This post marks the accomplishment of a truly mind-blowing milestone: today, we’re celebrating 100 EPISODES of Managing Made Simple!
We’re going to kick this celebration off by revisiting some of our “top plays” of the podcast, featuring advice on leadership from six of our favorite interviews from MMS.
Let’s get this party started!
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Alex Street
Alex Street is a storytelling coach who believes that when you share your story, you can change the world.
As an actor, youth pastor, and public speaker for more than 20 years, he knows firsthand how powerful storytelling is when it comes to personal development, business strategy, and creating authority.
Q: What does storytelling have to do with being a great leader?
It’s everything. I mean, it really is. We think leadership looks like us pointing in a direction, and then our team will follow us as we go there. But these days what we’re seeing—that maybe wasn’t so prevalent 60 years ago or so—is when you point in a direction and say, “Let’s go here,” whether that’s for a project you’re managing or it’s a long-term goal for your company, your team is sitting back going, “Yeah, all right…but why?”
The ”Why?” question is something that a lot of employees and team members are feeling more space to ask more than ever. And if you as a leader can’t answer that, then it’s going to be really hard to pull them along, and you’re probably going to lose some people along the way and have to replace team members.
This is where the storytelling aspect of this comes into play. We need to be so clear on why we’re going where we’re going right from the get-go—if you can tell that story from the start, then they don’t have to ask that question, and they’re going to be emotionally invested in the ride that we’re going on together.
So, what does it have to do with being a good leader? It really is about making the leadership journey easier than ever, helping people feel more invested than ever, and helping them understand they’re a part of making a difference here in your company.
Tracy O’Malley
Tracy is an Enneagram expert as well as a leadership, communication, and culture expert working with individuals, small businesses, corporate clients, and anybody else who wants to dive into how to become a better leader and have more fulfillment in their lives.
Q: What is the Enneagram, and how do people understand it?
Depending on who you ask, you’ll get all sorts of different answers. If you Google it, you’ll see that it’s an archetypal framework for personality, which is how I like to explain it. However, this doesn’t really explain how the Enneagram will serve you in leadership.
To me, the Enneagram is this framework that allows me to understand not just myself better, but other people better as well. It allows me to treat people with more compassion, empathy, grace, service, and understanding to create a win-win situation for everyone.
When we all have these different life experiences and perspectives, if we are locked into our own exclusively, we miss the boat on leadership, whether that’s in our home or in business.
That framework allowed me to realize that not everyone is motivated like me. Not everyone is fearful like me. And the first place I recognized that was in my home.
I have two kids who were teenagers at the time, and I realized that I only spoke in a way that would work for them if they were motivated like me and if they feared like me, and I knew that they weren’t and they didn’t.
With that in mind, the nine archetypes in the Enneagram allowed me to create eight other different “languages” for people that aren’t like me, that are motivated differently than me, that not only allowed me to communicate better with them—they also allowed me to learn a hell of a lot more about different perspectives, different experiences, and different strengths along the way.
In the corporate world, by observing things like quiet quitting, we’re starting to see that people aren’t motivated by the things that we used to think they were. That means we’re going to need a new language for interacting with each other.
What’s awesome about the Enneagram is if you understand your team members’ motivations and fears, you can speak directly to that thing. You can create a stronger sense of purpose. You can create more meaning in their work.
This is such a powerful tool for managers to connect those dots for their team members, because people want to be fulfilled. But when you’re in an environment where the person in charge or the person leading you doesn’t see you for who you are, that’s why we end up with things like quiet quitting.
New generations entering the workforce are explicitly saying, “I need to feel a sense of purpose. I need to feel like this work matters. I need to feel like I matter.”
And with that shift, the Enneagram is now a tool that you can use to make that happen and create that feeling for someone.
If you feel like you don’t understand what motivates this generation, give the Enneagram a try.
Corey Charles
Corey Charles is the founder of the Human Potential Accelerator. He’s a visionary leader, an inspirational speaker, and a catalyst for personal transformation. Unlocking hidden potential, empowering others, and igniting greatness within is his goal, and his bigger goal is to impact one million lives worldwide.
Q: Tell me about this goal of impacting a million lives and how you plan on getting there.
First, I want to really really clear: this goal isn’t about ego. I really hope that that number has to change pretty quickly; I hope we hit a million and then we have to go to five, then ten, then upward from there.
This goal came about because I think it’s not only important to give back, because I’ve been really blessed with some amazing people that have given back to me, but also to understand the ripple effect that impacting people in your life creates.
Even before I was in my training role, I was blessed to work a gentleman as his sales mentor. And I remember talking to him years later, after I’d been out of his orbit for a long time, and he talked about how much that mentorship had affected his life.
He told me that set of conversations we had allowed him to not only be a better salesperson, but also to move into leadership, to become a better leader, to be a better husband, and to be a better father.
In that moment, I thought, “Wow, that is an incredible ripple effect. Look at all those people that were affected by just a few small conversations.”
So if we as leaders can realize that we’re able to impact people on that level, I think it’s really amazing.
I talk about legacy and lineage a lot. And I believe that somewhere in my lineage, somewhere in my legacy, I will impact a person that changes the world.
It may not be someone that I talked to directly, but it could be a child. It could be a spouse. It could be a thing where I trained someone, who then trained someone else, who then trained someone else…in that lineage, there’s going to be someone that changes the world. And it is absolutely my mission to help foster that change.
Staci Millard
Staci Millard is a fractional CFO and business mentor for entrepreneurs who want to leave behind survival mode mentality and thrive in their small businesses. She grew and sold her first seven figure business before she was 35 while raising her two daughters. She prides herself not only in her experience growing her own business, but also the thousands of small business owners that she’s helped over the past 15 years.
Q: Where is one of the biggest places you see leaders get stuck when it comes to scaling?
In terms of scaling, the biggest thing I see leaders get caught in early on is this mentality of having to do it on our own.
We hesitate over hiring the support we need because we’re in a stage of figuring things out, and we don’t want to do it prematurely.
So instead, we end up waiting through the discomfort so long that when we do make that first hire, it’s not a great experience. Here’s what usually happens…
In this stage, we tend to hire doers: people who take on a little bit more of the workload, but aren’t necessarily strategic thinkers.
When we enter a later stage in business, all of a sudden, we realize this isn’t working. Why not? Because you don’t just need doers; you need somebody who’s a higher-level thinker. You need someone who can create more strategy behind things instead of just doing the things.
When you end up here, it’s almost always because you’ve made decisions up to that point by thinking about where you’re at, not where you’re going in the future. Instead of thinking about what you’re going to need, you’re thinking, “What do I need right now?”
Robyn Rapp
Robyn is a leadership development coach and facilitator, and she brings over 15 years of operating excellence at Google and the early-stage days of Slack. She enables talent to find renewed connection and commitment to their work, empowers individuals to stretch themselves into leadership roles, and supports working parents who hope to simultaneously prioritize their family and invest in meaningful work.
Q: Having been a manager yourself in the corporate world before you started coaching managers, is there something that you share with your clients that you really wish that you’d heard earlier?
Oh, the list is endless in terms of what I wish I knew earlier as a new manager, but one of the biggest ones that comes to mind that I try to impart to all of my clients, especially those who are newer managers, is that you really have to get comfortable with having hard conversations.
Whether that’s around performance or potentially how your team members are showing up, it’s an important thing; you can’t avoid it, and the faster you get comfortable with it, the better.
Is it uncomfortable to tell someone that you think they get defensive when they’re receiving feedback? A hundred percent. Yes. it’s awful. But is it important that you take the time to really develop that incredibly important skill of receiving feedback with your reports? Absolutely.
You and your team members will be better for it, even if in the moment it’s absolutely terrifying and awkward for all parties involved.
One of the things that I remind my clients about is that you have to remember that your employer isn’t paying you to be friends with your team.
It’s really excellent when that happens; it’s a beautiful thing! But when those two desires seem to be at odds with one another—wanting to be a great friend, and wanting to be a great manager—it’s important to remember which one we have a responsibility to deliver on, and which one we’re getting paid to do.
Jackie Koch
Jackie is the founder and CEO of People Principles. With over a decade of experience recruiting and scaling people ops for startups and small businesses, Jackie founded People Principles three years ago to help CEOs get the people stuff right.
Q: When clients come to you with an issue that they’re categorizing as an HR problem, what do you often find the problem actually is?
To be honest, it is usually a leadership problem.
I think the root of that can often be found in workflows; usually it’s about the way the work is being communicated and/or the way that people are working together.
It’s not a communication thing, though it has to do with the way work is being communicated—it’s actually got more to do with systems, the way stuff is translated between team members, or the way a task is passed off to whoever’s next in the process.
Beyond that, it could also be that the manager may just not be as skilled as they need to be at managing the team.
So that’s where I would start. I wanted to initially say the manager, but I actually think it starts prior to that with the ops issues and the systems. So if you’re having an “HR issue,” it’s more likely an operations or leadership issue.
Want to Hear More From Our Top Interviews?
Tune in to Episode 100 (WOO!) of Managing Made Simple to hear more wisdom from these six incredible people!
