Listen. Active listening is strikingly rare. It isn’t always required for day-to-day interactions, as we’re often more interested in information exchange and gathering the data and details that we need to function. But when trying to connect to people, we need to listen differently. We need to focus on making people feel seen, heard, and understood and not just on solving their problems.

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 Stephanie Judd and Kara Davidson.

Stephanie Judd and Kara Davidson are the founders of Wolf & Heron, a leadership development firm that leverages expertise in social psychology, influence, and facilitation. The partners have over 40 years of combined experience developing and delivering corporate training programs, public workshops, and executive coaching. Since launching in 2017, Wolf & Heron has rapidly scaled while attracting high-value clients in product management, sales, and marketing roles.

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?

Kara: One of the first times I was lead on a project, I was on my way to Atlanta for a work trip. In the airport terminal, I realized that I had left my laptop behind. Without getting into too much detail, I knew I needed to retrieve that laptop and get on a plane to meet with a bunch of executives. I decided to ask my CEO for a favor: “Will you get my laptop for me…and bring it with you to Atlanta?” Several hours later, he shows up to the office, laptop in hand, walks up to me and says, “Anything for the team.” That’s the type of team player AND the type of leader I want to be.

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?

Wolf & Heron: For us, as entrepreneurs, the way our business needs to respond to the market is always changing. That said, it was important to us to lead the organization with a set of shared values. We believe that by aligning on, communicating, and deeply knowing our values, we have a blueprint by which we can make decisions. Our values are our compass–they show us the way. By being aligned on our values, we can trust each other as partners, and our team members all know what to expect from us and what we expect from them. Also, because we made an intentional choice to operate by values that align with our personal ones, we are able to do business authentically and purposefully.

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

Stephanie: This is a question we often get when coaching leaders. I see a leader as having to wear many hats. The managerial hat is the administrative one. A manager focuses on checking the boxes, accomplishing the tasks, and reporting up and down the chain of command. The coaching hat is one that’s about creating connections. Good leaders are able to build relationships with their team members, their colleagues, and their superiors that are authentic, and help center the other person. By making those around them feel seen, heard, and understood, they empower these people to be the best versions of themselves.

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?

Stephanie: Earlier this month, I gave a talk on making people feel seen, heard, and understood. It’s one of the most valuable experiences a coach can provide a client, and often underdeveloped in leaders. When I coach leaders on how to more effectively make their team members (or rather everyone in their life) feel seen, heard, and understood, we focus on three key skills. The first is developing a discipline around designing relationships to be intentional, articulated, and flexible. The relationship is the container for the work achieved together, so a regular habit of checking in on the health of that container is crucial. The second is learning to listen deeply — to what is said, what is not said, and the energetic shifts underneath the words — and reflecting back what is noticed. The third is developing a deep sense of curiosity that is aimed at being exploratory and forward-oriented rather than information-seeking and solution-finding. I spend a lot of time working with leaders to help them refine the skill of asking powerful questions in extemporaneous conversation and resisting the urge to immediately provide an answer or solution to the problems that are brought to them.

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?

Kara: I ask powerful questions to better understand where people are coming from. What do they value? What are the outcomes they hope to achieve? Asking those questions helps in two ways. Firstly, I can consider and recommend some potential professional development solutions that will get them to where they want to go. Secondly, they can start to answer the questions for themselves, and self-identify the solutions. People are always more likely to trust their own conclusions. Professional development is something that can be a total waste if the people going through it don’t believe in it. When people are not just financially, but rather emotionally invested in their development, they’re more likely to see growth and a return on that investment.

Stephanie: I find that the best strategy is to model the skills. I know that my ability to inspire others through skills like building rapport, storytelling, and asking powerful questions showcases how effective those skills can be and motivates leaders to upskill in those same areas.

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?”

Design the Alliance

The first step is to get intentional about the relationships you have. Every leader should design an alliance with each person they interact with. Simply put, this is about creating an intentional, articulated, and flexible contract between both people that supports and empowers each other. The relationship is the container for the work that is achieved together.

Start by crafting the vision for your relationship; you get clear on what you want to DO, but more importantly, on who you need to BE as an individual and in a relationship with the other, to get it done successfully. And you make it crystal clear and explicit by writing it all down. This may mean discussing how often you will meet, what is expected from each of you, what each of you seek out of the relationship, and more. The second, and probably more important, step to designing a relationship well is ensuring that you check in on the health of that relationship frequently. Coming back to a conversation about what is working and what isn’t allows the relationship to stay flexible, respond to the changing environment, and thrive.


Active listening is strikingly rare. It isn’t always required for day-to-day interactions, as we’re often more interested in information exchange and gathering the data and details that we need to function. But when trying to connect to people, we need to listen differently. We need to focus on making people feel seen, heard, and understood and not just on solving their problems. Here’s how you can truly listen:

  • Focus on the whole person: what is said, and what is not said.
  • Listen below the surface: what makes the person come alive or withdraw.
  • Get out of your head. Don’t worry about what you should say next.
  • Stay unattached to being “right.”

Limit your words to restating what you hear or noticing the mental and emotional experience of the other person. This is a fundamental and powerful way to make a person feel seen and heard.

Ask Powerful Questions

One of the most transformative coaching skills is the ability to craft and ask powerful questions in extemporaneous conversation. If you want to help people move forward, focus on asking questions that begin with the words when, where, how, and sometimes what.

  • What would make you feel successful?
  • Where might you start?
  • How will you evaluate your options?
  • When will you know you’ve found what you’re looking for?

These questions are also future-oriented. They’re not designed to get the other person to simply rehash the past and tell you about things they already know.

Be Willing to Be Vulnerable

People do great work for the people they care about. Leaders who are willing to show their authentic selves to their people, and connect with them on a human level, are more likely to galvanize and inspire them. No one likes an overdog. Leaders who never share their own mistakes, growth moments, fears, and challenges, and instead convey an image of themselves as infallible and always prepared with the answer, are simply unrelatable; they won’t get a team to follow them, especially when the chips are down.

Create a Culture of Feedback

Leaders, when stepping into more of a coaching role, often struggle with feeling like the time spent with the coaching hat on simply isn’t “valuable.” Sometimes the conversations feel like they’re landing flat, or they have to pull teeth to get the other engaged in the conversation. If this is the case, there is a way out of it. Leaders should show their employees — and anyone they coach, for that matter — that they are interested in feedback. And like all feedback, it’s better served when shared in a timely and frequent manner. Every few meetings, ask your employee, “During these conversations, what do you find works particularly well for you? What value do you get from them? What would make them a more valuable use of your time?” Take that input, and then redesign the relationship to experiment with new ways of working together.

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?

Kara: Leaders should have authentic curiosity about their employee’s perspectives and acknowledge that their own perspective is just that–their own. As a leader to a multi-generational workforce, the key is to foster trusting and authentic relationships so that you can then ask each employee questions like, “What can I do to better support you? Where do you see yourself at this organization in the future? What excites you? What do you hope to learn from your colleagues?” and more. Each person is going to have a unique set of answers and responding to those answers in a way that shows you truly heard them is both radical and revolutionary; the best way to activate the collective potential of a group is to treat each person in that group as an individual.

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?

Kara: Once again, I’d come back to active listening and powerful questions. The best way to make people feel seen, heard, and understood is to listen to them wholeheartedly. Acknowledge their experience, reflect it back to them, and point out who you see them being in the midst of that experience. Then, ask questions that are aimed at getting them to think in ways that are new and different.

Leaders who treat their employees as humans and make them feel seen, heard, and understood are stronger support systems for their team members.

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

Stephanie: “What else?” This is one of my favorite coaching questions, and one that leaders should ask more often. When a team member shares a challenge they are having, asking this question encourages the team member to continue to explain and provide color. This gives the leader more context and a better ability to see, hear, and understand the team member. When the conversation moves into what to do about the challenge, the question puts leaders in the position of being exploratory and empowers their team members to generate ideas and solutions that resonate for themselves.

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

Wolf & Heron: “Fail fast.” As entrepreneurs, experimentation is essential. It can be so tempting to huddle inward and try to create the perfect product or service before releasing it into the wild. But the thing is, you can’t create the perfect thing without getting input from people. So, it’s important to find opportunities to fail fast and learn.

This applies beyond the world of product development though. It’s interesting to apply it to relationships as well. When we talk about designing the relationship, it’s fun to frame things as experiments to try. This forces a check-in mechanism for the relationship and allows for both parties to iterate along the way rather than get stuck in patterns that don’t serve the broader goals.

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?

Wolf & Heron: The best way to stay abreast to what we’re doing and what’s coming up, is to sign up for our newsletter at If you’re interested in some fun tips, tricks, quotables, and the sort, our LinkedIn feed is the place to be.

Thank you for giving us the opportunity to experience a leadership master at work. We wish you continued success and good health!