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Why are Some Questions so Difficult to Ask?

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It seems that some questions are difficult to ask. They must be because we see people taking forever to develop that habit of asking their clients more detailed problem questions.
What are we trying to do?
Selling is not complicated. There are logical steps that we go through when we buy things:
1. We decide were not happy with our current state. Whatever it is we have, or do not have currently, we decide we are not satisfied with it. That dissatisfaction creates a “need”. 
2. We go looking for something to improve upon our current state. During that process we make a number of decisions:
• How much we are willing to spend (budget)
• Quality of the product
• Features
• Where we will buy it - location and reputation of store
• After sale service - return policy etc.
• Warranty 
• Person you buy from - do you trust them? Are they helpful?
• Timing - when’s the best time to buy
3. We eventually get to the point where we are comfortable enough making a buying decision. We see enough value in the product that we are considering to offset the money we are going to have to invest.
Facilitate the buying process
Successful salespeople do a good job of facilitating those buying decisions. Given that the first step for the consumer is to come to the conclusion that they have a need, when you think about being proactive as a sales person the first step is to get the client to acknowledge a dissatisfaction of some sort.  Good salespeople lead conversations into areas where they know people typically are not satisfied or they are concerned with. Finding out how someone feels about their ability to retire on time is a great example of this because most people know they want to retire but don’t feel confident that they will be able to do so when they want, with enough money to do what they want. It's a known need but one many are not doing much about.
In order to really help the client we need to be proactive and lead the conversation to get their opinion on what they are doing now. This first step of the sales process is critical to the overall success and it’s also quite simple to do.  So if it’s really that simple that all you have to do is ask questions and let the client acknowledge the dissatisfaction, why don’t more people do it?
One reason may be because of a desire not to put the client on the spot. We don’t want to make them feel bad for having a dissatisfaction/need. After all, if I ask you how you’re feeling about your retirement plan and you’ve neglected it for years and feel horrible about that fact, I might make you feel embarrassed. While that is a potential risk, what is the alternative? Not asking essentially makes us an accessory to their lack of planning for their retirement. Most financial institutions have people and products that can help a client get their retirement plan on track but if we fail to initiate these conversations because we might make someone feel bad are we really providing the type of service that they expect?
So what else could it be?
The other reason people do not ask these questions is because of a lack of accountability. In some branches, it’s just not that important. Other things are, but proactively trying to help clients must be taking a back seat. Given the consequences, that is unfortunate especially when you consider that most people are comfortable with accountability. Think about it. It’s demanded that people find out some very personal and detailed information about most clients financial picture on a regular basis. If you’re doing a loan for somebody you’re asking them for information on how much money they make every year and  what other debt they are carrying. When you open up an account for someone in Canada anti-money laundering legislation demands that they are asked if they are a “politically exposed foreign person”. These are difficult and borderline offensive questions but they are asked routinely. Why? Because they are mandatory. That are not optional. 
So here’s a thought: why not make asking “how are you feeling about your retirement plan?” mandatory? Why not make asking how a client likes dealing at another financial institution a new rule everyone needs to follow whenever they see that a client is also banking at a competitors? Why not increase the accountability on some of these questions that will increase the likelihood of us being able to cross sell additional products?
It can be that simple. Make the asking of good problem questions an expectation. The questions are simple enough and the alternative is not to ask which has consequences to the client and the company’s service reputation. Set a goal for yourself or your team to be more proactive and then be accountable to doing so. You will like the results.

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