For salespeople, success is often painted as a numbers game, underscored by relentless pursuit and bold pitches.
Yet, beneath this surface, persistence and empathy emerge as catalysts for mutual success.
Academic studies have found that empathy improves sales behaviors like listening and adaptive selling, and also boosts sales outcomes. Moreover, making accurate, intuitive judgments about customer needs has been linked to better sales strategies and performance.
The convergence of persistence and empathy transforms challenging negotiations into opportunities for connection and partnership — and skeptics into allies.
Delving into the insights of professionals at Outdoorsy and ChowNow, their experiences highlight triumphs and reveal strategies that fuel success in sales.
By combining determination with a focus on understanding the client’s point of view, they demonstrate that the process of reaching sales targets is just as important as the end result.
ChowNow connects diners with independent restaurants across North America through a commission-free platform, offering branded ordering experiences.
Describe a time when you closed a deal with a tough customer. What strategies did you use to navigate the situation? How did you manage to close the deal?
There was a time when I was determined to partner with this restaurant group I admired. Surface level, they felt they were fine with their technology. Their software had the necessary components needed for their daily operation. My top three strategies involved active listening, utilizing my technical knowledge combined with industry expertise and maintaining conversational control. I always approach a deal from the prospect’s perspective. Actively listening and building trust was imperative before presenting any solutions. Showing I was genuinely curious and valued their needs opened up a collaborative conversation.
It was important to understand where the prospect had been, where they currently were and where they were going. Once I understood the past, present and future, I had a good sense of why they did business the way they did. I was able to use my expertise and present a creative solution to propel their business beyond what they thought possible. It’s natural for prospects to find every reason not to buy at first. Maintaining control of the conversation with a calm demeanor and leading my prospect through an incredible buyer’s journey concluded with us partnering.
“I firmly believe the number one reason deals are lost is speaking too soon.”
Would you do anything differently if a similar situation occurred again? If so, what would you do, and why?
Every situation is unique. No matter my experience or skill level, I will always continue to learn and try new techniques. You have to be open to new experiences. We all learn from successes and failures. However, from my years of experience and shadowing multiple reps, managers, executives and so on, I firmly believe the number one reason deals are lost is speaking too soon.
Listen to what they want and curate a solution specifically to what they need. If they don’t know what they need, at least hearing them out helps uncover a solution that will make sense to them. Overall, I would not change my strategy in a similar situation. With that said, one piece I would add once the deal is closed would be to utilize partnerships that could help them in other ways — even beyond my solution. If I can save a business time and money with my resources, I want to support them in every way possible. Customer experience is everything. Going above and beyond can truly set you apart.
What is the number one skill a good salesperson needs to cultivate to succeed with tough clients?
Empathy is the number one skill needed to succeed with tough clients. The tougher the client, the more challenging it can be to have empathy. The first step to actively listening is to keep all thoughts to yourself and empathize with your prospects, regardless of their demeanor. They may expose information or an experience that reveals why they think the way they do. It’s worth it in most situations. The tough clients often end up becoming the most loyal clients. Loyal partnerships lead to referrals, and before you know it, you have built an entire community of incredible individuals who support each other.
Outdoorsy connects adventure seekers to millions of idle recreational vehicles, complemented by top-tier insurance through Roamly, ensuring safe and memorable outdoor experiences.
Describe a time when you closed a deal with a tough customer. What strategies did you use to navigate the situation? How did you manage to close the deal?
Scene: I’m fresh-faced, in my first big-person sales job. Here was a challenge: a worldwide vehicle manufacturer, both personal and commercial, refusing to even acknowledge our existence. Why? Well, the huge tech company I worked for in the northern part of greater Austin had a wildly stale brand circa 2014.
Unrelated, my company rolls out a plan to reorg SMB accounts under corporate affiliates. The “lifers” said it was a waste of time. Dialing for pennies when they have quotas in the tens of millions.
Call me naive, optimistic or just dumb, but I saw an excuse to make contact with this account and redefine our brand through these smaller players who could influence the true DMs. So armed with nothing but a prayer, phone and printed paper leads, I started cold calling. My team thought I was DOA at this job. “Great call, rookie, that’s 1/100th of 1 percent of your quota!”
But lo and behold, after what felt like thousands of cold calls, something magical started to happen. Word spread up the ranks of this account. A couple of months later, they brought over $2.2 million in quarterly spending, all thanks to my elbow grease. That was truly a defining moment now ingrained in my DNA.
Would you do anything differently if a similar situation occurred again? If so, what would you do, and why?
I’ve told this story before but never actually told the true ending — and it’s not a heroic one. When this account was closed by the youngest person on the floor, I thought I was hot stuff. Unfortunately, that’s not how corporate America works.
My manager immediately calls me into her office. “Just how do you think I will be able to explain this ridiculous increase in my number?!” Crippled with confusion, I had no answers. I’ve never to that point — or ever — been confronted by management with closing too much business.
Ultimately, it was a great experience for me that really started my journey working for amazing startups in the Austin area, so I wouldn’t personally change it for the world. But if I could lend some advice to any young sales professional, run from the big corporate sales job, run from the fluorescent-lit cubicle farms, run from any job where your entire team has been around for decades and refuses to change, and most importantly run from managers that “like things the way they are.”
If you truly want to stand out in an organization and make an impact on your career, join a company where you aren’t just a cog identified by some employee ID number.
“When dealing with challenging clients, a salesperson must separate ego from strategy to steer toward favorable outcomes.”
What is the number one skill a good salesperson needs to cultivate to succeed with tough clients?
I always emphasize the nuanced role of ego in sales. Depending on context, it can serve as a catalyst for success or a stumbling block. Sales, by nature, attracts high-ego folks. The top performers reap the greatest rewards, garner the most accolades and ascend fast in their careers. This fosters a heightened self-perception, which isn’t inherently negative.
Yet, when dealing with challenging clients, a salesperson must separate ego from strategy to steer toward favorable outcomes. Handling demanding clients tests one’s ability to navigate beyond personal pride, as they often make unrealistic demands, have an arrogant demeanor and attempt to manipulate.
The instinct to assert dominance or “put the client in their place” often backfires. Difficult clients, wounded pride in tow, will defect to competitors — even if the alternative is worse. It’s a deeply personal dynamic.
By understanding the art of strategically checking ego, salespeople can wield greater influence. There are numerous ways to achieve this: staying calm and eliminating “I” as a pronoun. Balanced with subtle changes that lower the clients, like not laughing at bad jokes or cutting overuse of their name, is a winning combination.
