Courageous Leadership Strategies With Cindy Solomon

by | Jun 17, 2021 | Podcasts


Courage isn’t something you’re born with. It’s something you learn. Courageous leadership is an attribute that is sought after and that many say women don’t have. Today’s guest will prove that belief wrong. Join our host, Elizabeth Bachman in a fruitful conversation with public speaker, author, and leadership trainer Cindy Solomon, who generously gives us her take on leadership and what it takes to be a courageous leader. Learn the ins and outs of becoming a courageous leader and what it takes to be one from a woman who has made the journey herself.

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Courageous Leadership Strategies With Cindy Solomon

How To Take Action Outside Of Your Comfort Zone

My guest is Cindy Solomon, one of my favorite leadership experts. Before I get into the conversation with her, I would like to tell you that if you are interested in knowing how your presentation skills are stacking up, please take my four-minute assessment at That’s where you can find out where you are strong with your presentation skills and where perhaps a little support could help you get better results.

I am delighted to be able to interview the wonderful Cindy Solomon. She’s somebody I have been following for years and always loved meeting her when I listened to her. She gives me information. In our conversation, we talked about all sorts of ways of courageous leadership, as well as concrete suggestions for how you can raise your visibility. When I’m in Austria and I am nine hours ahead of the West Coast, if Cindy is doing a speech, I will get up at 2:00 in the morning to listen. She’s the only one I do that for. I have to say this is very much worth reading.

Courage is entirely personal. Only you can decide what takes courage for you. Share on X

Cindy Solomon is a Leadership Expert, best-selling author and a world-class speaker. She helps Fortune 500 companies build courageous leadership or at scale, which is better enabling their teams and organizations to compete and win during any disruption. With her Courageous Leadership keynotes and virtual and live leadership programs, Cindy has helped hundreds of companies around the world identify, nurture and leverage their leadership potential in both their frontline employees and their leadership teams.

Among her clients, she counts the 26 JD Power Award winners, as well as industry leaders such as Google, Alaska Airlines, UPS, Oracle, Wells Fargo, The Ritz-Carlton, and the list, goes on and on. This is part of the Pride Month series for Speakers Who Get Results. She has said that being out as a gay woman has made her so much more authentic in herself, and she has been able to embrace courageous leadership on her own terms because she has been true to who she is. That’s very important for all of us to remember. Without further ado, here’s the conversation with Cindy Solomon.

Cindy Solomon, I’m so happy I finally got you on the show. Welcome.

My pleasure. I’m excited to be here.

This is great. As I said in the intro, I have been watching and following you for a long time and I love running across you whenever I can. Before we get started on Courageous Leadership if you had a dream interview or you could talk to somebody who’s no longer with us, who would it be? What would you ask them and who should be in the audience?

Courageous Leadership: Courage can be learned. It’s not something you are or aren’t, it’s another decision-making skill or tool you can put in your toolbox.


That’s a really tough one because I have a list as long as my arm. I’m going to give you two because they are interested in different ways. The first one is Eleanor Roosevelt. She is probably my greatest idol and guiding light in the world. She became powerful and successful in a time when it was nearly impossible for women to do that. She didn’t have any of the outward attributes that were valued back in that time yet, she was courageous enough to step out of a predefined role, become the president of the United States and the voice of her husband who couldn’t do a lot of the work that she was doing on behalf of the country because he was in a wheelchair. She had to be his legs, eyes, ears and became a force of her own even after that role ended. She went to the UN created the Human Rights Commission. She never stopped changing the world for the better. I believe it was through her courageous acts that we have a better world now than we had before she was on it.

Who’s the other one?

The other one is Amelia Earhart. Partially, it’s because I want to know where the heck she is. We know where she ended up but I’m not so sure. Amelia Earhart was another one who stepped out of the traditional role of a woman and simply refused to take no for an answer. She found her path, her own way. She didn’t let any of the noes get in her way of her doing what she wanted to do, which was to be in the sky.

Both of them went ahead and did what they wanted to do. I often think that Eleanor Roosevelt never really planned to become what she became. She just did the next thing that was in front of her and, somebody had to do this, she got to step in and do it. Somebody had to do that, let’s step in and do that until she realized I have an identity of my own and grew into it.

I also think that she had a deep-seated need to make the world a better place. She wanted to leave it better than she found it. That value and desire helped her move forward even when the odds were against her.

She lived through two World Wars so there was a lot to make better. Speaking of Courageous Leadership. That’s a nice title, Leading with Courage. What do you mean by that? If you can cram it into the time we have.

I have to tell you the origins of it a little bit to answer that question succinctly. I’m a recovering Corporate Executive. I ran a 3,900 person sales and marketing team for a Fortune 50 company. When I left that world, I realized that I had 1,001 examples of terrible leadership. I could count my great leaders on one hand. I started thinking about the why of that. Why is it that good leadership and certainly great leadership seem to be so difficult to find and what is it that those handfuls of people do differently than the 1,001 mediocre or terrible leaders?

I started an accidental research project and I talk about this a little bit in my TED Talk. To date, we have interviewed over 9,000 people about what separates great leaders from good leaders or mediocre leaders? What is it that they do that allows them to develop and build the people around them in a way that’s so much better than many of those around them? What we discovered was this idea of courage. People talked a lot in our interviews about, “They had the courage to or I had the courage to.” Very rarely would they describe it for courage for themselves but when others were looking on, they did. We started this research project to get at the heart of what is courageous leadership and what can you do? We learned three amazing and important things during our 9,000 now-to-date interviews on the topic.

The first thing that we learned is the courage is entirely personal. Only you can decide what takes courage for you. It’s not something that you are born with, it’s something that you can choose to learn and go after. One of the things I love talking to you about this because you totally get this is when you think about Speakers Who Get Results. Some of us love speaking. I am one of them. It takes me zero courage to get on stage. I will knock people down to get on the stage. I love it so much. For other people, it would take them the courage to fight through their fear, anxiety and stress of being on the stage. I look to a quote from Rollo May that helps me understand this part of the research, it’s that, “Courage is not the absence of fear, rather it’s the ability to take action despite your fear.” For me, getting on stage takes no courage but for somebody else, it will take courage to get on the stage. Courage isn’t about being fearless. That’s a myth. If you are not fearful, you are just not paying attention, particularly in this day and age. It’s the ability to take action despite that fear or anxiety.

Courage isn't about being fearless. If you're not fearful, you're just not paying attention. Share on X

The second thing we learned that I think is equally important is that most of us don’t think were courageous. This was pretty stunning to me that only 1 in 3 of us believes we are courageous. When the reality is 100% of us are courageous. The thing that was most stunning to me is that there were no demographic differentials in that belief around courage except one, which was gender. One of the ways I illustrate this in my keynotes is, let’s say I’m speaking to a primarily female audience, how many of you believe you are courageous? About 20% or 30% of people will raise their hands and they usually are like, “I don’t know. I felt courageous earlier but not so much now.” “Jane, do you feel courageous?” I asked them all to close their eyes. Primarily female audience with their eyes closed, almost 100% of women will raise their hands.

It doesn’t matter where in the world I am and what the audience is. If I’m in a primarily male audience, which is most of the very senior executive leadership events that I do are primarily male, I asked the same question, “How many of you believe you are courageous?” One hundred percent of the guys raised their hands up. “I’m more courageous than him and him and definitely that guy over there.” When I ask them to close their eyes, nearly 50% of the men will bring their hands down. Culturally, women have been taught we aren’t courageous and if we are, don’t tell anybody. Men have been taught the equally destructive, “You darn well better be courageous. If you aren’t, don’t tell anybody.” We see how this plays out at work every day. Women will only apply for a job if they have at least 7 of the 10 qualifications. Men will apply with less than three and feel perfectly comfortable applying. It plays out in our behaviors.

The third thing we learned, which is the magical piece of all this, is that courage can be learned. It’s not something you are or aren’t, it’s another decision-making skill or tool you can put in your toolbox if you choose to go after it. That is the very long answer to your question about what is this thing that you are talking about. It’s the set of behaviors and skills that you can choose to go after in building yourself. There’s a great quote by Ruth Gordon that says, “Courage is like a muscle, it’s strengthened with use.” I think that’s true.

When you talked about people closing their eyes, for the men, the courage to be vulnerable and admit that maybe you are not totally certain, for the women, the courage to say, “I think I am,” even though with your eyes open, you expect to be slapped down if you claim courage. It is a cultural expectation. The way I can live with the news these days are I think a lot about history and historical cycles and where all this came from. I think back to where the whole gender norms started and many of them, does it still apply now, or is it centuries of history that we are still carrying the baggage for? One of the things I have heard you speak many times, you have mentioned about women getting in their way, which is a big part of the work that I do. It’s helping women get out of their own way. I would like to know what you do to help women learn to not sabotage themselves.

It’s less sabotaging themselves in my experience and more understanding the unwritten rules. That’s why we call our Courageous Leadership for Women workshops, The Unwritten Rules to Success. In my experience and I’m sure you see every day in the work that you do, we have a certain set of rules at the beginning of our clear careers. You put the time in, you say yes to everything, you achieve the results and overachieve the results. They are very clear black and white rules. Somehow in the middle of our careers, the rules change. Nobody tells us that the rules are changing, they don’t give us a new rule book but all of a sudden, those things are not nearly enough. They are the entry ticket then it becomes about your influence, relationships, ability to be visible and get known for specific things.

When we are teaching the skills of Courageous Leadership for Women, they are slightly different than for men because, for some reason, men understand this. They intuitively get this. I don’t know how they’ve got linear brains. There’s some back room where they all get together and say, “Here’s the new rule book.” For women, we seem to struggle with that transition. The first thing that we help women do is understand their strengths and how they relate directly to the business.

This is another fascinating idea to me because in a male audience, when I say, “Tell me your strengths.” Men will immediately grab the microphone and begin spouting their strengths that are, “I’m ambitious. I’m results-driven and self-starter, etc.” If you put a microphone in front of a woman in this situation and say, “Tell me your strengths,” they will generally broad-brush stroke and say things like, “I’m a good communicator. I am organized. I like to help people.” It’s these vague kinds of namby-pamby great. It’s good that you are a good communicator. I would hope so because you are getting a paycheck so you should be a good communicator.

When I asked those same women to pretend they are a man and describe that same strength, they will use the male words. Instead of saying, “I’m a good communicator,” they will say, “I’m especially good at taking people with disparate opinions, bringing them together, and getting them focused on a common goal.” They will immediately transition just by putting a male hat on into verbiage that more specifically details what they are great at, and then, more importantly, connecting it to the business. Being able to get comfortable with using that kind of language about yourself is what gets you the next role. It’s what starts to build your brand.

Courageous Leadership: Everything you want is just outside your comfort zone. Getting what you want is going to be scary. You need to take action on it in spite of the fear. Doing that every day will build your courage muscle.


When I ask women, “What does it feel like when you talk about yourself that way?” In an audience, I did this back pre-COVID with an audience of about 6,500 women. I said, “What does it feel like you are doing when you talk about your strengths that way? You are…” The entire 6,500 women said “bragging.” All together in a beautiful chorus. If I ask men that same question, they don’t even understand the question. They are befuddled by the fact that that would feel like bragging. It doesn’t even occur to them. They don’t even understand that word. It’s fascinating to me that that is one of the skills that women have to have to be able to get past that mid-point in their career, specifically describe their strengths, and vocalize it confidently with specificity and how it relates to the business.

I don’t know if your mom did this but my mom said, “Good girls don’t brag.”

My mom said, “Don’t toot your own horn.” That was hers.

It’s the same old thing. We are socialized that way. Also, there is a perception that the risks of failure for women are so much greater than the risks of failure for men. I always think about little boys are taught to be courageous and girls are taught to be careful. It brings me to one of my other questions for you, which is women within an organization, even if you are leading the organization, how can we gracefully claim the credit for what we have done without bragging? When women are perceived as bragging, the bar for bragging is way lower for women than it is for men. It is a tight rope that we walk. I heard you once talked about writing an email about your plans at the beginning of the week and then talking about your achievements, the boss email. Can you tell us about that? That crystallized for me. It’s something I was trying to say but I wasn’t nearly as concise as you are so I have totally stolen that from you ever since.

Spread it far and wide. I will tell you about the boss email, and then I will circle back to comment on your question earlier. The boss email is something simple, and this is especially valuable in our live virtual hybrid world that we are going to be in for a while, if not forever. The five-day workweek back in an office somewhere is going to be rare at least until 2022 and maybe forever. The boss email is something that is an accountability tool that we teach to leaders that you can ask your people to do for you but you can also do it for your manager.

Do one thing a day that pushes you a little bit because the more you exercise that muscle, the stronger it will become. Share on X

On a Sunday night, we all start the workweek, on Sunday looking at what’s ahead. It allows you to take three things that you want to move forward that week and share those with your boss and say, “Jane, I’m going to start doing a weekly update for you just because it helps myself stay accountable and I make sure that I’m working the priorities that you want me working. This week, my main priorities to move forward are…” It’s that short. “Complete the XYZ project with results posted next week. Utilize the time to develop Phil on my team against these two development priorities. I will let you know on Friday how I did.” It allows you to consistently be communicating with your boss so they know what you are working on. It alleviates some of the micromanaging that you are bound to get, particularly in a hybrid working environment. It also ensures that you are working on the right priorities that they want you working.

At the end of the week, on Friday night, before you close up shop, you send them another quick note, “Here’s where I’ve got to on these three priorities.” It holds you accountable and focuses you. It stops you from reacting to everything around you during the week and focuses on the most important things because you know you have to report back but more importantly, it becomes the map of your progress during the year. It becomes an incontrovertible piece of evidence for your annual review. That, in my mind, particularly for women, can be a game-changer because you now have a record with your boss of what you accomplished during the year. It also makes doing that annual review a lot easier but it also puts in black and white in your results rather than getting amorphous, “You need to work on it back at present, blah, blah, blah,” which is a catch-all for, “I don’t know what else to say to you but you are a woman and I’m not going to promote you.” This gives you incontrovertible evidence of your results throughout the year.

If you are on C-level, in theory, your boss is then the board, would you recommend that for someone who is C-level or running their own company?

If you are running the company, I would have everybody else doing it under you to have this big standard of the information flowing up. If you are in the C-Suite for an organization, I would argue that doing this once a month for your CEO, getting it on paper and record is important. I wouldn’t do it every week. I would probably do it once a month and I would keep it to two slides and say, “Here are my accomplishments for the month. This is what I’m working on next month. Here’s how far I’ve got.” Again, it’s written documentation of what you are working on and where you are getting results.

I had a client who created a giant merger for her company. She worked on it for five years. She knew it was her baby and it was a giant international collaboration. When it was launched, she spent so much time saying how great the team was that the marketing department forgot it was her baby and sent all the media requests to the brand-new manager who had only been there for two months. That was when she hired me. She erased herself from the picture by being so generous. You want to credit your team but you also need to claim credit for, “It was my idea. Hello?”


That goes back to your other question. I want to comment on that. You were like, “How do we do this so we are not perceived as bragging or aggressive?” I don’t think we walk that tight rope. I’m saying no to the tight rope. There are more upsides than downsides to being clear about your accomplishments. I don’t think you do it like the biggest jerk in the office does it but I think you do it clearly, consistently and with confidence. To give an example in the how-to world of the example you just gave is being able to say, “Here’s what I have been able to accomplish.” If she would have been doing those boss emails, that probably wouldn’t have been an issue. If she would have asked for time in front of the board to update them, make sure she’s the one doing those presentations so it’s clear. Obviously, it takes a village to do that to get a merger done but she’s the leader of that team. Being able to be clear about, “Here’s what we set out to do, here’s what we accomplished,” and it took the 30 members of the team to make that a reality, but being clear, it was your project and what you brought to the table to get it done.

Where could somebody start besides the boss email if you want to show up more courageously, be more visible and make sure that people are noticing?

There are three things you can do right out of the super simple gate. One is to get clear about your strengths, practice articulating them and how they relate to the business. Instead of saying, “I’m great at running projects.” You work on a statement that says, “I’m incredibly good at, and here’s what it does for the business,” it’s one sentence. Going back to that just to use the example that communication we talked about earlier, “I’m good at communicating.” That tells me nothing. If I’m your boss, I don’t know what to do with you with that. Instead, you say, “I’m incredibly good at taking a team with disparate opinions and ideas, creating a common vision and moving them more quickly toward a result regardless of the noise around them.” Now, I know what to do with you and I know where to put you where you can be of most value.

Get a group of friends together, talk about that and get used to having that roll off your tongue. That’s the first thing. Know your strengths. The second thing is to show up. When you show up to a meeting, share your opinion, prepare. One of the tools that we suggest in our programs is for two minutes before every meeting you go into, think about what’s the win for you in that meeting? What’s makes that time well-spent for you? By getting your brain focused on that, you show up differently to the meeting. To be able to try and get that result. It’s to share my opinion about this or to get a decision on that or to whatever it is.

The third thing about visibility is to stop asking for permission. Do not raise your hand. Have you ever seen a guy raise their hand in a meeting to be acknowledged? Absolutely, not. Lead with the punchline. Don’t apologize. Don’t put a whole bunch of fluff and words around it. Don’t go, “I’m sorry. Did I did?” because apparently, we have two seconds to be able to get a guy’s attention and to keep it. You have to lead with the punchline. “I disagree with that. Here’s why. I think the best next step is.” Get comfortable with clarity, which will help you become more visible.

I think that’s going to be one of our tweetable tweets. I’m on my third page of notes here. Cindy, let me circle back to something you mentioned in passing earlier. Executive presence, that’s a big piece of what I help people with. When somebody hears you don’t have executive presence and it probably means they don’t know what to do with you, so it’s like a catch-all phrase. Can you expand on that, please?

This amorphous executive presence idea has become the easy go-to, “I don’t want to promote you.” I’m going to say this phrase that apparently everybody now uses, and it’s going to keep you from getting promoted. We have all heard it. I heard it in my career. Men very rarely hear it by the way but women hear it all the time. What we have done is we have taken executive presence and we have defined the skills that it takes to be great at the things that we know are the end result, which is being heard and visible.

Are you talking about us, you or your company?

We have defined it as courageous presence and we have broken it into four specific skill areas. Relationship Presence, which is building your sphere of influence. You teach this to your clients all the time, which is hugely important. Communication Presence, which is how you show up, what you look like, leading with the punchline, etc. Core Presence, which is about understanding who you are and where you want to get to. Being clear about, “In three years, I want to be at this next level. Next year, I need a bigger span of control. I want an international assignment.” It’s having that core vision. The fourth is that Strength Presence, which is you’ve got to figure out what you are great at and go after roles that allow you to use that because, by the time we get to mid-career, we know what we are good at and what we are not. We know where our passion lies. It’s stunning to me how many women in particular haven’t taken the time to be able to do that strong statement.

It’s funny because, in the workshops, one of the examples we give is, “If I’m a CEO and I hired all of you, I have to know with detail where I can put you to get the biggest bang for my dollar. Until you can describe that to me, you are invisible to me. Until I know where I can use you in the best possible way but until I know where I can use your talents, you are baggage over here for me.” That’s what gets in our way more times than not.

There are so much gold here, Cindy. Thank you so much. I could keep you talking for hours but I know we both have hard stops. We will certainly be posting how people can find out more about you and so forth. Is there one thing we could start with? What’s one thing to leave us with?


One of the quotes that I use at the end of all my keynotes that I think is true is that “Everything you want is just outside your comfort zone and having the courage to realize that getting what you want is going to be scary. It’s going to take effort and it’s going to take you taking action despite the fear but doing that every day will build that courage muscle.” As Eleanor Roosevelt said, “Just do one thing a day that pushes you a little bit because the more you exercise that muscle, the stronger it will become.”

Cindy Solomon, thank you so much for being a guest on the show. You are one of my favorite people and I’m so happy to have you here.

Right back at you, my friend.

Thank you, everybody, for reading. Let me remind you that if you are curious about your presentation skills, your executive presence and how you are doing, you can take our free quiz at In four minutes, you can see where your presentation skills are strong or where perhaps, a little bit of support could get you some results. This has been Elizabeth Bachman. I will see you at the next one.


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About Cindy Solomon

Leadership expert, best-selling author and world-class speaker, Cindy Solomon helps Fortune 500 companies build Courageous Leadership at Scale, better enabling their teams and organizations to compete and win during any disruption.

With her Courageous Leadership keynotes and virtual and live leadership programs, Cindy has helped hundreds of companies around the world identify, nurture and leverage the leadership potential in both their front-line employees and their leadership teams. Cindy counts among her clients 26 J.D. Power Award winners, and industry leaders such as Google, Alaska Airlines, UPS, Oracle, Wells Fargo and The Ritz-Carlton, among others.

One of the most highly sought-after leadership speakers in the world, Cindy and her worldwide team of facilitators have traveled the globe sharing her provocative, and often hilarious insights on business, customer service and courage with tens of thousands each year. She is also the founder and CEO of the Courageous Leadership Institute, an organization that specializes in working with companies, nonprofits and associations to introduce and build Courageous Leadership skills at every level.

With clients ranging from financial services to aviation and healthcare to high-tech; Cindy and her team of worldwide Institute Facilitators deliver cutting-edge, blended learning programs and innovative, online MicroDevelopment programs that enable exceptional customer and employee engagement, generating impactful bottom-line results – fast.