Hard-Won Lessons on Rejection from 39 Years in Sales

I’ll be honest: when my pitch for last month’s column was declined, I was a little butthurt. I felt the topic was important, but my manager didn’t see the vision. Rather than nursing my bruised ego, I decided to pivot. In fact, getting shot down inspired this month’s topic: how to cope with rejection and not take feedback as a personal attack.

Nobody likes rejection, but it’s an inevitable part of any career — especially for those in sales. Robin Kennedy, executive manager of strategic partnerships at KHON2, has spent nearly four decades in the field. Here is what she has learned about picking herself back up after being turned down and finding the courage to try again.

Kennedy landed her first sales management role at age 23, working at a Macy’s in New York City. Since then, she has learned that success requires the ability to adapt to one’s environment. In a unique market like Hawaiʻi, she argues that technical pitch details often take a backseat to the strength of human connection. “Everything that I do in sales is related to relationships and strategic partnerships,” Kennedy says. “In Hawaiʻi, it’s all about who you know.”

Illustration: Ginny Williams

Warm Up the Cold Call

For many, the “cold call” is the most daunting hurdle in sales — the moment when the potential for rejection is highest. In Kennedy’s approach, however, a cold call shouldn’t actually be “cold.”

She maintains a prolific community presence, networking three to four nights a week and volunteering for various organizations. It isn’t just about handing out business cards; it’s about being a visible, helpful member of the community. “I don’t call what I do ‘cold calling’ because part of being an excellent salesperson is being out in the community and being seen,” she explains.

So, by the time she dials a high-ranking executive, she isn’t a stranger — she’s a familiar face from the last nonprofit board meeting or industry event. “It makes the cold call process a lot easier,” Kennedy says.

When “No” Feels Personal

Despite her high success rate, Kennedy is candid about the fact that rejection still stings. In an industry that often advises having thick skin, Kennedy admits that her passion makes her susceptible to disappointment. “When they say ‘no’, I take it really personal, like losing sleep over it, because I give so much of who I am to what I’m doing.”

This vulnerability, however, is coupled with a deep-seated belief in the value she provides. Kennedy refuses to sell anything she doesn’t “110% believe in.” When she approaches a business owner, she views the company as their “legacy.” If she knows her product can help that legacy, a rejection isn’t just a lost commission — it’s a missed opportunity for the client.

Instead of wallowing in self-pity after a failed pitch, Kennedy says she feels sorry for the person who turned down the offer. “I’m not spiteful,” she explains. “I just feel bad for them, like they made the wrong choice.”

The Reframe

A simple but powerful tip Kennedy shares is a shift in semantics. In her earlier years, she admits a “no” might have offended her and then she’d “probably go after their competitors.” Today, her mindset is more optimistically persistent.

“I feel like that’s probably the foundation of the salesperson that I am today — that no, isn’t, ‘no, never.’ It’s just ‘not right now,'” she explains. By reframing a rejection as “not today,” Kennedy removes the sting of finality and allows her to maintain the bridge for a future relationship.

Taking Constructive Criticism

Kennedy emphasizes that the biggest hurdle to growth is the human instinct to be defensive. “Most of how people think is a reaction to how they feel, right?” she says.

When receiving feedback, the goal is to listen without preparing a rebuttal. You should be “actually listening and not immediately starting to think of how to defend yourself,” Kennedy advises, although she admits this is easier said than done.

Second, she encourages staying in the conversation until the air is clear. Don’t just nod and leave as quickly as possible to avoid discomfort. “If someone’s giving you constructive criticism and you trust them, make sure you stay in that room and you communicate through it so you don’t go home crying, you don’t take it so much to heart that you’re carrying that with you on every call.”

A Message to Managers

Kennedy also believes that the burden of feedback shouldn’t fall solely on the employee. For criticism to be well-received, it must be offset with some positive recognition. She argues that managers are far more likely to see better results if they balance their critiques with a reminder of the employee’s value: “If someone is telling you how much they appreciate you as an employee, and that this [feedback] is to help you grow, aren’t you way more likely to listen to that?”

Find a Mentor

For those struggling to maintain momentum in the face of constant rejections, Kennedy’s final piece of advice is to stop trying to figure it out in isolation. “Find a mentor, find someone you can talk through it with,” she says, because “just bouncing ideas off” a trusted veteran can turn a setback into a breakthrough.

After 39 years, Kennedy knows that a successful career in sales isn’t about striving for a perfect record. It’s forged in the ability to pick yourself up after a rejection, refine your approach, and remember that a firm “no” is often just a “not today.”

Getting shot down is never easy, but for those of us early in our careers, these moments are where we actually find our footing. It requires humility to swallow your pride, figure out why your pitch didn’t land and learn from that experience. Rejection isn’t the final verdict; it’s an invitation to go back to the drawing board and try again with a better perspective.