Listen more, speak less. We must engage in active listening with genuine curiosity (and no judgment) to fully understand where the coachee is coming from, the situation, and the unique perspectives and insights they may have to bring to the situation.

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 R. Karl Hebenstreit.

Karl is a certified Executive Coach, Organization Development Consultant, and international speaker who has over 25 years of experience coaching leaders and their teams (from Individual Contributors to CEOs in myriad industries and sectors) to work better together and consistently exceed their organizations’ goals. He holds a PhD in Organizational Psychology and has authored two books: “The How & Why: Taking Care of Business with the Enneagram” and “Nina and the Really, Really Tough Decision.” Karl is motivated by seeing his clients achieve their full potential, professionally and personally.

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 was fortunate to be promoted into a formal leadership role at AT&T at the early age of 28 years old, where I was entrusted with managing a US-wide program and its 27 employees. I soon came to realize that I needed to rely on the expertise, insights, and experience of my team members who were closest to the 1,000+ associates for whom we were responsible — that I couldn’t do it alone and that I didn’t have all, or even the best answers. It was then that I also had the epiphany that different people had different needs and responded to different leadership styles — and that it was my responsibility to get to know them, their needs, styles, motivations, and aspirations, and to support them in achieving their goals, while leveraging their strengths and developing them to achieve their and our organization’s goals.

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 mostly agree with John C. Maxwell that all leaders’ primary roles are to know and show the way, while serving as a role model of the behavior that is expected of all employees in the organization. I have found that Simon Sinek’s “start with why” and Marshall Goldsmith’s “What Got You Here Won’t Get You There” philosophies are key to making this happen. In addition to needing a “True North” to navigate towards, people need to know WHY they’re being asked to do what they do, so that they can better align their own personal values to the organization’s ask, as well as understand how their own role contributes towards the ultimate goal or purpose of the organization. Where I may present a caveat to Maxwell’s saying is that sometimes leaders don’t fully know the way, or even know the best path to get there. This is where engaging our diverse employees who are closest to the work processes and customers, and who we hired and developed because of this expertise, is even more necessary to help co-create the way (the HOW) and possibly even a better or more appropriate way than could have ever been envisioned by a singular leader. Directionality is good, as long as we don’t get fixated on what we may (arrogantly?) believe is the ultimate outcome — in today’s VUCA world, the WHAT changes constantly and we need to re-evaluate and change course to make sure we’re working towards the real WHAT that is developing. This contradicts the traditional “command and control” way of leading and, instead, requires humility, vulnerability, collaboration, and reliance on the knowledge and expertise of our employees, who collectively know better. And leaders need to also come to terms with the fact that the expertise that led to their promotion to leadership may not help them be successful at their new level, where they must now lead and manage others.

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

I personally differentiate “leaders as managers” from “leaders as coaches” by thinking of them as two separate and overlapping roles. Leaders as managers are there to ensure that goals are being co-created, understood, and met, and that all the administrative aspects pertaining to meeting organizational systems, policies, procedures, laws, regulations, etc. (i.e., recruiting/hiring/on-boarding, goal-setting, constant feedback, check-ins, performance management) are being addressed. Leaders as coaches are there to coach an employee to success by NOT providing all the answers, but by empowering and supporting their coachees to come up with innovative, creative answers on their own (or at least co-create them). Employees need to know when they are engaging with a leaders as managers or leaders as coaches, so that they can understand what to expect from the engagement; leaders need to be explicit about what role they are taking on and what the expectations of the engagement are. This will prevent (or at least minimize) confusion and frustration for both parties, and lead to better results.

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?

Listening is definitely the number one skill/competency that leaders need to develop and practice when coaching. This is related to holding the coachee in high regard (supporting their agenda, not yours) and being there to support their development and success. Listening with genuine curiosity to the employee’s situation, challenges, and insights, and then asking powerful questions to help the employee see the situation wholly (and, ideally, from a different perspective) are also essential to the coaching process, enabling the coachee to develop and grow through their own insights, epiphanies, and self-identified actions (which are more likely to be committed to and followed up on, rather than explicit advice/direction from anyone else). And, speaking of follow-up, following up on the commitments or agreements to action that the coachee has made is imperative to the success of the coaching relationship.

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?

In addition to “catching more flies with honey rather than with vinegar,” we also have to take into consideration the READINESS of leaders — their awareness for and openness to development, upskilling, and reskilling; their ability to recognize the important of keeping themselves and their employees relevant, competitive, marketable, and up-to-date (if not ahead of the curve of new trends and developments). This is also related to the question of “Why would you want to spend resources to develop your employees, only to have them stolen by your competitors?” (the answer, of course, being, “How can you afford not to have well-skilled employees working for you and your customers?”). As referenced earlier, Marshall Goldsmith’s famous book “What got you here won’t get you there” implores leaders to continuously assess what’s necessary for their success in their (new roles) and continue their growth and development accordingly, to ensure success as the competitive environment around them changes and their new roles require. Coaching is an excellent way to get leaders to see this point of view. Asking leaders what their challenges and pain points are, what keeps them up at night, and then diving deeper to get them to inevitably come up with (on their own) development, upskilling, and reskilling as the answer will speed up their readiness and ensure proper focus in this area.

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?”

Coaching someone to do their own work really depends on their own intrinsic motivation. I rely heavily on the Enneagram model as a framework of helping leaders identify their own core motivation, and then realize that their coworkers, direct reports, peers, and stakeholders may each be driven by one of eight other factors. This model helps leaders and managers be better coaches and feeds into the top 5 ways to do so:

  1. Gain a better understanding of yourself. Coaching requires an understanding of “self as instrument” — and this step is the building block of emotional intelligence. Self-awareness, understanding how one comes across to others — and why they behave the way they do — is a crucial component of coaching. We don’t want to shut down or coachee, put them on the defensive, and prevent them from benefiting from coaching.
  2. Gain a better understanding of others. Once we have gained self-awareness, we can then work on understanding that others may not (and, in actuality, DO NOT) experience or perceive the world from our point of view. There is diversity in perspective that we need to tap into and leverage to fully understand the world we live in, as well as provide insights into the business situations and challenges we are experiencing.
  3. Select the proper/most appropriate strategy and approach for each situation. Now that we have an understanding of our own default perspectives and can see how others’ perspectives differ from our own, we can choose how to best motivate and engage our people by speaking to what’s important to them. We can better connect with our people by speaking their language, showing that we have taken the time to listen and get to know them, and are in tune with their needs and perspectives. This fosters inclusion of diverse perspectives and ensures the most appropriate action forward in any situation.
  4. Listen more, speak less. We must engage in active listening with genuine curiosity (and no judgment) to fully understand where the coachee is coming from, the situation, and the unique perspectives and insights they may have to bring to the situation.
  5. Ask powerful, mostly open-ended questions to help the coachee generate their own insights and action. Ask questions with genuine curiosity, from a place of humility and seeking to understand, and NOT from a place of judgment or arrogance. No one knows it all by themselves. Ask follow-up questions to ensure accountability and action on agreed-upon plans.

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?

Talk to them. Take time to get to know them. Build relationships with them. Find out what’s important to them. What are their values? What are their hot buttons? Where is there common ground (usually around purpose or mission of the organization)? Be explicit about your intentions in communication. Create agreements about how/how often to provide feedback to each other so it’s not misconstrued as attacking or puts others on the defensive. Multiple generations in the workplace concurrently is not a new phenomenon — it has always happened. Stereotyping and implicit bias is also not new and has been happening since the beginning of time. We need to stop it by treating others as individuals and understanding and honoring their unique gifts and perspectives, rather than assuming they all belong to a certain group and are all the same.

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?

Totally. Going back to my previous answer about top 5 ways that leaders and managers can be effective coaches, the two steps that leaders can take to develop and demonstrate higher levels of EQ would require them to:

  1. Understand where they and their colleagues are coming from (what are each party’s drivers, motivators, core values, hot buttons/triggers, strengths, areas for development, blindspots, energizers, etc.). Ask questions to really get to know them and build the relationship, setting expectations and creating healthy alliances.
  2. Practice openness to and acceptance of the diversity of perspective and experience that each person brings. Tap into and leverage those complementary strengths to co-create amazing results that are greater than the sum of their parts (gestalt).

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

“What do you need from me right now?” This is a really important question because it allows the leader/coach to find out what’s going on with their coachee, without assuming that they already know. The answer could be about a personal or professional challenge the coachee is facing, and it can help the leader prioritize or reprioritize goals and expectations around the coachee’s needs. It can also lead to seeing that there may be a disconnect or misalignment in understanding of current priorities and create the opportunity for co-creating a better solution/direction. It puts the coach/leader into the servant leader role, which is ideal for ensuring a coachee’s success and growth.

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

It’s all about readiness. I keep coming back to this mantra to remind me that people need to be ready to undertake a journey of change, transformation, growth, and development. And if they’re not ready, it’s not a reflection of you or them. People become ready on their own timeline and on their own terms, when the pain of changing finally becomes less than the cost/pain of not changing (or the pain/cost of staying the same is greater than the pain/cost to change). They may not be there yet, and that’s OK. People have their own journeys of self-discovery and awareness. You can’t (and shouldn’t try to) force it.

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?

The best way to connect with me is via my website: — it has my contact information, links to my books (“The How & Why: Taking Care of Business with the Enneagram” and “Nina and the Really, Really Tough Decision”), as well as a wealth of free resources for career management. LinkedIn is also a great way to connect:

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