowlight.

What’s one highlight and one lowlight of your career so far?

Content you might like

What’s your current understanding of RevOps?

Do you agree with the following statement? I have implemented new systems or technologies to compensate for hiring challenges at my organization this year.

How do you keep a team motivated in absence of leadership?

What are some ideas to keep up team morale remotely? Are there specific or structured adjustments you've made to counteract burnout/keep up productivity and mental health?

If you had a magic wand - what's the #1 daily business challenge you'd eliminate?