Career Notes 11.5.23
Ep 174 | 11.5.23

Jeffrey Wheatman: Sometimes you just need to open the raincoat.


Jeffrey Wheatman: My name is Jeffrey Wheatman. I am a senior vice president cyber risk evangelist with Black Kite.

Jeffrey Wheatman: Well, I think just like most people my age, I wanted to be an astronaut. I was informed that it would not work because my vision is terrible and I had to wear glasses. Uh, and in retrospect, I'm probably better off not, not being an astronaut. I was always a big science and math guy and then of course, when computers came out, I taught myself how to program not well, but I taught myself how to program and I think from there I was really off to the races.

Jeffrey Wheatman: I have a somewhat unusual pathway. I actually, believe it or not, started off managing a hardware store in New York City. I was selling plumbing supplies and electrical to a bunch of superintendents in the garment district and every day i got home and i was more and more unhappy and I decided one day i like computers i'm gonna go be a computer person and I put myself through a training class for Novell Netware 3, so i'm dating myself a little bit and i found out that i was having way more fun doing that then working in a hardware store.

Jeffrey Wheatman: So I first started out as a team manager for a company that installed color printers for M.C.S. Cannon back in the day, and what I quickly realized was while I was technical, I was much better at communicating about the technology to non-tech people. So I really found my sweet spot really is as an ombuds function between technical and business people. I built a bunch of consulting practices for some small companies. I ran, uh, network operations and cyber security, although back back then it was called information security at Martha Stewart in New York City and I did pen testing for a while and I realized I was not a super good pen tester, so that was sort of my sweet spot was that, that communication ombuds function.

Jeffrey Wheatman: I spent 15 years at a large IT advisory firm and I really, really enjoyed that, but what I found was I was so far from the solution from the problem that I didn't feel like I was doing a lot of good and I saw that organizations really struggling with third party risk and vendor risk and supply chain risk and when I stumbled across Black Kite, I really like what they were doing I reached out to my now boss who is our CEO and I said I think I can help you make this bigger, better, faster, more, and he agreed and, you know, 20 months in, I think we've had a lot of really good, good success and I feel like I am able to help people solve their problems at a much sort of granular and closer level than earlier in my career when I was, uh, you know, operating at the 50, 000 foot level.

Jeffrey Wheatman: One of the interesting things about my job is I do so many different things. My job is really to think about things and talk about the things that I think about. The one thing I've, I've learned in the last year or so is I'm very good at it at being a connector so I find people that have stuff to do and I find people that can do those things and I make a lot of those introductions. My dad taught me a long time ago, he said, any day where you don't learn something is a wasted day and I try to make every day an opportunity to learn something new even if it's a small thing.

Jeffrey Wheatman: I think that you can teach technology to people it's harder to teach them those softer skills and I think it's something that people constantly have to work on but at the end of the day you can be the best at your job, but if people on the other end of that transaction, for lack of a better term, don't understand why what you're doing is important or useful, they don't see the value there. I think being able to put yourself in the shoes of the other person. So empathy for what it is they are going through. I've had conversations with CISOs and I say, so did you talk to your business stakeholder and ask them why they won't do the thing you want? And their response is invariably, well, why would I do that? And I think that is a huge, huge issue, particularly in our career, because it, it comes across as, as wizardry for a lot of people, they don't really understand, they don't care, they don't understand why they should care.

Jeffrey Wheatman: There's a quote that's attributed to a couple different people that I paraphrase when you speak with someone, they remember how you made them feel much more than the specifics of what you told them and if you engage with your audience and they find you interesting, they'll invite you back and then you have another opportunity to share something, but if you don't engage them at that level, and they find you tedious or, or, um, or that you're talking down to them, they won't invite you back and then you potentially lose really good opportunities to communicate valuable pieces of information. Value pieces of data, pieces of intelligence, things that will help them make better decisions and be able to understand why certain decisions are more informed. I don't like to say better or worse, but more informed and more defensible and I just think that, you know, sitting in front of a technical console all the time while. That may be fun, does not demonstrate a tremendous amount of value for the person on the other end of that relationship.

Jeffrey Wheatman: I am definitely a lead from the front person. When I did manage people, I only had two rules. One, don't lie to me and two, don't put me in a position where my boss asks me a question and the best answer I can come up with is duh. I think openness, transparency, I think it's okay to let people know that you don't have all the answers, that you don't know everything. We're not perfect. We make mistakes and I I'm a, I'm a big believer in sharing those mistakes and I think it's important to open the raincoat as it were, and let people understand that we're not perfect, we all need help and then that way they feel comfortable coming to you and asking for help and the only way really to do that is to live the it's to live it right, walk, walk the walk and talk to talk.

Jeffrey Wheatman: If you find something you love, people will pay you to do it. And I think that loving what you do and really getting down in there and finding enjoyment, not necessarily in every second or every minute, but you do need to end the day feeling that you've accomplished something that you've done good that you've shared knowledge. I think, uh, the other tidbit I would give, especially for cyber people, I always tell people don't try to learn it all at once because you're never going to be able to absorb that kind of information so I think the key is find some stuff do a deeper dive if it's something that you really like maybe you can go deeper still but I always tell people you you wanna you wanna focus on some different areas across the board, but you're never going to learn everything really I think is, is, uh, is, is the point there.

Jeffrey Wheatman: I think broader than just my career, I would like people to look and say, you know, that Jeffrey Wheatman guy, the world is a better place for him being in it and I think that's, that's really what I try to get to. It's what I try to get my kids to think about incrementally, I hope the world is better. I hope people feel like they um, learn something from our engagement and I also, I don't on the flip side, don't ever want anyone to look back and say, you know, that guy was mean to me or that guy was inconsiderate or that guy was unfeeling or uncaring. It's a hard to answer, but I think just to sum it up, I would like the world to be an incrementally better place because I was a part of it.