The six regrets of the living and the power of executive wisdom

“It’s one thing to be clever and another thing to be wise” once said RR Martin.

In my thirty-year international career and ten years of being an executive coach, I’ve been able to reflect through a wide and divergent client base, the profound difference between ‘intelligence’ or ‘book smarts’ and wisdom. The Bible actually cites ‘wise’ or ‘wisdom’ on 2019 occasions – in complete contrast to ‘intelligence’ that appears just five times and ‘smart’, which never appears at all. According to many myths and ancient belief systems, there’s a profound relationship between wisdom and time – essentially, we need to earn the right to achieve wisdom through ongoing personal development, learning and the act of maturing.

Brazilian author and lyricist, Paulo Coelho notes that the secret of life is “to fall seven times and to get up eight times” and Chinese philosopher, Confucius believed we might learn wisdom by three methods – “the first, by reflection which is noblest, the second by imitation, which is easiest and the third by experience, which is the bitterest“. This statement echoes the sentiment that in order to achieve or experience wisdom, we need to have lived a life that has provided us with perspective and insight. It’s these insights, life experiences and moments that provide powerful discoveries that unlock the capacity for personal growth and as the saying goes, “A wise head on young shoulders” is the exception and not the rule. My father, a wonderful man, used to say that common sense, wasn’t always common –I wonder if this is the case when it comes to wisdom?

I’m lucky to have such an extensive group of clients and a broad network of professionals. I recently enlisted their help in answering the above question. All 80 participants have had interesting, diverse and phenomenal careers. The pool of participants was made up of CEOs, CFOs, CMOs, business owners and entrepreneurs, high ranking officers from our Armed Forces and senior partners and higher management. Life for all of them hasn’t always been a straight line to the top, and they all meet Confucius’s third method of learning wisdom; they have considerable life experience. They’ve earned the right to be able to look back and reflect. As part of my quest to understand wisdom, I posed a couple of simple questions to them all:

1.     From your current vantage point in life, with reflection and years of hard-earned experience, what are the two or three things you wish you had mastered earlier?

2.     And, knowing these things you could have mastered would have made you a more effective and complete leader or person, why would they have made such a difference?

I had no preconceived ideas of what each individual response would be, or, if there would be any similarities or patterns in their responses. And guess what? They didn’t let me down. I was able to review nearly 200 insights supported by humble, vulnerable and honest responses. As I read and re-read the responses it became astonishingly clear to me, that there are six recurring themes:

1.     I wish I had mastered a greater level of self-awareness and understood my impact on others.

2.     I wish I had learned to manage upwards and to develop networks and mentors.

3.     I wish I had kept my whole life in balance and prioritised what’s really important.

4.     I wish I had understood the techniques of powerful communication and active listening.

5.     I wish I hadn’t avoided developing new or critical skills.

6.     I wish I had understood the skills and techniques of building collaborative teams.

In appreciation of Bronnie Wares study on the 5 biggest regrets of the dying, I have called these the 6 regrets of the living. The real power of the responses is in the narrative around the why. Here are some selective comments by each of the regrets: 

I wish I had mastered a greater level of self-awareness and understood my impact on others.

“Learning the value of self-reflection has changed my life at work and at home forever. Asking your friends, peers and others about the impact you have on them and then having to look at yourself through a different lens, is the most powerful thing I have learnt in my life – and this was at the age of 34. I strongly believe it would have helped me, and the many others I know or have known throughout my life if I had just mastered self-reflection earlier. The exponential impact of such wisdom, can and could, change many other lives – particularly if a large portion of those people become better at it themselves or at least try to grasp the concept in their own way”.

“Being less self-critical and appreciating my own strengths more. Why? Well, perfectionist behaviour can be inhibiting whilst focusing more of what you are good at, can be very liberating! Constructive self-appraisal sets a positive-orientated tone and again, can be good role model behaviour for aspiring leaders. This is one that also benefits from sharing with teams and others to build trust and transparency”. 

I wish I had learned to manage upwards and to develop networks and mentors.

“The importance of building and cultivating a strong external network and managing upwards – until later in my career, I invested much of my time in the people within the organisation I worked for. Most of the time, I focused my energy on my team and peer groups. While this made for a good working environment and enabled me to do well at my job, it left a big gap in terms of my external network, and I feel I limited my career opportunities and personal growth. Once I started investing more time and effort externally, I found it opened my eyes to a more personal development opportunities and gave me a broader perspective of different organisations and people and issues that I was previously unaware of”. 

“I spent the early part of my career believing that networks were unauthentic relationships. I avoided networking events and judged leaders who were over-networkers. I’ve changed my view on networking as a necessary part of forming supportive business relationships to create mutual future opportunities. An effective network would have opened more diverse business and career opportunities”.

“I never developed close relationships with any senior leaders to provide mentorship, so I never received informal advice and support. Rather, I was very self-reliant making my decisions independently, without the counsel of an experienced leader. This could have better prepared me for key decisions, provide new perspectives and reduce the pressure on myself”.  

I wish I had kept my whole life in balance and prioritised what’s really important.

“Learning the value of work life balance, and how to continue to achieve at a high level without burning out – for many years I was focused on working harder, working long hours and over delivering as a sign of my self-worth to my employer. I delivered as much as I could and felt that this was a way of measuring success. It wasn’t just on myself – I pushed my team hard as well. As I ‘ve grown and progressed, I now have a strong view that the measure of success, is how sustainable the pace of work is over the long term. Ultimately, it comes down to how happy and engaged the team is – being able to focus more on getting a balance between work and play has made me a better leader and also more productive and happier. I now focus on the big-ticket items and coach and develop others to manage their time and priorities in a balanced way”.

“Easy to say this with the benefit of hindsight, but I wish I had been more effective at balancing my work and life. I‘ve been so committed to my work over the years that I have failed to pay enough attention to my own health and my relationships. It is a huge regret”. 

I wish I had understood the techniques of powerful communication and active listening.

“This is a trait I am least proud of and has got me into trouble in the past. I’m least proud of my ability to judge in seconds – and the worst part about judgement, is that you know it in instance when someone judges you. A question will always lead to deeper understanding “.

“Sounds simple, but it’s hard to listen without random thoughts popping into your head about what the person you’re speaking to, means versus what he or she is actually saying. Learning not to judge an idea because I don’t agree with it, is very powerful. Some of the best insights come from connecting ideas to your own thinking, even if initially the idea seemed to conflict. Good people don’t say things without good reason”.

“Seeing the results that the power of positive intent can have on me, and all things that make up my life gives me confidence. It trumps regret, resentment, immaturity, and all other negativity that we encounter in our lives. If everyone (or the majority) involved in something understand that the thoughts, actions, and words that are being put forward are all about improving something, obtaining a goal, bettering a process, and having a lasting and important impact for those involved, then momentum can be achieved and ultimately maintained for good”. 

I wish I hadn’t avoided developing new or critical skills.

Technology – “A late starter and largely bystander in early days, I witnessed others (young and old) embrace its capabilities quicker. I’ve been playing catch up for years, never really keeping pace with the increasing advances in technology. I‘ve worked hard to get myself into a place that I can hold a conversation within digital ecosystem without being or needing to be an expert, but without that effort I would have been one of the dinosaurs facing extinction in the working world”. 

Financial Language – “I’ve given insufficient time, energy and attention to mastering the language that business is based on – finances. Although I believe that without the right people you will not have a sustainable business, you also need to be able to speak the common language. Effectiveness at the executive level is based on it. The ongoing challenge for anyone in the business of people, is to be able to influence the right discussions, and to do that you must feel comfortable talking the language in an assured way. Financial language – new roles may have opened, different experiences may have been gained, and effectiveness enhanced”.

Financial literacy – “Beginning life as an educator and a musician, the world of finance was a mystery to me. Then changing careers to become a marketer, communicator, and then into leadership roles in commercial businesses it became a stark reality that if I could not read a balance sheet, I was incomplete as a business leader”.

I wish I had understood the skills and techniques of building collaborative teams.

“It’s all about trust. I wish someone had shared the importance of this earlier in my leadership roles. In my early roles, I was so hell bent on delivering outcomes for the business unit, that often my behavior was ‘my way or the highway’ within my team. Those that didn't want to comply or support my way of doing things, felt as if they were not welcomed in the team. It was never intentional, but I now know that this is how it would have been interpreted. The ‘brand’ of leadership I used to prioritize above all others, was making sure that I was ‘outcome orientated’. The problem with this? 80 percent of my team loved that driven style, but then the other 20 percent worked against me. I now know that if I had worked on gaining trust with all my team members when I was in my early leadership roles, I would have been able to convince many more to work together and more effectively. I now work on earning trust of the people I work with early in my dealings. I do my upmost to maintain the highest levels of trust. Knowing what I know now (based on 360-degree feedback sessions with my teams) I would be sharing this advice to someone early in their leadership career”.

“Understanding the deeper idea of identity and how critical it is to life, health, performance, resilience. While I feel I have long had a sense of this, it wasn’t until I was commanding a regiment of 800 personnel that I really understood it. The complexity and diversity of my workforce in terms of makeup and roles, was largely unparalleled. Our primary purpose was to combat related special operations. We had people being killed and grievously wounded. We had those struggling to keep up and those struck down by the sum of their experiences. Meanwhile we had ‘greyhounds’ who just kept surging, with seemingly endless pools of energy, talent and reserves. And then we had all their families, including those of the fallen. Every single one of them identified as a combination of elements. All had one or two elements in common – ‘army’, ‘commando’ and ‘Afghanistan’ etc. It took a team of clinicians and specialists working with my command group and other subject matter experts to bring some rigor to it, at least in our context. Once we better understood it, we were able to tailor our response to the individual and the various teams. This was all about human performance. At times, we were dealing with the broken end, trying to get them back to where they were, or at least, as close as possible. But often it was working out how to make the outstanding – how to find and hone their edge from a combat and problem-solving point of view. While I feel I have always been empathetic and willing to subordinate my needs to those of others, my ability to read teams, individuals and situations would have matured sooner. I think I could have helped more people through rough times as well as better enable those whose potential was being inhibited by the environment”.

“First and foremost, I wish I had mastered a deeper understanding of human behavior. Yes, I am admitting that even now I am often taken aback by what humans, say, do, and how they act. Why would it have made a difference? Because throughout my life, (whether in my personal relationships, being an employee, a marketer, a CEO, or board member) a greater knowledge and grounding in (human) behavioral science would have complemented my ‘gut’ instinct and accumulated experience and insight –which overall have been reliable”.

In conclusion, all the 6 Regrets are often the reason for a coaching intervention, and if we choose to, it is possible to master all of them, Alternatively, we may also choose to do nothing and shrink in our comfort zone. It seems that happiness is waiting for us outside our comfort zone so why do we still prefer shrinking? The answer is fear, fear of uncertainty, fear of failure or simply fear of not being good enough. Jeff Bezos, the founder of Amazon, came up with his own decision-making process, the regret minimization framework. The idea is simply to project ourselves into the future. Jeff would imagine celebrating his 80th birthday. At 80, by looking back in the past, his goal was to minimize the regrets he could have and through this thinking process he was able to challenge his fears. Fear is temporary, but regrets are forever. At 80, we will we regret our indecision and passivity while we had all our energies when younger. At 20, 30, 40 and 50 we still have all the capabilities to realize our dreams. So, let me end this article with 6 questions for you based on the wisdom provided to us by our successful executives. Its a simple scorecard ;

1 Have you mastered your level of self awareness and do you understand your impact on others?

2 Are you comfortable managing upwards and do you have broad networks and mentors who provide counsel when you need it?

3 Is your life in balance, are you valuing your health, well-being and relationships as well as your work?

4 are you genuinely interested in other points of view or are you a net transmitter?

5 Are you committed to learning as a lifetime pursuit or are you putting yourself at risk in the future by not continually reviewing new skills to understand?

6 If you lead a team, how would the team describe your leadership and is it a dynamic, high performing group or is it hampered by dysfunctionality and an absence of trust? 

I hope some of themes have resonated and I look forward to hearing your thoughts and perspectives in due course .I would also love to hear from Organisations and individuals who want their people and themselves to be the best they can be. Coaching programs which help clients address the 6 regrets of the living will be available in 2020.