Good Discovery Questions
- Dan Greenberg
- Dec 6, 2024
- 5 min read
I have spent the past couple of posts talking about discovery, but we have not talked much about what makes a good discovery question, and why.
Last post we discussed Neil Rackham’s SPIN Selling and the four questions that you can use to progress through a discovery cycle. The post before that we discussed the overall nature of discovery questions, and how to think about our preparation. Now, I want to spend a bit more time talking about the mechanics of the preparation and the questions themselves. It is impossible to keep all of the information and questions in your head and pull off a flawless discovery session without preparation. It is very important to put down on paper lists of questions that you want to ask a client so that you can internalize where you want to get to in your discovery focused conversations.
However, remember two things when doing this type of prep. The first is that you need a lot of situation and problem questions to set the stage and then fewer implication and needs / payoff questions because as you move towards the implication and value conversation it needs to turn into just that, a conversation, not a list of questions. The second thing to remember is that your list of questions is not sacred. The point is to prompt the buyer to lead you somewhere. Follow up and genuine curiosity are much more important than your questions, so long as you can keep the guardrails on and remain commercially relevant.
Let’s think about why we ask certain questions and what we are trying to get out of them. Let’s inspect some common questions and understand what is good and what is bad about them, and what that means in terms of your execution and your follow up after you ask them:
“What is happening in your business right now that is causing (x issue) to be a priority?”
Half of your job as a seller is to figure out why most of the people out there hang up on you and get angry when you keep bothering them, and don’t have the time for you, but this person you are sitting across the table from is actually taking time out of their busy life to talk to you. Time is valuable to decision makers, and even if it is not, mental energy is valuable to humans, so if someone is taking time and energy to talk to you, there is a reason. Why now? Why not later? What is being deprioritized in order to focus on this? It is your job to figure out that reason. The key with a question like this is follow up. This question by itself is not enough because most of the time you won’t get a full answer, but more importantly, the answer only tells you why they are exploring, and exploration is far from need, so while this is a good question, good follow up is key.
“What metric is suffering most as a result of the problem you are describing?”
Understanding why a decision maker is exploring a solution only means something if you can understand how they measure that problem, how important the problem is, and if solving it would likely cause other problems that are bigger, or seemingly bigger than the original problem. Metrics are a good place to start. If you understand the metric that the business wants to improve, how visible that metric is, how much people internally care about it, and what else it affects, you can start to make progress in having the right conversations. However, this question is not enough. It takes smart and persistent follow up to move from the metric that is suffering to the relevance, the visibility, the relative value, and the secondary effects.
“Tell me about your biggest challenges when it comes to (x issue)”?
This is a very open ended question and it allows the buyer to answer in a pretty unrestricted way, but at the same time it limits the buyer to the issue at hand. If your questions are too broad, you may not get relevant answers, or your buyer may feel overwhelmed by the possibilities and respond in an unhelpful way. Be aware of the level of breadth in your questions. It is important to open up the scope of your conversation to all potential answers that are relevant without being so broad that you end up at an irrelevant place. Again, with questions like this, follow up is key; once you understand the challenge, you have to go deeper. It is important to probe regarding the challenge and its details and its effects on the person you are talking to and their team.
“How is this decision going to be made? Who will be involved? And what does the process look like?”
It is always important to understand the process that the buyer has in place, especially in longer sales cycle deals. It is also useful to ask multiple people this question, and to ask them if they feel comfortable with the conversation and are able to help you navigate the internal process. Human nature makes most people naturally want to be helpful, and as soon as an individual on the buying side verbalizes a commitment to help you navigate the process, they become mentally invested in helping you. Make sure not to get stuck on the first level. If you ask someone about the internal process and they give you an answer, then the next thing you should say is, “and then what?”, and when you get an answer to that, you should say, “and then what”. This is a powerful way to influence your stakeholders to think about what they really need to happen to get a deal across the table. This will start them down the path of investing that mental energy into the deal itself.
The basic takeaway from all of the questions above is that you need the answers and they need to be asked, but they are generic. So it is important to inspect them and understand the positives and negatives so that you can do two important things:
Tailor them to the situation so that you can earn credibility and show the client that you know what you are talking about as you ask the question.
Follow up in an intelligent and conversational way that gets you the deeper information you need and let’s the client know that you are having a real conversation.
Discovery preparation is incredibly important, but it is not enough to just write down some questions. The key is to inspect what you really need to get out of those questions and think about how you will customize and position them in order to earn credibility, and how you will follow them up in order to learn the information you need to learn.
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