Lessons from a two thousand year old leader

Justin Hennessy
7 min readFeb 27, 2022
Image by Jehyun Sung from Unsplash

About two years ago, I began reading old classics, Stoic and Taoism philosophy. Ancient texts from all over the world, from all different periods and areas.

I am not sure why I started down this path. I suspect Taoism resonated with me and seemed an excellent way to move through life to minimise suffering and maximise “happiness” (a much bigger topic for another article).

Over the last few years, something has occurred to me that few new ideas have been created. We have many areas in life where ideas are rehashed, rediscovered and rephrased, but in essence, they are the same themes and underlying message.

A large part of my role as a technology leader is leadership. Before we delve into the ancient art of leadership, I feel it is essential to better define what I mean by leadership as it is an extensive topic and can sometimes be an overloaded term.

A common misconception of leadership is its only one’s “status” or tenure in a role or company. By this, I mean some believe that you have to have the title that goes with it to be a leader. I am in the camp that anyone can be impactful from a leadership perspective; it’s a mindset, an attitude and actions. Good leadership brings things like compassion, empathy, understanding, and curiosity to the forefront.

In her booking “Teaming, how organisations learn, innovate and compete in the knowledge economy”, Amy Edmondson describes BIG and LITTLE L leadership. Big L leadership is about having a role title and the associated responsibility and accountability. Little L leadership is when someone chooses to step forward, take action and own something without being asked.

This latter account of leadership is an area that I focus on a lot when coaching and mentoring people around me, my direct reports, my peers and even when managing upwards.

“What has this got to do with the article title?” you ask? I have just recently finished reading Sun Tzu’s Art of War and Wutzu’s “The sayings of”, and was struck by how insightful these texts were, even though they are over 2000 years old. I thought it would be interesting to take a few extracts from them and see how they translate and apply to leadership from my perspective in today’s knowledge worker landscape.

Attributes of a leader

Sun Tzu specifically refers to sincerity, wisdom, benevolence, courage, and strictness as qualities of the great general

The Art of War, Intro by Tom Butler-Bowdon, Page xviii

It is fascinating that even back as far as Sun Tzu’s period, the human equation was fairly well understood. He had a good handle on what motivates his troops, what helps to align and direct them to a great cause or north star. I have been a proponent of seeing people where they are, in their natural state. Instead of trying to affect change on them, I look first to understand how that person ticks then work on a path that I can journey with them as they identify what they are looking for in their growth.

Sincerity is being your authentic self, grounded, and working alongside your team as a companion rather than a “boss”. There are countless books on this topic that give examples of how to execute this. One such example is The Alliance, where Reid Hoffman talks about creating a “tour of duty”. A two-way agreement on how the person can add value to the organisation and their opportunities to grow. It’s such a big topic in today’s career landscape.

Benevolence is another crucial attribute for leadership. Gary Vee, a business and marketing entrepreneur, often talks about the need for kindness globally and especially in the workplace. Being compassionate and empathetic with your team is at the heart of creating a trusting, psychologically safe environment where you can balance supporting your team, delivering constructive and positive feedback and delivering on business outcomes.

On giving feedback back, David Rock has one of the best models/strategies I have found for conducting productive/safe conversations; he calls it the Dance toward Insight. This method has four key areas: permission, placement, questioning, and Clarifying. For years, this method has been the foundation of my conversations and has yielded excellent results in positive and difficult conversations; definitely worth a look.

Setting teams up for success

In an organisation, Law may mean the appointment of the right people who know exactly what they are accountable for and who have the resources to execute their mission.

The Art of War, Intro by Tom Butler-Bowdon, Page xix

Firstly, “Law” in Sun Tzu’s terms translates to “the ordering and partitioning of troops” instead of the present-day definition of the word. Law is one of Sun Tzu’s five “indispensable matters that had to inform a leader’s decisions” and is about identifying and positioning leadership and forming effective “teams” in his military. This quote resonated with me as it forms part of my primary strategy as a leader, and it is how I have achieved success in many roles to date.

When starting a new role, one of my first actions; is not to act. I see the first 30 days as a crucial opportunity to connect and quickly build rapport with my new team. Next, I look to observe, listen and understand the current environment, what is working, what is not, helping to enable me to stay relatively objective when the time comes for making decisions around change. I can produce more effective changes with a better understanding of the current state of things, including any historic “trauma” affecting members’ effectiveness and autonomy.

Once I have a good lay of the land, my next job is to identify, position and coach leaders or potential leaders. Sun Tzu’s idea is about the organisational structure and leadership to support that structure.

So, once I have connected with and built rapport with my team, I identify and position leaders to own my department’s different areas of responsibility. I create an environment of autonomy and look to empower my leaders as best I can. I first find that I need to dispel the “permission” problem, where people feel they need to elicit permission from me to do their jobs. Steve Jobs famously said he doesn’t hire smart people to tell them what to do. I believe wholeheartedly in this sentiment.

To help re-educate my leaders, I apply a method I learned from the book titled “Turn the ship around”. David Marquet, the author, used a technique of getting his leadership team to state their intent rather than ask permission when trying to action something. Instead of someone asking, “Can I proceed with X” you rephrase it to “I intend to do Y”. This achieves two things, it empowers the team member to state their intention and own it, and it also allows the Leader to give any feedback or observations on the intended actions. I treat my team as peers and trust that they are looking to do their best. I add value by empowering and supporting them in performing their role. You will be amazed at the results this brings.

Communicate or not communicate, that is the question

Orders should direct the soldiers; but while what is advantageous should be made known, what is disadvantageous should be concealed.

The Art of War, Intro by Tom Butler-Bowdon, Page xxix

Probably the most controversial point in this article given today’s focus on open, transparent and authentic communication, so let me explain. I struggle with this quite a bit. How much is too much transparency? When does transparency become unproductive?

One of the primary roles of a leader is to act as a heat shield or a noise filter for their teams. Given the volume of work that teams are now having to endure, any efforts to dampen the inputs and stimulus coming into teams will be valuable if done responsibly. I call this Select Transparency, and I use it not to conceal information from my team but as a way to articulate my desire to get the “best”, a subjective concept I know, information to the team for them to be the most productive and the least disrupted.

I have had a recent experience where some fundamental changes happened within a business I worked for, which I neither agreed with nor aligned to, but I still had to lead and support my team. So I chose to shield and filter the team from the actual realities and details of those changes as best I could and worked to help them reframe the situation and focus on what we could control. This was a true test for me to “get over” how I felt and think more broadly about the team’s needs, which helped.

There are many great literature sources around leadership, but old books are often discounted as they could be deemed outdated. Remember, there are few “new” ideas, and there are often things to be learned from the past, so try and expose yourself to something different for your next book. You may get some fantastic insights you didn’t see before.

Always be learning and growing, and enjoy the journey.

Originally published at https://justinhennessy.com.

--

--

Justin Hennessy

I am a technologist, an enabler, musician and I have an acute sense of the moment. https://justinhennessy.com