How 4 Boston-Based Sales Professionals Transform Rejections Into Learning Experiences

Rejection is a universal experience in sales, but harnessing each “no” as an opportunity for growth and later success is a personal yet necessary journey.

Written by Lucas Dean
Published on Jun. 08, 2023
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In sales, rejection is an inevitable part of the job. Channeling each rejection into something productive — an opportunity to hone one’s strategy, understand the prospect’s perspectives and transform unfortunate “no’s” into future “yes’s” — is the only way forward. 

Balancing the range of factors — methodology and cadence of outreach, data accuracy, the customer’s needs and the respective product’s ability to fit each use case — is not an exact science. Treating it as such can quickly prove a futile endeavor and a slippery slope into disillusionment. 

As one salesperson began his career, his penchant for quantifiable analytics was eventually proven unhelpful in coping with rejection. 

“I turned the entire selling process into a mathematical equation. I knew that if I spoke to 15 people, I would get one person to engage with me. This suggested that 14 people would reject me,” explained Robert Messana, Mention Me’s general manager of USA. “As I gained experience, I perceived rejection quite differently. When I fail to win a deal, I use rejection as a learning experience.”

The key to success and longevity in the sales field is defined just as much by empathy and openness as by persistence, due diligence and hardiness. Likewise, one’s ability to effectively reframe rejection is not determined by overarching data or precise methods and measurements but rather by considering what played a role in each success and failure. 

Only when serious consideration of each unique prospecting effort meets a healthy perspective on processing the unavoidable no’s can rejection become a positive force for growth. 

Messana and three other sales professionals shared their outlooks on rejection, their secrets to success and how they stay motivated when feeling down.

 

Amy Carpenter
Vice President, Strategic Accounts, Healthcare • Flywire

Flywire is a global payments network, payments platform and vertical-specific software solution.

 

Rejection hurts! Tell us about your personal journey dealing with rejection as a sales professional. How did you handle rejection at the beginning of your career? How do you handle it now?

I started my career in healthcare on the provider side of the world. Over the years, I actually evaluated and purchased software for my practices many times. I saw the sales process’s good, bad and ugly from a buyer’s perspective. So I never thought healthcare sales would be where I would end up spending the majority of my career! Once I made the jump to what some may say “the dark side,” there were rejections and not just a few. 

I took every rejection personally and doubted my ability to succeed in this business. I was very fortunate to have a seasoned sales leader at the time. He taught me very quickly how to use rejections to my advantage. I was not going to succeed in this role if I did not learn from each and every opportunity, won or lost. From him, I learned that listening is probably the most important skill for a salesperson to have. Too often, I was just showing up, following the demo script and hoping something fit. Active listening to understand and clarify a prospect’s needs not only tailor my meetings to meet their objectives but doing so also enables me to build trust and foster a more consultative sales process.

 

I was not going to succeed in this role if I did not learn from every opportunity, won or lost. I learned that listening is probably the most important skill for a salesperson to have.”

 

What are some key strategies you’ve developed to cope with rejection? Do you have any rituals, mottos or inspiration that keep you motivated when you’re feeling down?

First and foremost, I must learn from each opportunity. While it pains me, there will always be rejections. Learning and growing from those experiences is a must. Personally, I review all the steps in the process and understand where I may have missed the mark, skipped a step or mishandled an objection. I almost always know where I could have done better. If at all possible, it is great to get feedback directly from the customer. I find that this conversation not only helps me with other opportunities but also helps build and solidify the specific prospect relationship for future interactions. 

I also have to remember to celebrate my successes. As salespeople, we are always juggling many opportunities at all times. Sometimes it is easy to win and move to the next. We have to celebrate and learn from the wins as well. Winning is the motivation!

 

Tell us about a time when you were able to turn a “no” into a “yes.” What was the secret to your success?

Very early in my career, I had a significant opportunity with a health system. I believe I asked all the right questions, listened to the prospect, and understood their needs and pain points. The solution I was selling checked all the boxes to achieve their goals. We could even provide a significant ROI. Given all of these steps and projected results, I still got the rejection. I went back to the table multiple times and tried to get creative with closing the deal but still had no luck. The same sales leader I mentioned above told me to change my tact and give my prospect time to sit on it. Once again, he was right. Changing the power dynamics can positively impact and sway the deal your way. By trying this new tactic, I turned the no into a yes.

 

 

Andy Jones
Vice President of Sales • Stavvy

Fintech company Stavvy developed software that unifies workflows and simplifies complex transactions, allowing lenders to meet regulatory requirements and host remote signings efficiently. 

 

Rejection hurts! Tell us about your journey dealing with rejection as a sales professional. How did you handle rejection at the beginning of your career? How do you handle it now?

Experiencing rejection can be a painful experience, but only if you take it personally. At the start of my career, I used to take it personally when a prospect didn’t return my calls or went quiet. I would wonder what I did wrong and why they weren’t responding to me. This often resulted in frustration, which impacted my subsequent calls and emails, leading to a decline in overall performance. As I progressed in my career, I learned that it was not personal and most people have different priorities that they are working on. Being authentic in my approach allowed my prospects to communicate more effectively about their priorities and where I fell in those priorities.

 

Experiencing rejection can be a painful experience, but only if you take it personally … most people have different priorities that they are working on.”

 

What are some key strategies you’ve developed to cope with rejection? Do you have any rituals, mottos or inspiration that keep you motivated when you’re feeling down?

The key factor for me is to avoid taking rejection personally. This mindset significantly helped me in dealing with the challenges of rejection. I rely on a simple strategy to stay motivated: maintaining consistency and avoiding emotional highs and lows. Throughout my experience managing and coaching successful salespeople, I have observed that those who consistently apply a systematic approach to their daily routines and territory management tend to achieve the best results.

 

Tell us about a time when you were able to turn a “no” into a “yes.” What was the secret to your success?

The initial response in most outbound sales is often a “no.” To successfully transform this “no” into a “yes,” effective communication of your solution’s unique value and benefits is crucial.

Once you have the prospect’s attention, it is important to actively listen and understand their specific pain points and challenges. Be honest about whether your solution can genuinely improve their situation. If yes, emphasize the positive business outcomes and measurable metrics they can expect from implementing your solution. By highlighting these benefits, you can minimize the occurrence of rejections and subsequent “no’s.”

However, if your solution needs to provide more value for their needs, it is important to maintain honesty and transparency. Stay positive, professional and authentic throughout the process. A positive attitude can be contagious and may even lead the person to refer your business to others in the future.

 

 

Paddy Ivers
he/him/his SDR II • Allego

Allego’s all-in-one, sales rep-facing platform provides activated content, personalized training and learning opportunities to optimize sales teams for a virtual environment. 

 

Rejection hurts! Tell us about your personal journey dealing with rejection as a sales professional. How did you handle rejection at the beginning of your career? How do you handle it now?

I like to handle rejection with an emphasis on professionalism. It’s not personal; as a sales professional, my product is not a fit for everyone, and that is okay. When I started my career, rejection was so common that it was really a good thing — someone was at least giving an answer. Sure, it wasn’t the answer I wanted, but it was an answer nonetheless. Rejection is a part of life. If you look at being a sales professional as being curious, then it’s actually good because you are finding out something new.

 

What are some key strategies you’ve developed to cope with rejection? Do you have any rituals, mottos or inspiration that keep you motivated when you’re feeling down?

I try very hard to keep things even. I try never to get too high from success or too low from failure. In fact, I look at failure as the best teacher if you are willing to look at it and take away the lesson. Hearing no after no on the phone, in email or on LinkedIn can get to even the most hardened of us, but I remind myself that you often have to get ten rejections from prospects to find that person who needs what you have to offer. Every rejection is one no closer to a yes. I find that physical things will also keep me from becoming stuck. I work out, take ice plunges or play with my kids; even having a nonwork conversation with my wife or friends will remind me to be grateful that I even got someone to reject me.

 

I remind myself that you often have to get 10 rejections from prospects to find that person who needs what you have to offer.”

 

Tell us about a time when you were able to turn a “no” into a “yes.” What was the secret to your success?

I was once told on a call by a prospect, “I’m not interested,” and my response was, “Not interested in what?” The prospect had just heard me say my name and the company’s name, so I was curious about what had caused him to reach that conclusion. I expected the prospect to hang up, but to my surprise, he said, “Whatever it is you are selling,” so I responded, “Oh, cool, well, I’m not actually selling anything. This is a cold call to see what you might need. I don’t know if I could help you, but if you’ve got a moment to talk, even if I don’t solve your problem, I might be able to point you in the right direction.” We talked for about five minutes, and it turns out his problem at that time was not something I solved, so I pointed him towards a partner and wished him well.

 

 

Robert Messana
General Manager USA • Mention Me

Marketing tech startup Mention Me empowers brands to unlock the limitless potential of their fan bases. Its Referral Engineering approach helps customers connect friends and family with brands and promos, in the process growing a loyal customer base.

 

Rejection hurts! Tell us about your personal journey dealing with rejection as a sales professional. How did you handle rejection at the beginning of your career? How do you handle it now?

Early in my career, I made a decision to transition from the relatively “safe” world of financial analysis to the profession of selling. Being analytical in nature, I turned the entire selling process into a mathematical equation. I knew that if I spoke to 15 people, I would get one person to engage with me. This suggested that 14 people would reject me! I would then have to engage with four people to convert one into a sale, meaning I would have to talk to 60 people to make one sale. The average commission was $300, which meant I was getting paid $5 for every rejection, so why not get as many as possible? 

As I gained experience, I perceived rejection quite differently. When I fail to win a deal, I use rejection as a learning experience. Rejection can represent a failure on my part or my team’s part to adequately communicate my solution’s value and benefits. Determining what controllable variables could have led to a better outcome helps the seller refine their craft. It is important to be a student of the game and be on a continuous learning journey to maximize the value you bring to every interaction — both external and internal. 

 

What are some key strategies you’ve developed to cope with rejection? Do you have any rituals, mottos or inspiration that keep you motivated when you’re feeling down?

The perception and risk is the misconception that the rejection is directed at the salesperson personally. Keeping a healthy outlook is critical to coping with a career that will always be over-indexed toward failure. 

While that sounds inherently negative, consider some of the following thoughts that have kept me motivated throughout my career. 

In Major League Baseball, batting .333 — failing two-thirds of the time — will easily get you into the Hall of Fame. Rejection isn’t about me; it isn’t personal! Every “no” gets you closer to a “yes.” Reward yourself for successes, but also reward yourself for the negatives that help get you to those successes. Learn something from every interaction. For those so inclined, put on your role-based face. Keep a journal of funny interactions. Share the journey with colleagues.

 

 

Keeping a healthy outlook is critical to coping with a career that will always be over-indexed toward failure.”

 

Tell us about a time when you were able to turn a “no” into a “yes.” What was the secret to your success?

The first time I was able to accomplish this in a meaningful way was unforgettable to me and demonstrates the attributes of how to be successful over a sustained period of time-trust, commitment to customer success and personal accountability. I had been working with a prospect who informed me that they had taken the “safe” path by selecting my more established competitor. The x-factor was that I knew the competitor and their team extremely well and had observed them failing other customers who were doing similar implementations. I was also a subject matter expert in my solution and was confident it could support all of their requirements. 

I requested a meeting with the CFO, and as they outlined their decision criteria and how the competitor could check all of the boxes, I was compelled to suggest there was one variable that they had neglected to consider. I gave them my commitment that I would be personally accountable for making their project a success. This approach resonated since “safe” was one of their key decision criteria. The CFO walked me into the CEO’s office, and they changed their decision on the spot. The lesson is that you are the variable that can’t be replicated!

 

Responses have been edited for length and clarity. Images by Shutterstock