Top 9 Reasons Why Salespeople Lose or Win Deals

9 Reasons Salespeople Win Deals

Do you know why you win or lose deals?


How often, after losing a deal, do you ask yourself:

What went wrong? Was our product inferior? Was it marketing’s fault? Something I said? Something I did? Or something I didn’t do? Was the customer a time-waster? Did we get out-priced?

Over the years we have observed first hand why salespeople win deals. Here we outline all the right questions that should be asked. Also – it is imperative that these questions are posed before and during the sales cycle, not after the deal is lost.

Take a look at what we think are the top 9 reasons why you might lose or win deals.

1/ What is the Customer’s Problem?

Many salespeople rely solely on capabilities or features of their product to win deals. We can’t stress this enough: it doesn’t matter what product or service you are selling. It doesn’t matter what type of customer you’re selling to.

What matters is that your product or service is aimed at solving a problem. This is the key element of a client’s business case for change.

One of the most common mistakes salespeople make, is that they don’t fully understand
what problem their product or service is going to help solve for the client.

More often than not, salespeople go into meetings with the resolute intention of talking about their product or service. They think success depends on talking to as many people as possible about what they do and why they are the best in the market.

This belief is one of the biggest gaps that salespeople fall into. Not only does it risk quickly losing the interest of the client, (who wants to be talked at for an hour?) but it omits the obvious.

Your product/service might indeed be the best in the market. The real question is however:

WHY does your customer need your product or service at all?
What problem is it going to solve, and how big is that problem at the moment?

Most salespeople struggle to articulate the answer to these crucial questions.

Try asking them: “Why is the client buying our product?”

Normal answer: “Well they need it.”

Further investigate by asking: “Why do they need it”?

The likely answer will be: “Well, they just do – they looked really interested and said all the right things”.

And herein lies the gap the salesperson has fallen into. They don’t really understand the business case for the product or service. In other words, they haven’t grasped what problem their product can solve from the client’s perspective.

A far the more appropriate thinking process is: What problems/issues/challenges has my customer told me about? And, more importantly, how is my product going to help them deal with?

2/ What’s your Customer’s Decision Making Process?

Another noteworthy gap often overlooked at the early stages of the sales cycle is:

How is the decision is going to be made, when, and who makes it?

All too often salespeople assume it’s going to be a price-based decision. Research proves there will always be other factors that come into play.  You need to know what these are, and their order of priority.  It may be that price is the last on the list! Or at least it’s a secondary factor. In addition to how, you need to know when the decision going to be reached, and who will be involved?

Salespeople tend to invent their own timescale. They forecast business at the end of the month or quarter without first checking if, in fact, this is the customer’s timescale.

3/ What is the Competition doing?

Let’s face it – it’s unlikely the conversation the salesperson is having with the client is exclusive. In order to win deals, you need to be aware of what competitors are selling. What are their strengths and weaknesses? How do they stack up against the client’s needs? After all, if the client has a problem that you can’t fix, but the competition can, isn’t it better that you know this at the outset?

4/ What is the Value?

Another question you need to ask yourself to consistently win deals is: What’s the value to the client of you solving their problem? We put up with problems every day and our clients are just the same. While helping our client see the tangible value they will receive by letting us solve their problem, we can help tip the balance in our favour.

Sales people make recommendations to clients all the time. If they’re good, they’ll uncover a problem and present a solution. This is a recommendation with only half of its power.

By making the case for the tangible value of that solution, your recommendation becomes much more powerful.

Let’s look at a real-life example:

Say a client has a problem with their production line that is holding up customer orders. The solution is to fix / upgrade their machines. This alone could be viewed as an expense that the client can ill afford. The value to that client is that by increasing the production line’s productivity, they can raise the amount of orders they can fulfil in the same amount of time. As a result, this will measurably increase both turnover and profitability. If you can demonstrate that the investment in upgrading your client’s production line will directly contribute to the increase in profitability, why wouldn’t they say yes?

5/ Is there a Compelling Event?

Is there a compelling event that will help with the sale? If so, what is it? Some salespeople will tell you that the deal needs to close by the end of the quarter, or that the fix is perfect for the client. These are not compelling events.

A compelling event is a new product launch that the client needs a new service to support.

You need to get the client to believe that your recommendation fits into one of their compelling events in order to maximise the chance of success in the sale.

6/ Is There a Fit?

Simply – is there a fit between you and the company you are selling to? Why do you need to know? Not knowing how the client perceives you means that you are running a huge risk in the accuracy of forecasting the likelihood of winning the deal.

Some ways of testing how the client perceives you are:

  • Is there a cultural fit? Do both companies share similar values and working practices?  The client needs to know that you understand their market, their challenges and how they operate in order to have confidence and trust in what you are offering.
  • Are you one of many? If you’re one of many, what is it in particular that the client is looking for that is going to make the difference? For example, they might be going through a cost cutting exercise. You might be one of many and it’s all about cost. Are you really in that market?
  • Are you a problem solver? Can you solve their problem? Is that where your strength lies? We covered this earlier under: ‘What’s the Customer’s Problem?’. Finding out what pain the client is experiencing and whether you are in a position to alleviate it, will differentiate you as a problem solver.
  • Are you a trusted advisor? If you are, the client is probably sharing confidential information and you’ll be part of the decision-making team.
  • How Do You Know? You can measure exactly how the customer perceives you by simply looking at what access you have to the key people and the sorts of questions they ask you. If you’re selling a complex and premium product or service, you need to be talking to the CEO about company strategy, focus and future value, rather than talking to procurement about costs. On the other hand, if you’re selling ‘widgets’, then talking to procurement about cost, timescales or service levels is probably OK. It’s very easy to know where you are – even after the first meeting. Unless you can move forward, it’s going to be difficult to win deals.
In conclusion:
  • Can you measure how your customer perceives you?
  • Does that perception fit with what you’re offering and the type of company you are?
  • What do you need to do about that?

Spotting a client’s perception of you/your company/product early on, identifying if it is a weakness and therefore a risk, gives you the opportunity to do something about it before it is too late.

7/ Your Client’s Attitude

There is another aspect you can measure at the early stages of the sales cycle in order to win deals. It is attitude.

What is the client’s attitude towards you?

Are they negative, neutral, or fully confident? Have they had a previous disappointing experience with your company which has made they biased against you? One way of testing this is by observing how they behave. How helpful and co-operative are they? Also, how quickly do they respond to you?

If you combine the two elements of perception and attitude, you’re a long way to being able to decide if there is a fit. Knowing if there is a fit helps you to identify whether winning business with this client is realistic.  If there is no Fit – research shows that you are unlikely to win the deal.

8/ Levels of contact: Who are you talking to … and how often?

A common mistake when selling is that the salesperson spends the majority of their time dealing with the people they feel most comfortable with. This represents a huge risk. More often than not, this will be a conversation at a much lower level than it needs to be, especially when involved in more complex sales.

Dealing with a lower, more comfortable level is the easy option, but it’s not going to help win deals. No-one puts you under a massive amount of pressure. No-one asks you tough questions. In addition, those lower down the hierarchy will often tell you what you want to hear. Consequently, speaking to only these contacts can seriously jeopardise the success of your deal.

You need to know who are you talking to, the influence they have and where they fit within the decision making team.

Is the conversation constant and ongoing? Although all sales cycles are different, they have one common characteristic: more than one person will have a say in whether or not you the deal will be yours. These are referred to as ‘stakeholders’, and their level of influence varies considerably. The frequency with which key stakeholders are prepared to see you is an indication of how the sale is progressing.

Make sure you identify and are talking to stakeholders who fall into the descriptions below:

Decision maker

There will be one person who is the ultimate decision maker, in other words, the person who is going to release the budget. They are quite easy to identify – you simply ask the question. Failing to meet with the decision maker is a high-risk strategy. You need to present your final proposal to the decision maker at least once. If this isn’t possible, you have to be really sure that whoever is going to make the presentation to them is able to articulate the key benefits of your proposition.

Key recommender

This person will be judging the technical merits of your proposition. They can also act as gatekeepers: they can’t say ‘yes’, but they can sure as hell say ‘no’. The key recommender may not even be an internal contact. They could be a consultant, lawyer or some other third party that the client is using for recommendations or advice.

End users

The end users are those who have to implement your solution. They are often overlooked, yet they can have a huge influence. Their success links directly to the overall success of your solution. If they find your product difficult to use, or they don’t like it, the company is very unlikely to buy it, based on their feedback and opinion. However, be careful you don’t fall into the trap of thinking that because the end user is always available to see you, the sale is going well.


Ideally, but not always possible, you need to identify a sponsor – someone who wants you to win the deal and who will keep you updated on progress, threats from competition and any changes. Although they can’t make a decision directly, they are an essential ally. This person can fall into any of the above stakeholder definitions, internal or external.

In an ideal world, of course, the sponsor would be the decision maker or key recommender who helps you navigate through and ultimately win deals.


9/ How certain are you? A Confidence Test

How confident are you that this opportunity is going to close in your favour? The ability to meet stakeholders when you need to see them is a really good indication of where the sale is.


Bring all the 9 elements together and watch your chances of winning those deals skyrocket!