What I Wish I Knew Before Starting B2B Sales

We grow by accepting the mistakes we make and finding ways to learn from them. And by adjusting to what we learn means we have an opportunity to grow every day.

When I got into sales a few years ago, I quickly learned that sales is about asking the right questions and listening to what your prospects are saying. This sounds easy, but it is quite a challenge for many of us because it demands many of your soft skills like problem-solving and empathy.

How I approach sales now compared to when I got started is quite different. Over the past years, I’ve come to understand that sales is far more than just numbers and quotas; it’s about understanding people, empathizing with their challenges, and offering solutions that genuinely make a difference. In this post, I’ll be outlining the nuances of building long-term relationships, understanding prospect challenges, and the important lessons I learned from every conversation – good and bad.

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Building Long-Term Relationships Is the Key to Consistent Growth

In the first meeting, for me, it’s always about laying down the foundation for a long-term relationship. Before every introductory meeting, I do my research and find something about the prospect I can personally connect with that I can use during the conversation.

👉 For example, the other day, I was talking to someone who works in a building I used to work in a few years back. We started the call, made some small talk, and then I asked if the pool tables were still in the entry hall of that building because that’s where I often spent my lunch break back in the day. This was the easiest way to create a more relaxed environment before we even got to the sales part of the conversation.

👉 Another important point: Practice matching someone’s energy. When you are selling, it’s important to match the energy of your customer or client. Being too high or too low in energy can make them feel uncomfortable. The goal is to make the prospect feel at ease when talking with you.

It’s often the soft skills like awareness and empathy that make the difference.

Understanding Prospect Challenges = Higher Sales Success

During your first call with a lead, it’s not so much about what you are selling but the challenges they have and if you can offer them value. When you talk to a new prospect, you want to find out what exactly their problems are and if you, as a company, can be part of the solution.

For the first 15 minutes, let your prospect talk. Listen carefully to what they are saying and understand where their pain points lie, what they need, and what their potential objections might be. This way, you will be able to tailor your pitch to their problem.

How well you understand your prospect’s challenges will also determine the success of the next steps of your sales process. To make sure you get enough information during the first call, do your research and prep a set of meaningful and open-ended questions that will give you a good understanding of your prospect’s situation and where they are in the buyer’s journey.

One Bad Conversation Doesn’t Define the Outcome of the Next

One bad day doesn’t mean tomorrow is going to be bad, too. And one difficult conversation with a prospect doesn’t mean the follow-up will go the same way.

B2B sales can be tough, and there will be days when a prospect picks up the phone and won’t respond in a professional or friendly tone. But in these situations, it’s important to remember that bad days come and go. And one bad conversation doesn’t dictate the course of your next interaction. Even if you are going to talk to that same person again.

💡 A good example was the call I made the other day: I had to call someone who I talked with about four months ago, and I remembered that the prospect wasn’t very friendly. Naturally, I was not necessarily looking forward to this conversation. But I called them anyway, and in the end, we actually had a really good talk and booked another meeting.

Leave Your Ego at the Door and Learn to Take Criticism

If you want to get better, you have to ask others for feedback. And one great way to do that is by listening back to your sales calls with one of your colleagues.

Talking through your calls is probably already part of your training, but not every company uses these recordings consistently enough. Especially after you are post-ramp time.

Yes, hearing yourself talk can feel awkward, and sometimes, you will cringe at something you said (or didn’t say.) But before you sit down with your teammate to talk through specific points in your conversations, it’s important to prep concrete questions to get the most out of your feedback session.

Here are 6 specific questions you can ask that will help you improve your sales calls:

• If I could ask this question again, how could I rephrase it?
• Have you heard that objection before? How did you handle it?
• What is a discovery question I didn’t ask but should have?
• How would you have summarized this product feature to explain it more concisely?
• What do you think the other person was thinking when I said that?
• Could I have dug deeper here? If so, how would you have phrased your follow-up question?

In Conclusion—Sales Is Far More Than Just a Numbers Game

You don’t have to be a ‘born salesman’ to be good at it. Your success in sales heavily depends on your mindset, resilience, and willingness to learn.

A good sales process is prospect-centered and mutually beneficial. The best salespeople are empathetic listeners and problem solvers. They take the time to understand their clients’ needs and engage in genuine, meaningful conversations.

Sales isn’t about pushing a product onto someone who doesn’t want to buy from you. It's about building long-term relationships with people, learning about the challenges they are struggling with, and finding ways to help them do their jobs better.