The Courage Of A Leader: Stepping Up Even When Things Go Wrong With Amy Riley

by | Jan 12, 2023 | Podcasts

SWGR Amy Riley | Courage Of A Leader


“It often requires more courage to dare to do right than to fear to do wrong.” – Abraham Lincoln.

Courage is a quality a leader must have. Because a leader needs to have resilience and perseverance to overcome adversaries, in this episode, Amy Riley, the Author of The Courage of a Leader, dives into leadership and how to lead powerfully and effectively in stressful circumstances with courage. Amy also dives into the four pillars that courageous leaders demonstrate as they thrive in many circumstances. Tune in to this inspiring episode to learn how to create an extraordinary result in this world! Step forward with Amy as we set foot with the Courage of a Leader!

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The Courage Of A Leader: Stepping Up Even When Things Go Wrong With Amy Riley

Claiming the Courage of a Leader

My guest is Amy Riley, who talks about the courage of a leader. She’s written a book called The Courage Of A Leader. She has a podcast called The Courage Of A Leader. I wanted to ask her about leadership when it’s hard. What do you do if you make a mistake? What do you do if you can’t decide what the right thing to do is? Those questions were the ones that made me curious, and we had a very interesting conversation.

SWGR Amy Riley | Courage Of A Leader

The Courage of a Leader by Amy Riley

Amy L. Riley is an internationally renowned speaker, author, and leadership development consultant. She has worked with organizations such as Deloitte, Cisco Systems, and AON Hewitt, and has many years of experience working with leaders at all levels. Amy has a Master’s of Science in Training and Development with an emphasis on Organizational Development from Loyola University in Chicago, Illinois. She’s a Certified Professional Behavioral Analysis, also known as CPBA. She’s a Certified Tiara International LLC Coach and Certified in the Myers-Briggs Type Instrument, meaning that she’s got all sorts of certifications, which gives her all sorts of tools to help to see where an organization or a leader might be having some challenges and helping them get out of that tangle.

Amy’s second book, The Courage Of A Leader: How to Inspire, Engage, and Get Extraordinary Results, was released on March 23rd, 2021, and immediately reached number one International Bestselling status. Amy Riley is a really interesting person. I had a fabulous conversation with her. I know you’ll enjoy it, so here comes Amy Riley.

Amy Riley, I’m so excited to actually get you on the show. Welcome.

Thank you. I’m glad to be here.

This is going to be fun. Before I get into the many questions I have for you, let me ask you about your dream interview. If you could interview someone who’s no longer around, who would it be, what would you ask them, and who should be listening?

When I think about courage, which is a key theme for me and leaders, I think about Abraham Lincoln and the courage that it took to be the leader of our country at that time.

What would you ask him?

I’ll ask him about what gives him the courage to step forward, knowing that we’re never going to please 100% of the people 100% of the time. When leaders make big decisions, they’re hoping that 7% or 13% of the population that’s not going to be happy. Abraham Lincoln was looking at a percentage that was much larger than that. What were his convictions? What was driving him forward? What helped fuel him day after day to stand in his role?

I’m always thinking about the clay feet of the saint. I would love to hear what were all the backroom machinations, backroom deals, and things that were going on that allowed him. He didn’t make the decision to free the slaves in a vacuum. He had to bring the country, the congress and the senate with him. We see every day what a hard job that is. It’s easy to paint someone like that as a one-sided hero with a halo. I would love to be in this, and then I’d like to hear some of the things that didn’t make it into the hero story that he still stepped forward. He still said, “This is better for the world. This is my conviction.”

I’m curious how he would language and feel that conviction because I think when leaders are bold driving towards the results that they feel are most important for them, their team, and their organization. There is a strong commitment to something in the bigger picture.

Your special thing is the courage to be a leader. I know you have four pillars that you like to talk about. Tell us what those are.

The Courage of a Leader® 4 Pillars. The Courage To Be Authentically You. The Courage To Say What Needs To Be Said. The Courage To Trust The Legacy, and that, Elizabeth, is our own leadership legacy. The purpose of our leadership is what we feel we are called to contribute in the world and trusting that bigger picture commitment for ourselves. The fourth pillar is the Courage To Be Bold And Create The Extraordinary.

Authentic is a word that is used a lot. How do you talk about being authentically you? Not everybody knows what the authentic me is. What does that really mean? Take that apart for us.

I love working with emerging leaders and having this exploration about who you are as a leader. Some key inquiries are, “What’s our style? What words would you use to describe that? What are your strengths?” Our innate strengths are things that we have been good at since we were four years old. Now, there’s the more advanced version of that. What’s your story? What makes you who you are? We’ve all got a story. Mine is being from a small town, being curious, and wanting more exposure. What makes us who we are? What makes us tick? It’s owning all of that and leaning into it.

That particularly comes into play. I know this from my life and from all the executives that I’ve worked with. What happens when you start comparing yourself to what you think you should be?

It’s leaning into that and uncovering that. Sometimes, it’s something that we’re attracted to. It’s like, “I admire that in that person. I want to be that way.” There’s probably something there for us to take on that is authentically us. When we start to look out there like, “I should be like that leader. I should be like this.” We start putting all of the shoulds on ourselves. I like to remind people that the companies that research leadership competencies, there are 38 or 27 of them.

Do you mean a list of 38 different competencies?

Yes. We’re human beings. We are not going to be great at 38 different leadership competencies. What is your leadership about? We’re going to be most powerful when we lean into our innate strengths, passions, and interests. Play in that lane and not try to be 38 different things to everybody. Not the should-ing, but who are you? What is your lane? What is your unique contribution? Stay there.

We’re going to be most powerful when we lean into our innate strengths, passions, and interests. Play in that lane and not try to be 38 different things to everybody. Click To Tweet

Actually, that reminds me of a story I was just thinking of when I was starting out in the opera business. I worked as a stage manager and then as an assistant director before I started directing myself. I worked with a wonderful director named Colin Graham, who I loved. He was a major mentor to me. I used to think I was the kind of person that I do better if I had 24 hours to think about something.

I was listening to a conversation between Colin and a very famous conductor we were working with. Colin had an idea that he’d been thinking about. He went to the conductor and said, “What if we paused here? What if we changed the tempo of it?” The conductor said, “I don’t know. You know me. Let me think and sleep on it, and I can give you an answer tomorrow.” I thought, “You mean it’s okay to be the kind of person that does better if she thinks about it for 24 hours?” I could make a snap if it’s something I’m with, but if it’s a new decision, I’m always better off if I think about it for 24 hours.

It’s requesting that knowing that that’s okay.

In talking about all of this, we had a very interesting conversation when we were setting up this interview. We were talking about the courage to be bold and extraordinary. That brought up an issue that I’m helping 2 or 3 clients through. Quite often, you see women, especially if they’re in a very visible position, get stuck in a holding pattern where it’s hard to decide which direction to go. Let’s talk a little bit about the courage to take risks, make a decision, and maybe fail. This is something boys get taught early on. Boys get taught to be brave like, “If you fall over, pick yourself up and keep on going.” Girls were taught to be, “You fell. You hurt yourself. Be careful.” Let’s talk about that.

First, I love for leaders to be grounded in their leadership legacy and unique value. They’re like, “This is who I am. This is what I provide. I bring to every interaction and project to my work overall.” A footnote there, Elizabeth. By leadership legacy, this can be many things. This could be a new way of doing business, a new conversation, a set of improved processes, or a leadership trait. It’s like, “I bring innovation into everything that I do. I develop diverse teams. I solve complex problems.”

That leadership trait is what you bring, so being grounded in that is important. I’ve worked with many leaders on big decisions. A couple of pieces of practical guidance are getting clear about the results that you want from this decision and path, or whatever must be decided. It’s obviously getting input from key stakeholders in that. What is looking to be achieved here because it’s amazing how quickly that gets muddled with secondary and tertiary. It’s like, “We’re doing that. We should also do this.” Scope creep everywhere.

Scope creep, for our international readers, means adding more things to the plan which don’t belong there.

It’s thinking about, “What am I going to do to make this decision? What am I going to research? Who am I going to talk to? What survey am I going to put out?” Deciding these steps that you will take in order to make the decision. You take those steps, and then it’s time to make the decision. If we decide exactly what we’re going to do and what the due diligence needs to be, then we won’t let the due diligence go on too long. You’re like, “This is what I said I needed to do and figure out before I can make this decision. Now I’m here and it’s time to make the decision.”

SWGR Amy Riley | Courage Of A Leader

Courage Of A Leader: If we decide exactly what we’re going to do and what the due diligence needs to be, then we won’t let the due diligence go on too long.


What if it turns out to be a mistake?

Then it turns out to be a mistake.

The world does not end.

I get it. It’s easier to say that than to live through that. What kind of leader do you want to be? We respect and admire those leaders who say, “That didn’t work. We need to regroup. What did we learn? What are we taking forward? What are we not taking forward?”

What you just said is very important because the way you said that did not take the blame on yourself. There’s a difference between I said something that I should not have said, so I apologized and then making it right. I’ve hurt somebody. We made a decision. We went ahead. It didn’t work,” instead of, “It’s all my fault.” The other side of this that I saw and was taught as a woman is it’s easier to apologize, which depositions you and makes you less than. Girls are taught early that it’s easy to apologize first instead of owning the decision. If it didn’t work, it didn’t work. What did we learn and how can we fix things?

I’m not saying let’s pretend I wasn’t the one who made the decision but saying, “I made this decision. It didn’t take us where we needed to go. What are we learning from this? What are we taking forward?” There’s a difference there. I like that you’re pointing to this, Elizabeth, between owning it and standing in that, “I was the one that made this decision. It didn’t get us the results that we most desired here.” We need to regroup and then get it forward-focused.

Since we had this pre-conversation, I’ve been thinking about this a lot. This is something that’s up with a couple of my clients so it’s been very much on my mind. The other thing that you said, which I really liked, was checking with the key stakeholders without saying, “I don’t know what to do here because that’s not safe.”

It’s having trusted people you can talk to to say, “I’m not sure which direction to go.” Instead of saying that, you’re saying, “Let’s talk about where it should be.” I think it’s easier for a man to say, “I’m not sure what to do here. Advise me,” than it is for a woman because another thing that women are trained or socialized is you can’t show that you don’t know what you’re doing.

We can just go in and say, “I really want your perspective on this. This is going to have organization-wide impacts. It’s important that we get your perspective on this. What is your perspective?” Go into asking your questions and gathering information from the other person.

If you’re the kind of person who makes decisions by talking them out or talking them through, where is there a safe way for a leader to do this without de-positioning yourself but also staying strong? How do we talk about that?

I jotted down a few ideas. You could talk about that with a trusted coach like someone on this show. Who’s your trusted ally? That could be inside or outside of the organization, someone you can process with out loud. You can also help create safety and understanding by sharing what you’re doing. Sometimes, we go straight to the content of the conversation and we don’t talk about the process. You’re like, “I’m thinking out loud here. I’m going to process this out loud. Bear with me as you hear my thinking.” Let the other person know that that is indeed what we’re doing in that moment.

That’s a good point because I know, quite often, I will hear the answer come out of my mouth without having it consciously been in my brain first. I am a verbal process. I learned that. As a boss for so many years, I would tell my team, “If there’s something new, let’s talk it through. Challenge me. Bounce ideas back and forth because that’s the way I work.” Sometimes I wish I were the kind of person who would have an idea. It would be perfect. It would come instantly into my brain. I don’t think anybody actually does that, although there are people who pretend that they do.

Yes. It’s not a wonderfully wordsmithing iteration number one.

Let’s talk a little bit about trusting your legacy. There’s a great phrase I heard once where somebody said, “The self-doubt and Imposter syndrome comes up when you’re in a stretch position. It’s your back brain keeping you safe and keeping you small.” Do you have any advice for people who find that Imposter syndrome is coming up? They’ve stretched to a new position, got that promotion, and forgotten all the things that they did to get to that promotion. You were promoted for a reason. What advice can you give to some of us who have found ourselves in that position?

How do we get the reassurance and remind ourselves why we’re here and why we were brought into this position? That could be going to former co-workers. Get lifted up in those moments, knowing that it is not a needy or weak move. Having self-awareness in the moment of like, “I have some self-doubt here. How do I lift myself up so that I’m able to move forward powerfully?”

It’s not weak to ask for help.

It’s doing what we can and know to do so that we’re bringing our most powerful self forward and into the work ahead of us that we need to get done. Who are your go-to people? I have a folder called “Feel Good.” When I’ve gotten great feedback from a client and there’s been reported results on something that I’ve been a part of, I pull that over into the “Feel Good” email folder. I go to visit that folder in confidence crisis moments. We all have them because we’re all humans.

There was something I was going to say, and it’s just gone out of my head because I was so excited about the “Feel Good” folder.

There’s another piece to my response here. It’s also about the clarity of knowing what we want to achieve in this project and in this work and knowing who we are as a leader. Looking at that leadership legacy is like, “Is this going to get us to the results we said we want to achieve here? Is this what my leadership legacy would want in this moment?”

I worked with a female leader who really had to deal with some external pressure. She was in charge of implementing the ERP system, the enterprise-wide system. That was her leadership legacy. She did this in organizations and its fully optimized enterprise-wide software system. She was getting pressure from a senior executive, a very influential person in the organization, to speed up timelines.

I had to keep asking, “Maria, what would your leadership legacy want in this moment?” She said, “We need more benchmarking and dialogue. The leaders in this organization need to know more about this journey we’re about to embark on.” She decided to push back against the senior leader, and it got shaky like, “Is she going to stay in this position?”

It was the first of many times that she had to look to the legacy, the bigger picture commitment, to make her choice in the moment. Set aside the external noise, the turmoil inside of her and say, “If this is going to work, this is what I feel needs to be done in this moment,” and she did. It was fully optimized and implemented by year two. It’s an impressive timeline. They had to slow down to speed up.

That’s hard because there is a natural human tendency to skip the steps. The world is littered with projects that failed because people skipped some of the steps. Let me go to a slightly different aspect of this. What if you feel you are a leader and are not getting the recognition you deserve? This is the work that I do. It’s helping women especially get through the glass ceiling because, having made all the mistakes myself, I feel I’ve made all those mistakes. How do you get the recognition you deserve if you don’t feel like you’re getting it?

Think often an inroad for women to feel comfortable talking about this and creating visibility for themselves is to use the “we” language. It’s like, “I want to let you know about what the team has accomplished.” Thinking about what do others in the organization need to know about what you and your team are accomplishing.

SWGR Amy Riley | Courage Of A Leader

Courage Of A Leader: An inroad for women to feel comfortable talking about this and creating visibility for themselves is to use the “we” language.


There are business reasons for this. To think about the business impact of others fully understanding your capabilities, your recent successes, or what you can do. Hinging that on, “Here’s what others need to know so that we’re collectively doing the best work that we need to do here.” Starting with that “we” language.

Start with the “we” language, but also don’t forget to say, “I thought, I decided,” because it’s also quite possible to make it all about the team and erase yourself from the picture. I’ve had people do that. I’ve done that. Nobody actually recognizes that you were the one who decided it or who led it. If you feel you are being unjustly ignored or taken for granted, what can you do to step forward as the leader you want to be using your four pillars here? How can you get that recognition if you feel that you shouldn’t be ignored and you’re being ignored?

Some of it can go back to what we just talked about, saying what you and your team are accomplishing. Know that be grounded in who you are and what you are about and your value proposition. Find where that value that you bring is needed in the organization. It’s like, “I see we need XYZ. I bring this experience. It could have an impact on us increasing that capability, entering that new market, or whatever it is.” Where do you see yourself providing more and bigger value in the organization? Who needs to know that? Who are those influencers?

Does this go back to the pillar of having the courage to say what needs to be said, or is that something else?

There are a number of things that can fall under the courage to say what needs to be said. Whenever I share that one in audiences or big groups, I always see the nods because we can all think of a time that either when a leader did say what needed to be said. Unfortunately, more often when the leader didn’t say what needed to be said. It could be advocating for ourselves and our work. It could be having the back of a team member or a colleague.

Supporting a team member and saying, “I have your back.”

It could be like, “It’s time to make the decision now. This needs to be said. We’re going to go off in this direction. This is what we’re going to try. I’m saying that we’re moving forward.” I talked to many leaders about giving effective feedback and coaching in the moment that feels so hard. If we’re grounded in our intentions of, “I just want this person to perform better, have a great reputation, and do their work with more ease. I think they need this information in order to get there. Let’s have that conversation.”

Wonderful Janet Miller Evans says, “Feedback is an act of love.” We’ve all seen people who everybody knows where their failings are, but nobody ever said anything. You solve the problem by kicking them upstairs or they go off to another company. They make the same mistakes because nobody ever told them.

I had a time when I found out after about four months of engaging in the same behavior that something I was doing was not working for someone else. I felt so sad and discouraged. The moment I found out, I was like, “Why did we not have this conversation four months ago? I hate that I’ve been doing this thing that hasn’t worked for you. I would have wanted to know.”

Amy Riley, this is fascinating. If you find somebody who’s dealing with courage issues or stepping up to be a leader, where could we start? Let’s tie it up with a way you could start.

Reflecting on where your strengths are. What do people come to you for? What’s the unique value that you provide? This can take a little bit of reflection because sometimes it’s so innate. It’s how we approach and do things. We don’t think of it as anything special because it’s just there for us. In fact, sometimes we’re confused when it’s not there for other folks, but it’s not. It’s your unique strength. Reflect on where your value, interest and passion are. Where are you compelled to make a difference? Where those two lists overlap, that’s the area of your leadership legacy. Declare that leadership legacy and start using that as your guidance.

Reflect on where your value, interest and passion are. Where are you compelled to make a difference? Where those two lists overlap, that’s the area of your leadership legacy. Click To Tweet

Amy, thank you so much for having been a guest on the show. Amy also has a podcast. I spoke about that in the intro. If you liked this, please subscribe. Like us on Apple Podcasts. That’s the one that matters. Give us a review and five-star rating please, and tell your friends. Thank you very much, Amy Riley.

Thank you, Elizabeth. It’s my pleasure.

I’ll see you on the next one.


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About Amy Riley

SWGR Amy Riley | Courage Of A LeaderAmy L. Riley is an internationally renowned speaker, author and leadership development consultant. She’s worked with organizations such as Deloitte, Cisco Systems and Aon Hewitt and has over 20 years of experience working with leaders at all levels.

Amy earned a Masters of Science in Training and Development (MSTD), with an emphasis in Organization Development (OD), from Loyola University in Chicago, Illinois. She is a Certified Professional Behavioral Analyst (CPBA), a certified Tiara International LLC Coach and certified in the Meyers-Briggs Type Instrument. Amy’s second book, The Courage of a Leader: How To Inspire, Engage and Get Extraordinary Results, was released on March 3, 2021 and immediately reached #1 international best-selling status.