The Shortcut to Leadership Excellence
Interview with Scott Drake

Scott Drake

Scott Drake

Scott Drake is the Founder and Executive Director at JumpCoach, a social enterprise on a mission to make best-in-class leadership training available to everyone who needs it.

Scott’s journey into leadership was long, painful, and he made every mistake in the book. It took him 10 years to thrive as a leader and not feel like an imposter.

When he became a leader of leaders, he saw next-generation leaders making the same mistakes and having the same struggles. Selfishly, he couldn’t spend 10 years watching new leaders wreck his teams while they figured out how to lead, so he began searching for a faster way to teach leadership. That search turned into a five-year research project and the innovations that are now JumpCoach.

Prior to JumpCoach, Scott was Vice President of Technology for medical education disrupter ScholarRx, and his 25-year career includes stops at Microsoft in Redmond, Washington and start-ups in Silicon Valley.

For more about Scott, go to –


Read the Interview Transcript

Hugh Ballou: Greetings, this is Hugh Ballou, founder and president of SynerVision Leadership Foundation. We help leaders transform their skills to transform their organizations; therefore, we transform lives. SynerVision comes from the synergy of the common vision. As you know, leaders are the ones who hold the vision.

Our guest today is a leadership expert. He’s got some amazing things to share with us. Scott Drake, welcome. Tell us a little bit about yourself and your background and your passion for what you’re doing.

Scott Drake: Thanks for having me on. I really appreciate it. My background is I started out in life as a computer programmer. Like a lot of people, I always felt leadership was something I wanted to do. Leadership to me is working through others to get things done. You need things done, but you can’t or don’t want to do them yourself, so you choose to work through other people. The problem is I got into leadership through getting into some early positions, and I made every mistake in the book. It took me a few years to realize I just wasn’t a good leader. I was just making mistakes.

My passion for this came out of my desire to be a great leader and then failing. As I figured this out—it took me about a decade to figure out leadership, as I was promoted through the ranks at various companies—I had leaders working behind me who were making all the same mistakes I was. I looked at them and said, “I don’t have 10 years to watch you wreck my team while you figure this out, so there’s gotta be a better and faster way to teach leadership.” That’s what I did a five-year research project on. I left a role in medical education earlier this year to focus on this completely. This is where I will spend the next 15 years of my life, to really say how can we help people get better at this faster, get better at this skill of working through other people, instead of doing everything themselves?

Hugh: You may remember I come from a conducting background. The article in Forbes says about me, “What a musical conductor knows about leadership.” What does a musical conductor know about leadership? Well, it’s precisely what you just defined. We can wave that little stick all day long. Until somebody participates, we don’t have music. There are some similarities there. What is your special gift that you bring to the people who work with you?

Scott: Where I help the most is that I shortcut it. I looked at an engineer’s mind and said, “What is broken about this? Why does it take so many people so long to figure this out? Or, why do so many people not figure it out?” There is a lot of really good people who are not good leaders because they never quite make this shift.

My superpower is to help people shift quickly. That is about a mindset change. Also, we give them a scorecard, an equivalent of a map of the city of leadership that you now have to go explore. A lot of people struggle with leadership because they don’t have a clear picture of what it is. We solve what we consider a couple of simple problems, but they are really hard to get at through the 90,000 books on leadership on Amazon. You can’t find these shortcuts. We really do shortcut it so people can become effective quickly.

Hugh: The more time we waste, the more damage we can do. You were a computer programmer, did I hear that?

Scott: Yes, you did.

Hugh: I was in graduate school at 48, getting my masters in choral conducting. Half of the class were computer programmers. I said, “This doesn’t add up; this is the music space.” They said, “It’s the same skillset. You have an unforgiving structure. You have to be creative without breaking the rules.” It’s right/left brain simultaneously, which is a gift we bring as programmers and conductors to the workplace.

Talk about the relevance of strategy. A lot of people think that strategy is a waste of time, they don’t have time to do it, and it stifles their creativity when in fact I say, “No, that’s a container for your creativity. Now you can focus on being creative because you have this part worked out.” We haven’t talked about this. Talk about the relevance of strategy in your overall leadership skills. How do you make strategy come to life as a leader?

Scott: What strategy does is it makes sure you’re aware of all the moving parts. If you know there are nine levers, you know these are the only nine levers. A lot of people are overwhelmed because they think there are 80 levers. They don’t understand everything about it. To me, the more you can understand that these are the moving parts, and these are how they interact with each other, the more confident you can become, and the more creative you can become in how you play. You can see how Situation A requires you to respond in one way, and Situation B requires you to respond in another way. The more you can understand the strategy behind it, the more creative you can actually be, and the better results you will get.

Hugh: Everybody in leadership ought to teach middle school for a few years like I did. You learn a lot about leadership, like don’t turn your back on people, don’t pause too much, and don’t ask too many dumb questions.

Scott: You have to go where they are. You have to say, “What is going to get this person to do the things I want them to do?” It’s not about you and what you want them to do; it’s about them and what they want to do. You have to find a way to get them to do the things that you want them to do. It’s very similar to parenting as well.

Hugh: How you do anything is how you do everything, is what Richard Rohr says in his writing. Going back to strategic, there is the strategic plan for your operations so you know where you’re supposed to go. The leader says, “Here are the levers.” We don’t pull all of them because if we’re creative, we tend to want to pull a lot more levers and we won’t get anything done. There is that part about strategy. How do we become more strategic about ourselves in growing our skills?

Scott: Sure. Growing your skills is to recognize there is not one size fits all for leadership. Different leaders-

Hugh: Wait a minute. There’s not one magic pill?

Scott: No. There’s not one way to go about it. What works for Hugh may not work for Scott. What works for Scot with one t may not work for Scott with two. If you really want to be strategic, you have to recognize there isn’t a right way. A lot of people are looking for the right way to do something, and there isn’t a right way. It really is about the couple of foundational pieces that we help people put in place.

The first one is a mindset, shifting from what is called an expert mindset into a leadership mindset. The expert thinks they have to have the answers. They are trying to solve all the problems themselves. They want to be the heroes of the story. When you become a leader, you have to shut that off and recognize it’s your team who wants to be the hero of the story, so you have to become the hero maker instead of the hero. The first thing is to make that mind shift, recognize that you can’t be the hero all the time, and you don’t want to be the hero all the time.

The second thing is recognizing there really are these nine jobs and four goals. There is a scorecard we put together. Once you understand those two pieces, you have a foundation, and you can live within that foundation and be effective.

Then it’s a matter of over time saying, “What are the unique challenges I have? What are the opportunities I have? How do I need to adapt and adjust to meet the needs that I have uniquely as a leader?” That’s what we call wayfinding. That’s a process that we encourage people to get into, be in a continuous self-improvement mode so they are always adapting to their situation. When we talk about strategy and being a strategic learner and leader, it’s those three pieces coming together.

Hugh: What about people who say, “I read those books. I got it. I don’t need to study leadership.” How do you respond to that?

Scott: The challenges today are different than the challenges yesterday. Look at the work force today. You have a lot of people who have decided, “You know, the way we have looked at employment for the past 80 years doesn’t work for me anymore. I don’t want to participate in it.” Now we have this work force shortage. Your people are going to change. Your customers are going to change. Your industry is going to change. Everything about the world is constantly changing. If you don’t want to change and grow with it, you will become stagnant and get pushed out of the world pretty quickly. If you want to remain relevant and effective, you have to keep learning, especially if you’re a leader. You have to have fresh data to do what it is you need to do and that your mission is to do.

Hugh: You’re out there on the cutting edge, so you have to pay attention. That’s so important, Scott. What was true yesterday is different today. Our world really is changing fast. We are recording this in the latter part of 2021. We just had a massive exodus from the corporate work force. In September, almost 4.5 million people. I’m sure there are a number of them who said, “I’ve had enough of this. I want to do my own thing.”

Every year, half of the nonprofits that are founded will close. I think it’s a leadership issue. I’m a member of the Methodist Church. Before the pandemic, we were losing 1,200 people a week. That’s a leadership issue. Before the pandemic, 1 in 10 pastors would make it to retirement. They don’t have a track for leadership development in seminary. How do these people with great hearts, great purpose, running a community charity or religious organization, equip themselves with something they don’t get anywhere and maybe they don’t think is important?

Scott: Do me a favor. Rephrase that.

Hugh: A long question. We got people in the saddle doing really good work, but they are blind to the fact that they need to equip themselves to do the job they have been called to do.

Scott: Leadership is working through other people. If you look at Gallup studies, 10% of people are natural leaders. They are people who have a natural ability to work through other people in a healthy way, in ways that are empowering and encouraging, and people want to help them. There is about 10% of people who aren’t cut out to be good leaders. They may have some emotional or mental issues that they lack the empathy to understand people and help people. You have to want to help them to get them to help you. About 80% of us, we can learn it, but it is something we have to learn. We are not natural leaders, but we can definitely learn it.

But if you truly want to be effective working through others, if you want to amplify your impact, I can only do so much with my own two hands. I hit a point where I wanted to do more. I wanted to do things I couldn’t do with my own two hands. I didn’t have the skill or the desire to go develop those skills. I don’t have the time or energy to do all the things that need to be done. We just have to learn to work through others. It’s not a skill. It’s not something that most people are born with. Most of us are taught things growing up that make us bad leaders. They made us great workers. Hey, be the expert, find the answer, solve the problem.

As soon as you become a leader, that’s not your job anymore. You can’t keep doing that. You have to shift your mindset and objectives into something else. For those people, if you truly want to have an impact, if you truly want to do more than you can with your own two hands, then that is something you need to find. It’s not hard. It doesn’t take years to learn how to be a leader. It takes hours, weeks. It takes hours a week for weeks to get the foundation and the basics down.

Hugh: We’re in the work force. Everyone from that perspective sees it differently than the leader sees it. There is a difference in perspective. How do we accelerate our growth from this worker player to leader?

Scott: It is recognizing the mindset and accepting it. You choose. The biggest thing you have to do is choose. I choose to become a leader. I choose to start seeing the world and recognizing that how I saw the world before is not going to be as productive if my goal is leadership. I have to explore those mindset changes and be open to making them. You have to stop doing your old job.

A lot of us came up through the ranks. I was a great computer programmer. As soon as I became a leader of computer programmers, I had to stop being great at my old job. I had to say, “They are the hero of that story now. I have a new job, a new story.” It really does become about if you want to accelerate, it is a choice. It sounds simple, but it’s why emotional intelligence is so important. It’s why a growth mindset is so important. You have to recognize those triggers that make you want to fall back into that expert instead of letting you be that leader your team really needs you to be.

Hugh: Well spoken. Let’s go back to something you said a minute ago about learning the wrong things from the people who preceded you in your sphere of influence. What are some of the wrong things people have learned, and they try to emulate?

Scott: It’s not so much that I have learned the wrong things. It’s that when I was a kid, I was rewarded for getting good grades. If I work with somebody else, it’s called cheating. Hugh and I can’t always work together on this math test, or else I’m a cheater. My whole life, I have been rewarded for my individual efforts instead of collaborating with multiple people. That’s one of them. If you’re in middle school and have a question and go to an adult because they have all the answers. If you get your first job bagging groceries at the grocery store, and if you’re not sure what to do, you go to your supervisor. They are the supervisor because they have all the answers.

You get these false beliefs that the leader is the leader because they have the answers. What you end up getting into is you start thinking, If I am in the situation where I am the leader and I don’t have all the answers, is my team going to respect and trust me?” You start having some of these false beliefs that the trust or respect my team may have for me as a leader comes from my competence. Then what I end up getting in is a competency war with my team. I am trying to earn their trust through my competence, but they are trying to earn the trust of their boss, me, through their competence. We end up in a competency war. It’s that false belief of My competence is why I’m the leader, or the leader has to be competent, is what sets a lot of us up for failure. That’s what we have to unlearn, to move past so we can create space for our teams to be the heroes and for our teams to help us.

Hugh: It’s not your job anymore. Also, if it’s not your genius, it’s not your job. We have some of these myths that we say to ourselves about leadership. I hear people voice this one, “I have to be willing to do what I ask other people to do.” The operative word in that sentence is “willing.” You are the leader. What are some of the myths that really paralyze leaders in your experience?

Scott: A lot of it goes back to trust. You want to earn the trust of your team. David Horsager, don’t ask me to rally off his eight pillars of trust, but he wrote a great book called The Trust Edge. We want to be trusted and respected. We want the status of the leader. We feel like we get that through competency. There are a lot of other ways—clarity, being caring, generosity, looking out for other people—we earn the respect and trust of our team. Those are much better ways and much more effective ways, especially if you are building employee engagement, customer enthusiasm. Some of those things come much easier through those other mechanisms than they come through their own competence, which is where a lot of people feel like trust and leadership come from.

Hugh: Yeah. I like to say in some of my keynotes that we leaders actually set up problems because we haven’t thought through process, or we are not aware of the consequences of our decisions. How do you respond to that?

Scott: I agree. One of the big things is we teach leaders this concept called moments that matter. A lot of leaders are very unaware of the good or bad impacts that they’re having in very simple moments. If leadership is working through others, when does that happen? That happens in small interactions between people.

When I ask someone for help, that’s a point of delegation. When someone comes to me and says, “Scott, you asked me to do X. I’m confused, or not sure how to proceed. Help me get unstuck,” that is another type of moment that matters. Another is someone comes to you excited with an idea. They share that idea. You are wired as a human being to see every problem with an idea. As a leader, you have to recognize that and not just state all the ideas of what you think is wrong with the problem that the person is so excited about. You have to be curious and respond well in that moment that matters. Otherwise, what happens a lot of times is that we end up damaging motivation, relationships. We end up doing things that we don’t realize we’re doing.

A lot of times, we are trying to be helpful. People will say, “Scott, help me with this problem,” and I want to be helpful and help them with the problem. That is often the worst thing I can do. I maybe need to coach them through a process of problem-solving to help them get unstuck. But if I just give them the answer to the problems, then all of a sudden, they lost that opportunity for motivation, that opportunity to get that win for themselves. All of a sudden, I have the only brain that works in this organization in those small moments where good things or bad things happen, and the leader is often not aware of what they’re doing.

Hugh: Self-awareness is a big skillset. If you do a search, I almost used the G word, you’ll find 2.5, 3 million hits for leadership. You will find a huge number of resources. Lots of definitions of what leadership is. If you would catalog the styles, you have autocratic, transformational, servant leadership, authoritarian, charismatic, situational, transactional. Do you subscribe to any particular style of leadership that you teach?

Scott: We teach mostly in the direction of servant because our big focus is how do you build engagement? How do you get people to want to help you? The easiest way to do that 95% of the time is with servant leadership. It’s the idea that you’re going to let your team be the hero of the story. You will work through others to get things done. We talked a little bit about mindset. Some studies say that mindset is more important than style. No matter what your style is, if you’re thinking like an expert instead of a leader, if your mindset is wrong, then your style is less effective.

The other thing I found to be as important is the idea of mechanistic or organic management. Some problems are very routine, and you want to put processes in place; some are very creative, and you need to turn a team loose with the challenge. It’s about the ability to recognize when you need processes versus when you need to challenge your team. So we teach servant, but we teach that really heavy so they understand when processes make sense so they know when to put those processes in place.

Hugh: You mean you have to be flexible?

Scott: You have to adapt to the different situations you’re in.

Hugh: You talked about engagement with the team. How does the leader inspire a highly motivated, engaged team? One of the big challenges, especially with churches and nonprofit leaders, is engaging the board. How do you motivate and engage your team?

Scott: Fewer opinions about how. Lose the competency war. Challenge them to solve problems. You have problems that you need to be solved, but you don’t have the expertise a lot of times to go do them yourself. It’s really about saying, “This is the problem. This is how we’ll know a solution is good. These are the success criteria I’m aware of today. Go work on this problem.” But then be okay when they come back having done something slightly different than what you would have done. Recognize there is going to be a cycle there. They will go away and come back, and you will refine the standards. It may not be as efficient as if you would have done it yourself, but over time, you will get a lot more done if you can learn to let go and work through other people.

That is one of the big things. People get satisfaction, engagement by solving problems and helping you. So let them. Lose that competency war. Let them be competent. Let them be the heroes of the story.

Hugh: That’s a sound bite: Lose the competency war. Nobody likes a leader who is right all the time, do they?

Scott: They don’t like a know-it-all. Do you want to work for a know-it-all? Do you like sitting on a board with someone who knows everything and has all the answers? Scott is stupid and has nothing to contribute. You want to feel useful, and you want to contribute. A lot of times, we don’t recognize when we’re the ones keeping other people from contributing. So pay attention. Just start paying attention in some of those situations and pay attention to yourself. If you’re open, you may see that you do things that can be construed as stepping on other people’s toes, not letting other people have a chance to contribute.

Hugh: Is that about control or insecurity? Or are those the same realm?

Scott: It’s probably the same. A lot of people do go into leadership because they feel like they will get control. When I first got into leadership, yes, I can do things that I know how they can be done better. That’s okay to a point. I think it’s something a lot of leaders have to outgrow. I am happy with the solution that is effective, that gets the problem solved, more than I want the solution I would have done myself. You eventually learn that that’s what it means to be a leader.

Hugh: In the writing of Murray Bowen, psychiatrist, he has eight concepts of leadership. In those methodologies, there is the overfunctioning. The reciprocity of overfunctioning is underfunctioning. This is in the realm of overfunctioning. There is also the tension that when you delegate something, don’t micromanage. You want to mentor and not micromanage, if you agree with that. What leaders want to know is if it’s being done correctly. How do we monitor things so that we actually are satisfied that people are going in the right direction?

Scott: What is correct? If you can’t define “correct,” you can’t get anybody to help you.

I think there is a tension between efficiency and effectiveness, especially when it comes to delegation. I look at something that as a computer programmer, I could have done in two days. If I delegate it, I know it may take four or five days. I know that I am going to give this to them, ask for check-in points. Their work will go through six steps. At step #3, I want them to check back in with me to tell me what they have learned so that we can share what we’ve learned and adjust standards, trade-offs, cost factors, risk factors. We can do those things partially through the work, turn them loose, and come back for another check-in point. It will never be as efficient as if you had done it yourself, but you have to build these feedback loops and these processes into the work that you’re delegating off.

Hugh: It might be done better.

Scott: It will be. It may take a little longer. But then you get the thinking of other people. Your brain can only do so much. You can only be great at so many things. The more collective wisdom you can bring together and actually tap into, then collectively, things will be better, yes.

Hugh: I set you up for “What is the right answer?” One of the ways that leaders set up failure is not clearly defining the goal, what it looks like when it’s complete, and then mentoring people with the information they need to get there. Is that a way we set up the problem? Are there others around the lack of clarity?

Scott: I think a lot of management issues go back into lack of alignment. That is one of the key jobs we teach. If people aren’t aligned, that’s when you’re going to see people building the wrong thing. You will see people overbuilding, overengineering. You will see conflict between teams because person A and person B are working toward different standards. They have different goals in mind. If you are not clear on what the end state that you’re shooting for is, but also what is the quality, cost constraints, time constraints, that is where a lot of conflict comes from. Accountability issues often go to lack of clarity. I can’t hold somebody accountable if it wasn’t clear what it was we asked them to do. A lot of other management problems go back into that lack of clarity.

I want to say this again: You will never be perfectly clear at the outset. You have to have check-in points. You are always going to learn as you go through the process. You as a leader have to accept that I’m going to set you off right now with this. But in two or three days, we are going to know more. Come back and talk to me when we know more, and let’s adjust those standards, those trade-offs. Then come back again as you learn more. We are going to learn as we go through it. You can’t put the burden on yourself as a leader to be perfect when you delegate. It’s impossible. You can’t do it.

Hugh: That’s a great answer. That’s helpful stuff that people can take to the bank. Let’s talk about leaders and teams. I’m surprised to find even power leaders in corporations don’t want to do a course correction with somebody because they’re afraid of hurting their feelings. As the pleaser personality, they hem and haw around It, which sets up another failure because it’s not really corrected.

The analogy I use as a conductor is I stop the rehearsal and say, “Trumpets, that’s too loud. Take it down one dynamic level.” They’re not upset. They expect that. If I don’t do it, everyone is going to think, What is wrong with him? They’re in the back. They’re playing a loud instrument. I’m in the front. I’m the person with the perspective. Why are leaders hesitant to make those corrections you just talked about? What is some advice you can give people to be able to step up to that?

Scott: I don’t think anybody likes conflict. I don’t think healthy people like conflict, rather. There is the typical resistance to conflict that a lot of people have. And that’s okay. But it also goes back to accountability and the standards you set. A lot of times as leaders, we don’t have standards amongst ourselves as leaders.

One of my favorite exercises is to go to three people on a leadership team and ask them individually, “How do you know you’re doing a great job as a leader? What can you observe or monitor on a day-to-day, week-to-week basis that says, ‘I’m doing a good job. I’m a good leader.’?” Like you said, there are all these definitions of leadership. If the leaders themselves aren’t in agreement on what good leadership is, then it’s hard to hold each other accountable.

To me, one of the biggest things a leadership team can do is- We built a scorecard, and one of the biggest uses of that scorecard is it gives leaders a common language and structure to think about their jobs, how they balance their jobs. It puts them on the same page. It makes accountability easier. If Leader A isn’t doing this thing as well as we would expect, then we have something to base it on as opposed to just our own opinions on what leadership even is. That’s one of the tools we have put out there.

Hugh: Many variables here, but many factors to look at. I love you said there is no one size fits all. We have to be healthy. Managing self is critical for leadership. How can a leader quickly build and maintain trust? Trust comes from relationship, doesn’t it?

Scott: It does. I listened to a couple episodes of your podcast before, and someone brought up this quote that is one of my favorites, from Zig Ziglar, “You can have anything in life you want if you just help other people get what they want.” A big piece of trust is to grow your own empathy, grow your own emotional intelligence, recognize situations you do well, recognize situations you do poorly, but also recognize people and what they want. It’s being able to build good trust with them by caring about them and listening to them and seeing the world through their eyes and trying to help them get the things that they want, but it’s also saying, “I’m not going to damage trust. I’m going to make sure I’m behaving well in the moments that matter. I’m going to make sure I recognize my own triggers where I may respond poorly. I can work on myself so I’m not damaging trust that I worked so hard to build.” You can destroy it so quickly. It’s one of those things that can go away very fast.

Hugh: So fast. I think working inside of integrity breeds integrity. Working inside of relationship and trust. The culture responds to the leader in kind because we are setting the pace.

Scott, this is really helpful stuff. People can find you at What will they find there?

Scott: One of the best tools we have is a free interactive scorecard. It takes about 10 minutes with 39 questions. Based on that, it will show them the nooks and crannies of leadership, where they’re doing well, and maybe where they’re not doing well. Maybe here are your blind spots. A lot of leaders know they don’t know it all. What don’t I know? This scorecard will help them understand the full scope of what it means to work through other people to get things done.

What we also do is training, which is all on demand video training with assignments. There is a community version of that training that is free. We did that for smaller nonprofits and students. We wanted them to have access to the same training that we sell to companies and larger nonprofits. You can get into all of our training for free. It’s a great tool. If you need coaching, there are things along that line as well.

Hugh: Scott, what do you want to leave people with today?

Scott: My big thing is I am not a big follow the crowd guy. I am a cut your own path kind of guy. We need more of that, even in the places where the herd is common. To not be afraid of challenging the status quo is important. Think for yourself, and get out there and do the things that are going to light you up. For some people, that is more common things like get the job, do the normal stuff. For others, it’s go start the nonprofit, go into church work, whatever is going to make you happy. If it’s good for society as a whole, cut your own path, and do your own thing. We need more people who are thinking that way.

Hugh: Love it. Scott Drake, Thank you for sharing your wisdom today with our audience on The Nonprofit Exchange.

Scott: Hugh, thanks so much. I appreciate it.

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