EVALUATING TEAM FIT AND SHARED DIRECTION

Kip Boyle: 

Hi everyone. This is Your Cyber Path, we are the podcast that helps you get your dream cyber security job. I’m Kip Boyle, I’m here with Wes Reiner. We are experienced hiring managers of cyber security professionals, we have built many teams with cybersecurity people, and we’re going to share that experience with you. Now, if you want to give us feedback on the show, or if you want us to answer your question on a future episode, all you need to do is visit the show page. It is at anchor.fm/yourcyberpath. When you get there, you’re going to see a message button, it’s really obvious, you just click that and make sure your speaker or your microphone’s working and start talking and we will hear from you. All right, here’s the situation. You’ve found yourself a great looking job, you want this job, you’ve decided you’re going to apply for this job.

You’ve listened to all of our previous episodes, you’ve thought about technical fit and all the other things that you need to do. You’re going to, you’re going to craft a resume, you’re going to skip the cover letter, right? You followed everything that we said, but now you have to think about yet another thing, which is this, how do you know, how will you evaluate whether you are going to fit into this team? The one that has the empty seat. And, and I think you also need to ask yourself, do I want to go in the same direction that this team is going in? Because they’re headed somewhere and what is that direction? And do I want to be a part of that? And how do you do that? That’s not an easy thing.

Wes Reiner: 

These are good questions and I’m really looking forward to taking that on today in today’s podcast, it’s really about keeping the end in mind. What is our focus? Where are we going to from here? And I’m going to bring you back to life on the farm because life on the farm is how we do it.

Kip Boyle: 

And I got to say, I am endlessly curious about your farm life, it is nothing like my like. All right, lets hear.

Wes Reiner:

Farm life comes with chores, right? Animals come with chores, right? You’ve got to buck the hay bales, you’ve got to muck the stalls, you’ve got to clean up after these animals, you’ve got to keep them alive.

Kip Boyle: 

That’s why I don’t live on a farm. I remember now.

Wes Reiner:

That is not a one person job, that’s a family job, right? And so I try and be clear about what my goals are. My goals are not to take care of the animals, my goals are raise healthy children. And so my children have chores and the chores are to keep the animals alive.

Kip Boyle: 

Interesting.

Wes Reiner: 

I try and keep that end in mind and that’s not necessarily a job interview type thing, but understand that if you understand your goal is raising healthy children and you have the animals in order to help them become responsible young adults, then you’ve got your end in mind and that’s what we’re really talking about today is having your end in mind. One of my favorite quotes was from Ray Kroc in McDonald’s corporation when he said, “We’re in the real estate business, not the hamburger business.” Because he understood that when you own property in the middle of town, you sell hamburgers to pay the mortgage on it but once you own that outright, you have a valuable piece of land that is the center of town.

Kip Boyle: 

Okay.

Wes Reiner:

And he understood that.

Kip Boyle: 

Okay. So you’ve taken us some place deep, both in terms of parenting and in terms of business. I’ve heard Subway sandwiches is it has a very same philosophy that they’re really more into real estate and they sell subs as a way to pay their mortgages and whatnot. So it sounds counterintuitive, it absolutely does, but this is kind of deep magic, right? This is like a deeper way to think about something really important, which is where are you going to go to work and spend most of your waking hours?

Wes Reiner:

And that’s what we’re talking about today, is the deep stuff. The team fit and the shared direction. It’s the who you are, how does that fit with who we are and where are we going? Are we going the same direction? Right?

Kip Boyle: 

Yeah.

Wes Reiner: 

And when we get those two figured out, we’ve really rounded out the rest of that technical fit interview with team fit and shared direction.

Kip Boyle:

Right? And so if you’ve been with us in the previous episodes leading up to this one, and if you haven’t, I encourage you to go back and listen to them. When you get to the interview, your hiring manager is looking for many different things. The technical fit, the team fit, the shared direction and it’s often all happening at the same time. Now we’ve been breaking it down and in order to make it possible for you to understand the nuances and how all these things are different, but in the real world it’s all going to be going on simultaneously. Now we’re going to focus now on team fit and shared direction and it’s kind of a squishy thing. So Wes, tell me what team fit means to you?

Wes Reiner: 

I think it’s really about character, right? Character is who you are when no one is watching, it’s your integrity. It’s your ability to earn and maintain trust. One of the interesting things about work is that when I hire you, we’re going to share a reputation of sorts. Your reputation is going to start to blend with the team and the team’s reputation is going to rub off on you.

Kip Boyle: 

Yeah.

Wes Reiner:

So finding a really great fit is really important for both of us.

Kip Boyle: 

Yes.

Wes Reiner: 

That’s actually one of the reasons I invite candidates to interview with my internal clients before they join the team. Really, one of the interviews is completely dedicated to talking to people about our team. What do they expect? How do we deliver? And is that a good fit for you? You as a candidate as well?

Kip Boyle: 

Yeah. That’s one of the things I like about talking with you is the thoroughness that you use when you are interviewing people and the time that you invest, because you know it’s such a serious decision to bring somebody onto your team. And I got to say that when I’m interviewing people, over time I’ve become more like that. Early on when I was building teams, I was much more interested in getting somebody in quickly because I was feeling a lot of pressure to get work done and to not overburden the people who are on the team. But over time, I’ve learned that this is actually a much better way to do things.

Wes Reiner: 

That person’s going to be with you a long time, at least you hope they will.

Kip Boyle: 

Yeah.

Wes Reiner: 

And we’re going to invest a lot in training them up, right?

Kip Boyle: 

Yeah,.

Wes Reiner: 

Another key part of that interview, I actually invite you to a team meeting, right? I’m not interviewing you during that hour, I’m just asking you to observe what we’re doing here. How do we talk to each other? How do we talk about each other? What are the team dynamics? I realize as a job seeker, you’re looking for a great fit too. I want you to have all the information you can have to help you in that decision. This is a competitive marketplace and a healthy fit is oftentimes why a person would choose one job over another job.

Kip Boyle: 

Mm-hmm (affirmative). Yeah, so team fit super important and it’s a two-way street. So as a candidate, dear listener, if you are not evaluating your future job and making sure that it’s a good fit for you, not just that you are a good fit for them, then you might be setting yourself up for some disappointment down the road. Because if you’re going to work every day in a situation that is not a good fit for you, and you’re faking it all the time, that’s exhausting. And it’s inevitable that you are going to burn out and you’re just going to not like your job after a while. So, “Gee Kip, how do I know that?” Just take it from me.

Wes Reiner: 

Free advice.

Kip Boyle:

Yeah. 

There you go, for what it’s worth. Look, in order to evaluate team fit, just like you, Wes, I find it’s really helpful to get multiple perspectives. And so when I’m interviewing people, I involve others in the process. So for example, I typically don’t do the first phone screen, I have a recruiter from HR do that because I’m wanting the recruiter to sort of screen is this person a good fit for our overall corporate culture? And then if they’ve passed that screen, then the next interview is actually with a member of my team, not me because I want my team member to ask, “Is this person a good fit for our team?” Right? Because we have a subculture, right? We’re part of the larger company culture, larger organizational culture, but we have our own subculture and we want to make sure that people are going to fit there as well. Okay. So what are the specific things that you’re looking for in team fit, Wes?

Wes Reiner: 

I think you just brought some up, right? I want a person who knows what is right and doesn’t let go of what is right until a path is found that gets us to right, right? We don’t just ignore wrong things, we reserve judgment of right versus wrong for only those things which have a right and a wrong, right? Style issues are rarely right versus wrong, and we need to know the difference.

Kip Boyle: 

Right.

Wes Reiner: 

We need to know when we don’t know something, right, and we can say that, we can discuss it, figure it out and learn. That’s a humility, that’s a powerful characteristic of a person successful in our teams.

Kip Boyle: 

Yeah. I also think that that is an indicator of a person’s ability to think in more than just black and white terms, right? That they actually can see hundreds or thousands or millions of shades of gray because in my experience doing information security work, if you try to reduce everything to yes or no, if you try to make everything black and white, that usually doesn’t work very well.

Wes Reiner: 

That is a good challenge. Yeah. Sometimes we get to a conflict at work where the other person and I can’t reach a conclusion on our own, right? But we never use escalation as a weapon, right? We never yell at their boss, we don’t escalate on someone, we escalate with them, right?

Kip Boyle: 

Yeah.

Wes Reiner: 

We can say something like, “It looks like we’re stuck. I’d like to suggest we pull in my boss and your boss and ask our management for help on this one. Does that sound okay with you?” And that’s going to be a collaborative around and then up model as opposed to the escalation as a weapon, right?

Kip Boyle: 

Yeah. It’s the way we do things here.

Wes Reiner:

We practice humility in what we deliver, we turn to a trusted neighbor after putting in our best work and we say, “How would you make this better?” And by doing so, we have humbled ourselves to ask the person next to us how we can improve. We practice ownership, accountability, we stand up for what we’ve done and we deliver good work we can stand behind.

Kip Boyle: 

That’s a lot that you’ve covered. You’ve covered a ton of ground and I can see why all that’s important. But I think the challenge for us as hiring managers is being able to figure all that out, as well as the technical fit in a short interview. One of the things that you talked about that really stuck out to me and I would use different words, but I’ve said the same thing to my teams, which is, “Look, when you get into conflict with somebody, don’t ruin your working relationship with them just because you can’t figure out what to do. You’re going to be working with this person over the long haul, probably, so you need to guard your ability to work with them.” And so I say, “Trap the conflict, escalate it up to management and let us figure it out. And if we can’t figure it out, then we’ll trap it and escalate it until it gets to a level where it can be worked out.”

So that’s kind of the way I describe it.

Wes Reiner: 

Nice.

Kip Boyle: 

But I also think that a close cousin to that is candid respectful collaboration. Candid, because I want to hear the truth, I don’t want you holding back on me because you think you’re going to hurt my feelings or whatever, or because you’re holding onto something that you might use as a political weapon, so don’t do that. And respectful because look, it’s not fun for somebody to just say to your face a hard truth, you want to do it with respect if you want somebody to really listen to you and take what you’ve said to heart.

And then the last thing that I think is really important for team fit is we do not want to be Dr. No as an information security team. And so I always encourage my team to find ways to say yes, even if somebody brings you the goofiest damn thing ever, and you absolutely want to say no, take the time to unpack it and find out what it is that they really want. And see if you can find a way to say yes, if you can’t, oh, that’s fine. Sometimes the answer is no, but I think you get a lot of credibility by trying to find a way yes, if you can. All right. So Wes, what I want to know is how do you do it in an interview? How do you sort all this out?

Wes Reiner: 

If I were to add to that Kip, I would say that we do not put the no in technology.

Kip Boyle: 

Technology.

Wes Reiner: 

In fact, if you’re going to look at that word, I want you to put the ology in technology because that’s the study of, it’s the branch of knowledge of. And we as security professionals need to bring that learner approach to technology. And so give me the ology every day, I’d love it.

Kip Boyle: 

Give me the ology. All right, I got a new way to say it now. Thank you.

Wes Reiner: 

All right. So how do you answer these questions during an interview, right? It’s a tricky process. The best way to answer these questions is by asking other questions that expose these answers as a hiring manager, right?

Kip Boyle:

Okay.

Wes Reiner: 

If I ask, “Tell me about a time you didn’t agree with your management and you had to do it their way. What did you do and what happened?” You’re really telling me how do I work with the team? How do I follow up? How do I deal with right versus wrong and issues? If I, as a manager, ask you, “Tell me about a time you had to work with a difficult person.”

Kip Boyle:

Mm-hmm (affirmative).

Wes Reiner:

I’m looking for four parts, what was the concern, what did you do, what was the outcome and what would you do different? And we can work on taking on some of these interview questions, but just understand that if I’m looking for team fit, I’m listening for did you find a win-win? Did you escalate on someone or blow the other person up in some way? I’m looking for follow through, partnership and humility. I think you described that well.

Kip Boyle: 

Yeah. Now I want to be clear with listeners that what you’re hearing is this is what Wes looks for when he’s evaluating [crosstalk] building his team. And this is what Kip is looking for when he does the same thing. So we’re not speaking for all hiring managers, but what we are trying to tell you is this is how we think in general, right? There are things that are important to us and we have to screen for them, so don’t expect that you’re going to go into an interview and hear Kip or Wes actually pitching you these things. You might end up with a hiring manager who’s way more sophisticated than we are, or you might have somebody who’s not nearly as sophisticated as we are, because maybe they’re just earlier on in their journey and they’re still learning.

So in any event, typically you’ve got an hour to do this kind of an interview. This is a lot, how do you do it? How do you do it in an hour?

Wes Reiner:

I tend to run a pretty high energy interview. If I ask you a 22nd question with buildup and question, I’m looking for you to answer it in under a minute. And I want you to give the microphone back to me, right? If I can say that. Please don’t ramble for five plus minutes on a quick question, that limits our ability to finish the interview and that’s not going to reflect well on you.

Kip Boyle: 

Right, right. So in psychology, there’s a concept, I think it comes out of psychology. But in any event, wherever it comes from, it’s definitely a human thing, mirroring is a word that I’m thinking about, you might call it pacing. But the idea here is that as a candidate you want to be looking at the person on the other side of the table from you, is probably the arrangement that you’re in, and you want to match the enthusiasm of the interviewer. If the interviewer is going fast, you want to go fast, if they’re going slow, you want to go slow. But as a candidate, you’re probably feeling very eager, you’re very excited and so you might be outpacing the interviewer because I don’t know, that’s just how you’re feeling. And the interviewer might be actually encouraging you to talk a lot and you’re not because you’re just so excited. So it’s really important that you go in and you read the interviewer and you try to pace them.

Wes Reiner: 

So mirroring, to me, is the ability to reflect back to the person you’re talking to a similar energy and enthusiasm.

Kip Boyle: 

Yeah.

Wes Reiner: 

Pacing is different, pacing is the ability to match their verbal and idea pace, right? I’m looking for the candidate to follow me, follow my speed, follow my pace, right? If the candidate can’t accelerate to run with me in the most important conversations like interviews, they’re probably not going to run with my customers when they need to.

Kip Boyle: 

Okay. So you’re actually evaluating how they’re going to be with customers.

Wes Reiner: 

Very much so.

Kip Boyle: 

Yeah, that’s great.

Wes Reiner:

Let’s think about some examples of pacing. Kip, hit me with some questions, right, and I’m going to try and pace you-

Kip Boyle: 

Yeah, okay.

Wes Reiner:

– and mirror you if I can.

Kip Boyle: 

That’s great. Okay. Yeah. Here we go, I’m going to pitch just something. Okay. So, Wes, I don’t know a lot about the REST API, but I need to know that you understand it. It’s an important part of the way we’re architecting applications. So what can you tell me?

Wes Reiner: 

That’s a good question. With APIs, we need to make sure we’ve got two way mutual authentication. And I really like what’s going on with the Zero Trust Model, I think that’s the way to go. We need to authenticate at every level. So that might be the end of our lower pace question. Now you’re in a hurry-

Kip Boyle: 

Right. Yep.

Wes Reiner: 

– what would a faster pace question feel like?

Kip Boyle: 

Okay, here we go. Hey, Wes, what do you know about Python?

Wes Reiner: 

That’s my go-to language, actually, for scripting.

Kip Boyle: 

Great. Okay. What about Chef?

Wes Reiner:

I did it for three years at this company. I find it’s really useful for… What happened there was I gave you a quick answer, you gave long pause. I gave you a chance to give the microphone back, you didn’t ask for it back. And so I’m offering a second or a third sentence to follow on because you didn’t pick up the microphone when I gave it back to you. And it’s all about mirroring and pacing and reading your partner so that you’re meeting them at the level of energy they’re meeting you. Sometimes, if I’ve got a fast questioner and I need to give a quick answer, I might start with, “That’s a great question, thank you for asking.” Which is buying me three seconds to think about things before I answer the question.

Kip Boyle: 

Yeah, yeah. You can’t always know what someone’s going to pitch you.

Wes Reiner: 

One of the things I want to be careful of when we do you mirroring and pacing, I tend to be a chameleon sometimes, and I’m good enough at mirroring that sometimes I take on the other person’s accent by accident.

Kip Boyle: 

Oh, wow.

Wes Reiner: 

That’s not really cool, right? I speak a couple foreign languages, I was pretty good at pronunciation in those foreign languages because of this chameleon characteristic, but we really have to be careful of that in interviews and in the professional environment, right? It’s not going to help our cause, we need to be ourselves as we meet this mirroring and pacing objective.

Kip Boyle:

Yeah. I think if you’re going to actually pick up somebody’s accent or, or mirror them too well, I think the risk there is they’re going to feel mocked.

Wes Reiner: 

We don’t want that. [crosstalk]. We do not want that, it’s not the objective at all.

Kip Boyle: 

No, not a bit. You want to show respect. Okay. Thanks. [crosstalk]. Yeah, but you know what? That’s great because I’ve absolutely felt that before, but rarely have I ever talked about it. So I really appreciate that we can surface these deep issues on the podcast and I hope it’s going to help our listeners. All right, so that’s team fit. What about shared direction?

Wes Reiner: 

Shared direction? Very simply, what I mean by this is are we going the same place, right? Do your career and professional development goals line up with the role I have available and where my team is going, right? As a candidate, you have to bring realistic expectations. You tell me you want to be a director eventually, but you want to work remote as an individual contributor? That’s not really lining up, right?

Kip Boyle: 

Right.

Wes Reiner:

If you want to be in organizational leadership, you probably want to be closer to the core. If you’re happy being a technical expert, a remote role is going to be more successful and realize these are assumptions pre COVID 19, so it’s possible that those assumptions are out the window, but we’ll have to find that out in the next couple years as we watch the economy turn.

Kip Boyle: 

Yeah. Well, so that particular one may not be as well relevant going forward, but I think most people who have worked before COVID 19 became a thing can identify with that point. And really, it’s just the concept of making sure that you’re bringing realistic expectations and that if you’re not sure if your expectations are realistic too, put those on the table and and actually explore them. And in the same way, if you have this idea that you want to be a chief information security officer one day, which is fine, if that’s where you want to go, if you want to be in a senior decision maker. That’s a very different place than to be a senior individual contributor, it’s very different. And so you need to have a plan that’s more than just, “I’m going to come work for you, Kip and then stuff is going to happen and then I’ll have your job.” So you got to bring more realism to the situation than that and ask questions and get some help.

Wes Reiner: 

So I recently read Pete Carroll’s book, Pete Clay Carroll’s the head coach of the Seahawks, and he talks about win forever. And I love how he talks about how he built a plan for what he wanted to get, to the job he wanted, and then he executed on that plan to become the head coach of the Seahawks. And it’s a four hour listen if you’ve got the time, I found it to be really an interesting way to understand building that career path, career plan.

Kip Boyle: 

And I think that’s super important in our industry because I have rarely seen a single organization where you can have a long arc of professional development without going to another organization. So that kind of implies that you’re in charge of your own career progression and so you’re the one that’s going to have to make that roadmap. You can get help, of course, but I think-

Wes Reiner: 

Indeed.

Kip Boyle: 

– you just have to accept that it’s yours, right? It’s your primary responsibility.

Wes Reiner: 

It is.

Kip Boyle: 

Now there’s a lot of different types of jobs out there, some jobs are very process driven where we have to do the same thing every day. And there are some people out there who love that, that’s not me, that’s not the kind of job that I like. But there are things like regulatory requirements that force us to be in consistent behavior over the long haul. In contrast, other jobs are more undefined and so as a hiring manager if I’m looking for somebody to put into a role where the work isn’t very well structured, then the job description is almost kind of like, “Well, I want to hire a smart person to, to tell me what to do.”

So when you’re thinking about shared direction, that direction is something that you’re going to have to who ask the interviewer or the hiring manager about, right, in order to understand.

Wes Reiner:

Yeah. I think you can also get that from open-source intelligence, or OSINT, right? You can do your homework, this is what we call job hunting and that’s all about understanding what kind of company am I talking to? What kind of hiring manager am I talking to? What’s the culture there and is that a match for me? Right?

Kip Boyle: 

Yeah.

Wes Reiner:

There’s a lot of different companies and cultures and jobs out there, some jobs are the same, some jobs are never the same, every hour is a different new discovery of work. Some jobs require a team to deliver anything and the team needs to work together especially well, some jobs are entirely independent work and you can go and pontificate for hours to deliver a thing. Some are self-paced and you get as much done as you’re able to, other jobs are customer-centric and your workload is driven by others. Your role is more of turning them around quickly kind of a thing.

Kip Boyle: 

Mm-hmm (affirmative). Yeah, and we can just go on and on, right? I mean, you also need to think about the larger company fit, right? So some companies are very Monday through Friday, eight to four, eight to five, on the other end of the spectrum, there are companies where you can expect to be on call 24/7, and expected to do whatever needs to be done. You can encounter a company that has an up or out model for promotions and so if you’re not growing and promoting, then it’s not realistic to expect that you’re going to stay there over the long haul, right, you’re going to have to leave. And some companies are high tenure where they do expect you to be there for a long time, they don’t have a up or out, but maybe they’re going to keep you in the same role and maybe that’s going to get stale for you.

So think about that.

Wes Reiner:

Mm-hmm (affirmative).

Kip Boyle: 

Some companies want project managers to know scope costs and risks at a higher level, and in contrast, some companies are going to have project managers need to know every little detail of the delivery, and every little aspect of the architecture. But however, it happens, right? This is all part of fit. And so you should definitely be doing your homework to figure this stuff out and to the extent that you can’t figure it out, you should be asking questions.

Wes Reiner: 

You should. And maybe some of the best questions a candidate can ask when they’re interviewing are fit questions as well, right? And I call this the turnaround time of the interview, right, it’s that last 10 minutes of an hour long interview where they say, “Well, what questions do you have for me?” That’s a great time bring questions like, “Why is this position open?”

Kip Boyle: 

Yeah.

Wes Reiner:

“What characteristics would make a person hugely successful in this role? What concerns have you had in the past with people in this role? How would you coach them to be successful?” Right? And that’s a double win there because not only are your understanding, maybe, the characteristics that’s struggled in the past, but also how this manager handled them, right? So you get a double win on culture fit on that one.

Kip Boyle: 

Mm-hmm (affirmative).

Wes Reiner: 

All of these get to fit with your personal styles, fit with your manager, fit with the team and fit with the company, right? The earlier we can work these things out, the better it’ll help us and the hiring team make a healthy, really good long term match.

Kip Boyle: 

I’m going to say one more thing before we close the episode about the turnaround point in the interview. When a candidate fails to ask me questions when I invite them to do so, I’m not impressed. That’s really disappointing for me when that happens, because what that’s telling me, or strongly suggesting to me, is they’re not thinking about fit. They’re not thinking about are they going to get what they need out of this? And so I get a little disappointed and I just wonder if they really understand that important dimension of all this. Okay, Wes, any final thoughts?

Wes Reiner:

I think you bring up a good point that you need to have some questions to ask, but be prepared because some folks are going to walk out of 50 minutes of that interview and know that this was kind of edgy at best. And you can ask for feedback at that point, right?

Kip Boyle: 

Yeah.

Wes Reiner: 

If you think it was edgy at best, don’t ask the question, “What’s my day to day life going to be when I start working here?” Right? Because that might not be the right question, this is your chance to get some feedback if you think it maybe went a little sideways, right?

Kip Boyle:

Mm-hmm (affirmative).

Wes Reiner: 

If you think you had a slam dunk and you’ve got a pretty sweet opportunity here, then the question what things do you want to see in the first 90 days would be a great question to ask, but be prepared with pencil and paper. So you can write that down and take it home with you.

Kip Boyle: 

Yeah. Yeah, definitely. Great. Thanks, Wes, for those closing ideas. Well listen everybody, thanks for joining us today. If you liked the podcast, if you like what we’re doing, then I want you to consider our masterclass and you can find it at yourcyberpath.com. It’s called How To Get Your Dream Cybersecurity Job As Told By Hiring Managers. We have a really inspiring story to share with you, we had a student named Steve who got his dream cyber security job before he even finished all the lessons in our masterclass. And I think you should go check it out. If you go to yourcyberpath.com/steve, S-T-E-V-E, you’ll be able to read his story and if you want to, you can even check out his guest appearance on the insecurity podcast and let him talk to you about it. We’re really excited for him. So until next time, remember you’re just one path away from your dream cybersecurity job. See you later.