Idea 61b: Lessons from the Movies: How to Lose Your Best Customer in 10 Days (and how not to)


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In a popular movie by the same name, Kate Hudson’s character, Andie Anderson, takes on a challenge to write an article entitled “How to lose a Guy in 10 Days.” Andie’s character aims to do all the things “women do to push a man away,” and do it so successfully that she completes the task in 10 days.

The true comedy begins when Matthew McConaughey’s character Ben Barry simultaneously accepts a challenge to make “any” woman fall in love with him in 10 days. Ben, by contrast, aims to do all the things “that will cause a woman to fall head over heels in love” in 10 days. (Hold off on any of the comments on how reality does not work like this).

The chaos and confusion begin when Andie and Ben, as well as their associates and peers get involved in making one side win and the other side lose the bet. The scenes are sometimes comical, unbearable, and yet all too familiar. In some ways, the behaviors of both Ben and Andie, as well as their “charming” peers not only shine some humorous and light hearted comedy on relationships, but also illustrate some important facts about relationships – romantic and otherwise. I see some parallels between these scenarios and how companies form – and lose – relationships with customers.

Here is how to lose your best customers in 10 days (or not)

1. Misunderstand the real landscape of your customer

Ben and Andie are “set up” by people with bad intentions. Jealous associates and adversaries of Ben, decide to pick Andie as the “any woman” while knowing that she has the task to drive away any guy in 10 days. The two “love birds” accept their respective challenges while unaware of the real landscape of their relationship.

In many ways a loss of a great customer begins with a lack of understanding of the real landscape and of their actual needs and pain. What exactly do they do as a business? How are they structured? What are their internal agreements and SLAs with their customers? How does your solution fit into their needs? How do problems with your solution or service impact their enterprise organization? What makes your customer contact a “hero” to superiors? What motivates them to invest in your relationship?

A lack of understanding or unawareness of your customer and their business – in their terms – is a problem that your team needs to address. Use case notes, customer account history details, online research and training to be sure your support engineers and teams understand the real customer landscape and needs. Simply asking a customer – ‘what are you looking to accomplish in the big picture’ can reveal some important context for your customers’ actions.

2. Conflicting goals and requirements

In the movie, Andie is working to lose a guy in 10 days, while Ben is trying to win a woman in the same time span. They have conflicting goals and requirements, which leads to comedy gold in some scenes of the movie (the Celine Dion concert for example).

Having conflicting goals and requirements is another way to lose your best and most influential customers. Just imagine for a moment what happens when your team is personally incentivized to close tickets quickly? So your team benefits from focusing on providing your customers with quick and easy workarounds and hacks, instead of robust and tested solutions. What happens when your team’s goals for speed and time to resolution conflicts with the customers’ requirements for tested and validated solutions or other regulations that slow down the time to close a ticket? What happens when your customer wants a deeper understanding of the environment and best practices? As VP of Customer Experience, I work with teams who have had to accommodate customers with a wide range of specific requirements – regulatory requirements governing fixes, updates and upgrades, and times that systems can be modified.

Are your ticket system key performance indicators (KPIs) flexible and actually indicative of what the customer needs? Or are they maintaining a conflict between your team and your customers? If your goals and requirements continue to conflict with your customers, it won’t be comedy gold, but there will be tradeoffs with unexpected consequences.

Keep your customers happy by ensuring that your KPIs and metrics support their health and success, not just provide a measurement of your own speed and efficiency.

3. Overcommitment/Committing too early

In the movies, one of Andie’s breakup techniques involves overcommitting. Within the ten-day span, Andie moves her things into Ben’s place unexpectedly. She overcommits and commits too early in the relationship, a point she believes her readers can relate to.

Perhaps you are wondering about this point in losing a great customer, but for those who are responsible for communicating fixes, solutions, and software versions to the end customer, over-commitment also happens to be a big issue. Overcommitment can be a cause for a breakup with your customers as well and it may look like:
a. Overstating the value that your solution or service will provide
b. Over promising on the features of a hotfix, release, or workaround
c. Choosing an overly aggressive date with no margin or room for error
d. Implying a lower TCO to the customer than your business will approve
e. Agreeing to providing a date for resolution before understanding the RCA
f. Asking customer to do a customer case study before they have really experience with your product or your company

Avoiding overcommitment doesn’t mean that you need to pad dates and underwhelm them with proposed deliverables. It does mean taking in a healthy dose of reality and aligning with the tested mantra: It is better to under-promise and overdeliver than overpromise and underdeliver. Be sure to set customer expectations properly and refresh those expectations frequently. Put yourself in their shoes and work to understand their perspective and priorities. Internally, be sure to meet communicated dates without ambiguity and strive to beat those dates.

4. Miscommunication

Throughout the movie Andie and Ben have multiple episodes of poor communication, miscommunication, and even disinformation campaigns.

If you want to lose a customer in 10 days, separate your teams, sever communications between groups of differing responsibilities, allow miscommunications on dates, results, outcomes, expectations, and requirements to exist, fester, and perpetuate through the organization. And, if you really want to cement the catastrophe, follow in the footsteps of the so-called friends of Andie and Ben and engage in multi-channel disinformation that disputes previously shared or agreed upon data.

Avoid miscommunication by developing a process that keeps stakeholders informed, and redirects requests for updates and dates to a central repository or database of information. Share notes and status updates to minimize confusion and disputes over interpretations of customer requests. When in doubt, align with your leadership team internally before communicating critical information directly to the customer.

5. Avoiding help

In the movie, things appear to improve when Andie and Ben seek counseling. They attend couples therapy and as a result end up bonding with Ben’s family.

Along the journey, your relationship with your customer will need help. But, if you want to lose your customer in 10 days (or less), don’t seek out that help. Continue moving forward with the knowledge that you have, and with the limits of your team (even the best teams need help).

Seek out the help of industry experts, executive coaches within and without your organization, online training resources (Udemy is an excellent resource), or paid coaching. This training will help you and your team continue to improve your responsiveness to the growing news of your customers, old and new.

6. Mishandled difficult situations

After Andie and Ben return from a weekend at Ben’s parents, Andie tries to end her challenge to write the article and get out of having to finish her assignment. For his part Ben begins to forget about winning the bet and focuses more on an honest relationship with Andie. Unfortunately for both parties, they have forgotten the depths that their peers and adversaries will sink to in order to win or cause the other to lose. At a big event thrown by Ben’s firm, the adversaries from Ben’s firm and Andie’s boss set the stage for an unexpectedly chaotic “big reveal” of the bet with devastating consequences. An angry Andie and Ben handle the chaos poorly by scolding, chiding, and embarrassing one another from the stage in front of the crowd.

Difficult situations will always arise in any industry that involves software, services, and people. The key to losing a customer in these situations is to handle it poorly. Examples of poor handling of a difficult customer or customer situation include:
a. Scolding or embarrassing the customer
b. Complaining vocally or bitterly online or in public forums
c. Ignoring customer needs or burying them in process and paperwork
d. Being dishonest
e. Being disrespectful to the customer
f. Failing to honor communicated commitments or purchased products
g. Focusing on proving that you are right instead of on solving the problem

Practice how to handle difficult situations, rehearse hard conversations within the safety of your team, and look for ways to communicate without blame, anger, or disrespect. Be honest and thorough with your responses, and include empathy (genuine empathy) for them.

7. Wait until it is too late

The ending of the movie has Ben racing to catch up to Andie before it is too late. Of course, “How to Lose a Guy in 10 Days” has a happy ending. Andie and Ben resolve their misunderstanding and realize that life would be unhappy without the other.

Winning your customers is a great first step in the relationship, but keeping them happy and satisfied requires ongoing work. If you want to lose your customer in 10 days (or in 10 months) keep them waiting and guessing as to how you view the relationship. Allow peers and competitors to upstage and upset them with speculations on your silence and absence from the partnership and try to race in at the last minute to salvage it all. Unfortunately, unlike the movies, waiting until your customer has packed their bags is the wrong time for attention. It is often too late to save things when you’ve allowed steps 1-6 listed here and time to undermine things.

Of course, no one wants to lose a great customer, but if you choose to ignore and misunderstand their environment and real landscape, leave conflicting goals and requirements unresolved, overcommit too early (move too fast), allow miscommunication to exist and thrive, avoid the help of experts, and lastly wait until it is too late, you will lose your customer. It may not be in 10 days, but it will happen.

But, the good news is that if you want to keep your customer, when you’ve finished reading this article, get your team together and chase after improved communication, better goals and KPIs, processes that work for avoiding extremes in commitment, reduce misunderstandings, and coaching to improve individual outcomes and overall customer success.

Cassius Rhue
Cassius Rhue leads the Customer Experience team at SIOS Technology responsible for customer success spanning pre-sales, post-sales and professional services engagements. With over 19 years of experience at SIOS and a focus on the customer, his significant skills and deep knowledge in software engineering, development, design and deployment specifically in HA/DR are instrumental in addressing customer issues and driving success.


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