The first meeting with a prospective security leader usually goes one of two ways. Either the candidate does most of the talking and you leave impressed but not much better informed, or you ask a few careful questions and learn within an hour whether this is a person you want accountable for your program. The difference is preparation, and it is entirely on your side of the table.
These are the questions to ask a fractional security director in the first meeting, along with what a strong answer sounds like and what a weak one sounds like. You do not need a security background to use them. You need only to listen for whether the person in front of you thinks like an executive who happens to know security, or like a security technician who has been given an executive title.
Start With How They Would Begin
Ask the candidate what they would do in the first thirty days if you hired them tomorrow. This is the most revealing question you can ask, because it exposes the person’s instincts before they know what your organization looks like. A strong answer describes finding out what is true: walking the sites, reading what policies exist, pulling the guard contract, interviewing the people who actually run the building, and testing the controls everyone assumes work. A weak answer moves quickly to a proposal for cameras, access control, or a new guard vendor, and you should note that the candidate is recommending solutions to a problem they have not yet seen.
Follow that by asking what they would need from you to do the first quarter well. The right answer includes access to documents and people, a clear reporting line, an honest conversation about budget, and the authority to talk to anyone in the organization. If the candidate does not ask for anything, they either have not thought about it or they plan to work around you, and neither is good.
Ask About Testing and Assumptions
Ask how they would know whether your current security actually works. Listen for whether the answer involves verification or only review. A director who says they would read your policies and look at your camera coverage is describing a review. A director who says they would pull on doors after hours, call your alarm company to find out who receives the signal, watch the guard post at shift change, and run your incident plan as a tabletop is describing a test. My own position, which I built the P.R.O.O.F. framework around in Until Tested: Security Is Only Assumed, is that untested security is assumed security, and I want any director I recommend to think the same way.
Then ask what they have found in past engagements that leadership did not know about. Every experienced director has a store of these, and the examples they choose tell you what they pay attention to. Doors that never latched, badges still active for people gone a year, alarm signals that went to a disconnected number, evacuation plans that had never been walked. If the candidate cannot give you a single example, they may not have done the work.
Ask How They Talk to Leadership
Ask the candidate to explain a security risk to you as if you were the board, in two minutes, without technical language. Then actually time it. This is the job in miniature. The director will spend a great deal of the engagement translating exposure into risk, cost, liability, and continuity, and if they cannot do it in your first meeting they will not do it in the boardroom. A strong answer names the risk, says what it could cost the organization, says what it would take to reduce it, and stops. A weak answer wanders into equipment specifications or industry standards and leaves you no clearer on what to decide.
Ask also how they handle disagreement with an executive who does not want to spend the money. You are looking for someone who will make the case with evidence, document the decision and the risk that was accepted, and move on without sulking or going around you. A director who describes threatening to walk, or who says they have never had a recommendation refused, has either not led for long or is not being straight with you.
Ask About Vendors and Money
Ask plainly whether they receive any compensation, referral fee, or other benefit from any vendor they might recommend. Then ask them to put the answer in the agreement. A director who is paid by the guard company or the integrator is not evaluating those companies on your behalf, and independence is a large part of what you are buying. A candidate who bristles at the question is telling you something. A candidate who says of course and offers to disclose every relationship is telling you something better.
Ask what they think of your current guard contract without having seen it. This is a bit of a trick, and the right answer is that they would want to read it first, compare it to the post orders, and watch the officers before forming a view. Then ask when they last told a client to spend less on security rather than more. A director who has never done that is not looking at the whole picture, because most organizations I have assessed were spending in the wrong places as much as they were underspending overall.
Ask About Their Time and Their Other Clients
Ask how many organizations they currently serve and how much time each one gets in a typical month. You are not looking for a particular number. You are looking for candor and for a workable arrangement. Follow with what happens when two clients have a serious incident on the same day, and listen for whether the answer has been thought through. A director who has a plan for that, whether it involves a trusted backup, a clear triage rule, or a limit on how many retainers they hold, has been doing this long enough to have faced it.
Finally, ask what would make them decline the engagement. It sounds backward, but a director who has standards for the clients they take on is a director who takes the work seriously. Answers like leadership that will not give access, a board that wants reassurance rather than facts, or an organization that wants a name on a letterhead without changing anything are all signs that the person understands what the job requires. A candidate who says they would take any engagement is either new or desperate, and you want neither.
What to Do After the Meeting
Write down your impressions within the hour, while the answers are fresh, and note specifically which questions the candidate answered with evidence and which they answered with reassurance. Then ask for a sample of written work and two references, and tell the candidate you would like to pay for a single day on site before committing to a retainer. How they respond to that request is one more answer. A director who is confident in their work will welcome a test of it, and that is exactly the disposition you want in the person who will be testing everything else.
Go Deeper
For the full definition of the role, what it costs, and how it compares to the alternatives, start with What Is a Fractional Security Director? The Complete Guide. My book Fractional Security Director expands on the selection process and on what the first meeting should establish before any agreement is signed.
Commissioner William Epps is a former elected Fire Commissioner, federal law-enforcement supervisor, and firefighter since 2006, with instructor credentials in Hazardous Materials response, Active Shooter preparedness, and Stop the Bleed®. He spent seven years in federal law enforcement in physical security, executive protection, and incident command, and now serves organizations as a Fractional Security Director. He is the author of The Spirit of Saul, The Spirit of Pharaoh, and other practical books on security, leadership, and faith, built around one idea: knowledge should be practical enough to use when it matters.
Leave a Reply