The Dark Sides of Leadership

Full Circle Leadership highlights the strengths of eight diverse kinds of leadership. But each also comes with a shadow side.

Alanna Irving
Enspiral Tales


Full Circle Leadership is a framework for understanding the forms leadership takes in non-hierarchical groups, and for mapping project life-cycles in emergent environments without top-down project planning.

To learn even more, read the original article, extend it with patterns and loops, watch the video, or take a course.

Every kind of leadership has a dark side. Shadows can come out due to stress, conflict, or feeling undervalued. They can be exacerbated by overspecialisation in one type of leadership, to the detriment of empathy and balance. Shadows can represent the worst versions of ourselves, or simply what we look like on a bad day.

Through understanding shadows, we can better understand ourselves and each other. We can become more self-aware and learn how to ask for support and spot warning signs. The goal isn’t to eliminate shadows, but to understand and even embrace them.

The goal isn’t to eliminate shadows, but to understand and even embrace them.

As we delve into shadows, it’s important to remember that individual strengths and weaknesses are only part of the story; context also plays a huge role. No one can be their best selves in an unhealthy or unsafe environment. If the best sides of your leadership are not recognised or welcome, your shadow sides might come out instead. Below, shadows are examined both individually and systemically.

Eight Types of Leadership, Eight Shadows


Shadow: overwhelm

Sensitivity means opening up to input on all levels, observing and empathising with what’s going on around you. It’s about having your antennae out and spidey sense switched on. It’s a wonderful skill to have.

But think about this: while mind-reading could be fun or useful, it would be a cacophony if you couldn’t turn it off.

Highly sensitive people might cope with overwhelm in different ways: by reflecting a lot of emotion back, which is not always welcome, or by shutting down to gain a sense of control or a reprieve.

Signs of overwhelm include losing the inability to differentiate signal from noise, lack of a healthy outlet for all the insights or feelings you’re absorbing, poor boundaries (taking other people’s stuff on as your own), or the urge to either lash our or withdraw in an attempt to turn life’s volume down to manageable levels.

An unsafe environment for Sense leadership is one where vulnerability is seen as a weakness to be taken advantage of. If spaces for deeper listening are not created or respected, or being heard depends on yelling loudest, overwhelm is sure to follow.


Shadow: permission-seeking

Inquiry leaders are masters of asking questions. They want to connect to many perspectives, hear stories, and dig deeper to find out the full context. This is important work for consensus-building and socialising new concepts.

The problem comes when that never ends. It’s impossible to ask every person’s point of view on every topic, and feeling like you have to is debilitating. Strong inquiry leaders know when to stop asking questions and start moving forward. If that doesn’t happen, uncertainty rules.

Permission-seeking can come from fear or disempowerment. Maybe you think you can avoid blame for failure by conferring with every single person. Or maybe you lack mandate, never reaching the end of the chain you’re inquiring up.

In environments hostile to inquiry leadership, questions are taken as criticism and responded to defensively. You’ll never draw out the truth if past failures or mistaken assumptions are treated as shameful secrets. This will lead to a feeling of dissatisfaction and potentially lead you to asking more and more questions, creating more and more stress. Or you might feel you lack permission to contribute your inquiry skills and withdraw.


Shadow: distraction

Visionary leaders are inspired by what’s new and what’s next. But if you’re always looking toward that next horizon, you might not notice what’s right in front of you.

The thrill of creation, newness, and risk is seductive, even addictive—you can easily feel bored or even oppressed when reality starts catching up. Some visionary types are only motivated to work on what feels exciting in that moment, and can’t direct their efforts strategically.

Self-aware visionaries understand when to introduce new ideas and when it would just be a distraction. Visionaries without self-awareness may lack empathy for those attempting to focus on current challenges or responsibilities.

Visionary leaders are often the ones who create an initial spark and attract others to that flame. If you are always running off to start the next fire, you’ll either leave everyone behind or lead them on a wild goose chase. Effective visionary leaders step into operational leadership when the times comes, or hand over to operational leaders who complement them.

Bad environments for visionary leadership are where anything unfamiliar or risky is shut down and exploration is not encouraged. Visionary leadership can’t thrive when hemmed in by artificial boundaries. You won’t thrive without space for creativity and possibility.


Shadow: obsession

Passionate prototypers often take the form of the tinkerer, the hacker, or the inventor—those who latch onto a question and don’t give up until it’s cracked. This is fantastic for problem solving, but can easily stray into obsession.

When a concept is just emerging, it can be impossible to explain or justify it to others. You need space to experiment freely, brainstorm, and try things that seem a bit crazy. But if you are in that mode for too long, you become detached from the outside world, and risk building a solution to a problem no one has.

As technical specialists, prototypers often thrive when complemented by other types of leaders. Preceding you in the circle, it’s those who can create great specs, problem definitions, user stories, and briefs. Coming after you in the circle, it’s those who can measure viability, figure out implementation, and bring innovations to the world.

You need partners who can protect you from design by committee and defend the autonomy of experimental spaces. The shadow side of a prototyper can manifest as unwillingness or inability to work with these complementary leaders, and stubbornness about recognising their value.


Shadow: cynicism

Evaluation leaders care a lot about integrity. You probe for holes and weak spots to ensure that what comes after is built on a solid foundation. On a bad day, that can manifest as nothing ever being good enough.

In De Bono’s six thinking hats, the black hat is often labeled “evaluation”. You’re the devil’s advocate who spots dangers and difficulties. This can be a very useful hat to wear, but it becomes a problem if you use it too much or at the wrong times.

As an evaluation leader, you’re at your best coming from a place of care: for outcomes, for the vision, and for the truth. You’re at your worst coming from a place of fear or arrogance, prioritising being right above all else. Requiring that evaluations reveal perfection before a project moves forward results in paralysis, and focusing only on the negative damages relationships.

Healthy environments for evaluation leadership are where concerns can be raised and considered thoughtfully, neither downplayed and ignored nor trumped up and overblown. Looking at a group’s practice and culture around feedback is an excellent gauge. If it’s healthy and constructive, evaluation can thrive. If it’s defensive, broken, or nonexistent, shadows may emerge.


Shadow: ruthlessness

Operationalising is a process of negotiation with reality. When handled skilfully, it’s the art of compromising while staying true to the essential vision. But when the shadow emerges, the negotiator stops listening and starts playing hardball.

As an operational leader, I’ve often said my impatience is both my greatest strength and my greatest weakness. It drives me to keep up momentum and solve problems efficiently so we can ship, launch, open, or move forward. But too little patience can mean not enough empathy and openness. There’s a risk of rushing, missing important warning signs and getting things done at the cost of relationships.

Being an operational leader requires a certain level of decisiveness and confidence in the face of unknowns. A call must be made when it’s time to stop considering options and commit to action. But taken to an extreme, this can manifest as dismissiveness or shutting down other voices.

Operational leaders are complemented by those skilled in listening, dreaming, and holding space for ambiguity. You thrive in a culture that values finding the right balance between exploration and getting shit done. If your calls for realism are treated as just naysaying, it’s a sign your operational skills are not being valued.

Operationalisers are ultimately motivated by seeing work put into action—you’ll be forever frustrated in an environment constantly mired in distraction and last minute changes.


Shadow: bureaucracy

Maintenance leadership is about creating stability in an ever-changing world. Far from being static, it requires constant adaptation. The shadow side arises from trying to make the world adapt to you instead of the other way around.

Maintenance leaders love creating systems and procedures to make things more efficient and accessible. You think carefully about people’s needs and provide a map. The shadow arises when you start confusing the map for the territory.

There’s a great danger of limiting your perspective to what’s legible to your system. Instead of accepting that some cases don’t fit the model, your shadow side wants to get rid of them or make them conform.

When it goes wrong, we end up with classic bureaucratic frustrations: senseless rules, inflexibility, and everything moving at a crawl. A shadow maintainer ends up a taskmaster of conformity instead of a helpful guide through complexity.

Blame and shame cultures bring out bureaucratic shadows because people prioritise ass covering over effectiveness. The same goes for dehumanising approaches to metrics, resulting in everything being optimised only for what’s measured. Bad systems will get bedded in if there’s no healthy culture of feedback and questioning the status quo.

Maintenance is one of those paradoxical things where the better it’s handled, the less it’s noticed. If your true contributions is not recognised and valued, you won’t thrive. And if maintenance isn’t considered early enough in the process, you won’t be set up for success.


Shadow: meddling

One of the key skills of optimisation is staying with something long enough to deeply understand and improve it. Its shadow side is not knowing when to let go.

The term ‘perfectionist’ can have both positive and negative connotations. Similar to evaluation leaders, the shadow side can manifest as an impossible standard by which nothing is ever good enough. The beautiful side of optimisation leadership is the aspiration to reach the highest possible potential—but if pushed too far it can turn ugly.

As an optimiser, you may hold yourself to a perfectionist standard too. This can manifest as harsh self-criticism, or being judgemental of others, leading to detrimental negativity.

Optimisers have to strike a delicate balance between the inertia to stay at ‘maintain’ and the pull of sensing into the next journey around the circle. When not at their best, this balance is lost.

An environment where people get defensive and push back against suggestions for constructive change is not conducive to healthy optimisation. If consistently rebuffed, your shadow may show itself as increasing negativity or simply giving up.

Constructive Conflict and Developing Empathy Through Understanding Shadows

While diverse kinds of leadership can be complementary, they can also clash.

As an operational leader, my stress response is to want to lock down and clarify everything. This can come into direct conflict with others who seek more freedom and space when challenged.

By understanding and empathising with each other’s shadow sides, instead of setting up a recipe for disaster we can offer mutual support through stressful periods. And by coming to know our own shadows, we can work to reduce their impact, leading to better interactions and relationships.

Sometimes what I thought were shadows turned out to be valid unmet needs.

But it’s not the case that we should always seek to minimise or eliminate our shadows. They can be important signals. Sometimes what I thought were shadows turned out to be valid unmet needs.

I once left a company because I was the only one who sent out info emails about away days. As an operationally focused person, that was a way I showed care toward the team. The last straw came when I had to head to an away day immediately after a busy trip out of town and I didn’t know where the venue was because no one had sent out the information. If I didn’t do it, it didn’t happen.

I realised I would never be cared for in that way by that team. To them it seemed like overkill that this seemingly small detail caused me so much stress. In that context, my need manifested as a shadow, one that’d I’d have to minimise to get along with the group. Instead, I realised it wasn’t the right place for me anymore.

If two leaders with the same style are acting from their shadow sides, they’ll both be exacerbated.

It’s pretty obvious how very different styles of leadership can come into conflict, but too much similarity can be an issue as well. If two leaders with the same style are acting from their shadow sides, they’ll both be exacerbated.

For example, two visionaries caught up in distraction can pull a team in opposite directions and end up in a tug of war. Two leaders strong in sense/inquire can get caught up trying to facilitate and accomodate each other and never move forward. Two operationalisers can butt heads about implementation details, each trying to get the other to fit into their preferred structure.

Each leadership style is ultimately determined by what a person cares about most.

Each leadership style is ultimately determined by what a person cares about most—what seems important to them is what they notice and focus on. If we can continually recall that, despite any aggravation, others are acting out of care, maybe we can become more understanding toward one another.

Dealing with conflict and difference constructively often requires engaging with underlying power dynamics, and confronting deep fears about being unseen or undervalued. We have the opportunity to do this hard work and push through to solidarity, to declare “We’re all leaders here. Now let’s figure out how to work together.”

Letting go of ego—true acceptance and gratitude that other leaders do things differently—is the ultimate constructive alternative to conflict.


Here are some ideas for engaging with leadership shadows in your own work.

Individual: Shadow Sides

Review your Full Circle Leadership profile. What are your strongest areas around the circle? Reflect on their shadows.

  • Do you see a version of yourself represented there?
  • What can you do to change your habits or your environment to reduce the impacts of your shadows?
  • Are your greatest strengths and weaknesses actually two sides of the same coin?
  • What are your shadows trying to tell you?

Team: Stress Responses

  • Reflect: What behaviours or tendencies appear on your worst days? What does your stress response look like?
  • Share: What are the warning signals that you’re having a hard time? What might that look like from the outside?
  • Request: What do you want others to do if they notice your warning signs? Do you want to be approached, or given space? Held to account, or given encouragement? What are you asking for and opting in to?



Alanna Irving
Enspiral Tales

Exploring bossless leadership, collaborative tech, and co-op systems —