Discovery Dos and Don'ts According To One Guy
- Dan Greenberg
- Nov 8, 2024
- 7 min read
Basic curiosity is one of the best tools for improving your outcomes in sales. If you want to be great at sales, nurture your curiosity. Like any other muscle, it needs work. Read, watch, listen, observe the world, and think about how one occurrence or situation has implications for another. Although every situation is different, people, on the whole, generally respond to incentives in similar ways, so there is often insight that can be gained from observation of one situation and applied to another. That framework combined with genuine curiosity about the business results and outcomes of a buyer’s business can lead to very insightful conversations which provide a great deal of information to you, the seller.
It is much more effective to be a great business person who happens to be good at sales rather than trying to become a great salesperson in a vacuum. This is because being a great business person allows you to connect with a real decision maker on issues that make a difference to their business. This ability will allow you to add insight, and value, or at the very least commiserate with that buyer in a way that will open them up to a comfort level that will cause them to share vital information. It will also imbue you with the credibility necessary to allow you to both, ask additional questions, and be persuasive as the process progresses.
I have written in the past about earning the right to ask questions, and adding value to the conversation. Think about this like greasing the wheels. If you were to ask a potential future partner of yours, on a first date, how many kids they want and what they plan to name them, and then go on to tell them that you love those names and would totally want to use them on the kids you have together, and oh, by the way, you just happen to want the same amount of kids as they do, and maybe we should get started now…. Anyway, you get the idea, that is coming on pretty strong, and there is a pretty good chance the person on the other side of the table is going to call you out on it, or more likely, and even worse, finish the interaction awkwardly, and then ghost you.
Sellers do the equivalent of this all the time. They will ask obvious questions like, “what is causing the biggest problem for your business right now”, or, “what keeps you up at night that you need solved right now?” While there is nothing inherently wrong with those questions, they will ask those questions on the first interaction without earning any right to go that deep, and without even spending the time getting the buyer more comfortable socially. They will then proceed to tell them how magically, their solution happens to perfectly solve all of the problems that the buyer just mentioned. Not only is this not believable to the buyer, it is disingenuous, and irritating, and it causes the buyer to feel underestimated. In their head, they are likely thinking something like, “This guy thinks that I have this big problem which I haven’t even fully explained to him, and there is a perfect solution out there, and yet, I somehow have never thought about using it?” Basically, this kind of rapid discovery is irritating, lacks credibility, and essentially calls the buyer an idiot. On that note, let’s take a look at a few Discovery Don’ts.
Don’t skip steps: You have to earn the right to go deep in discovery. This can be done through social interactions and building relationships that allow for the buyer to feel comfortable talking. This can be done through conversational interactions in which you discuss insights and information and earn credibility by showing the buyer that you add value, as a person, outside of the products you sell, or that you share their understanding and even their struggles in business.
Don’t be a robot: Running through a checklist of questions is robotic, and makes buyers uneasy. I call it the “Uncanny Value Add Conundrum” (You can read about it in my post from July 5, 2023), but whatever you call it, making a buyer feel as if it is ‘discovery time’ and your entire goal is to gather information that you can then turn around and use to convince them of something you want them to do is a good recipe for turning buyers defensive, and argumentative. Discovery is a conversation, like the type that human beings have with each other. It should be about give and take, and it is important to follow cues and signals as to which direction the buyer is taking the conversation in, even if that direction has nothing to do with your preset list of questions.
Don’t mmhmm: If you have ever sat there explaining something to someone, while they respond with a constant stream of ‘mmhmm’s, ‘yep’s, and ‘that's an excellent thought’s, you know that not only is it annoying but more so, it is a signal that they are trying to reinforce that they are listening, but it doesn’t actually mean that they are present in the moment and really participating in the back and forth of the conversation; it simply comes off as performative. People are very good at picking up on subtle facial and social cues. Show them that you are listening with eye contact, and with follow up questions, and conversational value add. Don’t bombard them with ‘uh huh’s, and ‘I understand’s. And, for heaven’s sake, stop saying ‘that’s a great question’ when they ask you something. Not every question is a great question, and no one actually thinks you mean it.
Don’t let discovery end nebulously: Discovery is the foundation you will build your case on as the sales cycle progresses, so it is up to you to build a bridge between the two. Many sales people take notes during discovery, but then don’t wrap up and summarize their takeaways back to the buyer. If your takeaways don’t align with the buyer’s intended message to your questions you will end up off track. Summaries are really important, but what is more important is making sure that the client is brought-in on your version of the summary. If your insights and value-add is not relevant or actionable for the client, and if your summary of the discovery is not in line with how the buyer sees things then your discovery is not over. If, on the other hand, you do have buy-in, and alignment, don’t leave the interaction without making sure that there are clear next steps, and goals for that upcoming interaction.
In addition to considering these Don’ts I also wanted to write a bit more proactively and positively about some Dos. It is important to be prepared for discovery and think about the types of things you want to learn about. Here are some ways to think about that preparation.
Ask questions that compare their efficiency and productivity under multiple types of circumstances. You generally don’t want to ask questions that compare you to the competition. This is for two reasons. One, you don’t know the answer, and if they compare you unfavorably, you will either have to be agreeable or defensive and either is a bad look. Two, you don’t want to create an equivalency. You are not better or worse, or comparable, you are different, and competition should not be in the conversation. What you do want to compare, however, is how their business functions relative to other states; things like; “You mentioned that your marketing costs have gone up over the last couple of years; what do you think has changed in your business or in the landscape that is causing that increase?”, or, “what do you see as the most obvious way to improve the productivity of your team over the next 12 months?” These types of questions, when asked at the right time, ask business leaders to think about their business holistically, and discuss their thoughts about it as they compare to the status quo. Remember, discovery is all about building a case in your mind and the clients mind against the status quo.
Ask questions that introduce completely new information and insights into the mix and ask the client to evaluate their business as it relates to that new information. Sometimes the easiest way to get someone to speak openly is to ask them about something new that they have not had a chance to formulate thoughts on yet; the type of thing that they have to actually think about before responding. We have already talked at length about insights and how to use them, but you should incorporate them into your discovery as well, and see how your clients react to them with questions like; “Given the information we discussed about how your competitors have been using data, is your team currently working on new ways ingest and use this type of data to improve efficiency?” Make sure not to expose any implied ignorance, or lack of knowledge about this new information or insights, but be sure to challenge the client and find out how they think about the information.
Ask questions that focus the conversation on buying needs, and not on selling goals. In other words, focus the questions on what their business needs, and qualify those needs through follow up. The more you can focus on needs, and ideal outcomes, the more the environment of the conversation will be focused on buying needs as opposed to selling desires. Keep the buyer thinking about what is not great, but could be amazing by asking questions like; “You told me that onboarding and training are a slower process than you think they should be, but I’m curious which specific parts of the process are slowing you down the most, and what are your expectations for 12 months down the road?” Ask them to be specific about the problems, but not in a vacuum; it has to be in conjunction with the hopeful desired outcome that they are envisioning.
Lastly, ask questions about their goals and their goals for their team or the company. This is a common trope in sales training, but it is still worth mentioning. Ask the buyer to tell you what they expect from their team, and how that fits into the broader picture of the company at large. And, if you have a close enough relationship, ask the buyer about their personal goals for career growth, and how they think they can get there given their team goals. Measurement is important in these conversations, so you can focus on questions like the following; “What metric do you look at every day that tells you if your team is going the right or wrong direction, and what do you see as the most important lever in moving that metric?” It is important to be at the right point in the conversation and to read your buyer well. They should be very comfortable and open to discussion by the time you get to a question like this.
It is vital to be thoughtful about discovery. If your questions are generic, invasive, robotic, or overly simple, you are sending a signal to the client that the conversation cannot add value to their business. And, if you can’t add value to their business, they will have no reason to open up to you and have real conversations.

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