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How to be a Kind Leader in an Unkind World

How to be a Kind Leader in an Unkind World: A Manifesto

A Manifesto for educational leaders, non-profit directors, and others in the helping professions wishing to become a kind leader

To be a kind leader, Stay Kind Now.

Yep, that’s it.

Just Stay Kind Now.

To yourself, to others, to the world.  Be present in the moment, determine whatever act of kindness the moment may call for, and then look for your next opportunity to improve the world.

It’s that simple.

That challenging.

And that necessary.

Because when you are overwhelmed, overworked, short on time, money, and morale, kind leadership can guide you out of the maze and into a better world. Read on to learn what kindness truly is (you may be surprised), how it applies to leadership, and the six skills needed to become a kind leader.

Table of Contents

The Problem of Leadership for Kind Leaders

I’ve always wanted to be a kind leader, though I’ve only recently started using that phrase. I’ve spent over 15 years in higher education, about half of that in leadership positions. I worked my way up from the library front desk to the Dean’s office, earning a Masters and PhD on the side. 

In that time it’s become all too clear what educational leaders do right and what we do wrong. We need to change in order to sustainably make the world a more effective and humane place for those we lead and those we serve.

The Problem

As leaders who proudly (and occasionally smugly) prize impact over salary, we give our jobs 110 percent. We dream big in the face of scarce resources and dubious stakeholders. We care deeply about fixing or reforming our schools and communities. That’s because at times it truly feels like we hold their fates in our hands. 

Unfortunately, if you were trying to develop a recipe for workaholism, burnout, toxic team dynamics, vocational awe, cynicism and general failure, the mindset above would get you pretty close. 

Throw a pandemic on top, and almost any team or leader will be on the brink of collapse.

Where does that leave the average educational, nonprofit, or other mission-oriented leader? One who’s overwhelmed, overworked, feels attacked on all sides and is sometimes too paralyzed to make a decision? They want to help their team do great things and leave their communities better off, but there’s resistance and unforeseen crises at every turn. 

Many of us are barely treading water these days. All too often there’s nobody who is both able and willing to throw us a life preserver.

The Solution

The solution, of course, is held by other educational leaders. They have made it through one (or more) of those crises, and learned a healthy sense of perspective along the way. They know that it’s essential to put on their own mask before helping others, that empowerment defeats drama and advocacy beats office politics. 

Whether it comes to their strategy, people, systems, or resources, these leaders have a clear-eyed understanding of where they stand, where to go, and the decisions needed to get there.

These kind leaders aren’t saints or geniuses. They are simply practitioners of one or more of the key leadership skills that I’ve identified as crucial to accomplishing great things without burnout and drama. 

I’ve spent the last few years of study and real-world practice trying to figure out their secret sauce, and the Kind Leadership Guild is the result of what I’ve learned. It’s a model and community of practice that any leader can use to become more humane and effective in everything they do.

But before we go much further, we need to define some terms and clear up some misconceptions.

What is Kind Leadership?

 

Defining Leadership

For the purposes of this manifesto and this project, I define leadership as the work of individually and collaboratively making decisions focused on:

  • identifying systemic and cultural areas for improvement,

  • making strategic plans to do so,

  • mobilizing needed teams and resources to their best advantage, and

  • fulfilling your organization’s mission.

Pretty straightforward, right? It actually owes more than a little to Bolman and Deal’s four frame model of organizational leadership . As more of a practitioner than a theorist, I tweaked a few things here and there, and added a lot more emphasis on decision-making. As I’ll discuss in more detail further down, I believe that arriving at and executing solid decisions is the essence of leadership.

Defining Kindness 

Next up, Kindness is acting in an effective, humane manner with the goal of creating a better world for yourself and others.

If you’re like me, you probably haven’t really thought of what kindness is, though you know it when you see it. 

Add up enough acts of kindness over the course of a life, especially if you use a force multiplier like working or leading in education, nonprofits, or other “helping professions”, and with a little luck you’ll leave this campsite called Earth a little better off than you found it.

That said, kind intentions are not the same thing as kind impact, especially when one is in a relative position of power or privilege.

Most dictionary definitions of kindness don’t really consider the issues of effectiveness and humanity. However, in my opinion they are vital to ensuring that what you intend as an act of kindness is received as such. Consider whether a given action is going to be effective at the end goal of improving a situation, while also helping the person for whom you are acting to feel more visible, valued, and empowered as a human being. By doing so, your actions will be far more likely to impact the world both effectively and humanely.

Defining Kind Leadership

Now, combine these definitions of kindness and leadership, and we have an approach to leadership that has transformed my career and those of other leaders:

Kind Leadership is the art of consistently making humane, effective decisions in the present moment that could uplift and improve an organization’s strategy, culture, systems, and resources in service to the wider world.

Being supportive of a struggling team member is kind. So is setting clear boundaries and expectations and enforcing them. Encouraging your team to dream big is kind, but so is reminding them to work within the constraints of limited time and money. Pitching in to help with a crazy deadline is kind, and so is taking a break afterwards to replenish and celebrate.

Simply put, consistently leading with kindness in the moment (or “Staying kind now”, as I shorthand it) has the power to change the world.

Why does Kindness make for a better leader?

Now that we’ve discussed what kind leadership is, it’s time to consider three key reasons why it works so well in the messy and unkind world we inhabit. 

A Decision Framework

First, it gives you a framework to make decisions. 

I would actually argue that decision-making is the essence of leadership, both personally and professionally. Even if you’re not responsible for anyone else’s life or work, you are responsible for yourself. You have an obligation to make the decisions that will help you lead the most fulfilling life possible for yourself, those you know, and those who come after you.

“Perfect Decisions” don’t exist

Second, any leader focused on making decisions that uplift those people they lead and serve will quickly discover a key truth about leadership, and perhaps life in general. 

There is rarely, perhaps never, such a thing as a “perfect decision”. 

All decisions impact the world in both ways you can control and anticipate, and in ways you never would have guessed in a million years. To build a better world, you must overcome your hesitance and make peace with the 97% “right” decision, as well as, all too often, the one you judge to be about 50.1% correct. 

And then you will have to live with those “good-enough” decisions and make new “good-enough” ones based on what happens next.

A Kind Leader Avoids the Extremes

By balancing effectiveness at strengthening the organization’s efforts at building a better world, while also supporting and strengthening your team members’ abilities and morale by honoring their humanity, kind leaders naturally avoid the extremes. Rather than becoming too accommodating or too dictatorial, too cautious or too foolhardy, leaders take an approach of radical candor, and progress as the situation and their team indicates. 

In other words, you give people ample time and support to board the bus, but ultimately it will leave for its destination.  

The Six Kind Leadership Skills

The Kind Leadership Model is what us overeducated types call a conceptual framework, but you should think of it more as a set of lenses or skills you can use to understand and address any leadership challenge from a perspective of kindness.

Most problems lend themselves more obviously to one or two particular lenses, but it’s good practice to always consider any leadership challenge through all six. If nothing else, the Kind Leadership Model will help you to look at a problem from new angles, get out of your preconceived notions, and potentially implement a more effective and humane solution to your problem. 

Note–As we go along, I’ll link to other articles I’ve written that touch on challenges related to each skill, if you’re ready to learn more. I also freely admit that each of these six skills has been influenced by the work of others, so I am going to link to my favorite leadership thinkers as well. Leaders shouldn’t work alone, and I include myself in that. 

Presence: Becoming aware of opportunities for kindness now

Presence is the skill of mindful awareness of the opportunities and threats found in yourself and the wider world. Before you can effectively make decisions that will hopefully lead to a better world for you, your team, and those you serve, it’s important to have a clear, somewhat dispassionate understanding of your internal and external worlds as they are right now. Otherwise you’re building on a foundation of clouds.

When we decide that we need to become more present to tackle a leadership challenge, there are three levels of observation that need consideration. The first (and most challenging) level is ourselves. What are you thinking and more importantly feeling about your leadership challenge? What story do you tell yourself about this challenge? Does that story match the facts?

The second level where we need to figure out how to be present is with our teams.  The challenge here is less about realizing whether there is a challenge in a given area than it about getting your team to open up about the challenge. Finally, once you’ve got a basic understanding of what’s going on with yourself and your team around your leadership challenge (and this can easily take a few days, weeks, or longer depending on the problem), it’s time to turn your attention to the larger organization your team operates in and the community that it serves.

 

Learn more about Presence:

Feel your feelings, THEN respond

Kind and “Nice” are not synonyms

Know Yourself–and Who You’re Not

 

My favorite thinkers about Presence: 

The Conscious Leadership Group: I’ve attended a couple of their workshops, and their book gave me “permission” to pursue presence when I was at a key turning point early on as a kind leader.

Brave Leadership: A beautifully powerful book that helped me process the fears that paralyzed me. I laughed, I cried, and it was certainly better than the film adaptation of Cats. (Too faint of praise?)

Angela Kelly/The Empowered Principal–Being a Higher Ed type, I subscribed to her podcast about a year ago to learn more about the K-12 world. Not only has she been illuminating on that front, her leadership thoughts are relevant to anyone.

Foresight: Developing values and goals that lead to a better world

Foresight is the skill of envisioning an organizational purpose, values, mission, and strategy that could facilitate a kinder world. After all, once you have become sufficiently present to know where you and your team are when it comes to your leadership problem, the next obvious questions are, “Where do we need to go, and how do we get there?” The answer to that question may shift as you proceed along your journey, but you won’t know until start exploring what the destination could look like. 

The heart of the skill of foresight is determining the “good-enough outcome” for whatever leadership challenge you are facing, so you can start creating a strategy to get there. A good-enough outcome must be something that is at least largely within your and your team’s control to achieve, will likely lead to better circumstances for you, your team, and your organization, and must be inspiring enough to motivate you and your team to leave your comfort zones in the present moment to try to achieve something that may seem beyond your reach.

 

Learn more about Foresight

Eyes Forward!

You’re Always Living your Values

It (probably) Won’t Matter in a Year

My favorite thinkers on Foresight

Simon Sinek: All of his stuff’s great, and I watch his youtube channel regularly, but my favorite books of his are The Infinite Game and Start with Why. Both are great explorations of Foresight.

Michael D. Watkins: His classic The First 90 Days was my manual for planning my first 90 days at my current position. Any successes were due to my following this book’s advice, and all screwups were due to me ignoring it. 

Empathy: Coaching for an effective, humane team and culture

Empathy is the skill of coaching your team to use their unique strengths and challenges to create a more humane and effective culture. It’s about putting yourself in your team member’s shoes, then taking them off again as you guide them to greater success in their work. This skill requires a delicate balance between your perspective and needs, your team member’s needs, and your organization’s mission and goals.

Empathy isn’t about giving your team member everything they want, or about your becoming a martyr to their desires or complaints. Empathy seeks to understand, support, and clarify matters by establishing a safe space for honest discussion of uncomfortable topics, helping people feel heard by practicing active listening, and gently coaching them beyond needing support and towards creating a solution to your shared problem. 

Learn more about Empathy

Kind and “Nice” are not the Same

To lead your team to Greatness, Stand Back

Listening Solves most Leadership Problems

Some People Just Won’t Like You

My Favorite Thinkers on Empathy

Patrick Lencioni: I’m going to start this one off with a disclaimer–I still find a some of his management fables a little corny, and occasionally dated. I suspect it’s a generational thing. However, they’ve been around for decades for a reason–there’s truth there. If you’re struggling with applying empathy, go for The Five Dysfunctions of a Team. Good stuff there on healthy conflict, listening skills, and setting boundaries, even if it’s a bit hokey at points. 

Liane Davey: The Good Fight will teach you everything you need to know about nurturing productive team conflict. Her LinkedIn is worth a follow too. 

Michael Bungay Stanier: I literally turned his Seven Coaching Questions into a bookmark and carried it in my moleskine for 6 months. The Coaching Habit was one of the books that inspired me to try to turn my little leadership blog into something more. And The Advice Trap reminds me to keep my yap shut for just a few seconds longer. I’m still working on that one, but I’ve learned some amazing stuff when i can manage it. 

Stewardship: managing limited resources for maximum impact

Stewardship is the skill of designing and administering systems that sustainably drive your team toward your goals. Time, money, and softer resources like information and political capital are the most important currencies used to run your teams, and you rarely have as much of them as you need. Stewardship focuses on developing systems to efficiently manage each one of those currencies to achieve your goals with the most bang for your literal and metaphorical buck.

Learn more about Stewardship

Time Management Series: What do you Need to Do?

Why is this Worth Doing?

Who are you Doing this With?

When are you Doing It?

Who are you Doing it For?

Have you Done Enough?

My favorite Thinkers on Stewardship

Greg McKeown: Greg’s book Essentialism: The Disciplined Pursuit of Less got me through the worst of Covid. 

Celeste Headlee: Celeste’s Do Nothing is a vital corrective for all of us workaholics.

Advocacy: identifying allies and partners in kind leadership

Advocacy is the skill of promoting stakeholder decisions that will give your organization additional resources to serve its mission. In other words, it’s about working with stakeholders to negotiate for the time, money, information, and political capital needed to go after those big problems, assuming that those are the issues your stakeholders want you to tackle. It incorporates self-advocacy, serving as an emissary and “translator” between your team and your organization’s leadership, and developing alliances with other teams and leaders in your organization and community.

Learn more about Advocacy

Criticism is Golden

Leaders Need Advisors

Understand Before you Sell (or Network)

My favorite Thinkers on Advocacy

William Ury: Like a lot of you, I suspect, Advocacy is my weakest skill. Ury was the co-author of Getting to Yes, an excellent negotiation primer for those of us who aren’t natural negotiators. 

Seth Godin: Oftentimes, the most important person you need to advocate for is yourself. As I was emerging from a dark period in my leadership journey, I read a book of Seth’s called The Dip. He said something that you don’t often see in a leadership book–that if the destination is no longer something you still want, it’s ok to change goals. Something about the honesty of that statement gave me the determination to carry on.

 

Determination: making and implementing decisions that could lead to a better world

Determination is the skill of arriving at and executing decisions based on the other five skills, with the goal of a more humane and effective organization and world. It incorporates both common definitions of the word, by first determining a solution to the problem you face, and then having the determination to get that solution out of your head and into reality. In my exploration of determination, I tend to focus on acceptance of change and growth as a necessary pre-requisite for making a decision, the important skills and resources needed to make any decision quickly, collaboratively, and/or well (pick any two), and the central importance of effectively and humanely implementing your decisions.

Learn more about Determination

If you’re Indecisive, Rest

Change slowly or quickly–but with Intention 

 There’s not Always a “Right” Answer

My favorite thinkers on Determination

Peter Bregman: I really waffled on which skill Peter fit the best, because his amazing book Leading with Emotional Courage is another key influence in what I’m doing here, and you can find traces of his work in my thoughts on Presence, Empathy, and even Stewardship. However, like the Kind Leadership Skills, everything in Peter’s work is ultimately focused toward building the courage needed in yourself and your team to take action. What’s more determined than that?

Shelley Archambeau: I’ve recently finished devouring her recent memoir, Unapologetically Ambitious. If you are determined to do great things against imposing obstacles as a kind leader (and I suspect you are if you made it this far), read her story and apply its lessons. 

Conclusion

Kind leadership can change the world. I’ve seen it in my own leadership practice, and in the experiences of those I’ve coached. But kind leadership isn’t a solo sport. You need help to be an effective, humane leader.

That’s why I have my monthly workshops (free to list members!), where we all come together to work through case studies of the same kinds of normal yet frustrating leadership challenges we face every day. And it’s why, every three months or so, I lead a small group of leaders through an 8 week coaching experience laser-focused on the problems they are facing right now. If either of these sound like your cup of tea, just enter your email below to learn more.

If we can build a movement of leaders devoted to making a better world for their teams and communities, maybe, just maybe, we can make this world just a little less unkind.  Are you ready to do your part?

Stay Kind Now,

Sarah

Hi, I'm Sarah!

I empower library and educational leaders to heal their workplaces and to build a more educated and informed world in the process. 

Learn more about me and how I can help you. 

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