Clare Dillon Leadership Skills, Behaviours & Attributes – What Should We Be Looking For

Leadership Skills, Behaviours & Attributes – What Should We Be Looking For? #20 #cong21


 Leaders today don’t necessarily have the will, opportunity, or wherewithal to effectively lead us to a great future state. This article takes a look at just some of the skills, behaviours and attributes are needed for today’s and tomorrow’s leaders.

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Key Takeaways:

  1. Leaders aren’t cutting it today.
  2. 8 skills, behaviours & attributes I would like to see in today’s and future leaders.
  3. Some brief thoughts on how to develop them.

About Clare Dillon:

Clare Dillon is the part-time Executive Director of InnerSource Commons, the world’s largest community of InnerSource practitioners. InnerSource is the practice of using open source methods and behaviours to develop proprietary software within organizational boundaries. Clare has been involved with InnerSource Commons since early 2019, when she helped set up NearForm’s InnerSource practice. She is also a qualified coach and consults on future world of work skills and organizational change for a digitally transformed world. Previously, Clare was a member of the Microsoft Ireland Leadership Team, heading up their Developer Evangelism and Experience Group. Clare recently sent up Open Ireland Network as a community for people interested in the open ecosystem in Ireland. She also works with the OSPO++ Network to support the establishment of University and Government Open Source Program Offices globally, that can collaborate to implement public policy and trustworthy public services through open collaboration. Clare frequently speaks at international conferences and corporate events on topics relating to the open collaboration, future of work, innovation trends and digital ethics.

Contacting Clare Dillon:

You can contact Clare by email or connect on LinkedIn.

Clare Dillon Leadership Skills, Behaviours & Attributes – What Should We Be Looking For

By Clare Dillon

Why we need leadership?

The world has changed. A few years ago, at Cong, I shared ideas about how the “4th Industrial Revolution” is changing the way we work and live, but I didn’t foresee a global pandemic accelerating change monumentally. The world is more complex now than ever before. The world is in-undated with misinformation. The past is not necessarily a predictor of the future. Trust in our societal institutions is at an all time low. The ice caps are melting and inequality is rising. To tackle global problems, we are all likely going to have to dramatically change how we live and work, and it won’t be easy. Great leadership is needed!

But who is leading? What makes a good leader? And how do we create more of them?

Leadership is such a broad topic, that it is very hard to do the topic justice in a short article. So, I have limited myself today by focusing on some of the emerging skills, behaviours and attributes I feel are needed by leaders today. Some that are perhaps mentioned less often in the many traditional lists of Leadership qualities.

Who is leading?

The first topic I want to touch on is who is actually “leading” these days. There has been a lot of discussion over the past week about “world leaders” due to their gathering at COP26. In many of the companies I have worked with, there is a class of employee who get tagged as “leaders”.

I am starting to use a lot of quotes at this stage. In my mind, many of our so-called “leaders” these days have a lot of work to do on their leadership skills. COP26 coverage shows a staggering amount of hypocrisy, a shocking lack of diversity and representation, or even a lack of ability to stay awake to hear the issues.

What don’t these “leaders” do?

  • Lead by example
  • Upset the status quo or vested interests that pay/influence them
  • Advocate for marginal / minority positions
  • Give adequate representation to those they “lead”
  • Dedicate enough time / bandwidth to even consider the idea of personal development

I could go on. But fundamentally, I think many of these leaders don’t really understand what leadership in today’s world should look like. They are often not particular trying to lead people to a new and better place, as they are so often invested in maintaining the status quo. They are trapped in systems where they feel the need to maintain control over leading to an uncertain future. They certainly don’t often exhibit many of the qualities I list below.

In some ways, I have sympathy, what was required of “leaders” in the past was often stability, consistency, efficiency. But the world has changed, and what got us here is not what will get us where we need to go.

These days leadership is not just coming from people who have been tagged as “leaders”. Top down hierarchies and power structures obviously still exist, but many have proven that is it’s certainly no longer necessary to be appointed to a position of authority to be able to lead. In a time when anyone has the potential to lead, what should we be looking for in a leader?

What does a real leader look like?

I’ve included below some areas which I feel are necessary, but lacking, in much leadership today.

So here they are, in no particular order…

A Leader Can Inspire, Change and Sustain

Difference contexts require difference skills – but leaders these days need to know how to effect change when change needs to happen, but also how to effectively sustain and inspire people that need to keep wheels turning and make things happen over a much more sustained period of time. Some people are more skilled in one rather than the other. It’s important to think about leveraging different balances of leadership skills depending on the context.

A Leader is Trustworthy

Untrustworthy leaders can’t lead effectively, so it is worthwhile looking at what makes someone trustworthy. TheHarvard Business Review summarizes in nicely in this article on the Three Elements of Trust:

By understanding the behaviors that underlie trust, leaders are better able to elevate the level of trust that others feel toward them. Here are the three elements:

  • Positive Relationships. Trust is in part based on the extent to which a leader is able to create positive relationships with other people and groups.
  • Good Judgement/Expertise. Another factor in whether people trust a leader is the extent to which a leader is well-informed and knowledgeable. They must understand the technical aspects of the work as well as have a depth of experience.
  • The final element of trust is the extent to which leaders walk their talk and do what they say they will do.

This is perhaps a more traditional point. However, it’s worth noting that in the glare of social media, and amidst trends of transparency and openness – there are new standards that have to be met in order to be trustworthy.

A leader Understands Context

In recent years I have become a fan of two subject matter areas that help people understand the changing nature of the landscape they are operating in (Wardley Mapping) and how to choose a way forward depending on the context you are in (Cynefin Framework for Decision Making). I do not have the time to go into any details on either, but I would highly recommend folks look into each area to help understand how to better navigate our changing world. Some fundamental truths I have learned are that context matters, expertise is no longer always enough to get to the “right” answer to a given problem (indeed can incorrectly bias folks), and there is rarely a one-size-fits-all answer.

A Leader Knows How to Fail Well

Leaders can’t be expected to get it right all the time. They should know how to deal with failure, and in fact welcome it in stages of experimentation.

In the area of Complex Adaptive Systems, it’s well understood that experimentation is at the heart of how to find a path to the future. However, the thing with experimentation is that you have to allow room for failure. I can’t tell you how much resistance there is among leaders to the idea of allowing failure, or even mentioning it. So many people (and in particular those that have risen to become called leaders) have been conditioned to never fail, always be successful. However, real leadership gives space for failure, knowing it’s the best way to learn.

A leader is an Excellent Communicator

A leader brings clarity of direction, and that means bringing it beyond buzzwords and using tools other than propaganda mechanisms. What that means is changing rapidly in today’s world. An excellent podcast with Zak Stein on the Jim Rutt show recently talks about the dangers of mis-information and how we are all on a path to Mutually Assured Destruction if we continue to allow the information wars to continue in our societies unabated.

I would highly recommend it to help understand what is going wrong in our world, how “leaders” are inadvertently losing trust, and how the tried and tested mechanisms for communicating are being hijacked. Future leaders understand the difference between propaganda and education, between inspiration and manipulation.

Building on the point about empathy, leaders should practice nonviolent communication. As described in Wikipedia: nonviolent communication is not a technique to end disagreements, but one that focuses on effective strategies for meeting fundamental needs for all parties in a conversation. The goal is interpersonal harmony and obtaining knowledge for future cooperation. Notable concepts include rejecting coercive forms of discourse, gathering facts through observing without evaluating, genuinely and concretely expressing feelings and needs, and formulating effective and empathetic requests.

A Leader Engages in Open Collaboration

As with other points listed, this little point in itself is a huge body of knowledge. I would submit that whereas the past century prioritised competition and control, the future will depend on open collaboration to accelerate innovation and produce levels of inclusion and trust necessary to make positive changes happen. As a starting point, here are the five characteristics of an open organization (from ): Transparency, Inclusivity, Adaptability, Collaboration, Community.

Building on that topic, skills like consensus building, decision making, remote working, flexible working (e.g. working in asynchronous environments), effective incentivization, and community building are all related to this point. Each one could also be a standalone topic in a list such as this, with huge bodies of knowledge behind each.

I’ll also note here that I only relatively recently found out there the top level on Maslow’s hierarchy of needs above self-actualization, and that is self-transcendence or interdependence (pic thanks to ( We will never get to where we need to alone!


A leader impacts Diversity & Inclusion (D&I)

There has been so much discourse about D&I, I am not going to re-iterate the many reasons why increasing D&I in any team, and in particular in “leadership”, has been proven to be a good thing (better decision making, more innovation, increased profits, increased trust to name but a few). The point here is that good leaders don’t just “care” about D&I – they do something to increase it.

A leader is a Designer of Spaces

Another amazing skill is creating and maintaining spaces. I look at the list below from Leandro Herrero in this great Sketchnote by Tammy Vora, and I am struck by how often this is not done at all (not to mind done well) by today’s “leaders”.

Leadership Spaces

How do we get more, good, leaders?

Listed above are just some of the skills, behaviours, and attributes of the leaders we need for today and the future. I am sure there are many more, and I look forward to hearing more in Cong.

In recent years, I have been buoyed when I see amazing examples of leadership coming from unexpected places. Whether it’s the amazing grassroots campaign like Repeal the Eight or the young leaders of the Climate Justice mass movement, or the achievements of a small group of dedicated folks like the team behind Grow Remote, there are examples of brilliant leadership all around us driving changes that help shape our world for the better. These are just a few that spring to mind – there are many, many more.

And we need even more to solve the problems and address the opportunities our world is now throwing at us. Here is where the rubber hits the road…. Of this list of traits and skills (and I am sure there are more I haven’t even listed), who has them? How do we nurture them when we see them? How do we develop them?

Traditional education mechanisms are probably not sufficient. We could create a future of work “leadership course”, but there is a risk it would get packed out with “leaders” who are often trapped by constraints and circumstances that make it impossible for them to lead us as we need to be led. That’s not enough.  Perhaps we need to look at some alternative ways in which we can foster these skills.

There is so much great learning material and assets out there already, the challenge is often finding them and applying them to a given context. Looking at some “future of education” trends, perhaps what’s called for is a community, or a network of de-centralised education hubs, or opportunities for more peer-to-peer learning with some mutual curation and coaching. I look forward to discussing ideas of how we might address this at Cong!

Title Photo by Chang Duong on Unsplash

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