In this episode, we explore effective job search strategies with Caroline Wong, Chief Strategy Officer at Cobalt. Discover how focusing on what you can control - your resume, networking, interview preparation, and mindset - can lead to greater success in your job search.
Guest: Caroline Wong, Chief Strategy Officer, Cobalt
LinkedIn | linkedin.com/in/carolinewmwong
Host: Dr. Rebecca Wynn
On ITSPmagazine 👉 https://www.itspmagazine.com/itspmagazine-podcast-radio-hosts/rebecca-wynn
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Episode Description
In this episode of Soulful CXO, host Dr. Rebecca Wynn speaks with Caroline Wong about navigating the complexities of the job search process. Caroline emphasizes the importance of concentrating on elements within your control, such as crafting a tailored resume, leveraging your professional network, and preparing for interviews. She highlights how a positive mindset can help you navigate challenges and setbacks during your search. Caroline also shares valuable insights on evaluating potential employers, assessing organizational culture, and embracing change as a constant in one’s career. With practical advice and strategies, this episode equips listeners with the tools to approach their job search with confidence and clarity.
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Resources
Caroline Wong's Courses: https://www.linkedin.com/learning/instructors/caroline-wong
Caroline Wong's book, Security Metrics, A Beginner's Guide: https://a.co/d/391G2nH
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Job Search Mastery: The Key Focus Areas for Success! | A Conversation with Caroline Wong | The Soulful CXO Podcast with Dr. Rebecca Wynn
Dr. Rebecca Wynn: [00:00:00] Welcome to the Soulful CXO. I'm your host, Dr. Rebecca Wynn. We are pleased to have with us Caroline Wong. Caroline is Chief Strategy Officer at Cobalt, where she leads security community and people teams. . She hosts the Human of InfoSec podcast, teaches cybersecurity courses on LinkedIn Learning, and has also two books including the popular textbook, Security Metrics of Beginner's Guide. Throughout her career, she has been working to boost the number of women in the field and is an advocate for workplace equality.
Caroline, it's so great to see you again. Welcome to the show.
Caroline Wong: Dr. Rebecca. What a pleasure it is to get to spend some time with you today. Thank you for the invitation.
Dr. Rebecca Wynn: Right now a lot of people are in flux. There's a lot of people who they're getting laid off or they're finding that maybe a company they work for has had a lot of changes, whether it's culture or leadership changes.
How did you navigate that to get to your next level?
Because it's really been a struggle for a lot of people right now, especially in our industry.
Caroline Wong: I asked for a lot [00:01:00] of help and stayed dedicated just trying to put one foot in front of the other.
I was trying to be kind to myself. A job search is a process filled with rejection and takes longer than you think I found myself saying, look, I wanna try and acknowledge what's in my control and what's outta my control. What's in my control is the words I put on my resume.
What's in my control is. The people I reach out to, that I ask for help, that I ask for advice, that I ask for a perspective. What's in my control is how I show up to any interview and the energy that I bring to that interview and the preparation that I do for that interview. But there's also so many things outside of my control.
I don't control what roles are open at what [00:02:00] organizations. I don't control anything about who the hiring manager is, what their criteria is, what any of their different ways of thinking about me or any of the other candidates are. I don't control the other candidates and how qualified they are. So I think that, really was something that I tried to focus on, which is to say, Understanding what's in my control and what's outside my control, and trying really hard to focus energetically on the things that are in my control and try and let go of the things that are outside of my control.
Dr. Rebecca Wynn: When you talk about what's inside your control, Skillsets. One of the things I use the Venn diagram a bit to do, not only about philosophically and spiritually what I wanna do, but looking at what kind of businesses resonate with me, doesn't resonate with me and what type of people inside those businesses.
Cuz sometimes the business is right, but the people inside is not. Do you do something along those lines? Do you have some nuggets along those lines? [00:03:00] Did you share on how you work through that?
Caroline Wong: I'll tell you how I think about these things, I really wanna make a big positive impact.
as I was evaluating roles, I thought what's a job where I can positively impact, a lot of people. One of the roles that I was talking to was for a really major, very well established, very well-respected security company. they wanted me to train developers on secure coding.
I thought that's cool but I wanna have a bigger impact than that. Certainly something really important to me is, this a business that solves a really important problem? Do I think that this business can be wildly successful? this is also how I evaluate extracurricular activities.
[00:04:00] So advisory roles volunteer work where I put my time in mentoring or advisory work. I'll say do I believe in this organization's mission and purpose? Does that align with me? do they have a strong way to solve the problem.
Is this a real business problem are they solving it? Do I think this business is gonna be wildly successful? Thing number two is who are the people? I, try really hard to understand why have these people chosen to do what they do?
And what do they value? I want alignment. I work really hard to avoid and prevent is working closely with individuals who have values that are very, different from mine in ways that are unacceptable to me. Those are my two things
where can there be a [00:05:00] big impact and a lot of success which I think is a result of solving a really important problem. And then who are these people? What do they value and do their values align with mine?
Dr. Rebecca Wynn: One of the things I. I find always a challenge is, finding that the outward appearance of the company and the people is really the inner, I talk to people about not thinking about a job per se.
Obviously people want money But you need to be interviewing them. just as much. every time I've taken a position that my gut was like on run very fast. It has been a mess for me each and every time.
What do you mentor people around those lines? Because it's easy to say, I need this job. And then find out you're just in a horrendous position that takes away from who you are and takes a long time to recover from
Caroline Wong: Yeah. So first I wanna acknowledge that we as earthly humans, have physical [00:06:00] needs that need to be provided for. at any given time may be in a position where for some time we need to do work, that is not the absolute perfect because we need to take care of ourselves.
Maybe we need to take care of our families. And that, I think doing what needs to be done to provide is, really important. And we're in an economic atmosphere where there's not as many choices right now as there are at other times, points in time.
That being said, I think to the extent that we have choices, it is good to stay away from or get out of work situations that destroy your soul and make you feel bad. I have a joke metric that I suggest to people when they say, [00:07:00] Caroline, how might I go about evaluating a company culture?
And here's the joke metric. And it's a joke because first of all, people don't actually write this down anywhere. Second of all, it might be inappropriate for them to share here's what it is.
Look at the executive team and leadership and count the number of divorces in the past 24 months. Then look at the company and count the number of marriages and babies in the past 24 months. there are a million reasons wrong with that. I wanna address a couple of those assumptions.
Divorce is not bad. Marriage and babies are not good. They're just indicators. I personally am a divorced person. Getting divorced was the very best thing that happened to me it's simply an indicator. people in that phase get married and have babies [00:08:00] when there's a company culture that is supportive of healthy relationships outside of the workplace and work-life balance situation. I think that really toxic environments. You're gonna see divorces happening in leadership. It's, a joke, but a more realistic thing to do is just like you are interviewing the company.
Ask them for references. Ask if you can talk to someone who works for them or has worked for them. And there's two things that'll tell you thing. Number one, maybe they'll immediately give you five names and encourage you to do that. That's probably a good sign, even before you pick up the phone and talk to those people.
If someone's a little hesitant and weird about it, that in of itself, is a sign. But I think that just like when we are in a position where we're a candidate talking to a company about an [00:09:00] opportunity and, there may be a stage where they ask us for references of people we've worked for or with.
We get to do the same thing. that's an opportunity to ask for references. let me talk to someone who's worked on your team. Let me talk to someone who is a peer of yours. Let me talk to someone that you've worked for. And, there's those two data points. Thing one, how do they respond to that question and thing two, of course, when you make those phone calls how do, what do people share?
Dr. Rebecca Wynn: I think one of the things for us being CISOs, right? You, have been CISO, CIO, Chief Strategy Officer, I pay attention to who are they having me do my interviews with? Do they have me interview with five people who are gonna report to me? . I not against that, but how come the stakeholders.
Why aren't my stakeholders? How come I'm not really meeting with my peers? You're trying to make me more of a subject matter expert, not a person leading a division or team. I think that's the other thing is paying attention and quickly on who you're interviewing with. [00:10:00] Would you agree with that?
Caroline Wong: Absolutely. And when I interview for CISO roles, which I do from time to time for fun a really important question is how big is the team? And how big is my budget? Those are super important questions to ask, especially when you're talking about a security leadership role, because there's a difference between talking the talk and walking the walk.
It's easy for the words. We care about security to come out of someone's mouth. It's different for them to have allocated and approved. Headcount and budget if I'm talking about a CISO opportunity. Those are some of the first questions. The other really important question is what's turnover been like on the team in the past, 24 months?
It just indicates that there's a change. And the questions where, is the organization headed and does that align [00:11:00] with your skillset, your values, how you wanna make an impact?
Dr. Rebecca Wynn: Do you use something else besides LinkedIn? Do you use like when you go to conferences, cuz you speak at RSA and stuff like that? What do you find as a great networking to find those inner nuggets?
Caroline Wong: LinkedIn is my number one. I've never been a Twitter person. I use Slack a lot. LinkedIn is so cool because I will find myself connecting with folks that like maybe I've met and maybe I've never met. And, I think that, It's surprising to me if you reach out and ask a question, some people ignore you, some say, no
But some are delighted to have a conversation. if you're curious about, someone's perspective just ask.
Dr. Rebecca Wynn: I agree With, you a hundred percent on that. I, tell people, they're like, who do you mentor? And I said I think you seek out mentors. I have Ann Cavoukian and I know you and I have talked multiple times too, but Jim Routh, Theresa Peyton. And I said, [00:12:00] how did you get them to be mentors? I said, I asked they don't meet me every week, but I'm like, Jim, I really need, I'm struggling with X can I find 15 minutes or 20 minutes on your calendar so we can walk through it?
you just need to ask, but come with a heart.
Caroline Wong: one of the things I've been thinking about and learning about in the past couple of years is change. I think that as humans, it's really natural for us to like things to stay the same. Particularly if we have this impression that things are quote unquote good, we want them to stay that way.
I've come to accept this idea that change is constant and change is inevitable. And so I've been trying to shift my own mindset from one where if I perceive a particular stage to be quote unquote good and trying to like, hold [00:13:00] onto that. When change comes,
I try to recognize that like this moment right now. And now this moment right now, like they're different. It's new. None of us have any idea what's gonna happen tomorrow, and we always have an opportunity to look at things in a different way so that when change happens or when I can see change about to come, I think it's really natural again, for us to have a human instinct, which is fear.
Oh no. Something bad's gonna happen. Oh no, I don't know what I'm gonna do. That's natural. And I think that's our brain trying to protect us. And I think that change also presents opportunity. There have been changes in my life that happened that I did not ask for, that I would not have asked [00:14:00] for. There's a whole thing about.
I used to live in California now in the Pacific Northwest. And our decision to move was not something exactly that we chose. We had to do it. And I'm so happy where we ended up even when I got let go from Cigital, that was not something I would've chose. That was not something that I wanted.
what happened next turned out to be, beyond what I had imagined in a really, great way. And so I think that we have an opportunity to consider that change is uncomfortable we don't know what's on the other side and being on the other side and, what happens being really great, really amazing, really positive, really fulfilling.
That's just as likely as. Really terrible, really [00:15:00] scary, Like we just don't know. And in any given day, we can look for the opportunity and focus on the things that truly are within our control and to try and let go of some of those which are not, which there are always gonna be lots of things outside of our control.
Dr. Rebecca Wynn: Caroline, our time has flown by.
Caroline Wong: I do teach LinkedIn Learning courses and on my profile you can find links to view those at no cost. So I'd, invite folks to, to check those out and let me know what you think.
This is so great. Thank you so much for having me.