The Learning To Lead Show with Mark J. Cundiff

#19 From Discouragement to Empowerment: Five Strategies for Leaders. Reflections on my Conversation with David Pennington

• Mark Cundiff

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In this episode of the Learning to Lead Show, host Mark Cundiff reflects on his conversation with David Pennington. The discussion centers on key leadership lessons and insights from David, focusing on the importance of aligning work with passion, aiming for an 80% sweet spot in job roles, maintaining clarity and structure within organizations, adapting leadership styles to meet individual team members' needs, and ensuring a business's value isn't solely dependent on its owner. Mark summarizes these five takeaways and encourages leaders to apply them to enhance their effectiveness.

00:00 Introduction to the Learning to Lead Show

00:21 Guest Introduction: David Pennington's Diverse Leadership Experience

01:16 Key Takeaway 1: Understanding the Source of Discouragement

03:20 Key Takeaway 2: Aim for the 80% Sweet Spot

04:24 Key Takeaway 3: Clarity Beats Chaos

05:57 Key Takeaway 4: Adapting Leadership Styles

07:07 Key Takeaway 5: Building a Business Independent of the Owner

08:11 Conclusion and Call to Action


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LeaderNotes is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one.


Contact Mark at: mark@markjcundiff.com

Hello, welcome to the Learning to Lead Show. I am your host, mark Cundiff today's episode's gonna be reflections on my conversation with David Pennington Pebbles in the pond, coaching leaders who multiply impact across their organizations. I'm give you five key takeaways that I got from my discussion with David. One of the. Overall impressions I got was the fact that David had been both involved in the front lines of leading organizations, both in the church world and working at a school system, both public and private. He had experience in those sectors that enabled him to get a broad. View of different types of leaderships and different types of situations. Then the third area that he worked in was coaching and consulting small business owners. He's done a lot of that over the past decade. And so he has a perspective of looking at it from both the inside of being a leader, running an organization, and then also from the outside as a coach and consultant who's trying to help leaders better drive results for their organization. The first thing that he talked about that really got my attention is about the source of discouragement. One of the things that I run into with my conversations with leaders is that they're discouraged about the things that they're facing, discouraged about the pressures that they have from above them. Discouraged about how some of their team members are performing or not performing. How to get great talent on their team, how to keep great talent on their team. Lots of discouragement out there in the workforce when leaders are trying to move the organizations forward. He cited one of the sources of that discouragement often comes from misalignment, and I thought that was a interesting take. I hadn't heard that specific take on discouragement before. He said it's not from weakness or not from. Being incompetent or able to do their jobs. Many times leaders are doing too much, often doing the wrong things, tasks they don't love and aren't wired for. That combo drains energy and what fuels quiet discouragement. So I thought that was a very interesting take for all of us as leaders to consider are we doing the things in our work, in our jobs, in our career, in our business? That we love and are really good at doing. If we get drug into things that we're not really good at, that we don't really love doing, that can lead to discouragement, disillusionment, and cause us not to be focusing on the things that can add most value to our organizations. Here's one quote from David. He said, when you're doing things you like doing and you're good at doing it, it exhilarates you when you're doing the wrong things. Depletes you. So ask yourself that question. Am I doing the right things in my business? As a leader, am I focused on the things that I love to do and am really good at doing and delegating or getting other team members to pick up the ball on some of the other things that you don't like doing. The second thing you talked about was aim for the 80% sweet spot in your work. In other words, he said healthy, energized leaders spend most of their time. Where passion and strength overlap. So he's saying, when you are discouraged, if you'll get to the point where you can spend 80% of your time on the things that you're passionate about, that you're energized about, this'll move away from being discouraged and energize you and enable you to be more valuable to your organization. They challenges leaders to intentionally design their role so that roughly 80% of their time is spent on what they love. And are really good at and systematically offload the rest. You can't come in one day and just drop the things that are being taken care of by you. What you have to do is systematically train people, equip people, hire the right people to take those things off and offload them over a period of time. He said, you need to be about 80% of your time and energy in what you love doing and what you're really good at doing. The third thing that he really highlighted was that clarity. Beats chaos. Clarity beats chaos. You need to structure, have clear roles, and have clear metrics that matters. He said, whether you're in a church, school or business, confusion thrives where structure is fuzzy. If you read the book. Build a StoryBrand by Donald Miller. That is the whole premise of his book that if you confuse, you lose. He's talking about that in the marketing world, but he also carries that over into his business coaching practice that he has, and he talks about if you confuse, you lose. If you don't have clear messaging, not only in the marketing world, but with your people in your organization, then there's going to be frustration. There's going to be disillusionment. There's going to be. People out of align with the goals and the practices that you want to be having take place in your organization. Dave Presses leaders to keep org charts current. Define roles by responsibility, not just task, and also attach clear metrics so people know what success looks like. If you were to go out into your operation, to your business and ask your different team members what does success look like for them, what would they answer? If they did have an answer, would that answer be in alignment with the things that you would want them to be doing? He goes, how are you going to be successful if you're not even clear about what you need to do to be successful? The fourth thing he talks about. His great leaders must adapt their style to their people. Great leaders must adapt their style to their people. Meeting leaders only know one way to lead and expect everyone to adjust to them. One of the things he does in coaching his people is uses the DISC profile tool and other. Personality and leadership's trait tools to help guide his leaders that he's coaching. Dave teaches that good leaders flex changing hats depending on who they're leading. So each person gets what they need to thrive. And this is much if you look in the sports world, how many times coaches have to address different players in different ways in order to get the maximum out of those players. She said, you don't need to lead everybody the same way. A much more effective way is to learn your people and adjust. Some people really thrive with public praise and some don't like to be put out in the spotlight. They would rather you come to them one-on-one and celebrate the success that they're having. So learn that about your people. Learn the personality style. What makes them tick and what will drive them to give you discretionary effort. Lastly, he said, if the business depends on you, its value goes down. So this is talking about small business owners who someday might want to sell their business, he has an evaluation that he does to help companies understand the value of their company with the owner and without'em, and what it would take for them to maximize that upon selling time. So he takes'em through a process of learning how to make sure that the business is not so dependent on them, that when they pull them out of the business, when it's sold, that the business goes away, that devalues the business, makes it less profitable when you go to sell it. He says, the more the business is built on you, the less value the business has. So that's some things that you can think about there when you're. A solo business owner or a business owner of a organization that you want to sell someday. Maybe you wanna sell and get out and retire and enjoy the success that you've built, but you don't have an exit strategy. Dave would be an excellent person to get in contact with to help you with that. So as we wrap up today, I just want you to think about those five takeaways. How do they apply to you? How could you apply one of those this week to make yourself a more valuable leader? As Craig Rochelle tells us, when the leader gets better, everyone gets better, and so it's my hope that you get some encouragement, get some equipping, and get some practical steps that you can take each week when you listen to the learning of the lead show, if you liked what you heard today, please go and subscribe. Also, make sure to give us a rating and share with your friends. These help us get the word out about the Learning the Lead Show and help us grow our audience. Additionally, make sure that you go and subscribe to Leader Notes. That gives you the leader notes of every episode that we put out. It gives you a summary, gives you some practical guides and steps to take to put into place what you've learned on the show. Go, learn, grow, and lead. I.