Top Five Regrets of Executives 2023

Top Five Regrets of Executives

So often in the corporate career trajectory we believe that the higher up we get the more successful we become. Although if we’re not paying attention it’s easy to get caught up in the demands of the role and lose sight of what really matters.

How do you avoid getting towards the end of your career and living with regrets?

In 2012, Bronnie Ware, after her experience as a pallative carer, wrote the international best-seller ‘Top Five Regrets of the Dying’. This book is an extraordinary gift (and if you haven’t read it yet – what are you doing??) because whilst she shares insights from those close to their final days, her books provides the rest of us with a pathway – or a blueprint – about how to live our lives. It’s a conversation about life and purpose as much as anything.

(If you want to hear more about Bronnie’s lessons and insights tune into this podcast chat I had the fortune of having with her.)

Similarly, exploring the top regrets of executives gives us all a blueprint back to the things that matter in our work. Read through these below and consider how you’ll keep them front of mind in your career.

Let’s take a closer look at five of the most common regrets among executives.

Regret #1: Not prioritising personal lives

The higher up in an organisation you rise the more the role becomes part of your identity both at work and away from work. As such, it’s all too common for executives to put their personal lives on hold in the pursuit of career success. There may be seasons where this is critical – and the pursuit of work actually is a means to an end towards greater financial security.
Although all too many executives look back on their time and regret missing the small things in their personal lives (and we all know these small things are the big things in the end). This can happen because of the fear that prioritising personal life may be harmful to their career success.

Here’s the thing – those in your workplace want to know you’re human, setting boundaries and prioritising what matters in your personal life. And when you do it gives permission for others to do the same.

QUESTION: What is one thing in your personal life you will prioritise over work?

Regret #2: Not taking more calculated risks.

Fear of failure can hold individuals back from taking chances that could lead to greater success or innovation. However, taking calculated risks is essential for achieving long-term growth – for you, your team and ultimately for the organisation. It’s the role of executives to set vision, to inspire others with potential, to lead in times of uncertainty.
Taking more calculated risks requires the courage to be okay with things not working out as you may envision. Recognising that through the process you and your team will learn and grow the ‘muscle’ required to do it again. Uncertainty is not going away – invest in the calculated risks when it’s ‘right’ not just when it’s ‘safe’.

QUESTION: Where does fear of failure hold you back from take more calculated risks?

Regret #3: Not investing more in employee development.

There’s a saying that leaders fear developing their people in case they leave – although the far bigger fear is not developing your people and they stay.

Relevance, growth, and inspiration lead to greater discretionary effort and engagement amongst your people. Investing in employee growth is critical for business success. Full. Stop. Executives who are hesitant to provide opportunities for employee development miss out on valuable contributions, new ideas and loyalty from employees. Employee development is not just a nice to have in the good times, it’s a critical element of strategic planning. Continue to push the boundaries of quality development with a strong focus on application of learning. Hint: Find out more about our PT leading edge leadership development programs here. 

QUESTION: When was the last time you invested in creating quality, relevant, and strategic development for your team?

Regret #4: Not being more assertive in decision-making.

Indecisiveness can lead to missed opportunities and negative outcomes. Executives who fail to be assertive in their decision-making may regret not taking charge and making the tough choices when they had the chance.
Others will judge you not just in the decisions you make in the good times but in the decisions you make in the tough times. Once the tough decisions are made, back them up and be clear on expectations.

If that decision needs to change because the context is now different or you have new information, have the courage to make the call. Don’t regret meek or weak decision-making.

QUESTION: What area of your work would benefit from more assertive decision-making?

Regret #5: Not building stronger relationships with colleagues and employees.

Your network is your networth. The connections that we build require time, investment and courage. It’s easy amongst the sheer volume of work on your plate to put off the relationships side of your work and instead only focus on transactional connections with colleagues.
Although building strong relationships is essential for strengthening trust (which ultimately makes work faster) amongst colleagues. Executives who fail to invest in these relationships may miss out on valuable insights, opportunities for collaboration, and loyalty from others. It’ll take time, you may need to lean into tough conversations as you explore differing opinions. Although this investment is often worth it.


Use these five regrets as a blueprint for keeping the things that matter front of mind in your career. Have the courage to make these important things the pathway for how you’ll lead, decide and live as a leader.

Your career will thank you for it.