My Three Biggest Mistakes as a CEO

Posted on October 4, 2017

In the 25 years that I’ve led organisations as CEO, I’ve made my fair share of mistakes. Mistakes that have led to failed projects, funding loss, missed opportunities, and loss of good people.

Barring poor decisions that lead to catastrophe, I happen to believe that there is no way to be successful without having some failure AND (most importantly) learning from these experiences. In my workplace, mistakes aren’t highly confidential or spoken of in hushed tones. We find the new learnings and discover new solutions. If we want to develop, innovate, anticipate barriers to success and make better decisions, we also need to learn – and making mistakes along the way is all part of the process.

Let me tell you about my three biggest mistakes over the last 25 years and the lessons I’ve learned from them.

1.    Technology Mistakes

As CEO of a national not for profit federation, I decided to introduce new software technology designed to improve the experience of donors and supporters. We used our existing processes and engagement methods to drive the configuration process, setting up the new system to automate the older, manual one.

Mistake. I missed a prime opportunity to rethink how we did things. I should have put more thought into how we could improve our communication and methods of engagement through this process.


Our new system seemed clunky and old-fashioned from the start. Instead of focusing donor and supporter attention on our message, we confused and frustrated them with too much information and too many steps to taking action. This led to poor donor engagement.

Lessons I learnt

When introducing new technology, make sure the end result is much better than before. Give more attention to designing the ideal customer or consumer experience and less attention to ‘the good old ways’ of doing things. Hold everything up for evaluation and assessment. Ensure that the new system includes best practice technology and facilitates best practice relationships and outcomes. Configure your new technology to take advantage of exciting new opportunities. 

2.    Mindset Mistakes

As the new CEO of a national not for profit that was already performing reasonably well, my early focus was on refreshing the organisation. I initiated a busy program of reviewing and optimising systems, policies and processes.

Mistake. The extra workload and tight timeframe swamped our already-busy project management schedule.


We didn’t do the research and the thinking required to ensure that our decisions were in line with current sector issues or that we could meet future challenges and opportunities. We also dropped the ball on a critical project and compromised our reputation as a result of this initiative.

Lessons I learnt

When implementing a review process, you need both time and resources. Inject fresh, innovative ideas by encouraging research into best-practice methods and technologies, attending conferences and consulting experts. Have regular briefings with people in the field to ensure that management decisions are both useful and relevant.

3.    Communication Mistakes

I was leading a national organisation with multiple stakeholders and organisational complexity when I realised that legislative change (requiring policy and practice compliance) would result in a significant financial challenge to one of our related entities. I informed the affected entity and implemented the change. 

Mistake. By not consulting with all stakeholders, misunderstandings developed around several things:

  1. the reasons for change
  2. the impact of the change
  3. different ways to mitigate the change
  4. the new processes required for funding 


Some stakeholders lost funding and it took time to rebuild trust and work well together again. 

Lessons I learnt

In any change process, communicate early and widely. Engage directly-affected parties in face to face discussions, where possible, prior to making decisions. Work closely with each party as they move through the new processes to ensure positive outcomes for everyone.

Things I’ve had to un-learn as CEO

I’ve not only learnt important lessons from my mistakes over the years, I’ve also had to unlearn a few things. Possibly my most important unlearning has been in letting go of the superman CEO myth: the cartoon-like figure who stands alone to save the organisation and conquer every evil with precision, agility and superhuman skills!

While many CEOs are brilliant leaders and strategists, we all have a set of core strengths and capabilities and are acutely aware of our deficiencies. In my experience, a 'brilliant strategy' involves engaging the very competent and capable people around me. It’s in tasking the right person with a problem, or coaching and empowering people to step up and take on new responsibilities. It’s in getting my team to share new information and learn from each other’s unique experiences.

Social Impact Institute is all about partnering with others to help them succeed and increase their social impact. We rely on the expertise of our highly-experienced team members and partners, we stay up to date with best practice and evidence-based strategies, and we create and collaborate to elevate performance and achievement.

Social Impact Institute services are available throughout Australia, including Sydney, Melbourne, Brisbane and regional areas.

Call us on 1800 822 763 to have a chat and book your consultation.

David Jack

CEO Social Impact Institute

Share this page


Terms of Service
Privacy Policy