How to win sales: Your first two minutes matter most


For founders, success in sales starts right from the first moments of the conversation. Find out how to win deals by being prepared, understanding the client’s needs and genuinely engaging with your prospect.
As a founder who is stepping into the role of salesperson, your opening act is crucial.

Buyers make snap judgments, often deciding within the first few minutes whether to invest more time in what you have to say. That’s why it’s so important to make the best possible first impression during a sales conversation.

The key lies in your understanding of the buyer's pain points. 

If you can articulate their challenges and needs in detail within the first two minutes, you've already taken a significant step towards winning their attention and trust. This shows empathy and understanding right from the start.

Let’s take a deeper look at how to establish a meaningful connection in the first two minutes of your sales pitches, so you can set the foundation for successful sales.

How proper prep sets you up for success

Before you dive into a sales meeting, preparation is key. Every Tigera salesperson (myself included) must complete a comprehensive prep document before engaging with a customer. This is a fundamental part of our sales process for any account valued over $50,000.

The preparation document is divided into several crucial categories:

  • Desired outcomes: What is the client hoping to achieve with your product or service? This knowledge helps you tailor the conversation to meet their expectations.
  • Customer pain points: What pain is the customer experiencing and the consequences of not solving it.
  • Key stakeholders: Who are the stakeholders and who owns the budget
  • Decision making process: How will the customer make a decision? Who? What is the criteria for the decision?
  • Potential traps: When you know potential challenges or objections in advance, you can plan how to address them effectively.
  • Hot buttons: What are the key issues or features that will most likely catch the client's attention? Recognizing these can help you focus the conversation on what matters most to them.
  • Personal profile: Include a deep dive into the client's professional background. This involves understanding their role, responsibilities and even their influence within their organization. This research is about getting a sense of who they are as a decision-maker.
  • Organizational structure mapping: For substantial accounts, a detailed understanding of the company's hierarchy is essential. Knowing who reports to whom — and the internal company dynamics — can help you navigate the sales process and understand decision-making channels. What is the power structure?

When you do this level of preparation, it ensures you step into every meeting prepared to offer a solution that's been thoughtfully crafted to align with the client's specific needs.

Practice deep listening

Exceptional listening and the ability to ask insightful questions are the cornerstones of great sales relationships.

Even though the stereotype of salespeople is that they talk fast and are always on the move, the most successful ones are actually great listeners. 

Learn to tune in and understand the needs, concerns and expectations of your prospect. 

When your prospect speaks, every word counts. Your response must reflect that you have not only heard but also understood their perspective. The quality of your response is a direct indicator of how well you've listened and processed the information.

Asking the right questions is equally crucial. Don’t just fire off a checklist of follow-ups — engage in a meaningful exchange where your questions demonstrate a deep understanding of the client's situation and needs. Ask relevant questions that clarify your understanding and prompt the client to consider new perspectives.

An important aspect of being a good listener is humility. If you don’t know the answer to a question, it’s better to admit it than to make up a response. Honesty builds trust and credibility. You can always follow up with an answer later — but if you lose credibility, it’s hard to regain.

Don’t take shortcuts (even when it’s tempting)

Top sales professionals are committed to process and discipline. Success in sales is not just about charm or quick thinking — it's about rigor, preparation and using a systematic approach to every interaction.

This meticulousness extends to understanding the full landscape of stakeholders involved in any deal. Don’t just engage with one or two key contacts — the best salespeople map out all stakeholders who might influence or be impacted by the decision. This comprehensive approach ensures no crucial perspectives are overlooked, so you can offer a solution that caters to the needs of all parties involved.

Skipping steps or taking shortcuts might seem tempting, especially when you’re trying to speed up the sales process, but it often leads to missed opportunities and overlooked details that could be vital to closing a deal. The discipline to stick to a proven process — no matter the client or the size of the deal — is what sets the best salespeople apart from the rest.

Connect with your prospect using the pain-gain-fear framework

Building trust during sales conversations is crucial. Users are unlikely to buy because you have rattled off a long list of impressive product features. Instead, focus on connecting with your potential client.

Customers buy for one of three reasons - “pain-gain-fear.” Use this framework to guide your conversations, and map your strategy to one of these three dimensions:
  • Pain: Is there a task that is causing someone a lot of pain where they labor for hour or miss deadlines? If so, this is a strong motivator for a user to purchase a solution. Identify these pain points and demonstrate how your solution can address them.
  • Gain: Is a project going to get someone promoted and advance in their career? This is a strong motivator for a buyer. 
  • Fear: Is an event going to get someone fired? If so, how do they ensure that this event doesn’t occur and what tools can they use to mitigate risk? This is a strong motivator for a purchasing decision.
Building trust also means behaving with integrity. If your solution can't solve the client's problem, it's better to walk away than to mislead. This honesty fosters long-term credibility.

Furthermore, the customer needs to know that they can rely on you, especially in times of crisis. Being available and responsive, especially after they've made the purchase, reinforces trust and can lead to lasting relationships. When you close a deal, remember that you’re starting a partnership.

Use a hybrid approach to win over your first 10 customers

Gaining your first few customers is a pivotal moment for any startup — and as the founder, you should close the first ten deals yourself. 

To approach these initial sales conversations, I recommend a hybrid sales strategy, focusing both on “friendlies” as well as new leads that come without prior connections.

Friendlies are people within your network who know you and are likely to give your product or service a chance. They can provide the initial proof points necessary for your business. Their feedback can be incredibly valuable in fine-tuning your offering.

However, be aware of the risk of false positives. Because they have a personal connection with you, friendlies might be hesitant to provide brutally honest feedback, which is crucial for improving your product and your offer.

On the flip side, new leads can give you unbiased feedback. They provide a higher signal quality because their perspectives are not colored by a personal relationship with you, so their feedback is likely to be more honest and representative of the market at large. These customers validate your product in the real world and help you understand if there's a genuine demand for what you're offering.

From hello to handshake: Your guide to impactful sales openings

Your sales success as a founder starts in the first few minutes of any dialogue you have with a prospect — and those precious minutes need to be driven by meticulous preparation and genuine engagement. Essential points to remember:
  • Comprehensive preparation, including understanding client goals and organizational structure, is vital.
  • Exceptional listening skills and insightful questions form the backbone of effective salesmanship.
  • Build trust with empathy and integrity, and focus on addressing the client's specific needs.
  • Balance your customer acquisition approach by targeting both friendly contacts and new leads for unbiased feedback and market validation.
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