Elements of a Good Assessor

As assessors, there are some crucial elements that you need to incorporate into your style while you are in front of a client; whether it be the way you present yourself, the way you ask questions, or just the way you collect information. All of these issues can affect the quality of the assessment and how smoothly it performs.

The following are just some quick tips to consider as you are doing your assessment, making it as thorough and as painless as possible.

Be friendly but don’t be their friend.

This is one of the most helpful items that I have taken to heart. As an assessor, you want them to feel comfortable and divulge all information that you want from them. If they feel pressured or backed into a corner, you’ll get only short and sweet answers that, depending on the situation, will not get you the information you’re looking for. Try connecting to them at the beginning of the meeting. Ask them how long they have worked at the company and see where the conversation goes from there. Magically a repore starts to develop and the auditor wall will start to crumble.

Others things to bring up: weather, news (NOT politics), and opinions on technology. Also showing a sincere interest in what they do at their job also helps. People love talking about themselves!

‘May I see an example?’ should be your motto.

People can be a great way of gathering information, but the devil is in the details. Always be in a inquisitive nature and develop an uncomfortable feeling about information when you don’t have documentation to support it.

This is especially important when the client states that they are accomplishing the control or having certain processes around it. Not always, but usually you can trust employees to be honest if they are talking about deficiencies within their processes. The concern grows if they are saying that everything is fine and all of there controls are in place and working correctly. This is a clear sign that you need to gather documentation and further information on the status of findings.

If you get into an audit situation this becomes especially important, as everything typically needs some type of paper trail as to confirm the control is functioning and in place.

If they push back, attack!

Honestly, this should be a red flag while assessing personnel. If you think you’re getting resistance, it could be one of two issues. They could feel uncomfortable about the situation OR they could be concealing something. If they are concealing something, you need to dig even more, ask for examples, and confirm the content with others within the auditing scope.

Don't be afraid to as the same question more than once. For example, asking the configuration manager about pushing code into production might reveal that they have a uniform configuration management tool - and that's the only method of getting code there. Though when talking to the software engineer about this topic, they might reveal that they often put code into production in order to test it first.

I assume you know about assumptions!

Your whole job as an assessor is to gather facts and to interpret to the results - no assumptions included. This is still important even if you are familiar with the environment. Personally, I have to watch out for this if I'm involved with follow-up assessment for organizations. It is very easy to fall into presumptive questions if you knew the answer last year. The problem comes that you do not know if their environment has changed within the last year. Also injection your own presumptions into the assessment could bite you in the end.

Try and look at each assessment engagement as a separate issue. Even if you are familiar with the organization, ask the questions to their personnel again and let them answer the questions.

Let them do the talking.

Bottom line – you don’t get any answers when you’re doing the talking. Setup questions that allow them to describe the situation or process. For example, a closed questions sets up the yes/no answer – like “Do you do this within your process?”. Alternatively you need to ask open questions whereas they are forced to describe the situation from their own point of view - “Can you walk me through how you would typically perform this process?"

If it gets into a complicate section, utilize confirmation questions at the end - example "My understanding of the current situation is like this. Am I correct?". You want to make sure that the findings you are putting down are as accurate as you can record.

Don’t report the findings until the end.

I can’t tell you how many times I get after an interview the question of “So how did I do?”. The best strategy is to just say that you need to look at all of the information holistically before bringing out the findings. Let’s take a couple of scenarios.

Scenario 1 - “Mr. Client, you’re great and I see nothing wrong out of this interview.”

Client is happy that they’ve done their job in your eyes. The person then goes to gloat to his boss on the fine work they’ve done. This is until the next day when you discover a gaping hole in their process that wasn’t discovered until you looked at either the documentation or talked with another person involved. Now you have to retract the statement you did, the client has to retract their statement, and there is a bitter feeling in the air.

Scenario 2 - “ Mr. Client – you have some major deficiencies because of the findings I saw in this particular area.”

Now the client could fight back and try and justify their position, why they didn’t do certain controls, or why they think security is a joke! Additionally if you have to go back to the person to gather more information, they are going to be a closed book for information.

Bottom line – save the findings until the end where you can present all of them in an orderly fashion.

Practice good meeting facilitation.

Lastly, you should always practice good meeting facilitation while you’re performing interviews. Some examples are introductions, setting the tone of the meeting, good time management, keeping proper focus on the objective, and closing the meeting. This is important to ensure that all of the necessary information is gathered within the appropriate time frame.

I’ll elaborate on a future blog as to the details of some of the elements to a meeting and what I like to do to open and close a meeting.

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Keep in mind that these are all recommendations and general guidelines to an assessment. When the actual work is being performed, you are the general on the ground and no successful battle plan has been followed to the letter and the battle won. Adjust to the changes within the organization and environment and everything will complete successfully!

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Defcon – "And this is very illegal! So the following material is for educational use only."

I’m not a hacker, but I live with them. I took the pilgrimage to Defcon, attended by many of the world's best-known security experts, and felt much like the kid reporter in the movie “Almost Famous.” Among other (sometimes bewildering) presentations, Defcon showcases demonstrations of the latest discovered weaknesses in computer systems.

The big brew-haha this year was “The Anatomy of a Subway Hack” of the Boston T that got blocked. A federal judge ordered three college students to cancel a Sunday presentation where they planned to show security flaws in the automated fare system used by Boston's subway. I wouldn’t have thought this was any different than the presentation the SecureState team gave where we released various new tools, including SA Exploiter. However I guess when one of your slides proclaims: "And this is very illegal! So the following material is for educational use only," it draws attention to you.

At SecureState, we believe everyone (most especially those organizations trying to protect themselves) should have access to all information available. The belief is if you hide the findings (zero-day exploits) it’s not going to stop the bad guys who have the time and incentive to find the vulnerabilities themselves. It just keeps the good guys on the forefront.

Many organizations without the resources to properly research the latest and greatest vulnerabilities use penetrations tests to get the results of the research with the ability to see how it affects them specifically. Penetration tests are the foundation of security since you don’t know what you don’t know. Thus, keeping security problems secret, or the “Security through obscurity” idea, doesn’t protect the businesses relying on those systems.

In short, our goal at SecureState is to make security better. We don’t look to disclose things that can hurt people. That’s especially true if there is nothing they can do about it. Releasing exploits and tools gives researchers and ethical hackers the opportunity to learn from the experience we have, gives organizations a better idea about the attacks that are possible, and the steps they need to take to prevent them. The bottom line is that while there are risks, the public good is better served by having knowledge freely available. Besides, H4CK3RS are people too.

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