Minisode: How to Handle Imposter Syndrome with Jenn DeWall

Full Transcript Below

Jenn DeWall:

Hi everyone, it’s Jenn DeWall, and on this week’s episode of The Leadership Habit podcast, we are talking about a much trending topic, the topic of imposter syndrome. And it’s interesting. This is actually a topic that, you know, has been around for quite some time. It was actually coined in 1978, and people have been coaching on it, myself included, for many years. But I think as a result of much of the burnout that people are seeing or experiencing through COVID through all of these drastic organizational changes that we’re starting to see imposter syndrome take more of a center stage. People are starting to really relate to it. And we wanted to respond to the fact that there’s a lot of people that are really starting to resonate with this term. So this minisode is really just devoted to understanding what it is and also understanding what it may not be or what the root causes can be as well as how to overcome it, how you can do it as a leader, what you can look for on your team as well as what you can do in your organization.

What is Imposter Syndrome?

Jenn DeWall:

So let’s start with a basic definition of what imposter syndrome is. It is, or it can be defined as a collection or a feeling of inadequacy that persists despite evident success. It, another way it could also be known as self-doubt. There was a speaker that we worked with. She’s an author as well, Maxie McCoy. And she would absolutely say stop telling people that there is something wrong with them, but it’s just bad self-doubt or your inner critic. But it happens very commonly within more high achieving people, maybe more Type A, or your perfectionist where they’ve worked, worked, worked, but they somehow feel like they’re never enough. Even though they’ve got all of this evidence, maybe they have the title or the promotion, or they work at a big organization, insert whatever we think that Cigna would be. It’s still not showing them that they are there.

Another description for imposter syndrome can be described as feeling like a fraud feeling like, Oh my goodness, you’re in this job. Maybe you were promoted to a director, and you’re just walking on pins and needles, waiting for someone to expose you for not being that right person or the right fit for the role. Now, the important thing to note about imposter syndrome is that although the term itself was coined by researching women, it’s actually something that both men and women experience and it’s something that also transcends cultural borders. So we might find ourselves feeling— no matter whether we’re a woman or man— just feeling, Oh my gosh, am I really not enough? Am I fully capable of doing this? And let me just give you a little bit of context too. If you want to go and do your own research on understanding the origin, the imposter syndrome was actually coined by two psychologists, Pauline Rose Clance and Suzanne Imes, in 1978.

And they studied women and really found that these successful women just still felt like they were not able to, you know, really believe that they were successful. There was something where they were either feeling affirmed in the lines of, Oh my gosh, I’m still not there. But they also maybe didn’t study some of the things that would be really important to understand. There wasn’t a lot of diversity in terms of background in terms of race or class. And so that’s where people are starting to challenge a little bit of the notion of imposter syndrome, but in any event, go ahead, and I would encourage you to, you know, start to research more about this topic. Here’s how to know maybe if you’re experiencing something like imposter syndrome, again, imposter syndrome, being that collection or feeling of inadequacy, despite evidence of success. So what it can look like is, are you overworking and are you overworking so much because you feel that you have to prove yourself to someone, you have to show your value, show your worth.

And while this might feel like it’s serving you in some capacity because it’s proving that you’re enough, it can often lead leaders into burnout, where then they become exhausted. They likely are not showing up as the person that they are capable, capable of being, which then only reinforces the imposter syndrome. Another sign of what it can look like is maybe you find that you don’t believe in your opinions or that you have anything valid to share. So it could result in you not speaking up. Maybe there’s a little bit of doubt around the value that you can provide, or maybe you’ve had a past experience where you’ve spoken up. It didn’t go as planned. And so then you just decided that to protect yourself, we’re not going to do it anymore. In addition, it can also look like not asking for help. Imposter syndrome can also or can lead us to feel like we have to do everything on our own.

Because if we ask for help, they’ll see that we’re not deserving of our position, that we somehow are not perfect, and so on and so forth. I’m sure some of you can probably relate to that. We put a tremendous amount of pressure on ourselves as leaders to have all of the answers, to be able to do everything. Even though if we truly expected that from our employees, we likely wouldn’t. But if we did, we would then know that we’re creating burnout. We’re setting unfair expectations, but again, we are our own worst critics. Another way that imposter syndrome can show up or what it can look like is a lack of confidence and an error in your own decisions. You might second guess yourself. You might feel like, I don’t know if I’m competent enough to make this decision, or you have that fear of being found out.

Someone’s going to catch me soon, and they’re going to fire me, or they’re going to demote me, or what are the consequences that could come. And then also another sign of imposter syndrome could be risk avoidance. Maybe you try to go under the radar. Maybe you just try to take very small, easy steps into something, but you don’t really want to be in that vulnerable spot of doing something new or trying something big because you just don’t feel like you could do it. Even though, again, you might have this strong history of overcoming adversity, adding so much value, but yet we don’t even believe it. I mean, as a coach, I like to see it as, you know, if we thought about our resume and thought about all of our accomplishments, sometimes imposter syndrome can show up as half of a resume, meaning we might have all of this experience, but we completely forget about that.

Bias Can Cause Imposter Syndrome

Jenn DeWall:

And we don’t even look at it to say, look at this proves how worthy, valuable, competent, capable I am. We forget about it. So one thing that’s worth noting, and it really came about pretty strong, I would say in a recently circulated Harvard Business Review article on imposter syndrome that was published this February, is that we need to note that the root causes of imposter syndrome can vary. And that it’s not as simple as just saying, Oh, you’ve had some really bad inner self-talk, that’s what it’s happened. There can also be cultural perspectives that can create imposter syndrome within people. There can be bias. And again, this is from that Harvard Business Review article and bias in the sense of racism, a feeling that if you belong to a particular race, that there are certain ways that you can and cannot show up. And so then it gives you a little bit more of that anxiety feeling of inadequacy.And so we do need to note that it’s not only just about that self-talk that there could be other external factors that are also perpetuating imposter syndrome. So above and beyond competence, I should say are above and beyond, you know, just feeling like you’re good enough.

How Can We Address Imposter Syndrome?

Jenn DeWall:

So how do we address imposter syndrome? What do we possibly do to be able to navigate this very complex, inner working and feelings of inadequacy? Well, there are three ways that we can address it. We can start by looking at ourselves and first starting to think about some of the thoughts that you might be having now. Again, I don’t want to disregard that the fact that imposter syndrome can come as a result of bias discrimination, but we’re going to be talking right now about imposter syndrome in the form of self-talk. So imposter syndrome, if it’s showing up self-talk and you feel like maybe the self or the core thought is I’m not good enough to be a leader, then we have to challenge ourselves.

# 1 – Is it THE Truth or Just Your Truth?

Jenn DeWall:

And so the first thing that we can do to address it as a leader is to ask ourselves if what we’re telling ourselves is our truth or the truth. Sometimes our thoughts, because we have likely reinforced them multiple times, have continued to validate them and build these stories. They become so true to us. It’s like, it’s the only thing that we actually believe, even though we may not actually have factual evidence that validates it. So one of the first ways to challenge imposter syndrome, for example, is if you’re saying that you’re not, you know, they somehow promoted you by accident and that you’re not worthy of being there. Is that your truth? That’s driven out of maybe a lack of competence or confidence, or is that the truth? And if it’s the truth, you need to find evidence to support it. If you don’t have evidence to support it, then it could be an opportunity to challenge that truth and rewrite a new story.

#2 – Stop Looking for Perfection

Jenn DeWall:

The second thing that you can do to address imposter syndrome as a leader is to stop rewarding the idea of perfection and to stop setting perfection goals. Now we put a tremendous amount of pressure on ourselves to be able to know everything, be everything. And sometimes, that does come from a culture that rewards people for maybe being perceived as doing all of the things right. And if we truly believe that perfection exists, we’re ultimately setting ourselves up our teams and our organizations to fail because that just means that we think there’s a finite road to our development and growth and likely the second that we believe that is when we stop using our creative skillset, we stop innovating. And so we have to stop rewarding the idea of perfection. I’m sure yourself, you could think of something that maybe you may have had a misstep or a failure, and it provided a valuable lesson to you. Maybe that is really your opportunity to say that perfection. It’s not really a relatable or realistic thing that we can do that. If I had been perfect and not made these mistakes, then I wouldn’t be where I am today.

#3 – Act “As-If”

Jenn DeWall:

So number three, another way to combat imposter syndrome is to act “as if.” Now, maybe you’re about to go on stage, and you’ve never done it before. You’ve never presented to people. So what you could do is act as if you’ve already presented to, you know, hundreds of audiences, dozens of people, whatever that needs to look like for you. Act as if your success has already happened. So act as if it’s just embodying yourself in a visioning statement. So thinking about the vision of what success would look like, think about it, identify it, speak it in the present tense, and then act as if it’s already happening.I am a great leader. I am a great leader. And also, a practice that self-validation creates mantras for yourself that can, that you can use to guide you to build confidence. And that can help you overcome some of that anxiety that’s created as a result of poor self-talk or imposter syndrome.

#4 – Watch out for GAILs

Jenn DeWall:

Number four, if you want to combat imposter as a leader, you have to understand your energy drainers as it comes to your thoughts. The coaching school that I went to was called IPAC. So the Institute for Professional Excellence and Coaching would call these GAILs. These are the things that are all in our heads. So these are the things that we control, but by listening to them, they drain our energy. And GAIL is actually an acronym, and it stands for gremlins, assumptions, interpretations, and limiting beliefs. Now let me talk about what a gremlin is.


A gremlin is that pesky monster that’s in your brain, also known as self-talk. It could be giving that loop that, by the way, Jen, you’re not good enough. You’re never smart enough. You always say the wrong thing. Now the gremlin, again, they’ve likely come about for a beautiful reason. If I continue to tell myself that I’m not good enough, it may help me work harder because I constantly need to prove myself. The challenge is there’s a point that those gremlins stop serving us in a positive way. And once that happens, we see burnout. We see stress, low competence. That’s what we need to recognize. Do we need to re-examine our thoughts? So what are the gremlins that you have? Who are those pesky thoughts, or what are those pesky thoughts that are draining your energy or draining your confidence?


The next part of the GAIL is the assumption. What assumptions about a situation about yourself, about an individual, are you making? So again, this comes down to understanding what is true versus or true to you versus the truth. Are you assuming that something is going to happen? Just because it happened once, that’s not necessarily true, unless you can somehow back up that it will. If not, you have an opportunity to change. You do not have to adhere to that assumption. Understand that it can always be discarded.


The “I” in GAIL stands for interpretations. We all see, see the world through our own lens of our own experiences. Our failures, our family upbringing insert all of the ways that we are incredibly diverse individuals. And with that being said, we then see the world’s situations and events and our own unique way. Now the beautiful thing about interpretations is again, and they can be changed because we have to really ask ourselves, is this the truth? So, for example, let’s say that you’re looking for a job and you apply for this job. You go through the interview process, and then you never hear from them again, which many people, their first response is to say, I must not have been enough. I must have bombed the interview. And that’s how we’ve interpreted the situation. And why it’s important to be mindful of that is that interpretation is likely draining our energy and draining our confidence. Another way that we could look at it, let’s say that employer never called you back. It could be that they had to cancel the position. They could no longer hire for it because they had to make cost cuts, or maybe there was someone that was internal that was already going to get the job. If you cannot get to a confirmed truth to substantiate that interpretation, that means you have the opportunity to change it. So I recommend you challenge it, especially if it’s not serving you. And it’s only making you feel less-than or adding on to that imposter syndrome.

Limiting Beliefs

Now the final piece of the GAIL is your limiting beliefs. These are beliefs that we have about something that might prevent us from doing something. I could put it in a very simple way. It could be that because I’m a woman, I’ll never get to this level of leadership or because I’m a man. I can never share my emotions in some way. These act as rules for how we navigate our lives, and these rules again, we think and adhere and buy into them because they’re keeping us safe, right? Why bother with applying for the job? If I know that I’m not going to get it might as well save myself the heartache. The problem is, is again, these aren’t necessarily true. These might be old rules that we’ve adhered to from early childhood, or we’ve learned these lessons, but I would encourage you to challenge them. What are beliefs that you have that are keeping you playing small, that are preventing you from taking that risk? These are, again, things that can keep you caught into imposter syndrome because we’re, we’re telling ourselves that maybe we’re not as capable. We’re not as strong as we could be.

#5 – Self-Validation

Jenn DeWall:

The fifth way that you can address imposter syndrome as a leader is to validate your worth. Now, this is really important. I hear this often, and people can really struggle with trying to talk about their strengths and talk about what they’re good at. The challenge is, are you have to be able to believe in your worth. You have to be able to self validate to say. You know what? I am enough.

I know that many times throughout our lives, we’ve been conditioned to externally validate meaning, relying on someone else to tell us whether or not that we’re getting a right. And while we do need to do that, we absolutely always will. It can’t be lopsided. We can’t always just look for external validation. We also need to know how to tell ourselves we are enough. So one way to validate your worth and to challenge that imposter syndrome is to write down all of your successes. Some people might call this writing down and creating your own win-wall of all the accomplishments or the points of pride that you have, or maybe it’s just creating a great list of all the things that you’ve achieved, but write them down. Think about it. How could you use that in a moment of maybe where you lack confidence? You could pull it out and remind yourself. I am actually more than capable and confident in my abilities.

#6 – Find Your A-Team for Support

Jenn DeWall:

Six is to choose a team of support. Sometimes imposter syndrome can come up because we open ourselves up to feedback from everyone. The problem with that is that not everyone’s feedback should be treated equally. They may have a different experience. They may not have any experience. They may not even be someone that you trust or that you would admire, or they may just not be speaking from a place of love. And this is where it’s really important for you to choose your A-team of support who are the people that you want to maybe share these feelings with or share your missteps with. So then you can ask them, Hey, how did I handle this? And get feedback from them? Do not open yourself up to the feedback from everyone because they’re not all going to understand what you’re going through, nor is that feedback necessarily going to serve you. In some instances, that feedback can actually confuse you and leave you feeling more stuck than before.

#7 – Give Yourself Permission Not to Know the Answer

Jenn DeWall:

The last piece about how to overcome imposter syndrome as a leader is to give yourself permission not to know the answers. If you want to be a great leader, someone that builds trust someone, that’s relatable, show people that you are human, and there is no possible way that you are going to know the answers to every single thing, especially if you are continuing to change, to grow, to take risks. And if you want to be that innovative person or the creative person, you’ve got to get comfortable in the discomfort. And so it’s giving ourselves permission to not know the answers, as well as giving ourselves permission to not be the experts. We could have someone else on our team that could be a huge asset in one particular area. Instead of feeling like you, as the leader, also needs to be the expert, praise that individual for their strengths and leverage them for support. It does not mean that you are not enough. What it does mean is that you recognize and can see the strengths in others.

How Leaders Can Combat Imposter Syndrome

Jenn DeWall:

So how do you combat imposter syndrome on your team? Well, I just talked about the leader. You know, we have to talk about a few different things, but now we have to be able to identify it on our team. So the first thing is to have open conversations with your team, ask them what challenges do you have? What are your goals here? What motivates you and try to understand any perceived challenges or barriers that they’re having and actively listen to see if there’s any level of self-doubt, where they’re just not believing in themselves and see if there are opportunities where you can either coach them by asking open-ended questions or empowering questions, or that you can give them opportunities to prove it to themselves so they can see how great they are checking in with your team on impostor syndrome is important because if you want them to work, you know, the best that they can be, you want to remove any of that extra stress or mental clutter that could be clouding their judgment or reducing their productivity, or just adding to their overall stress.

Rewards and Recognition

Jenn DeWall:

So another thing is always to make sure that you’re taking time to reward. If you want to work on imposter syndrome with your team, make sure that you see your team, identify their strengths, contributions, give them recognition. No, it doesn’t always need to be some big cash bonus or a vacation. It can be simple words of affirmation. I appreciate you. The work that you did on this project really helped deliver an optimal client experience. We couldn’t have done it without you. Make sure that you are slowing down to see your team. This is a great way. When we can understand that imposter syndrome shows up on our team, then we can take steps to reduce turnover and improve engagement as well as morale.

Check-In With Your Workplace Culture

Jenn DeWall:

Now, the final thing is to check in with your culture. You know, as talked about earlier, you need to understand, there are biases that discriminate against people that create a cost, a culture where people do not feel included. You need to check in with that. So you can create an inclusive culture where different ideas, backgrounds, races, educational levels, skillsets, whatever that may be. Everyone should be able to have a seat at the table and feel valued.

Jenn DeWall:

And then the last piece for the organizational culture, if you want to reduce imposter syndrome, this is where listen up those with fear-based cultures, you really need to create a place of psychological safety. People can’t feel that if they make one mistake, they’re going to be fired. That’s only going to create a greater impact on imposter syndrome. You’ve got to create a culture that says we support you. We know that mistakes will happen. Here are the very specific ways that a mistake would lead to termination. It’s not just any mistake. We’re not that hardline, or maybe it’s looking at how you’re actually assessing your workforce.

Instead of doing the bottom 10% are gone at the end of the year. That can be a culture that fosters imposter syndrome. And again, think about what that can create. It can create ethical challenges as people might cut corners because they don’t want to risk being at the bottom. And it can also stifle the growth of your organization because everyone is competing with each other. And you’re creating a lot more mental challenges, too, for people such as depression, anxiety, stress, so on and so forth.

So this was our minisode. I know it was a little bit longer all about imposter syndrome, but I hope that if this is a challenge for you, that, you know, you take the time to really focus on the recommendations of being a leader, you know, checking in with yourself and doing that self-reflection and also understanding at a base level, you are absolutely enough and you are more than worthy, and you are incredibly capable of going after and achieving anything that you put your mind to.

Jenn DeWall:

Thank you so much for listening to this week’s episode of The Leadership Habit podcast. My name is Jenn DeWall. If you ever to connect with us about leadership training, would we love to serve you? We live and breathe leadership at Crestcom, and please reach out to us for a leadership skills workshop and find ways that we can support your organization. If you enjoyed this week’s minisode. Don’t forget to share it with your friends. Share it with someone that you might think is struggling with imposter syndrome, and last, but certainly not least. Please, please, please leave us a review on your favorite podcast streaming service. This is our way that we can reach more people and continue our journey to create and build better leaders.