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Painful Lessons Learned from Moving to the Sale Too Quickly

Updated: Feb 22, 2023

The best lessons in Sales are often the ones we draw from our biggest mistakes. Luckily, they eventually make you a better Sales Manager and business partner to your client. Here's a mistake that taught me a lot.

The best lessons learned are often the ones that still make you cringe today. They were real mistakes, resulting in unwanted consequences and took effort to smooth over. Yet, these mistakes are often the most valuable ones, the ones that you will never forget, nor repeat.

When I took over a sales territory from another Sales Manager as Business Development Manager, I started handling an insurance company that had repeatedly brought their annual Sales Kickoff Conference to our luxury hotel in the second week of January each year since hotel opening. The beginning of the year is a soft business period for most city hotels and booking this conference was very important to us.

The insurance client (let’s call him Tim), based in Toronto, used a booking agent, based in Vancouver (let’s call her Hannah), to manage the proposal process, select a hotel and eventually negotiate the contract. As I was based in Toronto, I was able to connect personally with Tim, but had only spoken to the agent on a few occasions over the phone. Tim was friendly, but vague. Despite my carefully crafted questions, he didn’t share a lot of insight into his priorities for a conference venue. I felt there were hidden barriers that he wasn’t sharing. At our third meeting, I wanted to find a way to uncover what he was concerned about. To engage him in a deeper conversation and move from the vague to the concrete, I brought last year’s conference contract along. I just wanted to see where his hesitation was coming from.

Big mistake.

Tim took a brief look at the sample agreement, stayed polite, but still did not offer more information. Ten minutes after our meeting my phone rang and a very (VERY) upset Hannah was on the line. She felt overstepped, he felt pushed into the Sale. I realized that what I thought was a pro-active and helpful approach was focusing purely on my interest to gain clarity on where we stood in the selection process, but did not fulfill any of my client’s needs.

I still feel the pain when I think of Hannah’s call.

Here are my main takeaways from this that made me a better salesperson and will hopefully allow you not to make the same mistake:

1. Focus on Providing Value

How do you become a trusted business partner to your client? By demonstrating that you are here to help realize their business goals, not yours. Saying “I care for you!” will not be enough. In each of your e-mails, conversations and meetings you need to do/say something that your client benefits from. This could be advice, a recommendation, sharing an article, connecting him/her with someone useful… anything that is useful to your client right then and there.

My client wasn’t benefiting from me wanting to review a potential contract. What I did was focusing on the sale, the transaction and as a result I fell from “Trusted Advisor” status to “Just another Sales Person” within seconds.

2. Reflect on the Purpose of Each Interaction

I should have asked myself:

“What am I trying to achieve by bringing the contract along?”.

The answer to that would have been

“Move closer to winning the sale.” or “Identify hidden obstacles to winning this sales conference.”

Most likely, deeper reflection on what the purpose of my action was would have lead me to the conclusion that me bringing the contract can also cause many unwanted reactions by my client. Most likely, I would have thought of other, better ways to gain more insight into my client’s mind.

Today, I scrutinize my messages and actions for purpose:

What do I want to get out of this? How is the client benefitting from this interaction? How will my client most likely respond? Is this relevant to my client or a waste of her time? How could I make this easier, faster and simpler for my client?

3. Never Take an Existing Client for Granted

Most likely you are thinking “I knew that.” And I knew that, too. But our full sales schedules and the necessity to develop new business often shifts our focus towards first time leads.

Think about it in financial terms: increasing customer retention rates by 5% increases profits by 25-95%. It is more expensive to win a new client than to keep an existing one, so consulting your existing client with the same detail and allowing him to move through the sales process at his own pace is key.

We did win that business, fortunately, and Hannah and I finally got to meet in person a few months later. She turned out to be just lovely.


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