This is the first installment of a four-part series on expectations in sales.
May 05, 2021
In his recent book, Why Startups Fail, Harvard Business School professor Tom Eisenmann described a broad set of reasons why some start-ups succeed while others don’t. Summarizing his research, he noted that VC investors and other start-up observers tend to attribute the success or failure to one of two factors: founder quality and opportunity (or product–market fit). While these two factors are important, they certainly aren’t the only forces at work.
The same factors that Eisenmann sees influencing start-up success also appear when we examine the success or failure of B2B SaaS implementation. In sales, it may feel as if implementation is not really your problem—you helped the customer identify a need and solve it, and now it is on customer success or tech support to handle future bumps in the road. However, for SaaS business success, you need to anticipate the factors that will help your customers realize their goals as they go about deploying and using your software. If you don’t, they are not going to be (satisfied) customers for very long!
Fortunately, research is ongoing to identify those very factors on an industry level. For example, an international team of researchers identified eight critical success factors for digital transformation at logistics service providers. These factors included:
This means that if you sell into an organization with strong leadership and employee skills development, that is accustomed to agile methodologies and is open to change, your software will have a greater likelihood of broad adoption, making it more likely that it will actually fix the problems it is designed to address. On the other hand, if you sell into an organization that is change-averse, with chaotic processes and conflict between business and IT leadership goals, they are unlikely to fully realize the benefits.
How do you understand what kind of organization you are selling into? Well, you ask them!
By this time you are probably used to the drill: the Maestro team has assembled some questions that work particularly well for uncovering each letter of DRIVE, and Expectations is no different.
On the first level of Expectations, the goal is to understand your contact’s personal perspective on the project. This is a little bit different from Impact, which looked at success from an organizational point of view. Impact assesses whether your solution aligns with their strategic vision and mission, examining how implementation would allow them to do their work faster and better while avoiding problems and risks inherent in the status quo. This is one part of surfacing success factors.
By the time you get to Expectations, there is some agreement that there is a problem you can solve or a situation you can improve, and the person you are talking to has some level of responsibility to maximize performance in that area. You can therefore focus more narrowly on the goals and desired outcomes for that individual (or group of individuals). You want to understand what factors are aligned to support their success and what factors will stand in their way.
A very straightforward question to start with is “What have you been asked to deliver?” This works best in a situation where the potential buyer is responsible for solving a problem. When a solution is already in place and you are trying to persuade them to switch, or when they are newly persuaded of the value of investing in a new tool that their superiors have not previously been aware of, it wouldn’t sit quite right. In those circumstances, you could try a broader question, such as, “What would you like to see happen?” or “What defines a successful partnership for you?”
Defining a successful partnership before it really begins is an essential precondition to customer satisfaction. The more specific you can get, the better. We’ve talked about Customer Performance Indicators (CPIs) before. What was true about measuring Impact is no less true about measuring Expectations.
For example, try asking your prospect “What are your measurements for success?” This question will turn up exceptionally informative answers that can help guide conversations not only during the sales funnel, but during implementation and onboarding, and throughout the customer relationship. These answers can even guide renewal and upsell/cross-sell conversations for your partner success team.
Let’s say that their answer is something like, “We want to reduce how much time we spend on X task by half.” To gather an actual CPI, you’ll want to follow up by asking if they know how much time they are currently spending, so that they will be able to measure again afterward and see if the deployment is successful. This type of question may also elicit an answer like, “We don’t know how much time we spend” or even “I don’t know what our measurements for success would be.” You are uncovering essential intelligence about success factors like the process standardization and knowledge resources at the organization.
When you get an answer like “I don’t know” about Expectations, it is a different kind of red flag from when you get an answer of that sort about other parts of DRIVE. Someone who doesn’t know if they have the Resources or doesn’t know the Velocity—the timeline that is important for implementation—may not be a decision-maker. Someone who “doesn’t know” when you ask about Impact may be a poor fit for your product or may just not be invested in solving the problem.
If they don’t know what success would look like or how they would measure it, however, it doesn’t necessarily mean you can’t close a deal with them. It does tell you that you will run into problems during- and post-sale because they do not have a clear mental roadmap of how they want the sale and implementation to turn out, and their organization is lacking key success factors.
This can result in unexpected obstacles turning up later, such as delays from IT or other stakeholders, or in a misalignment between the effectiveness of your solution in solving their problem and their perception of its effectiveness. You can mitigate against these risks, though, with focused inquiry in the second level of Expectations.
For example, you can ask, “What department could potentially slow down the process?” or “Of the people who need to be involved, whose calendar is the tightest?” These questions will mitigate against the risk of an inexperienced or naïve buyer who hasn’t seen the process play out before, and uncover well-worn (but not externally obvious) roadblocks in an organization where onboarding often does not turn out as well as they had hoped.
To solve for the risk of a misalignment on whether results match up to expectations—and the resultant challenges to CSat and churn—you can help the buyer dig into and identify their own personal goals in solving the problem. As Joel York at Chaotic Flow points out, the best way to understand why SaaS customers do or do not become well aligned with your offering is to ask them about their motivations.
If a prospect is leading the way on investigating and trying to acquire your product, you may have a champion who can successfully persuade other decision-makers of the value. They may also see alignment between their own career goals and the organizational value that will come from implementation. They can be a key ally in uncovering information about success factors and getting them in place if they have not been.
Your partnership with a champion brings mutual benefit. A great example of this within our example of digital transformation for logistics service providers is in the success factors of “employee training and skills development” and “leveraging internal and external knowledge.” If your Expectations questions have uncovered that they are lacking in these areas, you can partner to provide training to users as part of the onboarding process. This will greatly amplify their chances of success and earn you a grateful champion, satisfied customers, and more lifetime customer value.
To leverage some external knowledge on information gathering about Expectations, contact mastery@maestrogroup.co.
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