Be compassionate and warm. Do not be a hard ass because you saw some romanticized TV example of “tough love.” That isn’t coaching, it’s boot camp. That may have its place in personal development, but workplace coaching requires empathy and compassion.

The number one leadership initiative in any organization today is improved coaching. Coaching empowers employees, empowerment drives engagement, and engagement drives performance. At its core, coaching is about transformation. Leading distributed teams requires transforming how we coach and changing our play calls and playbooks to get things done. As a part of our interview series called “Moving From Command & Control to Coaching & Collaboration; How Leaders and Managers Can Become Better Coaches,” we had the pleasure to interview Sean Kosofskky.

Sean Kosofsky is the Nonprofit Fixer! He is a coach, consultant, trainer, and strategic advisor. For the past 30+ years, he has helped a wide variety of causes, campaigns and candidates raise millions of dollars and transformed nonprofit organizations and leaders. Find him at

Thank you for joining us to explore a critical inflection point in how we define leadership. Our readers would like to get to know you better. What was a defining moment that shaped who you are as a leader?

I learned a lot about how to run nonprofit organizations by watching it be done poorly. My boss (and best friend) was a brilliant strategist but really struggled as a CEO. His addiction to alcohol almost destroyed the entire organization. Every day was a lesson in how an organization survives a shock to the system.

John C. Maxwell is credited with saying, “A leader is someone who knows the way, goes the way, and shows the way.” How do you embody that quote as a leader?

I don’t think leaders always “know” the way. We paint leaders as wise, but they don’t need to have all the answers. Holding leaders up on a pedestal may only reinforce the aura that they are naturally wise. Leaders make mistakes and should be able to course-correct like anyone else. Humility is a huge part of what leadership is about. That said, I do believe leaders need to model the behavior they hope to inspire and they should be patient and willing to teach, guide, coach and be committed to learning. I hope in my 30 years of nonprofit leadership I have held myself to high standards and inspired others to commit to a life of service.

How do you define the differences between a leader as a manager and a leader as a coach?

Managers are hired to get results. When you are managing work or people, the goal is to get results. In business, that can be revenue, but in nonprofits, it is mission attainment. I think coaching is a way of helping people get results and grow by seeing their own power and helping them overcome challenges. In many ways managing and coaching are interchangeable. You do need to let people grow and fail in order to develop them.

We started our conversation by noting that improved coaching is the number one leadership initiative in any organization today. What are some essential skills and competencies that leaders must have now to be better coaches?

I do believe coaching is underrated. There is only so much improvement to expect from training and managing. The biggest bang for your buck to develop high-performing and high-potential staff is coaching. Essential skills 1) You have to be OK with allowing people to fail…even spectacularly. The goal is that if you let an employee fail, they fail forward and learn something — and get better. Letting someone fail out of laziness or carelessness is not OK. 2) One of the most important parts of coaching is listening and observing. The way you structure your advice, feedback, and prompts are based on the real world, not some survey or questionnaire coachees complete 3) A third critical part of coaching is tackling mindset issues. People get hung up on the term “mindset” as if it has to do with lacking confidence. Mindset issues are ways we limit ourselves. Great coaches are listening for mindset issues that may limit an employee’s success.

We’re all familiar with the adage, “You catch more flies with honey than with vinegar.” How are you inspiring — rather than mandating — leaders to invest in upskilling and reskilling?

Vision. You need to inspire people to want better for themselves. Many employees are already motivated, but you sometimes need to show people a vision of what’s possible for them and it helps them reassess where to spend their energy. It can’t always be about money or notoriety. Sometimes it is really about making the world better and solving problems. Sometimes that means helping people see that their long-term value is not working where they are now!!! In nonprofit organizations vision isn’t just about social change, it is also about building confidence and transforming yourself for your career and for your family.

Let’s get more specific. How do you coach someone to do their best work? How can leaders coach for peak performance in our current context? What are your “Top 5 Ways That Leaders and Managers Can Be Effective Coaches?”

Each person is different. If I am coaching a fundraising professional, they will get different advice than a communications director for a lobbying organization. But to get specific, here are 5 things managers can do to be effective coaches. 1) Be compassionate and warm. Do not be a hard ass because you saw some romanticized TV example of “tough love.” That isn’t coaching, it’s boot camp. That may have its place in personal development, but workplace coaching requires empathy and compassion. 2) Authenticity matters. People don’t want platitudes and buzzwords. They want real-life stories and lessons and the messy way things worked themselves out. 3) Make time: You need to schedule dedicated time to coach. Doing it on the fly will shortchange the experience. Will good coaching happen on the fly? Yes. But good managers make time to develop their people…with an appointment. 4) Mindset, Toolset, Skillset. These three areas must be addressed. Tackle the limiting factors. Use devices and tools to give shortcuts to the coachee and have them practice and role-play so they get better. 5) Spend money. You may have to put a budget behind coaching if you want to see change. That may mean classes, courses, retreats, apps or subscriptions to things to deepen the learning.

We’re leading and coaching in increasingly diverse organizations. And one aspect of workforce diversity on the rise is generational diversity. What advice would you offer about how to effectively coach a multi-generational workforce? And how do you activate the collective potential of a multi-generational workforce?

In some ways, all workers have similar aspirations and goals. Some are just closer to retirement or have seen many a wide variety of organizational situations. I have managed interns and later career subject matter experts. Managers cannot manage or coach everyone the same. Each employee needs a customized approach while using the same knowledge base. People aren’t widgets. We must help them based on the organization’s goals and their own.

You’re referring to emotional intelligence, in a sense. What are two steps every leader can take to demonstrate a higher level of emotional intelligence?

Emotional intelligence is rooted in empathy and humility. We must appreciate that people have a very wide range of experiences. One worker may speak four languages and have come to the US as an asylum seeker. The next person may be struggling in silence with a pre-existing condition, or trauma. Radical curiosity is key. Suspend judgement. Smile. Lean in and be curious about people. Demonstrate compassion and employees will be more likely to open up.

Words matter. And we’re collectively creating a new leadership language right now. What are the most important words for leaders to use now?

I don’t love the premise of this question. Words matter. Actions matter. Gestures matter. Body language matters. It all matters. We tend to think the time we are living in is exceptional. It is not. For me, to meet the moment, you must be committed to dismantling racism, sexism, ableism and homo/transphobia. That is the single biggest signal you can send that you are a trusted coach…even to white cis-hetero men.

I keep inspiring quotes on my desk. What’s your favorite “Life Lesson Quote,” and why does it mean so much to you?

I have so many. But my favorite right now is “Rigid structures crack” from I.F. Stone. Have standards and morals, but be flexible in leadership.

Our readers often like to continue the conversation. What’s the best way for readers to connect with you and to stay current on what you’re discovering? Join my email list or follow me on social.

Thank you for a meaningful conversation. We wish you continued success with your mission.