An introvert’s guide to sales and fundraising

The quieter approach to sales.
The quieter approach to sales.
Image: REUTERS/Thomas Peter
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When I imagine the quintessential salesperson, I think of an extroverted, persuasive, life-of-the-party charmer who—by sheer force of charisma and personality—is able to convince people to buy a product or service. I’m not alone in thinking this; it’s a widespread belief that an extrovert makes the best salesperson.

Fortunately for me, an introvert who is often engaged in salesmanship, this belief isn’t justified.

Research actually shows a “weak and conflicting relationship between extroversion and sales performance.” In fact, an analysis that surveyed more than 4,000 salespeople found no correlation between extraversion and sales performance.

As the CEO of Uncharted, and the person responsible for sales, partnership-building, and fundraising, I’ve had to leverage the most strategic parts of my introversion to raise capital and keep our organization financially healthy. What follows is a “introverts playbook” for sales and fundraising. When you’re an introvert, you can’t necessarily rely on flashy persuasion, but you can focus on a different type of selling—one based on genuine interactions, long-term relationships, and commitment to details.

I write this for fellow introverts like myself, not to say that an introverted approach is superior, but to show the practical and fruitful ways this disposition can be the foundation for a strong sales strategy.

Focus on the hidden 85%

Most people think sales is about being able to give a persuasive speech.

But in a given sales cycle, only 15% of my time is spent face-to-face or on the phone with the prospect. The other 85% of the time is spent prospecting, emailing, responding to email introductions, researching a prospect, preparing for a meeting, drafting a proposal based on what I learned in the meeting, following up, answering questions over email, updating the proposal, and following up again. The competitive advantage for introverts is in this hidden 85%. Here’s how to nail it:

  • Know that methodical preparation beats a charming personality. I’m not the most charming or charismatic salesman you’ll ever meet. But my research before every conversation, phone call, and in-person meeting with a prospect is exhaustive. My goal is to understand how prospects think, what their priorities and goals are, and what language they use. I’ll be able to better connect with them in our in-person meetings if I have a head start in understanding who they are and what they care about. For my first meeting with prospects, I’ll spend time scouring their organizations’ websites, their LinkedIn profiles, their social media, the first page of their Google search results, and any mentions of them in the press. Often our first point of contact within organizations are not the final decision-makers. Instead, they will escalate the sale decision to someone more senior in the company. Before meeting with these final decision-makers, I’ll go even deeper by asking my original points of contact (the decision-makers’ colleagues) about the psychology of the decision makers. What do they care about? What motivates them? How should I approach the conversation? What should I make sure to say? What should I avoid saying? Then I’ll spend time diving into online research to identify any articles they’ve written, podcasts they’ve been on, and speeches they’ve given. What are the common themes between their tweets over the last 90 days? Doing most of the legwork before the meeting means I feel more confident going into it.
  • Be more of a detective than a motivational speaker. While extroverts may spend their time emulating the charisma of the late Apple CEO Steve Jobs, I try to be more like Sherlock Holmes, gathering data and searching for clues that will help me unlock the sale or investment. During every phone call, I type verbatim notes in the prospect’s CRM-software profile. During in-person meetings, I take notes in a journal. As I am walking from the meeting to my car, I dictate into my phone everything I didn’t write down so I can upload it into that person’s CRM profile. Names and ages of prospects’ kids? That’s documented. The small talk at the beginning of the meeting about what they did that past weekend? Documented. My impressions on what they care about and what motivates them? Documented. What my next steps are? Documented. My goal is to capture as much information as I can so I can resonate with them better, connect with them more deeply, and understand the path we might take to join forces through a sale or investment.
  • Long-term follow-through is more valuable than short-term persuasion. Being meticulous about follow-through is not technically difficult, but it’s hard to consistently pull off. It requires building a business-development infrastructure: systems, CRMs, processes, tasks, internal deadlines. The success of Uncharted’s business development is more a function of our behind-the-scenes organization and follow-through than it is a function of wowing people in in-person meetings.

How to nail the 15%

No matter how good you are at research and relationships, sales will require at least some in-person interactions. Keep in mind:

  • Active listening > active pitching. Charming extroverts might be tempted to use the time spent on a phone call or in a meeting to pitch their products or services. Introverts might use that time instead to hold space and listen, understanding the priorities and needs of the person they’re meeting. I aim to spend the vast majority of my conversations with prospects listening and asking questions, especially early on in the conversation, so I am not pitching Uncharted or explaining what we do without having extensive context.
  • Sales is more translation than proclamation. My goal during the majority of a meeting is to understand the language and cultural context of the prospect so when the time comes to communicate Uncharted, I can effectively translate who we are and what we do into understandable terms. What Uncharted creates doesn’t change, but how I talk about our services does change based on the cultural context. For example, I start all my meetings by asking what success looks like for a potential partner: “If we were to fast-forward one year from now and you looked back and declare this partnership an extraordinary success, what happened?” Their answers become the anchors around which I structure my explanation for how Uncharted can help them. I’ll emphasize dimensions of our work that address these goals, while glossing over other elements that aren’t as relevant.
  • Don’t lose sight of the human. In conversations with prospects, I’ve often felt pressure to make the most of our limited time together: get my point across, demonstrate Uncharted’s value, and convince them to commit. But I’m learning the importance of in-person meetings is often overestimated; there is so much pressure to “nail it” in each meeting that often salespeople lose sight of building a long-term relationship. In one hour-long meeting with a prospective investor, we spent the first 30 minutes discussing mindfulness. I had recently started a mindfulness practice, and I knew she had been meditating for years, so I shared a few of the challenges I was having, and she shared some advice. Our conversation spun off from mindfulness into parenting and yoga. We eventually got around to discussing the possible investment in Uncharted, but connecting on the human level was more important to me, so I was willing to throw out my agenda to further build a relationship.

The Takeaway

Sales can be terrifying and uncomfortable; I’ve found that it’s easy to overthink things and psyche myself out. No matter if I’m about to walk into a meeting to try to close a $1 million sale or if I’m meeting someone for the first time at a happy hour, I ask myself: What is just the next small courageous step I can take?

Ultimately, sales is about two things: understanding someone’s problem and exploring how you can help them solve it. Sales is less about persuasion and charisma than it is about human-to-human problem-solving. Make it all about them: be a giver, not a taker.