Closing a Tough Customer- My Experience!

I started my career in sales and have been working for the past 33 months. During the later part of the journey, I did some customer success and realized the pain of closing a tough customer.

Over a while, I have heard & read various content on why a bad client is not good for business, its effects, etc. I am not going into that stuff but would share my experience of realizing how messed up it can be. I am dividing this post into three parts 1. Background 2. Customer 3. The moment you release you messed up!

Background:

If I am honest, I have closed a fair share of tough customers in my previous company, where I started my sales career selling SaaS solutions. With a completely separate customer success, I never really realized the consequence, at the max had to be available for an escalation call, deal with an angry account manager (to whom I would later send a pizza - thanks to Swiggy) and that’s about it. I had the impression that no money is bad money and the only thing that matters is the target, commission, and the high of closing a deal.

Then things changed I moved to an early-stage startup, with a small team and shared responsibility and as the saying goes old habit die hard, I continued with my approach of closing any deal that comes across. Initially, things went well with minor hiccups and clients closed were a good fit for us until a year later.

The Customer:

It was around the end of the quarter and the probability that the deal would push to next quarter was high to make the matter worse there were two separate accounts both linked, once the first account would close the other would follow.

The requirement was not complex but they wanted priority support, a dedicated account manager (basically we were doing the whole setup). We did used to come across such requests with other customers but they would be satisfied with our existing support structure.

I had a gut feeling that it will not be the same this time, and to add to that, the buyer… let’s just put it this way, was not a very pleasant person. Nevertheless took the plunge, verbally accepted the terms and closed the deal.

Post closure initial onboarding had few hiccups here and there, I remember our CS guy being pissed at me as the client needed individual training for each user and some customs reports. Well, it was not that bad.

The moment you realize you messed up!

After around a month, our main CS guy had to go on a sabbatical for around a month and I shared responsibility of a few customers, including “the special one”.

My initial reaction was how hard can it be? Most of the onboarding is done, they are using the tool, it would be mostly review calls and some minor support. Alas, I was wrong. It turned out to be a nightmare. To keep it short below are the few things I faced.

• Extreme nitpicking of product
• Hand holding each user on every step
• Every morning opening up the inbox only to find multiple emails from them on top
• What was supposed to be a monthly call turned to weekly and then to almost every alternate day. Sometime weekend too - they had Saturday working :(
• There were moments when I felt I was working on their payroll

After managing them I realized the cost of such a customer, it is not only about the amount of effort and time that goes in handling them but also how it takes a toll on your mind, which puts you off and affects your productivity.

For me, the silver lining is that it’s never too late to learn a lesson. I’m glad I learned this early on. Now before closing any customer, I ask myself - would I want to deal with them after closing the deal? If the answer is no, I politely let them know that we would not be a good fit :)