Episode 178: Am I Leading Well? How to Honestly Evaluate Your Leadership
Have you ever asked yourself, “Am I leading as well as I could be?” In this reflective and practical episode of The Today Counts Show, Jim explores how to take an honest, constructive look at your leadership, without slipping into self-criticism or complacency.
Join us as we break down:
Key markers of strong leadership: What traits and actions truly make a difference, and how to measure them in your own style.
Uncovering blind spots: Discover how everyday habits, team dynamics, and unforeseen gaps can hold you back—plus, what to do about them.
Feedback that fuels growth: Learn where to seek meaningful feedback—from peers, mentors, and direct reports—and how to act on it.
Building a personal leadership audit: Walk through a simple framework for evaluating yourself across ethics, empathy, strategy, and more.
Setting growth goals that stick: Define realistic, actionable steps that will accelerate your leadership impact—no overwhelm, just progress.
Whether you’re stepping into a formal leadership role or already guiding teams, this episode gives you a trusted, compass-style approach to measuring—and leveling up—your leadership. Tune in to start leading with clarity and intention, because your influence starts with self-awareness.
Get a copy of Jim’s new book: Story – The Art Of Learning From Your Past. A book designed to challenge, inspire, and guide you toward greater leadership and purpose. Discover how your past shapes your leadership. Order your copy today or Get the first seven pages for free!
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Today Counts Show Episode 178
Preview
Jim Piper: “What you ignore becomes more.” Maybe you had your feelings hurt and you’re just putting it off. You’re going, “You know what? I’m a big boy. I’m a big girl. Those things shouldn’t bother me.” And maybe they should or shouldn’t. But for the integrity of relationships, we often need to have the hard conversations.
But it’s important for me to take a look back to see how well I managed my time, how well I seized opportunities, how well I invested in doing the right things, the things that matter versus just—
Appreciating our Sponsors
Winston Harris: Hey, before we jump into the podcast, we want to thank all our donors and supporters who make the Today Count Show possible. It’s through your generosity that we’re able to shape leaders through this content and this podcast. And be sure to like, subscribe, and follow wherever you find yourself coming across this content. All right, let’s get to the podcast.
Introduction
Jim Piper: Welcome back to the Today Count Show. As usual, we’re talking about leadership today. Let me start by asking you a question: What have you learned about your leadership this past week? Was it encouraging? Was it disappointing? And was it frustrating? Or are you just happy to get past another week, another week that ticks by?
The Three Dimensions of Leadership
When I talk about leadership, I tend to think in terms of dimensions—three specific dimensions. The first I think about is your person, yourself. The second I think about is our people—your people, the people in your life, people in my life, our life. And then I think about our place in this world, in this life. You could view it as your workplace, your profession, a season that you’re going through, a project that you’re working on, an opportunity that is in front of you. That kind of thing. So it has different applications.
Self-Reflection Through Weekly Questions
I ask myself: How well did I lead myself last week? How well did I take care of myself? How well did I engage in the important relationships in my life? And how well did I navigate those? How well did I lead those? And when I think about my mission, my project, my season in life, the opportunities, my clients, all those kinds of things, I ask: How well did I lead in these last week?
Asking yourself these questions—what is that? That’s evaluating. Evaluating is a fundamental practice, a discipline of all very conscious leaders who are trying to get better at what they do, both for themselves, their relationships, and those that they lead in their place of work.
Evaluating Leadership: Lag and Lead Measures
So I ask myself these questions: How did I do in hopefully making adjustments for the future? When I look back, those are what we call lag measures. In other words, I can’t really do anything about it. But it’s important for me to take a look back to see how well I managed my time, how well I seized opportunities, how well I invested in doing the right things, the things that matter versus just doing a lot of stuff.
So this evaluation piece is important, but it’s a lag measure. The score is already up on the scoreboard. But by doing that, hopefully I can learn from it at least a little bit and then make adjustments for next week. And when I make those adjustments for next week, we call those lead measures. These are activities, these are decisions that will be leading me into the future. I trust that these are as good or better than how I practiced them last week.
Planning Proactively with Calendars
So they’re proactive decisions. They are decisions that you make ahead of time for the coming week. You then enter those decisions—whether you call them appointments or blocking time or whatever it might be—you enter them on your calendar. In the world we live in today, many of us, most of us, probably all of us use a calendar in some way, shape, or form.
And of course, calendars themselves have evolved in the last X amount of decades to a place of incredible opportunity that can actually improve our lives versus be some kind of nagging idea about “I got this appointment, I got that appointment.” But when we make decisions ahead of time, then we’re being proactive and we are prioritizing our week ahead.
So this process is part of the shaping and executing of our lives and our leadership.
The Importance of Quadrant 2 Activities
In practice, I call it a playbook, an actual document. That’s not what we’re going to be talking about today necessarily, but this activity of evaluating the last seven days and then planning the next seven days—you can go out farther than that, of course—I call this a quadrant 2 activity.
Stephen Covey, if he didn’t invent the quadrants, he definitely made them popular. Four quadrants, obviously. Quadrant 2—the definition of quadrant 2—is activities that are really, really important, but they’re not urgent. They’re not like they have to be done right now. And that’s the problem. Things that don’t have to be done right now, we often put off.
The Trap of Quadrant 1
We put off for what? Well, we put off for quadrant 1 activities, which is what has been labeled urgent and important. But here’s the thing: The reason why our quadrant 1 box is often full and we’re running around hurrying and scurrying and living off adrenaline is because we have put off and ignored quadrant 2 activities—quadrant 2, important but not urgent.
And when we ignore those things, they tend to pile up into quadrant 1, where now everything is urgent and everything is important. So when I think about this activity that we just talked about—evaluating and planning—well, that’s obviously a quadrant 2 activity.
Planning for the Next Week
Now, some people still enter into their next week without any planning, believe it or not. Maybe that’s you. And hopefully, if that’s you, maybe I can talk you into a different way of living. You might say, “Oh my gosh, I already feel, Jim, like you’re putting all kinds of armor on me that I don’t want. It’s too heavy for me. You’re choking out the life in me if you’re going to schedule out every minute of every day.”
Well, let me finish though. It is like scheduling out every minute. But remember, you can schedule fun time. You can schedule relaxing time, rest time, all those kinds of things. So bear with me.
Examples of Quadrant 2 Activities
For example, what might be ideas or activities or examples of things that are really important, but they’re not urgent? What are they? You can think about it yourself as you’re driving, as you’re walking, as you’re listening and watching this, as you’re cleaning a house, whatever it might be.
So let’s consider the really important side of this equation first. Really important might be things like reading. Reading is important.
This episode is not about the importance of reading. I probably need to do an episode about why reading is so important. Whether you enjoy reading or you don’t enjoy reading, most introverts or many introverts enjoy reading, and many extroverts not so much. But whether you enjoy it or not, reading is a really important thing to do.
Writing is an important thing to do. You might say, “I hate my penmanship.” But writing is still an important thing to do.
Exercising, taking care of your body. When you take care of your body, it has a way of taking care of your mind and your spirit, your outlook, your attitude.
Hard Conversations as Quadrant Two Activities
I already mentioned evaluating, planning. Maybe there’s a hard conversation that you have been ignoring. That’s quadrant two.
Those conversations where you need to apologize. Those conversations where maybe you had your feelings hurt and you’re just putting it off. You’re going, “You know what? I’m a big boy. I’m a big girl. Those things shouldn’t bother me.” And maybe they should or shouldn’t. But for the integrity of relationships, we often need to have the hard conversations. When you avoid those things, they usually come back to haunt you.
What about praying? What about working on a big project that you need to block time for and start working on bit by bit? That’s quadrant two activity.
What about an important family event or studying for a class that you’re taking or an advanced degree that you’re trying to earn? Or maybe you’re trying to make a comeback in your life and you’re trying to take care of some of those other certifications and graduations that maybe should have happened when you were younger. If you’re after a comeback, man, I applaud you. I am standing up and I’m excited for you.
The Benefits of Investing Time in Quadrant Two
So when you invest time in doing that, that is quadrant two activity. Healthy people, growing people, maturing people, healthier people spend a lot of time in quadrant two. In fact, I would say that if you do find yourself moving up the ladder, so to speak, however you would view that, I think you will notice—and if not, maybe I can encourage you—the more time you have to spend in quadrant two.
So it’s really kind of anything that, or maybe an important meeting. Not meetings—I would say some meetings are not quadrant two—but there are some meetings that are very important to not only attend but to be prepared for and engaged in, would be another idea of quadrant two.
So anything that prepares you, that strengthens you, that encourages you, that gets you ahead of the rat race—or better, even out of the rat race. These are the kind of things that we would call quadrant two.
Visiting your doctor is a quadrant two activity. Your dentist, as silly as it sounds. When you brush your teeth, that’s a quadrant two. When you shower, that’s a quadrant two. And when you take care of yourself and your relationships and the other people and places that count on you for production, these are quadrant two activities.
The Danger of Ignoring Quadrant 2
The second part of the equation is what makes practicing quadrant two difficult.
Let me pause there for an effect. Let me help you think about that. So you’ve got a good idea of what quadrant two activities are and why they are so important and why they need to be scheduled in your life. But if something’s not urgent or life-threatening, then it can be easily skipped. It can be easily put off. But the problem with skipping and putting things off is skipping becomes a way of life. I call it skimming.
Skimming becomes a way of life, and it then becomes a habit. That begins to shape you to where you have very little quadrant two life of evaluating, planning, getting bigger. And then you can get into really bad habits of pleasure seeking, just everything’s urgent. You’re running around with your head cut off. You can have bad habits of eating, lack of exercise.
And what happens is sooner or later, when you ignore quadrant two activities—those things that build you up, encourage you, strengthen your relationship, improve your profession, all those kinds of things—when you put those things off, they, by necessity, slide into your quadrant one, and they become urgent and really important. And of course, the simplest example of that is your physical health. If you ignore your physical health for too long, you’ll find yourself in a really bad place. And sometimes it’s too late.
Practice 1: Weekly Evaluation and Planning
Jim Piper: The first one is, I tell you what, I’m going to cover two practices on this episode. I think that can really help you. The first practice is block time each week to evaluate the previous week and to plan next week. Let me say that again. I want to challenge you for the new discipline. Once a week, block time to evaluate your week and then to plan your next week based upon what you’ve learned about your behaviors and all those things that go on around you by evaluating.
In other words, how do you do that? Well, you do that by asking yourself questions like this: When I look back at my calendar for last week, how well have I been taking care of myself, my person? How well have I been doing that emotionally, spiritually, physically? How well have I been doing that? Mentally? You can apply that to your relationships. How well have I taken care of my relationships last week and my place in life?
Another way of going about this is I can say also, how have I done the positive? But I can also ask this second question: In what ways have I wasted time on things that really don’t matter?
Then a third question that I can ask in the evaluation is, are there bad habits that I have acquired? Am I starting to see some bad habits that can become addictions if I’m not careful? Are there bad habits that I’m seeing developing that I have acquired that need to be addressed? Are you eating too much? Have you stopped exercising? Are you drinking too much? What about your language? How’s your language? Are you doing hard things or are you ignoring hard things?
And then here’s another question: Am I putting something off that needs to be addressed?
A Principle to Remember: What you ignore becomes more, what you address becomes less
One of my friends said something that really caught my attention probably a couple years ago. In fact, he was Clint Peas, and he was somebody I interviewed on the Today Counts Show. I’m not sure what episode that was, but he said, “What you ignore becomes more.” Well, that made sense. “And what you address becomes less.” So what you ignore becomes more, and what you address becomes less. Wow. That is a great principle that can hover over the evaluating and planning process.
Okay. So the first thing I’m going to ask you to do, to challenge you to do, is to block time each week for evaluation for the past and then planning for the future for the following week. When should I do that? Well, I don’t know how you do your calendar, but for me, what works best is—it takes me about an hour. Sometimes it will take longer than that, sometimes a little less than that. But it takes me about an hour, and I do mine on late Thursday afternoons.
I look at everything from Sunday through Thursday, and then I start again from Friday. Actually, I guess I look seven days to seven days, but I do it generally on Thursday afternoons. I’ve tried other times like Sundays, but I find that I’m more consistent at it when I do it on Thursday afternoons. You can obviously do it whenever you want to do it, but for me, that’s what works for me.
Practice 2: Using Your Calendar as a Planning Tool
All right, let’s talk about the second practice that I’d like to challenge you to do. I’ve talked about evaluating, and I’ve talked about planning, but I don’t think you can do that really well if you don’t use a calendar as a planning tool. So that’s the second thing that I want to share with you: Use your calendar as a planning tool.
Most people use their calendar to write down appointments. That’s what they use it for. Well, what else would you use it for? That’s the problem. What I want to do is I want my calendar to be a partner with me. So I use it not just as a recording tool, but a planning and evaluation tool, not just an appointment reminder tool. Ideally, what I’d like to see you do is to plan out your entire week.
You may say, “I don’t know what you’re talking about.” In other words, you probably already have some appointments for next week, but you’ve got all kinds of time in and around those appointments that are unaccounted for. I want all of that accounted for. You might say, “Well, how do you do that?” It’s going to take some practice. It’s going to take some time. Blocking.
But sometimes we scatter appointments all over the place when we could start learning, what do I do on Mondays best, Tuesdays, Wednesdays, Thursdays? We’ll talk about that in another episode. But for right now, what I want you to do is think of your calendar as a friend, as an accountability partner, as somebody that helps you both evaluate and plan. Because if you don’t write out what you do, then how can you really evaluate it? I’ll talk about that in just a second.
The Importance of an Accurate Calendar
So what I’m trying to say is when you are filling out your calendar for next week, think of everything. Rest. You might even want to put bedtime on there, because if your bedtime is sometimes nine o’clock, sometimes twelve o’clock, sometimes ten o’clock, people will tell you that that’s not healthy anyway. So if you can establish a general time that is good for you to go to bed, I’d put that on there. You don’t need to put your sleep time in there.
Whatever time you get up in the morning to start the day, from the time you get up to the time you go to bed, how have you planned that day out? If you can’t put specifics down, you can at least block time. That’s rest time, downtime, appointments, block times for projects, and other quadrant 2 activities.
Here’s the second part of that: Often we make plans and they do not turn out as we had hoped. So we just throw the baby out with the bathwater. We don’t start planning because people interrupt our day, we get hijacked from here to there. People just quit. They say, “Jim, it doesn’t work.” No, it works. It works. If you stick with me in these episodes, it works. It really does work, because you’ll also teach people how you work best, how you get more done, how you get the right things done. You have to teach the world how you work as well.
Update Your Calendar to Reflect Reality
So here’s what I’m saying. Here’s the second part of it: I want you to make sure that at the end of each day, your calendar reveals what really happened. Otherwise, you can’t evaluate. We cannot evaluate last week if the calendar doesn’t tell us the truth. If we’re simply trying to use our memory, that’s not going to work.
If we look back and we look at a calendar that does not really reflect what happened, or 40% of what happened, or 30%, or even 50%, or even 60%, even 70% of what happened, it’s not going to give us the data we really need to evaluate. So at the end of each day—because otherwise you’re going to forget, and if you can do it in real time, that’s even better—when your lunch appointment goes from 60 minutes to 90 minutes, you need to change it. Say that went 90 minutes. If that created a domino effect, you need to put that domino effect.
If you had to cancel an appointment and reschedule it, make sure that all of that is done accurately. Maybe you put down two hours to run errands on your calendar. Maybe that’s not a quadrant 2 activity, but it was quadrant 1 stuff that you needed to do. You had to pick up whatever you were doing, and it took you three hours, or it took you one hour—whatever it took you to do, that’s what you need to adjust in your calendar.
Make sure that your calendar reveals what really happened, not what you planned. This will help you identify habits, behaviors, patterns of how maybe you are letting others control you instead of you. And the idea is that if you can discipline yourself, you’ll be surprised what you can do and how much healthier you can live.
Recap of the Two Key Disciplines
All right, so let me recap. Often when I am meeting with leaders, I ask questions about last week. After I ask questions about last week, I ask questions about next week. And in the beginning, many of these—and these are good leaders, these are effective leaders, these are friends—many are trying to remember last week because they did not make a commitment to these two disciplines that we have discussed on this episode.
Discipline one: Evaluate and plan.
Discipline two: Keep a detailed calendar so that you can do that, so that it will actually work.
So let’s say it again. Make a commitment to weekly evaluation and pre-planning. Make a commitment to that. If you sometimes feel like you’re just running from one week to the next and you feel like your life is a little bit out of control sometimes, and you feel stress rising, and you’re short with your family and friends, and you’re not taking care of yourself—all of these are symptoms of ignoring the two things that we’re talking about.
Why Commitment Matters
Make a commitment to weekly evaluation (lag measures) and a commitment to plan and move forward with lead measures. And then second, use your calendar as your evaluation and planning tool. Make it exact, make sure it’s accurate. Make sure at the end of the day it reflects the truth of the day, not just how you hoped it would go.
Turning Plans into Reality
But of course, wouldn’t it be nice if the plan became the reality? Wouldn’t it be nice that if you planned out your week, it actually went as planned? Here’s my promise to you: That can happen most of the time, but it will take some time to learn how to do it well, because we haven’t talked about how you create margin and those kinds of things, but we’ll work on that as time goes by. So that’s the goal.
Think about that. You plan a week and it goes as planned. What if that happened 80% of the time? Wouldn’t that be great? So let’s start here.
Outro
Winston Harris: Hey, thank you so much for joining us on the Today Counts Show. We have so much more planned for you. So stay tuned and stay connected on Instagram, LinkedIn, Facebook, and subscribe on YouTube. And remember, today counts.
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