Ask The Hard Question Upfront

My dad is the first sales person I ever learned from, and I learned a lot from him. He is now a semi-retired non-practicing lawyer, a businessman, a consultant, and an advisor, but he has sold a lot in his career, and knows what he is talking about. One of the first, and to this day most vivid pieces of advice that he ever gave me is that the most important thing you can do as a seller is find a quick “no”.

When he gave me this advice, it made intellectual sense. I mean, if it’s not gonna happen, then find out quickly and move on. But, as I have advanced in my career, the advice has become more and more meaningful and appealed to my understanding on a number of different levels. Not only does finding a quick “no” value your time and resources, as a seller, it makes you a much better seller because it allows you to confront scary and difficult issues upfront, and avoid hiding from them.

When thinking about how to spend our time as sellers it is easy to get lulled into equating relationships with opportunity. We all do it. It is soothing to our subconscious brains, it is easy to explain to bosses and internal teams, and it is just frankly more pleasant to talk to those who want to talk to us. The problem is that the people who are pleasant, and nice, and agreeable usually aren’t the buyers. Sure there could be a small amount of overlap, but the people who want to spend time talking to us are usually not the people who have enough internal sway to buy from us. This is not to say that there are no nice individuals who have decision making power within buying organizations. What I am saying is that we, as sellers, tend to gravitate towards the easiest and most pleasant conversations, and those tend to be negatively correlated with the ones that will get us closer to deals.

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Objections and contentious relationships are often good. Real objections that are focused on the core of discussion and the reality of how a solution will interact with a problem are good because they mean the buyer is engaged, and thinking about a solution. Buyers who never object rarely buy, however, most eventual buyers object at some point in the process, because they have true concerns that they want ironed out before committing to buy.

Challenging your clients on their current viewpoints and on what is and is not acceptable to them is very important because it draws out responses that tell you if the client is serious or not, and if so, what their boundaries are. The reason that ‘challenger sellers’ are able to outperform other categories of sellers, in the well known Challenger Methodology study, is partially because they challenge conventions, but it is also because they learn the boundaries of their clients much better than those who do not challenge. Challenging is, in and of itself, a discovery tool that allows sellers to build a map to help navigate the buying organization and their concerns. That is why earning the right to challenge is so important. The challenge conversations need to be open and honest in order to draw that information out of the buyer.

Discovery is not a discrete act, and it is not a one way question asking expedition. It includes the ideas of ‘earning the right to ask questions’, ‘earning credibility’, ‘imparting commercially viable insights’, ‘asking the right questions’, ‘engaging in authentic social interaction’, and ‘learning from the client.

There is a very important difference between the clients comfort zone, and their firm boundaries. Firm boundaries are places that a client cannot or will not go, like spending more than their bottom line allows, or implementing a solution that will fundamentally change a core tenant of their business, or implementing a process that introduces an unacceptable business risk. If you advance to later stages in the process and introduce ideas and solutions that cross these lines, or lines like them, you will lose credibility and control. On the other hand, the client’s comfort zone is more about the status quo and the things they are comfortable with and understand in the moment. These are things like a current process or way of solving something, or a specific vendor that they are used to, or a company belief in an aphorism or assumption that helps them achieve success. These lines should be challenged, and crossed often. Clients who remain in their comfort zone rarely make status quo challenging decisions, so it is your job to challenge assumptions, and established realities, and the only way to learn the difference between these two major categories, and where the lines are, is by getting to “No”.

The process of getting to “No” early helps define boundaries, improve the conversation and make you a better seller. We will spend a lot more time focusing on that, and on Jim Camp’s “Start With No” concept in a latter article, but for now, I want to look more at the other benefit of challenging and asking tough questions, which is that it helps you learn which deals will not close so that you can spend your time on ones that might.

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The key is that early on in the relationship, but after you have already earned a degree of credibility, it is important to search for the buyer’s boundaries by asking some scary and aggressive questions. This boundary finding tactic will help you understand if a deal is possible as well as what the rough outline of the area that the deal can fall within is. Once you have done that, you will understand the boundries and shape of potential deals.

You have to be willing to ask your client why a deal won’t work in order be sure that a deal can work.

An example:

“It looks like we are talking about all the right things, and we are on track to meet the agreed upon timetable, but I have to ask, if we were to get derailed, what would the most likely reason be?”

This type of question can seem like it would put negative thoughts in the buyer's mind, but it's important because the answer tells you how to proceed. It also has an added advantage. Once the buyer verbalizes potential impediments, it makes them more likely to take those impediments seriously and help to overcome them.

Another example:

“We have spent some time talking about your issues and the potential solutions, but we have not talked about the value of solving this problem for you. I want to find out if it really makes sense for you business to solve this problem now, as opposed to waiting.”

This is just an example, but it is a version of challenging the client on a potential problem with the deal that is not yet on the table. The answer gives the seller needed information, but it also causes the client to verbalize exactly why they need to solve the problem quickly. Or alternatively, why you need to move on.

The best salespeople ask hard questions and confront risk, they ask about procurement and legal, and finance. The ask about the things that will derail the deal, they ask about objections, and they ask about what happens next, and next, and next, if we agree on price.

They don't hide from the potential problems. This overt and direct confrontation of problems is respected by buyers, and conveys a sense of confidence that makes the deals that can happen more likely, and the deals that can’t happen more noticeable.

Get to "no"