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  • Matthew Jenkins

The art of the "Daring Leader"​

Leadership is a funny old thing. It’s a title, a status, a ‘thing’ that people aspire to achieve and something that people get promoted into the world over. At the same time however, it’s something that by all accounts, is relatively poorly understood or able to be clearly explained. The concept of “leadership” is pretty vague and ambiguous.


As the University of Sydney found in a study they completed a few years back, ask one hundred people the question “what is leadership?” and you’ll get almost one hundred completely different answers. How is that the case when people and organisations alike rely on “leaders” the world over to navigate the performance of their organisations?


I’ve recently finished reading ‘Dare to Lead’, a leadership book by researcher and author Brene Brown. In it, Brown makes a call for brave and courageous leaders but not in the “once more unto the breach dear friends” mode but rather, one of vulnerability and curiosity. It’s a message that echo’s the words of Simon Sinek who equally speaks of leaders needing to be “curious and vulnerable” and also nods to the work of Patrick Lencioni too who speaks of leaders needing to ‘go first’ when demonstrating vulnerability, the very foundation for building trust within a team.


Amongst varying anecdotes and personal stories shared throughout the book, Brown shares her interactions with Colonel DeDe Halfhill, Director, amongst other things, of Leadership Development in the US Air Force, and how the concept of leadership has changed over the last 50 years within the US Military. Brown recalls how Colonel Halfhill’s current leadership curriculum centred around working with leaders on items such as “tactical, operational and strategic leadership” yet looking through archived documents (as far back as 1948) Halfhill discovered a Military leadership that was schooled in things like “humanness” amongst other things. 


These archived Military teachings spoke of “belonging, feeling, compassion, confidence, kindness, friendliness and mercy” and even included the words “love”, as in “love your men”, were littered throughout these once revered Military leadership documents. A far cry away from the more sterile teachings the current leadership doctrines promoted.


What Brown articulates so nicely is that “the words we use matter” and that at the end of the day leaders deal with people! Yes, leaders are required to know and understand operational, tactical and strategic things but underneath all this sits people.


People come with emotions, feelings, fear and a whole host of other things that fall way outside of anything tactical, operational or strategic. As Brown so eloquently sums it up, leaders are required to “invest a reasonable amount of time attending to fears and feelings, or squander an unreasonable amount of time trying to manage ineffective and unproductive behaviour”.


When you strip it back, Leadership comes down to two things; mindset and behaviours.

It’s having a mindset that that values getting the best out of peopleIt’s behaving in a way consistent with how you want your people to behave


Simple? Yes. Easy? No!


Why brave and courageous leaders?

If you don’t know much about Brene Brown you should probably know that at heart, she’s a research professor, a good one at that by all accounts too. That’s where her latest book started. Brown wanted to put together a “no bullshit book” on what it means to be a daring leader. A chance to pull together years of research and at the same time settle an inner desire to be a better leader herself.


Essentially what Brown found consistently common in much of her research was that the world needs “braver leaders and more courageous organisational cultures”. She shares this because common issues faced by leaders and organisations alike could be linked to 1) an inability of leaders in being brave, and 2) a distinct lacking in organisational cultures centred around courage. Brown’s research discovered:


An avoidance of gritty conversations and getting the bottom of real things that impact business. Skipping over feedback and creating a place of artificial harmony;Avoidance of talk relating to the “feelings” that come about when change happens and instead ends up leading to time being spent fire-fighting the subsequent behaviours that come out to play;Lack of emphasis on building trust based relationships and the resulting amazement over why people don’t feel they are understood or valued;Failure to create an environment where people feel they can take risks and instead operate from a point of fear of being shot down or ridiculed;Living with one foot always in the past, where people are limited and scarred by the events or interactions that have gone before them;A culture where blame is too easy to apportion and where accountability is easily hidden away from;Where leaders jump straight into finding a solution rather than first asking the question “why” and making time to properly understand where a root cause might lay;Where values are something that get stuck on a wall, rather than things that get lived, breathed, evidenced and exampled day-in-day out.

Essentially, what Brown spells out so neatly in Dare to Lead is that leaders become all too happy to settle at a six out of ten, paralysed by fear rather than truly striving for excellence by doubling down and getting under the skin of what it really means to be a daring leader.


What daring leaders do!

In Brown’s words, daring leadership can be simplified down to four core things. Things you have to have a mindset to value, and behaviours that need to be promoted and actively demonstrated. They are:


* Vulnerability

* Values

* Trust

* Resilience


What she means by this is that leaders need to be willing to be vulnerable and value vulnerability in others. Leaders need to know and make decisions by their values and surround themselves with people that share similar values and that can hold them to these values when they are slipped from. Leaders need to place value in trust based relationships and understand the intrinsic link between trust and vulnerability. Leaders need to work on their ability to be resilient and actively teach resilience to their workforce so people are equipped to ride out the storms that will inevitably hit organisations and people more than we may be willing to recognise it.


Brown’s book is deep and full of wisdom and teachings for the modern leader but when stripped back the messages are relatively simple and largely common sense. Nothing in Brown’s research is rocket science but it is hard. It goes against what leaders have been taught in days gone by about ‘taking charge’ and ‘leading from the front’ and largely comes back to stripping yourself bare. As Brown nicely puts it, daring leaders lead with a “soft front and a hard back” not a “hard front and soft back” as many leaders have become prone to demonstrating today. As Brown beautifully crafts, “Great leaders make tough people decisions and are tender in implementing them”.


Vulnerability and Daring Leadership:

On the subject of vulnerability, Brown shares her findings of how leaders often hide behind myths in their natural avoidance and discomfort at being vulnerable. She shares how leaders often view “vulnerability as a weakness”, how they often put a barrier up through the claim “I don’t do vulnerability” or “I’m fine going it alone” and their preference not to “let people in”. Hard front, soft back! When leaders are able to be vulnerable though, good things happen. Brown explains that the resulting good that can come from vulnerability includes “adaptability to change, hard conversations, feedback, problem solving, ethical decision making, recognition, resilience” and a host of other things that constitute daring leadership.

As Brown nicely articulates, leaders need to find the “courage to get curious and surface emotions and emotional experiences that people can’t articulate or that might be happening outside their awareness”. For Brown, it comes down to ‘Daring Leadership’ over ‘Armoured Leadership’.


Armoured Leadership is:

Driving perfectionism and fostering fear of failureBeing a knower and being rightHiding behind cynicismUsing criticism as self-protectionLeading for compliance and controlWeaponising fear and uncertaintyRewarding exhaustion as a status symbol and attaching productivity to self-worthCollecting gold stars


Daring Leadership is:

Modelling and encouraging empathy and self-compassionBeing a learning and getting it rightModelling clarity, kindness and hopeMaking contributions and taking risksCultivating commitment and shared purposeAcknowledging, naming and normalising fear and uncertaintyModelling and supporting rest, play and recoveryGiving gold stars


Values and Daring Leadership:

On values, Brown has a clean and simple definition of “Know my values = know me. No Values = No me”. She outlines that “sharing values is a massive trust and connection builder for teams” and that the job of a leader is to create an environment in which connection can be achieved, trust fostered and vulnerability willing and able to be demonstrated.


In Brown’s view, values should be “so crystallised in our minds that they don’t feel like a choice – they are simply a definition of who we are in our lives”. She continues that in the difficult moments we come across in life “we know that we are going to pick what’s right, right now, over what is easy”. For Brown, for leaders, for people in general, it’s about “choosing what’s right over what’s fun, fast, or easy”. It’s practising values over professing about them! A favourite quote from the book is simply this when it comes to values…. “Regardless of the values you pick, daring leaders who live into their values are never silent about hard things”.

How true that is!


In Brown’s conclusion around values, she shares that people who are values driven, or want to be values driven, have to operationalise these values into “behaviours and skills that are both teachable and observable” and that leaders need to do the difficult job of “holding themselves and others accountable for showing up in a way that is aligned to these values”.


Trust and Daring Leadership:

As mentioned already, trust and vulnerability go hand in hand. Unlike the common misconception that first you have to trust in order to show vulnerability, leaders need to first demonstrate vulnerability in order for people to then trust. As Brown shares, the “slightest inkling that someone is questioning their trustworthiness is enough to set total vulnerability lockdown in motion”. Once that happens, people are completely unable to hear or process anything that’s going on around them, they slip into “emotional survival mode”. A leader’s job is to show vulnerability themselves in order to develop trust from those around them and in their position as leader. Soft front!


Trust in organisations is not nice-to-have, it’s a complete must-have. As Brown highlights through her research findings, failure to have trust based relationships and organisation’s can literally fall into total disrepair. Brown’s studies show that when leaders build trust based relationships at the heart of their organisations the bottom line returns for business can be as much as three times greater than those who don’t prioritise trust in their organisations. In a study of the ‘100 Best Companies to Work For’, trust between managers and employees was the “primary defining characteristic” of these workplaces and organisational results benefitted greatly because of this.  


As Brown cleverly shares through her own personal experience as a leader and also through her findings, daring leaders demonstrate trust not through the big actions they take but through placing value in, and remembering, the small things. Leaders can’t demand that an employee simply trust them. Trust is earnt. It’s earnt through the small things like remembering children’s names or asking how an ill relative is doing. These are small things. They aren’t strategic, tactical or operational but are equally as critically important in the grand scheme of things, possibly more so, and as proven through research studies, can be directly linked to the bottom line performance of an organisation too.


Resilience and Daring Leadership:

Finally, on resilience, Brown shares an interesting view that leaders don’t spend enough time teaching people to be resilient and that often resilience is taught and experienced in reverse. She likens it to being taught how to land a parachute jump only after you’ve hit the ground. A retrospective look back on what went wrong. In reality, vast amounts of time is devoted up front in teaching a person to land a parachute jump ahead of going through the actual land experience itself. For Brown, resilience should be taught by leaders this same way. Prepare people for what might happen because “if we don’t have the skills to get back up, we may not risk falling” as Brown nicely puts it. 


Resilience is needed not so much for the huge events that happen in life, although it is needed there too, but it’s more commonly needed in the everyday interactions and events that create the need for us to repeatedly “bounce back”. In a world where we are now “on” almost 24 hours a day and the pressure to juggle so many things consistently builds around people, it has become all too easy for people to become overwhelmed and “for them to subsequently fall”. The infamous straw eventually breaks the camel’s back.


Brown talks about resilience and the need to be in tune with our emotions and be curious to what’s going on around us when under pressure. It’s about equipping ourselves to “respond” rather than “react” and teaching ourselves, as daring leaders, to look for the signs that show we are struggling. For Brown, it’s about the need for leaders to be curious, to seek information first. To be able to be vulnerable and rely on trust based relationships and our values to help weather the storms that occur in every day organisational life and to educate and support employees in better understanding what’s going on around them so that the subsequent “falls” happen less frequently and are easier to live through.

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