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Why are Transformative Leaders Sometimes Bad Bosses? Hope University and the Need to Boss-Up

Updated: Dec 29, 2021

by Jessica Riddell

eight herons flying in a vee formation

The academy does not train people to be bosses.

Scholars? Yes. Educators? Sometimes. Leaders? Sure. But bosses? Rarely.

When academics move into positions where they are expected to manage staff and build dynamic teams, the skills they have developed as researchers, teachers, and leaders do not always translate easily into these new roles. As one of my favourite Canadian university presidents is wont to remark, “the only equation that matters is people.” However, when successful scholars and award-winning educators find themselves managing HR issues without the appropriate skill sets (including performance assessment, conflict management, and trust-building frameworks), a myriad of problems can and often do arise.

Institutions often assume managing people is intuitive rather than intentional; and yet, even with the best of intentions, poorly trained bosses can cause significant harm.

As I write elsewhere, “there is no such thing as a naturally gifted teacher” (Riddell, 2019).

The same statement is true about bosses.

There is no shortage of work done on leadership in the higher education sector and beyond. There is even a theory of followership. The first follower principle, coined by Derek Sivers in his TED talk “How to Start a Movement” asserts that a leader “needs the guts to stand out and be ridiculed.” But, Sivers argues, the first follower is crucial to “transform a lone nut into a leader.” Interestingly, Sivers posits that in starting a movement, the leader embraces the first follower as an equal. As the movement is made public, new followers emulate the first follower, not the leader. Nurturing the first few followers as equals, Sivers argues, is essential to nurturing the movement. To further complicate things, research around followership in academia suggests that followers often see themselves as leaders, an identity that shifts in different contexts (Billot et al., 2015).

Academics can (and often do) read diverse books on leadership. However, people management – by which I mean navigating the complex dynamic of employees and employers within complex organizations – is almost never discussed in academic circles (with the exception of business schools, who are often indulged for their “business-speak” and then promptly ignored). A lack of management training has caused countless challenges for academics who have thrived as scholar-leaders and are then thrust into positions where they need to design job descriptions, hire and train employees, build teams with diverse stakeholders, engage in staff and admin performance assessment, and manage inter-personal relationships and conflict. Add unionized environments, multiple collective agreements, and entrenched politics and this becomes downright disorienting.

The reasons why we do not train academics to be bosses are plentiful and some of them are very compelling. Over the past few decades, the neo-liberal narratives have threatened to transform universities into corporations, students into customers, and education into a product. We need to be attentive to these movements and combat them heartily. Universities – counter to what education “futurists” like Ken Steele argue – are not businesses. In Canada they are publicly funded institutions that serve a social purpose – and their moral contract to the broader society necessitates that they operate outside of the influence of corporations and beyond the control of governments.

an ornate plumb line over a compass sigil on a map

And yet. Universities are complex systems that need thoughtful, nuanced, and empathetic approaches when navigating collegial governance and bicameral systems.

The solution, however, is not more management classes for aspiring administrators. This path only perpetuates the mission drift of universities and dilutes the values that differentiate universities from other social institutions.

The solutions are more complex; in the following case study I will apply American professor Bréne Brown’s framework of scarcity and shame (from her influential Daring to Lead series) to understand the journey of a flawed-to-reflective boss (spoiler alert: I am that boss).

I failed in my first role as a boss with my first employee.

Just as Sivers points out about the first leader and the first follower, I treated my first employee as my equal. We co-designed their aspirational job description, I gave them carte blanche to dream and scheme, and put them in charge of a small team of volunteers. They kept calling me “boss” in jest and in meetings with others, and I kept chafing against that term, preferring instead to reframe their role as a valued collaborator and co-designer.

Only in hindsight do I realize how much harm I caused by erasing the boss-employee relationship.

I thought I was creating a movement – an organization built in the spaces between universities that was student-centred and focussed on transformative and inclusive education with a social justice trajectory.

But I was actually building an organization – albeit with that same mission. And I had an employee who needed boundaries, onboarding and ongoing training, clear expectations and deliverables, regular performance assessment – and most importantly, regular and consistent access to me. But I did not explicitly teach them to collaborate across complex organizations, how to act in a professional manner, how to upskill for difficult conversations, nor did I provide guidance on what corporate stewardship is and why it is important. Quite frankly, I was not taught that myself and had to figure it out along the way (which of course means that it was

large crack in a highway surface, blocked off by traffic cones

intuitive, unexamined, and totally unhelpful to anyone else).

As first boss and the first employee we started off with a shared purpose. But we lost alignment, in part because I unintentionally reproduced systems of scarcity that I had internalized from working in and across institutions that are chronically underfunded and under-resourced.

Scarcity, according to Brown, means “there’s never enough blank, never enough time, never enough people, never enough clarity, never enough, never enough, never enough.” In a scarcity-driven culture “leaders use fear and uncertainty to drive productivity. We could lose the accounts, we could shut down, we could do this, we’ve got to do this. It is exhausting, it is unrelenting, and it does not drive productive, innovative, creative thinking.”

I was 100% guilty of this mindset.

Working for years within institutions with declining provincial funding, precarious enrollment, and multi-year structural deficits, the scarcity seeped into my bones. The “never enough” mantra drove me to work harder, sacrifice my research, compromise my health, and go the extra (pro bono) mile because I thought that if I tried my best, I could help save the university. Writing it down makes it seem a bit ludicrous (a junior faculty member making $50,000/year teaching extra courses for free to over-enrolled classes was not going to make a dent in the long-term sustainability of the university).

Nevertheless, because I did not have the language to name or claim it, I reproduced scarcity in my own leadership. And then I inherited a fledging consortium that had very little grassroots buy-in and a lot of people demanding metrics to justify “the bang for their buck.”

That informed the hustle – and the harm.

Dry outdoor faucet with spiderwebs on it

For Brown, “[In] scarcity-driven armored leadership cultures … our perceived value is often tied to our performance, [so] we tend to hustle for our worth. Now, one of I think the hardest relationships to manage is the person who is constantly hustling for their worth, constantly vying for validation that they’re good enough, that their work is important, that they’re a contributor. And you often see that in scarcity-based cultures.”

I am 100% guilty of this mindset, too. It is something I must unlearn every day.

When organizations operate in a scarcity model, shame is “baked into the walls” (cf. Brown). And in my refusal “to boss” (both as a verb and as an identity) and my insistence on co-design (coupled with benevolent neglect), perpetuated behaviour from my first employee that was, according to Brown’s framework, driven by shame:

“Shame shows up at work [as] back-channeling.” If you have ever shown up at a meeting only to realize the decision had already been taken, you have experienced back channelling. In virtual meetings, new forms of back-channelling have become pernicious. Texting amongst people during meetings is toxic behaviour. When you see faces change on-screen (laughter, a smile, a distracted face) and it has nothing to do with the energy of meeting, it is obvious to everyone else in the meeting that something is shared, secret, and exclusive.

“Favoritism is shame in action, because the people that are subjected to your favoritism and not part of the favorites feel smaller, diminished, less than, put down.” This is clear from who is backchanneling, but also shows up in inside jokes, social media shares, and other micro-actions that demarcate insider and outsider status.

“The invisible army. This is when I come to you and I say, ‘We’ve all been talking and we really think you should reconsider,’ my first question is: ‘Who’s we?’” When someone share issues without naming the interlocuters and claiming the conversations, it puts the person receiving feedback on the defensive. And that is never a good look.

“Perfectionism … is absolutely a function of shame. Perfectionism is the 20-ton shield that we carry around, if I look perfect, work perfect, turn everything in perfectly, do it all perfectly, I can avoid or minimize shame, judgment, and blame. Any kind of management tool where we’re tying people’s self-worth to their productivity, you are as good as what you produce, shame in the walls.” This one resonates especially, I think, for academics who have been rewarded for producing [insert publications, grants, awards, prestige]. When we work within conditions of scarcity, we are always asked to prove our worth and account for our place in the budget line. And it quickly moves from “we don’t have enough [X]” to “I am not enough.”

“Gossiping. Let me tell you, if you’ve got a gossiping issue, you got a shame behind the wall issue. Teasing, shame in the walls; passive-aggressive behavior, I would look for shame.” When school-yard behaviours and spicy millennial ripostes are pervasive in work cultures, it bakes shame into the deep culture of the organization.

backlit silhouette of a woman with long hair

While I saw this behaviour manifesting in my first employee, it felt yucky, but I did not yet have the framework to draw the line between shame-based behaviour and the erosion of trust that was happening. American author and Founder of Insight Coaching Charles Feltman describes trust as “choosing to risk making something you value vulnerable to another person’s actions,” and he describes distrust as deciding that “what is important to me is not safe with this person in this situation (or any situation)” (quoted in Brown, Braving the Wilderness).

In my case, I reproduced a scarcity model, which led to the shame-based culture; with no training to upskill for difficult conversations and an inability to call out or “call in” toxic behaviors, this reproduction of the model led to irresolvable tensions. To compound the issue, the team of volunteers under the first employee followed them (as Sivers predicted) and reproduced the behaviours they saw modelled.

When trust is lost, things snowball. I struggled hard to recapture a shared purpose with weekly check-ins and alignment exercises, but it was too little, too late. The more I chased, the more elusive alignment became. The damage had been done, and trust was lost on both sides.

The first employee left for a new job that was stable and well-funded (compared to the original job on a short-term contract with soft money from an external funder).

This should have been a happy ending – but it was not.

I experienced deep grief and feelings of tremendous loss for a relationship that I had highly valued. I have had to learn to sit in the discomfort of this and ask, what do I do with this shame? I thought I was a transformative educational leader – and my professional identity was inextricably bound up with this belief – but it turns out I was a terrible first boss. As Brown remarks, “we do not have the skills culturally in this country around accountability, we just shame the shit out of everyone, we have cancel culture, we literally do not know how to hold ourselves and others accountable” (Brene Brown, Podcast Part 1of 2).

Two white ceramic tea bowls on a wicker mat with a wooden ladel

As I was sitting in the sadness, I discovered the Buddhist practice of “inviting Mara to tea”. American Psychologist and Buddhist teacher Tara Brach tells a story of the “Demon God Mara, who attacked the then bodhisattva Siddhartha Guatama with everything he had: lust, greed, anger, doubt. Having failed, Mara left in disarray on the morning of the Buddha’s enlightenment.” However, Mara was not vanquished for long, and had a bad habit of turning up at the most inopportune times.

“Instead of ignoring Mara or driving him away,” Brach recounts, “the Buddha would calmly acknowledge his presence, saying, ‘I see you, Mara.’ He would then invite him for tea and serve him as an honored guest. Offering Mara a cushion so that he could sit comfortably, the Buddha would fill two earthen cups with tea, place them on the low table between them, and only then take his own seat. Mara would stay for a while and then go, but throughout the Buddha remained free and undisturbed.”

This is a remarkable story because it helps us to name our shame, claim it whole-heartedly as part of our human imperfections, and aim this knowledge into generous and generative spaces.

This is not an easy proposition, especially for those of us who are conflict averse.

The first step is to name the shame. Canadian author Ann Voscamp shares: “Shame dies when stories are told in safe spaces.” Writing gives discomfort a narrative shape, and by doing so helps me understand the contours of the shame so I can learn from it.

Next, we can reflect on the advice from Nigerian scholar and public intellectual Bayo Akomolafe: “The times are urgent; let us slow down.” Pausing to reflect on the context within which we find ourselves helps to locate and centre the discomfort. In my case I had to grasp the concept of the scarcity model and recognize how I had been unwittingly reproducing shame-based systems. (Let me tell you, that was a hard guest to invite to tea).

And then, and only then, can we aim this discomfort into new spaces to do better and be better. Once I understood the shape of the problem, I could design systems that value the spirit of curiosity, critical reflection, and open-mindedness.

No one needs another management course from a team of well-meaning consultants.

We already have the language within the academy to become better bosses.

We have design principles in the scholarship of teaching and learning: Students as partners (SaP) scholarship warns against the dangers of erasing power differentials. UK scholars Healy, Flint, and Harrington (2014) argue: “Building partnership learning communities requires critical reflection on and consideration of key issues within specific contexts of practice:

• inclusivity and scale

• power relationships

• reward and recognition

• transition and sustainability

• identity (8).

While I have worked extensively with the students as partners model in my teaching and educational leadership , I did not initially connect the dots in managerial spheres.

Brown's BRAVING acrostic via

We have access to research-informed leading practices. Brown’s BRAVING framework – a result of a huge body of research – provides excellent tools for building trust, combatting armoured leadership, and upskilling for difficult conversations. The BRAVING is an acronym that outlines the key values for healthy work cultures: boundaries, reliability, accountability, vault, integrity, nonjudgment, and generosity.

As a failed first boss, I have become an intentional and reflective second boss.

For one, I listened to Brown when she said: “leaders acknowledge the fear and uncertainty, they name it, they normalize it, with the goal of not leveraging it or using it, but de-escalating it.” Before, I named the messiness and disruption of building a movement but did not de-escalate or mitigate the emotional and cognitive labour of working in flux.

In my second time around, I have been careful about setting clear boundaries, spending more time onboarding, sharpening my focus on ongoing training, paying more attention to clear expectations and deliverables, and designing regular performance assessments. Most importantly, my new team has regular and consistent access to me. Onboarding now includes explicit discussions on how to collaborate across complex organizations, how we ground professional behaviours in shared values and social norms, how to upskill for difficult conversations, and guidance on what corporate stewardship is and why it is important.

When the academy is run by people who are not trained to be bosses, toxic cultures flourish. But when we slow down, centre ourselves in our discipline, listen to experts, and anchor our values in daily practice, we create the conditions and systems where all bosses and employees at Hope University can flourish.

Works Cited

Akomolafe, Bayo. “The Times are Urgent, Let Us Slow Down.” Victoria BC April 26, 2019,

Brach, Tara. Radical Acceptance (2003).

Brown, Brené. “Daring versus armoured leadership, Part 1.” Daring to Lead Podcast.

--. Braving the Wilderness: The Quest for True Belonging and the Courage to Stand Alone

Healy, Mick, Abbi Flint, Kathy Harrington, “Students as Partners: Reflections on a Conceptual

---. 2014. “Engagement through partnership: students as partners in learning and teaching in


Riddell and Langevin, “Designing for transformative learning in covid and beyond through

student partnerships.” April 26, 2021


Sivers, Derek. “Talk How to start a movement.” TED talk 2010.

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