Closing Questions
You must be willing to ask hard questions and you have to be willing to lose the deal. Pace, persistence, and bravery are very important in sales, and the lack of any of the three can adversely affect your deals. If you don’t move conversations forward, if you don’t push buyers outside their comfort zone, and if you don’t ask hard questions, buyers will make decisions without you.
I have alluded to the concept of asking scary questions in recent articles, and I want to spend more time focused on it today. You have to be willing to ask the client what is going to cause the deal not to happen in order to put yourself in the best position to make it happen.
“What are the things that are causing a delay and making it so you can’t agree right now?”. “If you don’t end up agreeing to work with us, what would likely have caused that decision” Yes, those questions are bold, and scary, and they could bring the entire deal process to an end, but if you don’t ask them, any deal that was destined to hit a roadblock, will end up hitting that roadblock anyway, and you will spend a lot of time, resources, and energy before you learn that.
Of course, you may worry that asking these types of questions may force negative thinking and bring problems to the table that would not have ordinarily come to the surface, but any serious buyer has already confronted possible issues with a deal. Deals that have structural issues will eventually be derailed by those very issues, and the only way the issues can be fixed is by asking about, understanding, and resolving the problems. You give yourself significantly more opportunity to make a deal by surfacing potential problems. Here is how that plays out:
A. Deals with no structural issues:
If you ask the tough questions, the buyer will give you the real answer, which is that there are no problems, then you can focus on progression towards a close since the buyer has just reinforced to themselves and to you the idea that the deal is fundamentally sound.
If you do not ask the tough questions, you will move forward as planned. You will get lucky sometimes and a deal will close but without introspection from the buyer you will not trigger the clarity around the fundamental strength of the deal and you will be susceptible to losing to competitors with their own fundamentally sound deals.
B. Deals with structural issues:
If you ask the tough questions, you will surface the structural problems on your own terms in an environment you control. You will give yourself and your team a chance to address those problems and find a path to a mutually beneficial deal.
If you do not ask the tough questions, any deal that would have stalled due to structural issues will eventually stall. You will be blindsided and less able to course-correct. You will have invested more time and energy into a deal that likely will not close, and your buyer is also likely too feel that they have been strung along to the end before finding out about the issues.
It’s easy for a buyer to say that everything is great and that they are interested in buying. That means they will spin their wheels later on, and put in the hard evaluation work later. Later is easy because it is something we don’t have to deal with at the moment. But this is why pace, persistence and bravery are important in sales. Sellers must be willing to ask scary questions in order to challenge clients to really think about if they are interested or not. If a prospect is not fully engaged, they will say they are interested because that costs them nothing in the moment. However, it does cost you, the seller, a lot. That prospect will do the real evaluation and investigative work later when you are not in the room. And if that happens, you have lost your chance to be influential. That is why it is so important to directly ask scary questions in person and in the moment.
Deals that move slowly don’t happen for two potential reasons. The first reason is causally reversed and it is that the deal is moving slow because the buyer is not that interested and they are just stringing you along.
But, the second reason is important and it is one where the pace causes the problem. When a deal moves slowly, the people who were excited about it originally lose excitement, because the solution does not remain new. The risk never lessens, but the excitement abates, and you need excitement and opportunity to overcome risk. People within the buying organization start to think that maybe there is an issue with the deal, and wonder why it isn’t moving, and before you know it, you have a bunch of people on the buying side with doubts and concern about risk, and with zero excitement.
This does not mean that there is no such thing as a long sales cycle. It is not about the time from start to finish, it is about the pace. You can have a deal that takes 28 calls, 13 meetings, 142 emails, 6 demos, and 4 social outings, and takes 11 months, but the pace has to be there. It needs to move from interaction to interaction, and more importantly from topic to topic, and stage to stage. And all of this is accomplished by persistence, and by asking scary questions that engage people, and cause them to think about real answers.
When a buying organization spins their wheels, they may hit roadblocks that they don’t want to deal with. If you allow the conversation to lose momentum because of those roadblocks, there is a good chance you will lose the deal. You have to get them thinking about how they are going to make it happen in that very moment when they are interested in and excited about making it happen.
Here are some examples of questions that do that type of legwork:
Let’s say we agree on a price, what is the next step in the process?
Are there any legal or procurement steps that we should start working on now to get the ball rolling?
Looks like we are on the right track, but I want to cover my bases here; if something were to derail us, what’s your best guess as to what it would be?
What steps need to be taken on your side for us to wrap this up this month?
These questions may seem a bit mundane, and forced, but it is the timing and the manner of the ask that is most important, not the questions themselves. When you have a buyer who has had a real opportunity to work through all potential structural issues in a deal and there is agreement and excitement to move forward, you must transition the conversation to the details around how to get the deal done, rather than the old conversation about if it is the right deal. Your job is to align your team and the buying team and create one team where the goal is to get across the finish line logistically, given the assumption that the real fundamental decision has already been made.
That transition of conversation has to happen with pace or you will lose momentum. If you are unable to make that transition, it means either, there are still outstanding fundamental issues with the deal itself, or you never had a serious buyer to start with.
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