I’ve found in early discovery sessions with stakeholders – regardless of the organization, industry, personalities, problems or other nuances – we’re striving to accomplish essentially the same things. Further, for any situation, there are a few basic questions or cues that can help us make sure we cover them all.

Because of their value and range of application, I’ll refer to them as “golden questions.” I’d like to share my list of golden questions – and a few simple keywords to help remember them.  In return, I’d love your feedback on what you might add, or edit on your own “golden questions” list.

Before I get started, here are just a few guidelines.

  1. I intentionally kept the list short. I’d like to restrict it to maybe the 5 or at most 7 golden questions, applicable to the initial scoping or discovery. Any more than that would become difficult to remember. They key to this being useful is not to script our discussion, but to remember to cover the areas each question represents during our discussion.
  2. Every question should have a clear and distinct purpose – something it will help us discover.
  3. I’ll be purposely generic in the wording to ensure the intent is clear. Think of these more as cues than a script. The timing and specific phrasing of each question may different depending on context of the discussion. I don’t want to remember the wording, I just want to remember the ideas!

So, here we go –

1. What is the problem we need to solve?

Every solution begins with a problem to solve. While it can be tempting to assume we know what the problem is – that we even know what the solution is, it is important to develop a contextual understanding of the problem. If you don’t have a solid understanding of the problem, you’re essentially trying to hit the bulls-eye while blindfolded.

Keyword: PROBLEM

2. What is the cause of the problem?

This is a close follow-on to our first question. Once we have a good sense of the problem, we get into one of the trickier parts of the conversation – trying to identify the cause. Often, stakeholders and even analysts will mistake symptoms for causes, which results in solutions that only partially address the problem. In other cases, stakeholders will mis-diagnose based on only a partial view of the problem.

Keyword: CAUSE

3. Who will we need to consult as we analyze the problem and proposed solution?

Once we know the problem and objectives, we want to get input and verification from those who are “living the problem.” This questions puts us on the critical path to learning who our stakeholders are, and what areas and processes in the organization we anticipate being affected.

Keyword: IMPACTS

4. How will we define and measure success?

Once we have an understanding of the problem domain, it is time to begin discussing properties of the solution, or, in other words, what success looks like. This is the question that leads to our business objectives. A close companion to this question is, how will we define “done?”


5. What are the biggest challenges or roadblocks might we expect to encounter?

Even though we’re in our first discovery session, it isn’t too early to try to learn what our audience is most concerned about as we move forward. This type of question can be useful to identify potential risks and challenges the solution team might encounter. These could be political, financial, resource-related – any type of risk or challenge with want to be mindful of from the beginning.Asking the question also demonstrates to the audience that we are mindful of their concerns.  At this early stage, we shouldn’t expect an exhaustive or complete list of risks, but we will come away with a much better idea of the audience’s priorities and mindset regarding the solution.

In some cases, I’ve seen this question asked in a more generic way to good effect – for example, “What else should we be mindful of as we begin our analysis effort?” or, “What have I not asked you about that you feel is important for us to know as we move forward?”


If it makes it easier, just remember the key words as cues:

  1. Problem
  2. Cause
  3. Stakeholders
  4. Objectives
  5. Concerns

Well, there you have my list of golden, go-to questions. Please feel free to add your own in the comments or share this post with those you think might benefit from it. Happy elicitation!