“Leadership starts with clarity—and the courage to act on it.”

In this episode, Craig Anderson takes the mic solo to share the three leadership mistakes he sees time and again: outsourcing your vision, waiting for certainty, and over-indexing on empathy. Drawing from decades of experience and recent coaching conversations, Craig reflects on why leaders must stop looking for consensus and start setting direction. He opens up about times he made the wrong call, how he course-corrected, and why taking imperfect action is better than standing still. Craig also unpacks how empathy without accountability can stall a team—and what it really looks like to lead with both compassion and conviction.

Whether you're navigating your first strategic plan or struggling to have hard conversations, Craig’s insights will help you evolve with confidence and purpose.

After You Listen:

• Connect with Craig on LinkedIn
• Subscribe to Craig’s "The Evolving Leader" newsletter
• Download Craig’s “10 Tips to Level Up Your Leadership” guide

Key Takeaways:

• Vision starts at the top—not in a group vote
• Leaders grow by acting, adjusting, and learning
• Empathy means being honest, not avoiding discomfort

Things to listen for:
(00:00) Intro
(01:18) Stop crowdsourcing your vision
(02:38) The cost of indecision
(05:44) A real story about making the wrong call
(08:52) When empathy becomes avoidance
(11:31) Building empathy into your leadership style
(12:41) How to hold high standards with kindness
(13:41) The most empathetic thing might be a hard truth
(14:38) A call to action for evolving leaders

Episode Transcript

This has been generated by AI and optimized by a human. 

[00:00:00] Craig P. Anderson: After two hours of debate and discussion, I looked around the room and realized. We hadn't made any progress at all. Welcome to Executive Evolution. I have over 25 years of leadership experience in corporate America. I learned a lot of lessons the hard way, and I created this podcast so that you won't have to today on Executive Evolution.

[00:00:25] Craig P. Anderson: We're doing something a little bit different. It's Craig Anderson solo episode. So get ready. We're gonna go through what I believe to be some of the. Biggest leadership mistakes. I see we're gonna cover three of those today. We're gonna talk through them and talk about what you can do to evolve past them as a leader.

[00:00:41] Craig P. Anderson: And that story I kicked this off with, we're gonna come back to in just a few minutes. It's really important for us as leaders to have things like a clear vision, to not wait for certainty, to realize that life is often uncertain and realize there's a difference between empathy. And actually moving your business forward.

[00:00:59] Craig P. Anderson: So we're gonna break those down today in this episode of the podcast. Our next episode will go back to our normal interview format. But I've seen these things a lot in working with clients over the last few months, and it's really the beginning of leadership, and you need to evolve yourself into a point where you build a leadership confidence in leadership acumen to move through these things.

[00:01:18] Craig P. Anderson: The big message up for all of you here today is that leadership mistakes are learning opportunities. I'm not expecting any of you to never make a mistake. We don't evolve from perfection, we evolve from experience. So it's okay for us to make mistakes. We don't evolve from perfection, we evolve from our mistakes.

[00:01:34] Craig P. Anderson: But what's important is we have the self-awareness to see those mistakes. So today I'm gonna walk through these three common leadership mistakes I see, and how you can work to move past them. We're gonna start today with flaws that I see in my work. With small businesses not-for-profits in developing the strategic plan for the business.

[00:01:53] Craig P. Anderson: Now, maybe if you're a not-for-profit or a, you have a board that's kind of giving you the strategic vision, but you're really the one who's gotta execute it. And certainly in a small business it comes from you. But I see a lot now that people don't wanna take a stand. As the leader and say, this is the business that we're building.

[00:02:09] Craig P. Anderson: This is the vision we're going after. Instead, they want to get buy-in, they wanna get acceptance. They want to get kind of this consensus building exercise where everybody sits around a table and that gets to the story. I kicked off this episode with, you know, I sat down with the leader of this organization two or three weeks before we actually met with her team to kind of work out the details of the strategic plan.

[00:02:31] Craig P. Anderson: And I said, you know. Uh, what we really wanna do is get very clear for you what you're building over the next three or five years. That's the strategic plan. This has to be a vision that you own. It has to be a vision that you are building into. But she insisted that she really wanted the team to come together and that that's how she could get the team behind the vision is make them all feel participated as participants in the development of that vision.

[00:02:56] Craig P. Anderson: And I really pushed back against it, but she was adamant that this is how she wanted the session to go. I said, well. It's gonna take us a lot more time and I think we'll have some challenges. But you know, your team, let's see if we can pull this off. So we sit down at the beginning of the day and she kind of throws the door open.

[00:03:12] Craig P. Anderson: And you can imagine with five people sitting in a room, what happened? Everybody had an opinion. Everybody had something they thought was more important, and honestly they couldn't agree on anything and we wasted hours. Trying to build this thing and piece it all together, and quite frankly, what we came up with wasn't great, and we had to go back and make some adjustments to it.

[00:03:33] Craig P. Anderson: Why does this happen? Because visions are something that the leader has to create. You are the one who defines the vision for where your business is going. You are the executive director or president who's driving your philanthropic mission for your not-for-profit. Certainly. If there's some work maybe around the details, but if it's not your vision that doesn't have a hundred percent of your strength and commitment behind it, and you're not providing that clarity to.

[00:03:59] Craig P. Anderson: The people in your business, they're gonna be all over the place. 'cause everybody's gonna have their own piece of an agenda that they want to drive forward. It's okay to invite input. Heck go talk to people one-on-one before you finalize things. But it's got to be your vision. It's not a democratic process to set a vision, and I'm really sorry to have to inform some of you of that, but this is on you as the leader.

[00:04:20] Craig P. Anderson: It is your responsibility, it's your vision. So now I don't do these sessions until we have hammered out a solid vision from the leader of what the business is going to look like five years from now. And I can tell you having just come off three days with a team developing their strategic plan, because what we do is we kind of have the leader strategic plan, and then we build departmental ones underneath that.

[00:04:42] Craig P. Anderson: It's an entirely different experience when that leader is laser focused. So you start to evolve as a leader. When you stop asking the team, what should we do? And start saying, here's where we're going. Help me get there. That's what builds by and that's what builds a team that is coming together to build your business.

[00:05:00] Craig P. Anderson: So next up, another big mistake I see with a lot of leaders that I'm coaching as I'm working through plans with them is this kind of idea that we have to have certainty before we can act. We live in a chaotic world. Setting aside how people may feel about our current situation. In general, it is always a world that is going through chaos and unpredictability.

[00:05:21] Craig P. Anderson: There's things we just can't see, and if you as a leader, get stuck waiting for perfect action or perfect plans. You're never going to really see the success of what you're trying to do. You start getting into paralysis analysis, progress starts to stall. You know, we're just a, last week was, was the anniversary of the D-Day invasion and you know, had Eisenhower Dithered and not made a decision and just kind of wiffle waffle around and said, well, maybe not today.

[00:05:49] Craig P. Anderson: Maybe not tomorrow. I'm not sure. I'm not sure. It's never going to move forward, you know, he famously said. Imperfect action beats perfect in action every day of the week. So. It's really hard though, I think for us to always see that and we, we want that clear path. We want to have that specific information.

[00:06:09] Craig P. Anderson: But what you really have to do as a leader is get as much information as you can, and this is how I coach. I. People as they go through these kind of challenging decisions is, look, we have to find the best viable path forward for the business. There are things we're not going to know. You know, I, I have another client I work with.

[00:06:27] Craig P. Anderson: They have a lot of changes that are kind of external to them, that happen to the business, so you might be tempted to wait. You can't always wait because thing, you can't control the timing of other people's decisions. So what you have to do is sit down and really think through the options that you have in front of you and have a timed focused time to do that.

[00:06:47] Craig P. Anderson: Really get the options out there. Look at the information you have, and then commit to a path, start moving forward. It may not be the perfect path, but it's gonna be a path that you're using that's driving your business in Extremely forward to the next level. The final piece of that is actually saying to yourself, okay, I'm watching this.

[00:07:08] Craig P. Anderson: I'm having self-awareness about it. I'm watching what happens from reaction to this path that we've sent. Make sure you're pulling your team in to talk about these things. What's happening? What's moving forward? You know, I can think of a time I stepped into a leadership role of an existing division of a business, and I thought I had this really clear plan of how we should go forward, and it was very clear and it was very decisive.

[00:07:30] Craig P. Anderson: Also, it was wrong. We pushed it out there. Probably one of the things that was a learning opportunity for me, there is leadership teams that are new to you may not challenge you as much as you want them to, and this group didn't and they just jumped on what I said. I missed some red flags, but it became quickly apparent that it was the wrong decision.

[00:07:49] Craig P. Anderson: I was getting that feedback from the team and then we made the adjustments and we changed what we were doing to better reflect what the market would bear. So move forward with that imperfect information, move forward. Don't get stuck in paralysis analysis, but also make sure you're keeping your fingers on the pulse of everything that's going on in your business, which is why it's so important to have leadership team meetings on a consistent basis.

[00:08:12] Craig P. Anderson: Make sure those meetings are cascading through the organization, so information is moving up and down in your organization so you can react quickly if you pull the wrong trigger and it's okay to pull the wrong trigger, that's when we make those mistakes. You know, we evolve as a leader when we act on what we know now, not what we hope to know in the future.

[00:08:31] Craig P. Anderson: And when we're open to saying, Hey, maybe this wasn't the greatest idea based on the feedback, I'm gonna pivot and I'm gonna move forward. That's how we began to grow as a leader, and that's how we keep our business moving forward. If we're not moving forward, we're just standing there waiting for the waves of chance to push our business around and we're gonna make mistakes, it's not gonna work out well for us.

[00:08:52] Craig P. Anderson: So that's that. The next piece that I see, and hey. I talk about this a lot. I talk about the importance of empathy and leadership, and I do think it's important to have empathy as a leader. A lot of people are going through a lot of things in our organization. You know, I've even talked about before, you know, I posted this out on LinkedIn recently.

[00:09:13] Craig P. Anderson: You know, when you're doing layoffs, you know, you don't have to be a jerk about it. You can do layoffs with empathy, but you have to do the layoff because you have to go with what's dictating, what's going on in your business. But a lot of times what I see is we're talking about leadership, empathy so much that that's become the predominant way that we're viewing our business and we're viewing our leadership role and we start to think, well, empathy's the only thing that matters.

[00:09:39] Craig P. Anderson: So we start to make excuses to say, well, they're going through a tough time. I'm not gonna talk to 'em about this right now. Oh, some of these things happen. I can't make this change right now. Even when it's the right business decision for your business, we have to make. The right business decisions. If we have an underperforming employee, certainly have that empathic conversation.

[00:10:01] Craig P. Anderson: Certainly sit down with them, talk about the facts, ask them what's going on so we understand what their situation is. Make adjustments. Hey, if you need to give them a week off to kind of get whatever straight, they have to get straight, that's the right thing to do. But if they come back and we're consistently seeing this pattern, you can still feel empathy for them.

[00:10:20] Craig P. Anderson: But at the end of the day, you have a business run if that person can't perform under the situation that they're in. You may have to make a tough decision. Sometimes we use the idea of empathy, that we wanna have this empathy to actually not make the decision. And it's really not about them, it's about us.

[00:10:36] Craig P. Anderson: It's about our discomfort in making tough decisions. And I see this so often, it turns into this idea of, well, it's not gonna happen again. They'll figure it out. And I see this with leaders all the time where they just kind of hands off the situation and say, well, it's just a situation that's going on.

[00:10:53] Craig P. Anderson: It's gonna go away. Problems don't age well. I talk to a lot about this with my clients, deal with it in the moment, have empathy as a leader, but realize sometimes I. That empathy isn't gonna work for you, and what's really gonna work for you is make the right decision for the business. We don't have to treat people poorly in this process, but we also have an obligation to our business, and frankly, we have an obligation to the rest of the team, and we have an obligation to our clients, our customers.

[00:11:20] Craig P. Anderson: True empathy is about making decisions that ultimately serve the mission for your business. That. Not just, you know, in the moment of something we have going on. So build this into your leadership style. Build empathy in, but realize sometimes you're gonna have to do things that may not feel kind, may not feel like empathy, but are the right things to do.

[00:11:39] Craig P. Anderson: And it's tough. It's one of the toughest things for us to do as we grow into a leader. So how do we deal with this practically as leaders One. We have to be, we go back to what we talked about in the first point is one, have a clear vision for the business. This is what success looks like. Help people know how to put in context.

[00:11:56] Craig P. Anderson: What the most important things are, they need to be working on the, the projects that are most important, the objectives we're trying to achieve so they can make those decisions. Make sure people understand how their role in your business aligns with achieving those objectives. So there's clarity. Sit down with your team.

[00:12:11] Craig P. Anderson: If it's just you and a bunch of people under you, or if it's you through your direct reports, make sure your direct reports are doing this, that we are having. Regular, weekly one-on-ones with our team to make sure people are on track and achieving their objectives. Give feedback in the moment. Help them catch them doing the right thing.

[00:12:27] Craig P. Anderson: Catch them doing the wrong thing. Treat them with respect as you do it, but also set the standard and the expectation for what is okay and what good performance looks like. When we run into problems, now we have a solid rubric. For understanding, this is what success looks like. This is where you are. What do we need to do differently to try and get you into the place we need you to be?

[00:12:46] Craig P. Anderson: And we wanna make that effort. But if we can't get them there, we have to make the tough decision. And you know what? In many cases they realize they're not performing as well and they need the, the invitation, if you will, to make the move to get somewhere where they're gonna be able to perform. Be that another role in your organization.

[00:13:03] Craig P. Anderson: Or a role somewhere else. And that's really also a piece of empathy is just saying, this is not working. That's actually the most empathetic thing you could do, as opposed to just letting people kind of meander along performing poorly. Because there's also the empathy you have to consider about for the rest of your team who are looking at a low performer, seeing them continue to move along and wondering why they're working so hard.

[00:13:25] Craig P. Anderson: So these are tough decisions that we have to make, but leadership means being kind, but clear, not just being kind. So I encourage you to think about that. So these are the three leadership mistakes I've been seeing a lot lately. I wanted to get on here and share these with you because I think they're so important.

[00:13:41] Craig P. Anderson: Again, the mistakes. Don't crowdsource your vision. Own your vision. It's you. It's your business. You have to set where we're headed as a business. Two, realize. Waiting for certainty is a fool's game. You have to pull the trigger. You have to make the decision. Set the course, have the self-awareness to see what's going on, and if you made the wrong decision, realign, readjust, get on the right place.

[00:14:04] Craig P. Anderson: And then finally, overweighting. Empathy. Empathy is important. Empathy and kindness have their place, but you have a business to run. And sometimes the most empathetic thing you can do is tell the person you're not performing. Here's how we gotta get back on track. But if you're not gonna be able to do that.

[00:14:19] Craig P. Anderson: We're gonna have to make a move that's gonna be tough for both of us, but it's the right thing. So, which of these really show up for you in your leadership style? I'd encourage you to think about that. If you're watching this on YouTube or seeing this somewhere else, you know, drop some comments with your thoughts of where these show up for you in your leadership style.

[00:14:37] Craig P. Anderson: And finally, there's a link in the, in the show notes here for downloading my free leadership guide, 10 Tips to Level Up Your Leadership. I really encourage you to do that. Those are things that are some of the best practices both for me and from the people I've interviewed on this podcast to understand how you can become a better leader.

[00:14:55] Craig P. Anderson: And if you're really feeling stuck, shoot me an email. Let's jump on a call and let's talk about what you might be able to do to move forward. Remember, you can go from being an accidental leader to being the greatest leader of all time. It's about building your competence, confidence, and calm, and avoiding the kind of mistakes we talked about in this video today.

[00:15:13] Craig P. Anderson: Thanks for listening, and we'll see you next time on Executive Evolution.