25 Questions to Ask During an Information Security Interview

What follows is a list of questions for use in vetting candidates for positions in Information Security. Many of the questions are designed to get the candidate to think, and to articulate that thought process in a scenario where preparation was not possible. Observing these types of responses is often as important as the actual answers–especially when interviewing for customer-facing positions.

I’ve mixed technical questions with those that are more theory and opinion-based, and they are also mixed in terms of difficulty. A number of trick questions are included, but the goal there is to expose glaring technical weakness, not to be cute. I also include with each question a few words on expected responses.

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Where do you get your security news from?

Here I’m looking to see how in tune they are with the security community. Answers I’m looking for include syndication feeds for solid sites like liquidmatrix, packetstorm, rootsecure, secguru, astalavista, whitedust, internet storm center, etc. The exact sources don’t really matter. What does matter is that he doesn’t respond with, “I go to the CNET website.”, or, “Steve Gibson’s home page”. It’s these types of answers that will tell you he’s likely not on top of things.

If you had to both encrypt and compress data during transmission, which would you do first, and why?

If they don’t know the answer immediately it’s ok. The key is how they react. Do they panic, or do they enjoy the challenge and think through it? I was asked this question during an interview at Cisco. I told the interviewer that I didn’t know the answer but that I needed just a few seconds to figure it out. I thought out loud and within 10 seconds gave him my answer: “Compress then encrypt. If you encrypt first you’ll have nothing but random data to work with, which will destroy any potential benefit from compression.”

What’s the difference between HTTP and HTML?

Obviously the answer is that one is the networking/application protocol and the other is the markup language, but again–the main thing you’re looking for is for him not to panic.

How does HTTP handle state?

It doesn’t, of course. Not natively. Good answers are things like “cookies”, but the best answer is that cookies are a hack to make up for the fact that HTTP doesn’t do it itself.

What exactly is Cross Site Scripting?

You’d be amazed at how many security people don’t know even the basics of this immensely important topic. We’re looking for them to say anything regarding an attacker getting a victim to run script content (usually Javascript) within their browser.

What’s the difference between stored and reflected XSS?

Stored is on a static page or pulled from a database and displayed to the user directly. Reflected comes from the user in the form of a request (usually constructed by an attacker), and then gets run in the victim’s browser when the results are returned from the site.

What are the common defenses against XSS?

Input Validation/Output Sanitization, with focus on the latter.

What’s the difference between symmetric and public-key cryptography

Standard stuff here–single key vs. two keys, etc, etc.

In public-key cryptography you have a public and a private key, and you often perform both encryption and signing functions. Which key is used for which function?

You encrypt with the other person’s public key, and you sign with your own private. If they confuse the two, don’t put them in charge of your PKI project.

What kind of network do you have at home?

Good answers here are anything that shows you he’s a computer/technology/security enthusiast and not just someone looking for a paycheck. So if he’s got multiple systems running multiple operating systems you’re probably in good shape. What you don’t want to hear is, “I get enough computers when I’m at work..” I’ve yet to meet a serious security guy who doesn’t have a considerable home network.

What is Cross-Site Request Forgery?

Not knowing this is more forgivable than not knowing what XSS is, but only for junior positions. Desired answer: when an attacker gets a victim’s browser to make requests, ideally with their credentials included, without their knowing. A solid example of this is when an IMG tag points to a URL associated with an action, e.g. http://foo.com/logout/. A victim just loading that page could potentially get logged out from foo.com, and their browser would have made the action, not them (since browsers load all IMG tags automatically).

How does one defend against CSRF?

Nonces are an accepted, albeit not foolproof, method. Again, we’re looking for recognition and basic understanding here–not a full, expert level dissertation on the subject. Adjust expectations according to the position you’re hiring for.

What port does ping work over?

A trick question, to be sure, but an important one. If he starts throwing out port numbers you may want to immediately move to the next candidate. Hint: ICMP is a layer 3 protocol (it doesn’t work over a port) A good variation of this question is to ask whether ping uses TCP or UDP. An answer of either is a fail, as those are layer 4 protocols.

How exactly does traceroute/tracert work at the protocol level?

This is a fairly technical question but it’s an important concept to understand. It’s not natively a “security” question really, but it shows you whether or not they like to understand how things work, which is crucial for an Infosec professional. If they get it right you can lighten up and offer extra credit for the difference between Linux and Windows versions.

The key point people usually miss is that each packet that’s sent out doesn’t go to a different place. Many people think that it first sends a packet to the first hop, gets a time. Then it sends a packet to the second hop, gets a time, and keeps going until it gets done. That’s incorrect. It actually keeps sending packets to the final destination; the only change is the TTL that’s used. The extra credit is the fact that Windows uses ICMP by default while Linux uses UDP.

If you were to start a job as head engineer or CSO at a Fortune 500 company due to the previous guy being fired for incompetence, what would your priorities be? [Imagine you start on day one with no knowledge of the environment]

We don’t need a list here; we’re looking for the basics. Where is the important data? Who interacts with it? Network diagrams. Visibility touch points. Ingress and egress filtering. Previous vulnerability assessments. What’s being logged an audited? Etc. The key is to see that they could quickly prioritize, in just a few seconds, what would be the most important things to learn in an unknown situation.

As a corporate Information Security professional, what’s more important to focus on: threats or vulnerabilities?

This one is opinion-based, and we all have opinions. Focus on the quality of the argument put forth rather than whether or not they they chose the same as you, necessarily. My answer to this is that vulnerabilities should usually be the main focus since we in the corporate world usually have little control over the threats.

Another way to take that, however, is to say that the threats (in terms of vectors) will always remain the same, and that the vulnerabilities we are fixing are only the known ones. Therefore we should be applying defense-in-depth based on threat modeling in addition to just keeping ourselves up to date.

Both are true, of course; the key is to hear what they have to say on the matter.

Describe the last program or script that you wrote. What problem did it solve?

All we want to see here is if the color drains from the guy’s face. If he panics then we not only know he’s not a programmer (not necessarily bad), but that he’s afraid of programming (bad). I know it’s controversial, but I think that any high-level security guy needs some programming skills. They don’t need to be a God at it, but they need to understand the concepts and at least be able to muddle through some scripting when required.

What are Linux’s strengths and weaknesses vs. Windows?

Look for biases. Does he absolutely hate Windows and refuse to work with it? This is a sign of an immature hobbyist who will cause you problems in the future. Is he a Windows fanboy who hates Linux with a passion? If so just thank him for his time and show him out. Linux is everywhere in the security world.

What’s the difference between a risk and a vulnerability?

As weak as the CISSP is as a security certification it does teach some good concepts. Knowing basics like risk, vulnerability, threat, exposure, etc. (and being able to differentiate them) is important for a security professional.

Cryptographically speaking, what is the main method of building a shared secret over a public medium?

Diffie-Hellman. And if they get that right you can follow-up with the next one.

What’s the difference between Diffie-Hellman and RSA?

Diffie-Hellman is a key-exchange protocol, and RSA is an encryption/signing protocol. Blank stares are undesirable.

What kind of attack is a standard Diffie-Hellman exchange vulnerable to?

Man-in-the-middle, as neither side is authenticated.

What’s the goal of information security within an organization?

This is a big one. What I look for is one of two approaches; the first is the über-lockdown approach, i.e. “To control access to information as much as possible, sir!” While admirable, this again shows a bit of immaturity. Not really in a bad way, just not quite what I’m looking for. A much better answer in my view is something along the lines of, “To help the organization succeed. ”This type of response shows that the individual understands that business is there to make money, and that we are there to help them do that. It is this sort of perspective that I think represents the highest level of security understanding—-a realization that security is there for the company and not the other way around.

Are open-source projects more or less secure than proprietary ones?

The answer to this question is often very telling about a given candidate. It shows 1) whether or not they know what they’re talking about in terms of development, and 2) it really illustrates the maturity of the individual (a common theme among my questions). My main goal here is to get them to show me pros and cons for each. If I just get the “many eyes” regurgitation then I’ll know he’s read Slashdot and not much else. And if I just get the “people in China can put anything in the kernel” routine then I’ll know he’s not so good at looking at the complete picture.

The ideal answer involves the size of the project, how many developers are working on it (and what their backgrounds are), and most importantly — quality control. In short, there’s no way to tell the quality of a project simply by knowing that it’s either open-source or proprietary. There are many examples of horribly insecure applications that came from both camps.

What’s the difference between encryption and hashing?

Encryption is reversible, as long as you have the appropriate key/keys, and the size of the cyphertext roughly matches the size of the plaintext. With hashing the operation is one-way, and the output is of a fixed length that is usually much smaller than the input.

Who do you look up to within the field of Information Security? Why?

A standard question type. All we’re looking for here is to see if they pay attention to the industry leaders, and to possibly glean some more insight into how they approach security.

Bonus: Scenario Role-Play

For special situations you may want to do the ultimate interview question. This is a role-played scenario, where the candidate is a consultant and you control the environment. I had one of these during a Google interview and it was quite valuable.

So you tell them, for example, that they’ve been called in to help a client who’s received a call from their ISP stating that one or more computers on their network have been compromised. And it’s their job to fix it. They are now at the client site and are free to talk to you as the client (interviewing them), or to ask you as the controller of the environment, e.g. “I sniff the external connection using tcpdump on port 80. Do I see any connections to IP 4.2.2.2?” And you can then say yes or no, etc.

From there they continue to troubleshooting/investigating until they solve the problem or you discontinue the exercise due to frustration or pity.

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Feel free to contact me if you have any comments on the questions, or if you have an ideas for additions. ::