Amanda and Ashley talk about their experiences as women in the cybersecurity and technology industries. (Spoiler alert: it’s on the up-and-up!)

In this episode:

  • “When did you stop taking notes and start to actively participate?” [01:35]
  • The ‘average’ woman’s experience in traditional industries and decision making [05:45]
  • Communication is a two-way street [10:10]
  • Qualifiers and comfort while being wrong [18:32]
  • Ashley and Amanda accidentally stereotype themselves! [22:13]
  • A reminder of why DEI is worth fighting for at your organization. [27:10]

Additional Resources:

  • See Yourself in Cybersecurity: How 3 Experts Transitioned into InfoSec | Security Insights Podcast, Episode 27 (Show Notes)
  •  A Candid Conversation About a Career in Cybersecurity: Q&A With Amanda Wittern (Blog)
  • More about Amanda Wittern, Deputy Chief Security Officer (LinkedIn)
  • Meet your host, Ashley Stryker
  • Join the conversation!

Ivanti Security Insights podcast - S2E29

“When did you stop taking notes and start to actively participate?” [01:35]

Ashley Stryker [00:00:06] Welcome back to Ivanti's Security Insights: where best-practice cybersecurity meets real-world workplaces and roadblocks.

Ashley Stryker [00:00:14] I'm your host, Ashley Stryker, and with us today is the lovely and charming deputy CSO Amanda Wittern. Amanda – hi! Welcome back.

Amanda Wittern [00:00:24] Thank you for having me.

Ashley Stryker [00:00:26] I think it's just going to be you and me on today's episode.

Amanda Wittern [00:00:30] You know, we've got the really important people here.

Ashley Stryker [00:00:34] We do, you know! And, I think this does give us a lovely opportunity to dive into some of the conversation [that] we kind of started, then had to drop with one of our previous episodes – where we're talking about hiring and in InfoSec in cybersecurity, and how your own journey kind of made its way there.

Ashley Stryker [00:00:54] We touched on [it] briefly and promised to bookmark talking about the woman experience in cybersecurity. And you know what? I guess today, that it might be a pretty good day to start that off, don't you think?

Amanda Wittern [00:01:09] I remember that part of our conversation. I think I made the comment that, as part of my journey into information security, I would not ask questions and scribble down notes in some of my meetings, because I felt as a woman, it might come across poorly to ask questions. I believe that was the starting point?

Ashley Stryker [00:01:34] That was, so... Let's start there, then. At what point did you just decide to say, "Screw it, I belong here? I'm going to not only take notes, but also participate?" Was there a moment, or a...?

Amanda Wittern [00:01:47] Yeah, I'm really excited about this. I'm really excited about this conversation. I'm excited to start telling that story.

Amanda Wittern [00:01:54] I think that, you know, as we're talking about this, I want to point out that some of these struggles that I went through are struggles that a lot of people go through – not just women, but unrepresented people in the workplace.

Amanda Wittern [00:02:13] And really, I hope that while we [Amanda and Ashley] have come in as the "all important people" – as women – certainly, I want to have a message out to really everyone, including the men, that this conversation is for everyone. Because, I don't believe I've ever come in contact with anyone in my professional career that has purposefully treated me poorly.

Amanda Wittern [00:02:39] So, yeah, honestly, I think what the moment that we're talking about here, where... I realized that I could be respected – or rather, I would be respected as a woman, despite my reservations of appearing as a stereotype...

Amanda Wittern [00:03:06] Can I back it up a little bit, right? A women in tech – originally, I worked in the finance industry, and fintech startups, and that kind of thing.

Amanda Wittern [00:03:17] There's always a lot of pressure in being part of those industries – or any industry where it's the case, to be as successful [as others] – to have the same amount of respect, to contribute as much, to make a statement or a place for yourself.

Amanda Wittern [00:03:35] As a woman, that pressure is always on. It might be self-inflicted, right? And, I guess, that's really where the journey is.

Amanda Wittern [00:03:46] So, I had this mentality through my academic career – through my professional career. It was always, "Got to look smart. I've got to look capable. I've got to keep a cool head about things." Right? And then there was this situation, the "aha moment."

Amanda Wittern [00:04:03] I'm sitting in this room – myself, running this consulting project. It was myself and 11 men – very intelligent, knowledgeable, competent professionals. They were talking about something that I did not understand, but I needed to.

Amanda Wittern [00:04:28] And I... At some point I realized, we're all very passionate about what we do, and we enjoy telling people about our passions, whether it's work or your hobbies, right? And so, in my mind, I'm like, "I bet this person would actually like to tell me this stuff."

Amanda Wittern [00:04:48] So I asked, "Roll this back a little bit. I actually don't know what that is. So help me with that!"

[00:04:56] And, the entire room became animated! It was no longer like the consultant, the auditor grilling questions. It was, "Wow, somebody wants to know this!"

Amanda Wittern [00:05:10] And after we had spent two days, 10 hours in this room together, one of them reached back out to me a few days later and said, "You know what? We have never had someone come in and show true interest in what we were doing."

Amanda Wittern [00:05:27] And it hit me that actually I earned more respect. I was more a part of the conversation, [and] I had a bigger impact by just asking the question. Why was I so hesitant for years?

The ‘average’ woman’s experience in traditional industries and decision making [05:45]

Ashley Stryker [00:05:45] Well, yeah! And that was about to be my next question to you – do you think that was a "you" thing, or do you think that was representative of similar issues from other women in those kind of situations?

Amanda Wittern [00:06:01] I do not think that my situation, my experiences are unique. This is a... You know, I mentioned the word "stereotype." It really is a stereotypical view that women kind of impose on themselves, right? We do feel like... I had mentioned this extra pressure, but that can come from all kinds of places.

Amanda Wittern [00:06:28] There are certainly parts of the evolution of our society, the sort of entrenched kind of mental frameworks that we have progressed so rapidly from – you know, 20, 30, 50 years ago. The transition, it's rapid! So, society has had very little time to make very impressive... Make these huge strides towards equality and inclusiveness. So, I'm sure some of it is that mentality.

Amanda Wittern [00:07:04] I don't know if you've gone back and seen some of the cartoons from our childhood. But, let me just tell you, sometimes it's a little jaw dropping that even many years ago, there was sort of this entrenched view of the stereotypical relationship between men and women. So, maybe that's part of it.

Amanda Wittern [00:07:25] Another part of it is that, women – for a reason that someone smarter than me would have to explain – are very hesitant to be wrong. That's a pretty common characteristic across women. Men seem more likely to say something that they're not sure of and then own when they get it wrong, than a woman is, who would rather....

Amanda Wittern [00:07:52] And again, we're talking in generalization, right? But, women prefer to take in all of the information and then make a decision, so that our need to digest everything before contributing, before saying something means that we are unsure of ourselves, until we feel comfortable with knowing everything we have.

Amanda Wittern [00:08:20] Parts of it is communication, too. At least for me personally, I was aware that I could say things that were disadvantageous to my position. And so, I'm always cautious about that. These are common themes that women face in the workplace.

Amanda Wittern [00:08:42] So, I would absolutely say... and underrepresented people, right? This spans a wide variety of common characteristics that we really got to figure out the way around.

Ashley Stryker [00:08:56] Right. And as I was thinking through some of my own personal experiences in that – I, too, have seen people's eyes light up when you just ask them, and you're willing to just... You're willing to be the student for a moment, instead of constantly having to prove, "Yes, I belong here. Yes, I know what I'm doing."

Ashley Stryker [00:09:14] And, if you just go to people and say, "Yes, can you tell me more about this thing that you clearly find so interesting [that] you're willing to spend your career doing it," [then] it's amazing [to see] the doors that open, when you do take that initiative and kind of own that. It's really remarkable.

Ashley Stryker [00:09:36] But I'm wondering more... This is my first time working at a large tech company. In general, we serve cybersecurity and I.T. operations, and those traditionally male-dominated end users.

Communication is a two-way street [10:10]

Ashley Stryker [00:09:55] As somebody who has seen both sides of the coin within a... traditional, male-dominated sector outside of tech – and then one that's in tech – have you noticed that there are any differences in stereotypes of women that either hold especially true, or are a different subconscious way of approaching things for women in technology, particularly in cyber and I.T., than is [present] in other industries?

Amanda Wittern [00:10:30] I think that... the mentality of women remains consistent regardless of the industry. We have certain characteristics and tendencies; we carry those with us. We're challenging ourselves to overcome them, no matter where we're at. However, there was a difference in the mentality of the opposite sex and –

Amanda Wittern [00:11:00] Again, I'd like to reiterate, I think people are good. I don't think that I was intentionally slighted in any way.

Amanda Wittern [00:11:07] But when you have... For example, the financial industry – it is very established. There is not always a push for change – for new, improved, cutting edge, that kind of thing. When you have those types of institutions in place, there are traditions that have been passed forward from times where we maybe were not as progressive.

Amanda Wittern [00:11:38] So, for example, the a board of a bank has traditionally been white male, between a certain age, right? And you have to make active steps... You have to put in effort to break out of that mold. So the financial industry has more of a challenge with that than the technology industry.

Amanda Wittern [00:12:09] When you're in technology, it's the next best thing. It's new; It's exciting. There's change. You have to be open to adapt to every scenario that comes up. I found that that sort of mentality – that forward-thinking – seems to foster an environment where it doesn't matter your background.

Amanda Wittern [00:12:39] Do you have the idea? Do you have the capability? Are you excited? Are you enthusiastic? Are you curious?

Amanda Wittern [00:12:48] It doesn't matter who has that idea. Everyone can, because technology is so new. Some of the things that we're pushing into space and... All of the stuff. Because of that, there aren't those entrenched traditional structures of people – and that, I feel, gives more opportunity.

Ashley Stryker [00:13:12] I have noticed that there is a willingness to.... experiment, to try new things, to try different approaches that has been lacking in other industries that are much more traditional. I worked in legal for a time, and introducing new concepts and new ways of doing things was more challenging than I had expected – to be tactful there for a moment.

Ashley Stryker [00:13:41] That's really encouraging to hear, though, that that [mentality] creates this open opportunity for women to really break through into this truly developing and cutting edge industry.

Ashley Stryker [00:13:53] So what do you think – let's start with ourselves, then. How do we, as women or as previously disenfranchized groups, attempt to break into an industry as powerful as technology, even as it is accepting? What can we do to better facilitate and find the places where we can grow and then advocate for ourselves, and then find the advocates who can help us?

Amanda Wittern [00:14:23] Yes, that is a really good question. I have been involved in women's initiatives in the past. I'm still actively an advocate, so I'll share some of the things that I have been taught and that have really been insightful, and then some of the things that I've learned.

Amanda Wittern [00:14:43] Communication is a huge factor in how we [as women] are able to present ourselves to other people, and there are big differences in how men and women communicate.

Amanda Wittern [00:15:02] For example, when a male receives a compliment or recognition – "Hey, you did a good job!" –  they accept it. "Oh, thank you. I appreciate that."

Amanda Wittern [00:15:17] When a woman is given the same kind of recognition, we will have a tendency to say, "Thank you; I had an excellent team" – and transition the focus from themselves.

Amanda Wittern [00:15:31] Now, there is no right way. In fact, they're both completely acceptable ways of responding. We need to be aware, however, that they are perceived differently.

Amanda Wittern [00:15:48] I'll keep giving you a couple of examples, but I do want to pause for just a moment. It is... I do not have the answer on who is responsible, in that scenario, for doing... for recognizing that those are both equal responses.

Amanda Wittern [00:16:08] So, in that scenario, the woman is no longer the focus – and thus elicits less respect – than the man who owns it, who claim that.

Amanda Wittern [00:16:25] So from the root, to give her communicator of the recognition the compliment if they are male, it is often perceived that the woman was... [that she] earns less respect. It was a "weaker" response, [one] that we would consider that a weaker response. And so, it can be perceived differently. Right.

Amanda Wittern [00:16:54] The reason I want to pause is because I don't know who in that scenario is ultimately the responsible party for making that exchange more equal.

Amanda Wittern [00:17:06] Is it the woman who should say it, in such a way as the man did, because we realize that that's what makes us... That's how we get equal footing?

Amanda Wittern [00:17:17] Or is it the giver of the recognition, who realizes that what the woman said was not an indicator, or that it's...

Ashley Stryker [00:17:26] Not a weak response? Yeah.

Amanda Wittern [00:17:28] Right – I don't know that answer.

Amanda Wittern [00:17:31] Let me give you a couple more examples, and let me just tell you that I cannot speak to who would be the person to make the change, to make the shift.

Ashley Stryker [00:17:44] That was part of why I framed the question to you the way I did, was because I recognized while there are some things that we ourselves can do to take ownership, there are other things outside of our control, in the environment that we are in, in the workplace that we're in, in the industry that we're in – that they have to shift as well. It's kind of a meeting-halfway.

Ashley Stryker [00:18:02] So just with that general recognition of, what can everybody do here?

Amanda Wittern [00:18:09] Okay, and I apologize for leaping forward there. It's just... it's just such an important thing to express, so that when you and I are talking, I would never want to say that this perception or this conversation is, "Men are bad; men should be doing this differently." 

Qualifiers and comfort while being wrong [18:32]

Amanda Wittern [00:18:32] I also want to make the point that women are not in any way bad for doing these things. That response is perfectly acceptable by the woman, right? This is exactly right. It's a communication... It's a collaborative effort.

Amanda Wittern [00:18:50] So like I said, I apologize for jumping forward, but I really want to make sure that this community, this conversation with us fosters a positive environment. So thank you – a constructive environment. Yeah, absolutely.

Amanda Wittern [00:19:09] So another example, I sort of brought up, where we [as women in general] are not confident in being wrong. We're not comfortable with being wrong – that's a hard one! I don't –

Ashley Stryker [00:19:31] We're back to, "Is this a woman thing, or is this a me thing?" Because I personally am not comfortable being wrong, but...

Ashley Stryker [00:19:39] But, if I'm starting to think about it, it's not so much a discomfort of being wrong, so much as it is a reluctance to speak until you're sure.

Ashley Stryker [00:19:48] Oftentimes, men are more comfortable giving answers and responses when they're not as certain of an answer. Women tend to wait until they have more of the information before being certain of the answer.

Ashley Stryker [00:20:04] So, it has been my experience that in those kind of situations – because the woman in question needs more time to respond with confidence – they, in the meantime...

Ashley Stryker [00:20:18] The team runs with the initial response from the one, so that by the time the other woman participant is ready to contribute and is like, "No, guys, this is actually the correct response!" – they've already carried it off halfway through, because the man was willing to put forward his idea first.

Ashley Stryker [00:20:34] And that's, that has been... Again, this is grossly generalized, but that has been an ongoing and recurring theme in my own professional career. That was what I was thinking of when you brought up that situation.

Amanda Wittern [00:20:46] Well, let me make a comment on that before I give you maybe one final example. There's actually two parts to what you're talking about, and they both contribute.

Amanda Wittern [00:20:56] There is a hesitation to be wrong. There's a hesitation to be wrong that is separate from a woman's tendency to be less vocal.

Amanda Wittern [00:21:08] That doesn't mean that they don't come into play at the same time.

Amanda Wittern [00:21:11] An example of being wrong, and then women being afraid to being wrong is, "Does that make sense?" – right at the end of what we say.

Ashley Stryker [00:21:23] Oh, I say that all the time!

Amanda Wittern [00:21:25] "Is that...Oh, did I communicate that? Did you, did I say something wrong? Does that make sense?" Right?

Amanda Wittern [00:21:32] That what I'm talking about, an example of where women don't want to be wrong. We were uncomfortable with it. Whereas, you're also absolutely right. We prefer to...Typically, we like to absorb all of the information and speak when there is an appropriate time, to not cut people off –those types of things that contribute [to communication perceptions]. So there's two parts there.

Amanda Wittern [00:21:58] But, let me give you one one last example, and this is from personal experience. Women can be self-deprecating, and sometimes not even realize that they're doing it.

Ashley Stryker [00:22:09] You and I have talked about this, in fact! Yes, yes, we can.

Ashley and Amanda accidentally stereotype themselves! [22:13]

Amanda Wittern [00:22:13] Our conversation was actually pretty funny, because we both... we've both done it in different ways. You have made active comments – and I'll let you share those – versus me, who was unaware I was doing the exact same thing.

Amanda Wittern [00:22:32] So in my particular case, I would ask... Daniel [Spicer], he's the more technical one – versus me, which is more risk compliance. That is perpetuating a stereotype that is absolutely untrue.

Amanda Wittern [00:22:50] It framed him – as the man – as the more technical [person], versus me – the woman – who has more soft skills. It's absolutely not that way.

Amanda Wittern [00:23:00] My technical expertise is in fintech and blockchain and digital assets. His expertise is networking infrastructure – more infosec-oriented kind of thing.

Amanda Wittern [00:23:14] So, while I was good intentioned with what I was saying – trying to express how he and I complement each other – I was reinforcing a stereotype without even realizing it! There was self-deprecation there, completely unintentionally.

Amanda Wittern [00:23:30] But when you brought it up in our conversation, it was a jaw-dropping moment. It was an aha moment – that even after all of these efforts that I've been making over the years for that equality, I was still… I still have things to learn!

Ashley Stryker [00:23:46] And it was a beautiful moment, too, of the.... It's a perfect example, I think, of acknowledging that these things run deep and it's often not intentional.

Ashley Stryker [00:23:59] I did not intend – by any means! – to belittle my deputy CSO! That was a, "Oh, holy crap. You're absolutely correct. I am so sorry" [moment].

Ashley Stryker [00:24:10] So I was... there were lots of apologies, and Amanda, you were like, "No, no, no, no, it's fine! This is – I can completely see how you got there!"

Ashley Stryker [00:24:22] That was an interesting conversation that you and I both had, to kind of unpack how we got to that point. Then, that was the genesis of several of our conversations on how you accommodate and account for these sorts of things within a modern environment, even with the best of intentions. So, that was... I thought that was... That was why I was snorting earlier, because that was a perfect example.

Ashley Stryker [00:24:48] And then, I actually have a habit of self-deprecating humor.

Ashley Stryker [00:24:54] I tend to put people... That's my default for putting people at ease, because nobody can get mad if I'm the one who's getting the the joke made of them, right? It's something that's cross-cultural, that nobody can possibly feel offended if it's me who's the butt of the joke, first of all.

Ashley Stryker [00:25:11] Second of all, it makes people feel more comfortable and less intimidated, because if I can admit to fault – if I can admit to being wrong – then that means that they're also comfortable taking shouldering blame in certain situations where it may be appropriate for them to do so.

Ashley Stryker [00:25:29] Or, you know, it's a great icebreaker, too, because it makes people realize that I'm not going to be that... "auditor at the table" kind of moment. It's going to be a, "Hey, we're all in this together. We're all partners in this. Let's just go to town" [philosophy] and break the ice that way.

Ashley Stryker [00:25:47] But, in recent months, my boss and I have been discussing this. And while I'm in marketing – I'm not directly in cybersecurity – it's, to mention your point earlier, it's a woman issue.

Ashley Stryker [00:26:01] We think... We suspect...

Ashley Stryker [00:26:03] We worry that people who don't know me already – so a thought leader, [or rather] not thought leaders [but] internal executives and hire-ups and "the Powers That Be" as I so lovingly refer to them...

Ashley Stryker [00:26:15] [Those internal leaders] might not understand that this is my.... not a defense mechanism, but it's just a quirk. I'm just as capable and competent and confident as someone who doesn't do that. I know exactly what I'm talking about in my arena and what to do and where to go.

Ashley Stryker [00:26:32] But the self-deprecation is an accommodating mechanism. We [my boss and I] worry that I could be seen as... I could be taken less seriously; my proposals could be subject to flaws.

Ashley Stryker [00:26:45] Am I trying to mitigate what I'm worried about as a critical response right off the bat? If I start off with that – as opposed to letting someone bring critique to it – am I just trying to head the pain off at the pass and assume that there's flaws in it by presenting it first?

Ashley Stryker [00:27:01] Is it... And is it a "me" thing, or is it a woman thing? So, self-deprecation is, I know... That's been my professional theme of the last month or so, I think.

A reminder of why DEI is worth fighting for at your organization. [27:10]

Ashley Stryker [00:27:11] I wanted to close with a question to you which is been asked on messaging boards everywhere, [with] the subtext [that] everybody recognizes that DEI [Diversity, Equity and Inclusion] initiatives – [it] seems to be the buzzword. Everybody wants to invest in companies that can show this.

Ashley Stryker [00:27:37]  But there's hard... You're often asked to show, "What is the business case like [for DEI]?" There's this underlying subtext of, "Well, why should we even bother? Besides it being the right thing to do, why? What does it bring to the table?"

Ashley Stryker [00:27:50] So I wanted to put it to you, Amanda. What do you think? Inclusion and explicit, intentional inclusion of women and other underrepresented voices, traditionally underrepresented voices. What does that bring to InfoSec specifically?

Amanda Wittern [00:28:06] I do not have to give my opinion on this, because there are endless statistics about how much more how much more efficient, creative.... more ingenuity that teams from any profession are, when there are women, when there is more inclusion. I don't have to give my opinion.

Amanda Wittern [00:28:37] Statistically, there is a higher return on investment: companies make more money; companies save more money; companies are more agile, in that they are able to pivot faster in the market and identify market trends more quickly.

Amanda Wittern [00:28:58] Now, this is stuff that I would encourage everyone to just look up. There's so much information out there that I don't even... It's not opinion. This is statistically the case. There's so much out there.

Amanda Wittern [00:29:14] This is not just because women have all of this stuff; it's because together, in an inclusive environment, we all have strengths that can be brought to the table, and that makes a difference.

Amanda Wittern [00:29:31] Women have strengths, they have characteristics. They have ways of looking at things, perspective. They have things to bring to a team. They have things to bring to leadership that... A business needs a group, needs a team, needs to make things as effective as possible.

Amanda Wittern [00:29:56] So, yeah, I like this question, because it's a really easy answer. What benefit is there to having women there? And really, the question is, "When is there not?"

Amanda Wittern [00:30:15] There are absolutely limitless reasons that it's a benefit – and we have a great sense of humor, in my opinion.

Ashley Stryker [00:30:27] Yes. I mean, yeah. I mean, you and I definitely do. Well, if we can get Daniel to crack a smile [while recording]. If we can get him to actually laugh on recording next time – you guys should really hear our pre-recording sessions! They're pretty.... But, well, we'll. Well, we'll bring our baller sense of humor.

Ashley Stryker [00:30:48] And with that, thank you, Amanda, so much for taking the time to talk with us about this. I've been really excited for this one.

Amanda Wittern [00:30:58] And I appreciate. I appreciate you having me. I mean – I'm just kidding. I'm just kidding. Thanks for that, Ashley.

Ashley Stryker [00:31:09] No, of course!

Ashley Stryker [00:31:10] And thank you, guys, so much for tuning in today. We really appreciate it.

Ashley Stryker [00:31:17] We'd love to hear about your experience, particularly working with women and other underrepresented voices in cybersecurity. If you'd like, we'd love to hear about it. Please join the conversation online. You can follow us @GoIvanti. Check the show notes on your podcasting platform of choice for all of the resources that we have, including, I think, a blog that you wrote explicitly for October 2022 in Cybersecurity Awareness Month. So please do take a moment to check that out.

Ashley Stryker [00:31:56] And if you found today's conversation remotely interesting, entertaining, insightful – even a little bit! – please share it with your friends, your colleagues, your coworkers. The more times you share this, the more the algorithm loves us, and the more we can talk to other InfoSec folks like yourself.

Ashley Stryker [00:32:15] So with that, we're signing off. Stay safe, and we'll talk soon!