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Sales is Just Like Dating: First Impressions, Authenticity, and Finding Your Groove

How to Close Deals by Being Your True Self

Obamacare sales

As a sales entrepreneur for the last 13 years—and trust me, it feels like forever—I’ve always seen parallels between the sales process and dating. Both require making a strong first impression, navigating the nuances of connection, and ultimately, closing the deal. The common thread? People buy from people they like. Period. Whether you're pitching a product or asking someone out, the principles are strikingly similar.


But here’s the thing: being likable doesn’t mean putting on a show. Trying to act like someone you’re not often backfires. People can sense inauthenticity, and it’s a surefire way to lose trust.


Instead, the key is finding your unique strengths—your authentic self—and using that to build meaningful connections. It’s not about being perfect; it’s about being real. Much like in dating, there’s a wide range of qualities people find appealing, and the same is true in sales.


In this article, we’ll explore how to make the most of your personality, avoid common pitfalls, and cultivate genuine client relationships that lead to lasting success.



First Impressions Set the Tone


Whether you're selling a product or trying to land a second date, your first impression is everything. People buy from people they like, and that initial encounter is your chance to make a lasting impact. The secret? Be likable—but don’t overthink it.


Think of this moment as the foundation for everything that comes after. Dress appropriately for the situation, prepare a clear value statement, and most importantly, be genuine. Whether it’s a warm smile, a firm handshake, or a confident opening line, focus on creating a connection right away.



The Danger of “Trying Too Hard”


When you try to be what you think others want, you risk coming off as fake or even annoying. Authenticity is key. Pretending to be someone you’re not—like mimicking “new money” or post-glow-up energy—is a surefire way to lose trust.


Authenticity means embracing your quirks and strengths without overcompensating. People can sense when you’re trying too hard, and it creates a barrier instead of a bridge. Instead of focusing on how to impress, focus on how to connect. This will naturally make you more approachable and trustworthy.


Everyone Has Their Own Flavor of Likability


Think about your circle of friends. Each person brings something unique to the table—whether it’s humor, intelligence, reliability, or wisdom. In sales, the same principle applies. Lean into your strengths and let your natural personality shine.


Steps to Put Your Personality Forward While Building Client Relationships:


Identify Your Strengths: Are you naturally funny, empathetic, or a great problem-solver? Recognize your unique traits.


Practice Active Listening: Show genuine interest in your clients’ needs and concerns.


Be Honest: Share your thoughts openly but professionally. Clients appreciate transparency.


Show Your Passion: Enthusiasm is contagious. When you’re passionate about what you’re selling, it’s hard for others not to feel the same.


Be Relatable: Use stories, anecdotes, or shared experiences to build rapport.


Follow Through: Reliability is a cornerstone of likability. Do what you say you will, and do it well.


Authenticity Paired with Competence Wins Every Time


Being yourself is only half the battle. You also need to know your stuff. The best salespeople are those who combine their authentic charm with deep knowledge of their product, their industry, and their clients’ needs.


Competence builds confidence—both yours and your client’s. Stay informed about the latest trends, anticipate your client’s questions, and provide solutions that align with their goals. This combination of authenticity and expertise makes you a trusted advisor rather than just another salesperson.



A Real-Life Example of Authentic Sales Success


Take the Southern gal with the soothing voice who worked on my sales team, Keri. Her secret? Authentic kindness and rock-solid knowledge. She didn’t try to be anyone else—and that made her the top salesperson on the team.


Her voice was a natural asset, but what truly set her apart was her ability to make people feel cared for. She paired this with a deep understanding of the product, which allowed her to answer questions confidently and provide tailored solutions. Her authenticity created trust, and her competence sealed the deal.


Be the Best Version of You

Your job isn’t to be everything to everyone. It’s to figure out what makes you special and let it shine. In sales, as in life and love, the key to closing the deal is being genuine and confident while bringing your A-game.


The Many Faces of Likable Sales Personalities


There’s no one-size-fits-all when it comes to likability. Here are some common sales personalities that clients tend to respond well to:


  1. The Charmer: Full of warmth and humor, they make every interaction enjoyable.

  2. The Educator: Knowledgeable and patient, they focus on teaching rather than selling.

  3. The Problem-Solver: Analytical and resourceful, they shine when solving complex issues.

  4. The Connector: Relatable and empathetic, they excel at building relationships.

  5. The Visionary: Passionate and inspiring, they help clients see the big picture.

  6. The Trusted Advisor: Balanced and reliable, they focus on providing long-term value.


The key is finding which personality type aligns with who you are and amplifying it. People like different things, and your authentic self is likely to resonate with the right clients.


Helpful Resources for Finding Your Sales Personality

If you’re just starting out in sales or looking to refine your approach, these resources can help you discover and develop your unique strengths:


  1. HubSpot’s Guide to Developing Your Sales Skills

  2. Daniel Pink’s "To Sell Is Human" – A great read on understanding the human side of sales.

  3. MindTools’ Personality Quiz – Identify your strengths and how to leverage them in your career.

  4. The Salesman Podcast – Insightful interviews with top salespeople to help you learn from the best.


Take the time to explore these resources and reflect on what makes you unique. Your authentic self is your greatest asset—use it to build trust, foster relationships, and close deals.

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