Elicitation — Planning Conversations

Rick D.
6 min readApr 27, 2021



In the previous article we covered what elicitation was, a few examples, how you might use it, and how you might defend against it. If you haven’t read that article, you can find it here. In this article, we will cover how to plan conversations around the elicitation before diving into the third article on the elicitation techniques.

Planning Conversations

Planning conversations can be a little bit awkward at first, to some, it may even seem weird because it is not a common practice. While you can’t plan every aspect of the conversation, key items you may be able to plan:

  • What happens if the target is unresponsive or just shy?
  • Different streams of conversation that get the same result
  • Information you are willing to give about yourself that will assist in eliciting information.

An unresponsive target is sometimes difficult to understand, and we may feel that it is us they don’t wish to speak with. This could be true but could also be the furthest from the truth. We just don’t know, as Chris Hadnagy likes to say.

‘Just because you know the “what” doesn’t mean you know the “why.”’

This is important and pertinent in understanding our boundaries. When dealing with an unresponsive or shy target, it is best to avoid the conversation that made them unresponsive. Talk about something different, with the hopes of guiding the conversation to the information of interest without upsetting the target, and remembering that if it doesn’t work out, at least there was a good conversation. The goal is to always leave them feeling better, not bullied, or interrogated. Ways that you can do this include:

  • Build the conversation around the information you are looking for
  • Don’t dive right in
  • Plan past the information gathering phase

Diving right into eliciting may seem a little awkward, especially when using some of the techniques that require a little more rapport such as flattery. Additionally, if you end the conversation with a “Gee, look at the time!”, right after you have gotten the target information, this may leave the individual feeling awkward as well. It’s important to plan around the information and focus on having a successful conversation that leaves you and the target both feeling good afterwards. This may seem difficult at first, but you will get the hang of it.

It’s also important to plan different streams of conversation. Ask yourself this question; have you ever had a conversation that went exactly how it was supposed to? I don’t mean a short, pointed question that has only one answer. I’m talking about the conversation you get into, thinking it will only last a few minutes, only to realize an hour later that you are still talking? This is because conversations are dynamic and sporadic. They rarely go as we had hoped. We must plan for this in our conversations. It is best to not just focus on the target information you are after, but also the myriad of different paths you might have to take to arrive at the destination.

The final thing to consider in your planning is the information that you will give about yourself to build the conversation and the rapport between the target and yourself. This can sometimes be hard because what we consider valuable about ourselves, the target may not, and that is fine because this really is all about them. We must be willing to give information that the target will find valuable or relatable to get the information we desire from them. Consider this information every time you plan an interaction. Understanding the value of the information you are attempting to get will help you understand what elicitation technique may be best to get that information.

“Pretexting is a more compassionate and productive way of entering a conversation because it entails doing something incredible, almost radical: taking a moment to think about the other person’s emotional needs.”

~ Christopher Hadnagy — Human Hacking: Win friends, influence people, and leave them better off for having met you

Here are some steps that we can take to plan through each of these considerations and how we might think about them:

  1. Consider the issue you are trying to solve or the information you are trying to obtain. The What. Write it down!
  2. Write out the expected end goal of the interaction, what does success look like, this is important. (Remember, success isn’t always getting what you want. Sometimes, success is merely knowing that you have left someone better off for having met you.)
  3. Write down and understand the states of the conversation
    a. Where you want to start. What is the first thing you plan to say to bump the target? Why?
    b. The direction the conversation will go. What happens if it doesn’t? How do you get it back on track?
    c. The emotional state the individual needs to be in.
    d. The emotional state you need to be in or appear to be in.
    e. Where the conversation will take place, and why?
    f. What part of your personality do you need to portray? Remember, honesty is important, the more you let go of who you are the more difficulty you will have appearing genuine.
  4. Practice!

Chris Hadnagy (Professional Human Hacker), in his latest book “Human Hacking: Win friends, influence people, and leave them better off for having met you”, has a step-by-step process for building out your pretext that he has coined PREPARE.

  1. Problem: Identify the problem you are trying to solve.
  2. Result: Specify your desired outcome.
  3. Emotional State: Identify the emotions you want to see in your subject.
  4. Provocation: Anticipate the emotions you need to project or display.
  5. Activation: Define your pretext.
  6. Rendering: Determine the where, when, and how.
  7. Evaluation: Evaluate your pretext and ensure that it will leave the subject better off for having met you.

To better understand the PREPARE process and how to use it successfully check out Chris’ book here.


Finally, practice! By practicing the conversation with yourself in a mirror, two things are going to happen. First, you are going to think of ways that the conversation may take a turn, things that you would say in the situation or in the moment, and even things that would make you shy away from speaking to you if you were in the target’s shoes. Second, you are going to think of better, more efficient ways to work through the conversation. Practice also builds confidence, it does this because you begin working through errors and kinks in the wording and flow. I want to caution you here, it is important to not memorize the conversation you are planning, you don’t want to sound rehearsed, this makes conversation awkward.


Planning conversations can be a little difficult, sometimes awkward, but always rewarding. We often undervalue our conversations and therefore spend little time considering how to be good conversationalists. Even if learning how to perfect elicitation techniques is not on your to-do list, learning how to plan a good conversation should be. You may find that the reward for doing so is far better conversations with greater feelings of connectedness and mutual understanding for both you and our conversational counterpart. If you take nothing else from this, remember, planning and practicing conversations prior to execution is the best way to consider the conversational counterparts emotions, needs, and wants before and one the best ways to build strong connections.

Written By: Richard Davy ~ Professional Social Engineer and OSINT Practitioner

Don’t forget to checkout PERSINT and learn how Open-Source intelligence gathering can make your pretext stronger.

Stay tuned for the next article in the Elicitation series where we will start digging into the techniques of elicitation.



Rick D.

Professional Red Team operator, Social Engineer, and breaker of things. I like writing about adventures Red Teaming, Social Engineering, and Hacking…