Introducing Deena

I am Dr. Deena Kara Shaffer. I'm very unfancy about the whole doctor thing, so Deena's great. My pronouns are she/her. I will spend a lifetime trying to perfect the elevator pitch—can we just soften the anxious edges around that? It's hard to sum up a life and all that one cares about.

I am the CEO and founder of Awakened Learning. In this sweet business of ethical entrepreneurship, I teach and coach learning strategies, as does my growing team—to students of all ages, stages, years, programs, identities, and pathways. I also teach parents learning strategies, because learning happens a lot at home, and there's often friction around homework, grades, and unmet expectations, and attention that is fractured.

I want to include parents as nudgers and encouragers of the learner. I teach learning strategies to educators, chosen families, administrators, CEOs—anyone I can share learning strategies with, I do.

I'm also adjunct faculty at Toronto Metropolitan University, where I co-created and teach the Learning and Happiness course. I do lots of other things too, like writing. I'm the best-selling author of Feel Good Learning. My second book is coming out next week at the time of this podcast interview. I also speak, publish research, and do everything I can to sing from the rooftops about the alchemy and transformative power of learning strategies.

What Does Leadership Mean to You?

I am in a constant wrestle with leadership because I don’t like how it’s been performed on me or to me over the years in many different spaces. I’ve had leaders who were curt, who led from anger, from adrenaline and scarcity. You can’t do thoughtful work if everything is at go-times-a-thousand. No matter what you call yourself, you’re still two bodies in a room, sharing a nervous system.

I try to glean from those experiences the kind of leader I want to be. I'm much more interested in small L leadership—the kind enacted, not in hierarchical spaces. The principles that guide me are not prescriptive or finite—they may change a hundred times depending on what I learn and unlearn.

But I am forever guided by kindness—not to placate anyone. I am a punk human in every space—but kindness because I know life is suffering. I’ve experienced that, and I’m not interested in workplace dynamics that are complicit in more harm. People hurt enough from their personal lives and systemic roadblocks.

So I ask: how can I get the sh*t out of people’s way? That’s my interest in being a leader.

In formal roles—when I’ve been a director or manager—I want this person to be paid the maximum amount of money and have the best possible title, and I’ll put my body and my title on the line to make that happen.

As the leader of my own business, I insist on paying people excellently, being super transparent with my team and families, and creating many access roads. The families who come to see me are worried about their kid, and I don’t want to take advantage of that worry. I don’t use sales funnels, I don’t run ads—nothing salesy. It’s all word of mouth because someone’s life has changed.

If a family can’t afford one-on-one support, there’s group learning. If they can’t afford that, I say: don’t worry about it. Get my book for $18. I’m so interested in creating access. To me, leadership is about getting all the baggage out of someone’s way. Being the person who says “yes” to what others are driven by. That’s what I care about.

How Do You Lead With Empathy?

I was a director at York University for two years. I loved the team. I was in service and supportive. If someone needed to work from home because they had a sick kid, the answer was yes. If their partner worked night shifts and they needed flexibility outside the formal hybrid arrangement, the answer was yes.

Does it make your life easier? Does it make your work more doable? Then the answer is yes.

Some people would say, “Aren’t you worried about being taken advantage of?” I’m just not going to spend my minutes worrying about that. The alternative—being hard-nosed and creating more rigidity? No thanks. I’m going to trust in 99% of people’s good nature and say yes.

How Do You Engage and Motivate Learners and Your Team?

For me, in every direction, it always starts with relationship at the centre. I would never start a meeting with action items before asking how people are doing and what’s top of heart and mind.

There’s no point in sharing a strategy with a learner who’s coming in absolutely stressed, rushing, racing in. They need a moment to settle and know that you are human, that they can connect with you.

The best strategies come out of an encounter that is deeply relational. I know this in my bones, thanks to the brilliant work of Indigenous educators I've been lucky to learn from. If decolonization is to mean anything—not as a checklist but as a lived practice—then relationship and the time invested in relationship is the first principle.

I don’t use people to get clients. I don’t use strategies to “convert.” I don’t even want to use that language.

Parents and families come to Awakened Learning because they hope something will feel different. They’ll feel different in how they’re met. Their student will feel different in how they’re served. And that happens—over and over again.

Students who say school is so hard—when they are met with zero judgment, zero shame, zero “you should already know this”—they shift. Think about how we talk about time management and procrastination. “You should just manage your time better.” Well, if it were easy, people would already be doing it!

There’s no singular way. I think the Awakened Learning strategist team sits in that space with the student. By the end, the student walks away with a whole toolbox of strategies—but it’s born out of relationship first. Being really heard, non-judgmentally—that’s where it all starts.

What are you driven by?

I’m driven by the desire to somehow participate in both creating less harm and creating more ease—for humans everywhere. The way I can do that is through something related to how learning and teaching happen—for everyone involved in that experience: students and learners themselves, parents and chosen families, the people around a learner, educators, and decision-makers or leaders. All of those people are part of what I think about when I consider the work I want to do. It all comes back to creating ease.

What is a piece of advice you might offer that you wish you had heard when you were younger?

First, for anyone who’s looking around and thinking it seems like other people are "making it happen"—whether you’re seeing just snippets of their story or it looks like things are unfolding easily for them—be really clear that it’s never linear. There are always layers of stories: who gave them a helping hand, who slipped them a few extra dollars, who championed them, who they knew, what they fought for over the past 12 years to make something happen. There are always so many unseen layers. So just know: what it looks like is never what it is.

And second—and I’m learning this in middle age—sometimes we find ourselves looking for the grown-up in the room. And that “grown-up” could be any age, but we think: Somebody’s got to know the answer. Somebody’s got this figured out. But… not a chance. Nobody does. There is no grown-up in the room. I’m not saying that because I wish other people knew it—I’m saying it because I’m still learning it, over and over. And when I find myself thinking everything is chaotic, or how is this so messed up, I start searching—maybe it’s this podcast, this mentor, this class, this person’s advice—but what I keep learning is: we’re all still figuring it out.