IN GOOD COMPANY: What 11 CEOs would do differently if they were starting their careers again

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Steve Atkinson, CEO and Founder, would outsource company finances to the experts. What would you do?

Established business leaders have a clear vision, defined goals and a drive to always be better.

Just because they know what they want today, however, doesn’t mean that has always been so.

All successful business people have made mistakes along the way; turns in the road which, if they had their time again, they may have not taken.

We asked executives from a range of companies and industries what they would do differently if they were starting their careers again.

Here’s what they said.

JD Sherman, COO of Hubspot, would have travelled the world

JD Sherman, COO of Hubspot/ supplied.

“If I could wind back the clock, I would have taken some time off before I jumped into starting my career. At the time, I was eager to get cranking and I started my first job just one week after graduating from business school. However, many of my friends chose to head off on round-the-world trips, enjoying their last crack at real freedom before they entered the ‘real world.’ They still talk about those times when we get together, and I realize that I missed an opportunity by not doing the same. My 50-year old self would like to go back and tell my 25-year old self that life is a balance, and opportunities like that don’t come up very often. I think I’ve finally learned that lesson — a bunch of my world traveling friends are taking time off next month for a fishing trip, and this time I’m going!”

Tim Reed, CEO of MYOB, would think bigger

“If I were starting my career again there are many things that I’d do the same: work overseas, study, find mentors, listen and learn, push myself, grab opportunities, follow my passion, join a tech start-up in Silicon Valley … but there are also things I’d change. I think the main thing that I’d change is that I’d think bigger. I put my heart and soul into what I do and on reflection there were times when the target of my passion was too small. The amount of impact your work can have, and therefore the value you can create, is directly related to the size of the problem you’re trying to solve. Today when I invest in start-ups the first question I ask is whether they are aiming to solve a small problem, a big problem or a really big problem. I like the latter.”

Taryn Williams, CEO & Founder, WINK Models would learn to delegate earlier

Taryn Williams / Facebook

“If I was starting my career again, I would learn to delegate much earlier. I spent the first 2 years of business trying to do everything myself – payroll, BAS, website updates, bookings, invoicing, talent meetings and more. As the company grew it was really hard for me to relinquish control and accept I couldn’t physically be across it all. I became a bottleneck, standing in the way of my own company’s growth. By insisting on being the ‘doer’ and key point of contact for everything, I was preventing us from being able to scale and succeed.

“When I realised this, I took steps to bring about change. I built systems and processes that allowed me to delegate to my employees. I created a system for regular WIP meetings and clear lines of reporting. As it all came together I learned to let go. It was hard but watching my team win without me was incredibly validating. Now my team often works autonomously. They have learned to come to me only when they really need to and usually armed with solutions. Delegation isn’t without risk but it’s a path full of rewards and one I wish I had taken sooner.”

Luke Anear, founder and CEO of SafetyCulture, would set up for growth from day one…

“From a pure tech point of view, if we had built our technology stack on Amazon Web Servers (AWS) from the beginning, that would have saved us over a year. We could have made better technology choices with more experienced team members onboard earlier. Our greatest challenges came from our architectural decisions that were made early on.

“Startups usually don’t have a clear idea of what the core user metrics are going to be when they start, and we could have benefited from going after our core user metrics sooner than we have. Having someone early in the data science and analytics area would have helped us find the metrics that matter most and then double down on those areas.

“If I was starting out tomorrow, I’d start building a growth team from day one. Engineers who are focused on growing the engagement within our products. I’d also hire a senior architect and I’d look to leverage existing technologies as much as possible rather than building everything ourselves.”

… and he adds this about general attitude:

“I’m not big on regrets and very much believe that everything I have experienced in life has brought me to this moment right now.

“With that said, if the older Luke was going to provide some wise counsel to the younger Luke it would probably be something like this:

Choose a goal that makes the world a better place, whatever that means to you. Don’t worry so much about how it’s all going to work out, put that energy into your work. Learn to self-assess effectively, understand your strengths and your weaknesses, and play to your strengths. There is no need to convince anyone that your idea is a good one. They either will get it, or they won’t and the synergy that comes from the people that share your vision will be the ones that matter most to you.

There is no substitute for hard work, but allow it to happen in cycles. Sometimes you need to work 18 hours a day, and that is ok, but other times you can back off a little, and let the ideas come to you, rather than you chasing them down all the time.

Be patient. Good businesses take time to build, and you don’t need to worry about when it will happen, just focus on making it happen. Bubbles come and go, but the fundamentals don’t change. Building great companies stand the test of time and will overcome adversity. Sometimes they will even thrive from the adversity.

Look for the synergies in life, nature and business. Look for the exceptions, not the patterns and look to create a new paradigm, rather than extending the status quo.

Daniel Flynn, co-founder and MD of Thankyou, would try to enjoy the ride

Photo: Daniel Flynn, co-founder of Thankyou/ supplied.

“We’d enjoy the journey more, rather than always being so focused on achieving the next success milestone.

“For Jarryd, Justine and I, the first few years of the Thankyou start-up journey were tough and results took a lot longer to come than we expected. We were pretty inexperienced, naive and optimistic, which worked to our advantage in most situations, but also played against us a bit when we didn’t grow as quickly as we (naively) imagined we would.

“Passion for our cause is what drives us, and in the first few years when we didn’t get business deals we were deflated because to us, every unsuccessful deal was money that wasn’t going to help people in need. But experience has taught us to use the setbacks to motivate us, and today we define success as the ability to turn stumbling blocks into stepping stones, rather than a particular point or destination.

“Don’t get me wrong, it’s great to have big goals and dreams that you’re focused on working towards, but it’s so important to make sure that you take the time to enjoy every stage of the process – even though at the time they may seem small and insignificant. “

Stephanie Christopher, CEO at The Executive Connection, would take more risks

Stephanie Christopher

“If I were to start my career over and do anything differently, it would be to take more risks in my earlier career. I started my career as a speech pathologist and if I had commenced my corporate career earlier, I may have been afforded many exciting opportunities and perhaps had the chance of an overseas posting.

“We often end up progressing careers we are no longer passionate about even when we realise we have other interests and desires. The thought of changing career track and going back to study in another field can be scary and it can be tempting to stay within your comfort zone.

“I now know there is no time limit on shifting a career path and it is important to keep learning and growing. Find your strengths, diversify your skill set and always remember your skills are transferable. Don’t be afraid to take some risks and don’t hold back on pursuing what compels you.”

Jo Buston, founder and CEO of Inspiring Rare Birds, would asked her mentors more questions.

Jo Burston, founder and CEO of Rare Birds/ supplied.

“If I were to start my career again, I would ask more ask more questions (and more of the right questions) of people who were smarter, more successful and who emulated the entrepreneur that I wanted to become. While I always had many hobbies — I surfed, I had a motorcycle, and a bronze medallion — I would have liked to have tried even more new things.

“I started my first business at 32, which now seems late, although I always still feel 32! Perhaps I could have started my business journey in my early 20s or even during high school, when risk had little or no downside. The issue was that I didn’t have any business role models around me that I could have learned from. I also would have loved to have learned to code during school — unfortunately there were no opportunities!

“Looking back, I wouldn’t have listened to my English teacher, who blatantly told me that I would not amount to much. He had favourites and I wasn’t one of them. It affected my belief in myself at school, which in hindsight was quite damaging, as I love reading, poetry and theatre.

“I would also have read more books — business, philosophy, poetry and the arts — creative thinking in all formats. As a teenager and young adult, I would like to have been less averse to the opinions of people who I didn’t care about and those who didn’t care about me.”

Steve Atkinson, CEO and Founder of would outsource and delegate sooner

1. Delegate sooner
“In the beginning I’d wake up early each day and do 5 or 6 people’s worth of work. By not outsourcing I was slowing growth and also creating a lot of frustration. As an owner of a company your efforts should be on developing systems for scale rather than doing unnecessary things.”

2. Seek out those who can add value and provide mentorship
“Finding a successful business owner to shadow in those early stages of development is something I wish I had done sooner. Doling so has given me insights into what profitable companies do well and how. In the beginning I did it all myself, learning the slow and hard way. I’ve since learnt there is no shame in asking the big questions from those who are more advanced than me. It saves time and the learnings are great.”

3. Outsource company finances to the experts
“It took me 3 years of owning my first company to realise I needed financial assistance. I now have a bookkeeper, accountant and financial controller, which may sound expensive, but it is not. For as little as $35 p/hour you can employ someone to manage the books and good financial advice easily pays for itself. Again it comes back to delegation and seeking the advice of experts. Don’t hesitate as it will only add delay and set you back.”

Jodie Fox, co-founder of Shoes of Prey wouldn’t stick to a ‘careers guide’

Photo: Co-founder of Shoes of Prey, Jodie Fox/ supplied.

“When we started out with Shoes of Prey, I stuck to a ‘careers guide’. It was the early days of online retail so it wasn’t so easy, but I should have picked up the phone or travelled to secure meetings with people who I thought had jobs that were absolutely amazing.”

“Other things I would do differently:

    • Follow my heart more
    • Chase my dreams
    • Actively look for mentors
    • Know that anything I was passionate about is possible — it’s just not all contained within a careers guide
    • Do more research”

Julie Stevanja, co-founder and CEO of Stylerunner, wouldn’t avoid difficult conversations.

“It’s business. There are going to be unpleasant things to deal with. Once you mentally accept that responsibility and decide to live up to it, you will face difficult issues head-on and get better at resolving them quickly, calmly and resolutely.”

Chris Ridd, MD of Xero Australia, would be more assertive about his values

“Don’t compromise on your core values. It’s hard when you are young but I wish I had been more confident in my early years to stand up for the right values that were important to me. My advice is to lead with integrity and genuine passion. That counts for a lot in a company’s success these days because I don’t ultimately think that you can fake it.

“You also need to be very actively looking at what you are worth and stay informed about new opportunities, even if you are happy in your current job. Also, back yourself in the early years and don’t stay in the same company for too long.”

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