Q & A with Jan Jones: How Prevalent is Impostor Syndrome with Executive Assistants?

In this article, author Jan Jones, discusses how prevalent Impostor Syndrome is within the executive assistants profession. 

FlyPrivate is a proud partner and associate of Jan Jones. Jan brings valuable, actionable information to executive assistants across the globe. We hope you enjoy her blogs as much as we do! 

FlyPrivate: Our readers are asking about Impostor Syndrome. Have you discussed this topic with executive assistants and have you seen much evidence of it in the EA profession?

Jan Jones: The Impostor Phenomenon in High Achieving Women” is an article written in 1978 by psychologists Dr. Pauline Rose Clance and Dr. Suzanne Imes. They introduced the term in that article. They interviewed over 150 high achieving women throughout the US. Women who had earned a Ph.D. in various fields, who were all respected and recognized for their accomplishments. Unable to accept their success, these women doubted they had legitimately achieved success through their own talent. They felt it was a fluke, or the result of a lucky break. Feeling undeserving, they feared they would be discovered as being a fraud – an impostor – pretending to be something they weren’t, fooling people into thinking they were smart and accomplished. Hence, Impostor Phenomenon, or Impostor Syndrome.

Impostor and Imposter are both acceptable ways to spell the word. Impostor is the original spelling. It’s important to understand that Impostor Syndrome is not a disease. A syndrome is a group of symptoms for which the underlying cause has not been defined. A disease is something that has a clearly defined cause behind it.

Originally, Dr. Clance said that in her clinical experience men experienced Impostor Phenomenon, but much less frequently and with much less intensity than women. Subsequently she revised that to say that males are just as likely as females to experience it. Other studies have borne out these findings.

Slate magazine says “Impostor Syndrome has been rediscovered and named the workplace anxiety du jour for women.” Perhaps that’s why some EAs are experiencing it, think they should be experiencing it, and want to know more about it.

I’m not making light of Impostor experiences for assistants, but I don’t want them to feel they should suddenly diagnose themselves with it because it is the new “workplace anxiety.” Honestly, standards have not always been rigidly applied and there are typically no advanced educational degrees required for the administrative role so, in general, why would assistants feel like frauds in not living up to expectations that haven’t been overly rigorous?

EA/PA trainer Adam Fidler said there are assistants today who don’t touch type and many struggle with spelling, punctuation and grammar. A quick look at social media posts by assistants bears this out all too well. Low entry barriers resulted in under-valuing of the assistant role because the impression is that anyone can do it. Career EAs and executives who have the privilege of working with high performing EAs know that “anyone can do it” is bunk, yet it is still a widely held misconception.

Assistants I’ve met who experience Impostor Syndrome the most, tend to be in tech-dominated sectors, where some executives have gone from the college dorm to company founder, or CEO. These are high-level executives with impressive degrees, who hired their assistant not for experience, but because they too have a degree and there’s a personality fit. (One inexperienced EA told me her executive hired her, saying “How hard can it be?” Another told me “He hired me because we had great chemistry. He didn’t care about no prior experience”). But the degree has not trained the assistant for the fundamentals on which the EA role is built. As these assistants go deeper in the role, they are surprised by how steep the learning curve really is to excel as a true executive assistant. So they worry they’ll be found out as not deserving the job, or the responsibility given to them. They won’t meet their executive’s expectations and live up to the promise on which they were hired. Many do succeed, but it’s a harder row to hoe, especially when expectations are high from senior executives in fast paced, unpredictable environments, who underestimated the requirements for the role of the executive assistant.

This is an interesting topic to discuss, because Impostor Syndrome does not easily resonate with me. Like many EAs, I know with certainty that where I am professionally is the result of hard work and commitment, putting in the time and effort when it would have been convenient to ease off, or take a short cut. I worked harder than most, accepted responsibility, put up with a lot, dealt with daunting challenges. I said yes when it would have been easier to excuse myself and say no. Like so many dedicated assistants, I willingly did things that by all accounts were not my job, so I could step-by-step build expertise, make myself visible and increase my value. I readily allowed my mentors to stretch me beyond my comfort levels because I knew it would set me up for the success I wanted.

The people who experience Impostor Syndrome also put in the effort and hard work to reach extraordinary success in their professions. So what separates them from those of us who succeed, but don’t experience Impostor Syndrome?

To probe deeper, I spoke with Liz Solomon, who works closely with Dr. Daniel Goleman, the Emotional Intelligence luminary. Liz is the co-host of Dr. Goleman’s podcast. She is a highly accomplished Goleman EI certified coach and corporate workplace strategist, with a Master’s Degree in Organizational Psychology and Family Therapy. Liz is insightful, strongly empathetic and compassionate.    

LS: Underneath Impostor Syndrome is a very clear statement of ‘I don’t belong here.’ So it raises a deeper question of not belonging and if so, what is that related to? What we call Impostor Syndrome could translate to ‘I’m executive assistant to an executive or thought leader who the world adores. I’m here by proxy. Did I earn this or did I just get lucky?

More specifically, It could also look like ‘I come from a family that worked jobs that were not so high profile, or well paying, with as much responsibility as this. How did I get here when my family of origin didn’t have such opportunities?’

Impostor Syndrome asks us to probe deeper into our own definitions of success. We all come from different environments, cultures or groups of origin where success is defined in certain ways and we all find ourselves in different circles of people who have varying levels of success or profiles in the world. In the context of belonging, I think there’s a lot in there around power and confidence.

JJ: Confidence! I’ve talked with technology sector assistants who have never been an assistant before. They’ve been hired by executives who never had an assistant before. Because they’ve never worked with an assistant, the executive doesn’t really understand what the job requires. They’ve hired somebody without experience who is thinking ‘Wow, how did I land here?’ I’ve met assistants working for high profile executives who seem stunned that they got the job because it’s truly above their proficiency level. With determination and hard work they do well in the role, but the means by which they arrived there contributes to their lack of confidence. They wonder if they truly measure up, or deserve to be there.

LS: I hear two things there. If we’re talking about coming into an environment like Silicon Valley for example – where the majority of people within organizations have Ivy League educations – then it increases the likelihood that someone without an Ivy League education would feel excluded or ‘lesser than’. Impostor Syndrome is one way this signaling around status and belonging manifests, which adds many more layers to the conversation. 

JJ: Interesting that you mention feeling ‘lesser than’ because I heard about an assistant who decided she needed an MBA so she could feel she belonged at the executive table. It immediately reminded me of your comment that Impostor Syndrome carries a statement of ‘I don’t belong here.’

LS: The second thing I hear is about being hired into a role without clear expectations or ways to receive feedback. If the person hiring doesn’t know what the job entails, and if there’s no explicit acknowledgement of that, then it’s hard for the person being hired to know if they are succeeding. While some roles take time to define themselves, there should, at the very least, be a transparent conversation. It’s reasonable for someone hiring an EA to say ‘I don’t know exactly what this job is yet so I’m giving you the wherewithal to make it up on your own. Here is when and how we’ll check in to know how it’s going.’

Communication and feedback go a long way – particularly in moments of ambiguity. If I don’t know how I’m supposed to be performing, and also don’t have any indicator of whether my performance is satisfactory or not, then it is especially hard to feel confident. 

JJ: Correct, because you have no real benchmark. This is your first time in the role, let alone working for such a senior person, so that could be it. These assistants also wonder how will they compare to assistants with prior experience working in a similar role? Will their performance be deemed inadequate by comparison? Will their executive regret hiring them?

LS: I think people are also plagued by Impostor Syndrome because of social media and the presentation of an ideal identity and the degree to which people question themselves or feel a deep inadequacy. There is a lot of research showing the detrimental effects on confidence – particularly that of women – as a result of social media and idealized images.

JJ: So how do you help them to overcome something like this?

LS: One approach is strengths-based coaching.

  • What are the strengths that you have? 
  • When have you been in a situation before where you haven’t felt totally clear about what you are doing, or felt a lack of confidence?
  • How did you rise to the occasion?

Just helping people, if possible, to see the pattern of their own ability to thrive even in situations where they might not be feeling inherently confident.

I would probe into beliefs around success and status.

  • What does it mean to be successful?
  • Who is “allowed” to be successful?
  • In terms of status, what does this role mean to you?
  • Is the power that comes with this role familiar to you?
  • What is hinging on you doing well here?

Those questions can give you a lot of information. Someone might say ‘This role is the best paying job I’ve ever had and it might allow me to start a family in the Bay Area for the first time.’ That tells us there is a lot hinging on that role and doing well in it – which lets us know that anxiety is likely to be heightened.

JJ: Performance anxiety. Can I really match the expectation? People ask me this a lot, particularly when they want to know how I supported Tony Robbins. They ask how did you manage to support somebody like that? I tell them that apart from experience in the role, the only way I could support him was to know with absolute certainty that I’m as good at what I do, as he is at what he does. If I didn’t know that about myself, I couldn’t support him, or any executive, at that expected level.

This question comes up frequently and I wonder why, but obviously it’s something of interest to people. What’s interesting to me is that not many assistants will be in the situation of supporting someone like Tony. There’s so much interest around a situation that many would rarely be in, so I assume their interest is about how they would measure up, and how would they thrive in that environment.

LS: I’m curious how you make sense of that question because under that I hear desire – a wanting to work for someone like Tony – whether that’s feasible or not. How do you make sense of that wanting?

JJ: I think it’s natural to want to progress to a higher level than you are and I admire that about them, that they see potentially they have the ability to be there. Even if it’s not their reality right now, that they think ‘Maybe I can do that and if that’s the case, how would I do it?’ I tell them instead of focusing energy on getting a job with someone like Tony, start with how can you apply that to where you are right now. How can you take that to the next level from where you are, and give your executive that experience of someone who might be supporting a Tony Robbins?

LS: Did you ever have a moment when you were working with Tony, where you felt like an impostor or were anxious that you shouldn’t be there?

JJ: No, not with Tony, or ever. I struggle to comprehend the question because the idea of feeling like an impostor is alien to me. It’s why I wanted to get your perspective, since you coach so many high achievers.

LS: Of course, that opens up a whole Pandora’s Box of why not. Why don’t you have those Impostor Syndrome feelings? I’m reflecting on our first conversation and in the short time I’ve known you, my sense about you is you have a deep internal well of confidence, that you are a person who is willing to just put yourself in front of things and just ask for what you want. In that way, especially when it comes to women, and women working with powerful men, you are probably the minority.

JJ: Maybe that’s why I keep getting that question! How do you work with a man who is so powerful? Many assistants have told me they would be too intimidated. Tony is so visible, people see the power he can generate. The interesting thing is that I worked with executives like that long before I got to Tony. They were not as famous, but they were millionaire and billionaire types with personalities very similar to Tony. From the outset, I was confident I could hold my own with any of them.

A while back I read about how when we are children we lack acceptance by our family, friends, teachers, so we carry that over as we grow older. It’s this lack of acceptance that we’ve experienced that may contribute to the Impostor Syndrome of we don’t belong, or we won’t measure up.

LS: Yes, I think that childhood trauma and conditioning is one piece. Another piece – and I’m doing a training in this right now – is family constellations which look at systemic issues like generational trauma. For centuries, people and cultures have had to ask ‘Am I safe? Am I safe to have a voice, am I safe to be visible?’ There are so many places beyond our own childhood that impact our confidence and sense of power in the world – trauma that we inherit through generations, through our DNA, that we are still bringing into our lives and into the spaces we occupy.

There’s a lot of angles to come in on this topic. One of the starting places can be to ask people “If you’re not the person for the job, who is?” Through this line of questioning you’ll start to understand what are the beliefs people have about who is allowed to or not allowed to occupy that role. Then you can extend that further by looking at the organization reinforcing those beliefs, are they coming from inside the person, or is it a combination of both? There would be some coaching around where is that true and where is that not true. While there are real skills that you need in order to do the job, there are so many stories we tell ourselves – passed down to us from the environment or unexplored places deep within our own psyche – that could put someone at a disadvantage.

I also find that sometimes people who feel Impostor Syndrome have separated themselves from their own journey. They discount how they got to where they are. They don’t give enough merit to their own choices or talents. Many people with Impostor Syndrome are asking “Do I deserve to be here?” This is a loaded question.  

JJ: I’m lucky to be here is quite different than I don’t deserve it.

LS: It is. On the one hand, the gratitude is very freeing. Being appreciative automatically changes how we relate to ourselves and what is around us. On the other hand, being grateful allows us to begin to examine the role of luck and of privilege in our own lives. This is part of emotional intelligence – bringing more awareness to ourselves and to our surroundings. Hard work, luck, and privilege often weave together in ways we can’t always pinpoint or understand.”

A 2020 KPMG study “Advancing the Future of Women in Business” surveyed 750 women across corporate America. It found that women feel Impostor Syndrome at “milestone moments,” such as making a career change, or receiving a promotion. So it’s not surprising that EAs have told me they feel like an impostor when they’ve received a promotion, started a new job, been recognized for an achievement, or a bonus. They question whether they are up to the challenge. “What if someone else turns out to be better, or more deserving than me?” “If I don’t measure up, I’ll be found out and branded an impostor.” I typically respond by asking if they misrepresented themselves or pulled some swindle to get an opportunity. If not, then why assume whoever gave you the opportunity didn’t know what they were doing when they selected you? Why assume they showed poor judgment in betting on you? If you landed the opportunity fair and square, there’s no reason to feel like an impostor.

There will always be situations that challenge you. You reached for the opportunity knowing you have what it takes. Running into challenges doesn’t make you an impostor. It shows you bravely went outside your comfort zone to do something remarkable.

Even if you have been hired or promoted beyond your capability, or arrived in a job that’s more challenging than you thought, to me it simply says you have more to learn. At various times in life we all do. If I’m not as good as I need to be, then I’ll get busy improving myself and prove I deserve the success I’ve earned.

I’ve heard that when people let go of self-importance, they feel less of a fraud. Perhaps it will help if we stop feeling more important than we are. Corporate strategist Matthew Cross calls it, The Myth of the Impostor Syndrome™. It’s something I’ve observed in some EAs who say they experience Impostor Syndrome. My initial impression is that they’re not that good, nor have they achieved a particularly high level of success in the role to warrant feeling like an impostor. There are EAs who are far superior in performance, yet they don’t feel like an impostor. Don’t let ego allow you to misrepresent yourself and cause you unnecessary suffering.

What about the element of luck? Are we lucky to have executives who believe in us and encourage us to try? Does serendipity factor into success? I think they are contributing factors along with karma. If you agree with philosopher Seneca that “Luck is what happens when preparation meets opportunity” then you probably believe that we make our own luck, however we happen to do it and whatever the contributing circumstances are. We have it because we deserve it.

What are some other ways you can conquer feelings of being an impostor, or avoiding those feelings in the future? Remind yourself of what you’ve accomplished in this role and others. I particularly like Liz Solomon’s question “If you’re not the person for this job, then who is?” This will help you to clarify your beliefs about who is allowed to occupy the role you are in. Have you been praised by your boss or your colleagues for a job well done? It means you bring something worthwhile to the table. You are good enough and worthy of being heard.

Don’t underestimate yourself. Attribute your success where it belongs – to your efforts to apply yourself and strive for your goals. Grit and perseverance pay off, sometimes in big ways, sometimes smaller. Give thanks that your hard work and effort paid off. You know what it took to get where you are. As Liz said – don’t divorce yourself from your journey. Don’t entertain the myth of the Impostor Syndrome. You are here because you are accepted. You earned it. You belong.


©The CEO’s Secret Weapon. The ideas expressed in this article and any text extracted from “The CEO’s Secret Weapon” are the intellectual property and copyrighted to Jan Jones. All rights reserved. No unauthorized usage or duplication by any means is permitted without the express consent of the author.

Author: Jan Jones

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Jan Jones is the author of “The CEO’s Secret Weapon How Great Leaders and Their Assistants Maximize Productivity and Effectiveness.” The book has received widespread acclaim from executives and executive assistants worldwide. Jan spent 20+ years as an esteemed international executive assistant to well-known business people, including Tony Robbins, the world’s #1 business and life strategist. Jan continues to champion the executive assistant profession with her writing, consulting and speaking. She offers timeless, practical advice that is relevant to the day-to-day role of the executive assistant. 

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The CEO’s Secret Weapon: How Great Leaders and Their Assistants Maximize Productivity and Effectiveness

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