Why Pitches Fail: How Strategic Sales Conversations Win Clients

If you want more clients, stop pitching and start having strategic sales conversations—they’re the key to lasting business relationships.

Every day, LinkedIn provides me with a number of pitches. Most of the people pitching me believe that I need their help to convert prospects into clients. None of the salespeople know me well enough to know that I was selling newspapers door-to-door when I was 12 years old.

The Early Roots of Real Sales Experience

When I started selling newspapers, someone (I don’t remember who) told me that if I knocked on doors and asked people to buy, I would make more money and tips. I knocked on every apartment in my territory and sold so many papers that I was unable to deliver the Sunday paper on time because I had so many customers. I also made friends with the people who lived in my apartment complex. This was relational sales, even though most of my relationships were transactional.

At 15, I was making cold calls for a not-for-profit that organized bike-a-thons. Despite being much younger than my co-workers, I was the only person on the team to set up a bike-a-thon. At 17, I was selling B2B enterprise-level deals in my family’s staffing firm. You could say I started my career early.

Sales Lessons From the Streets of Hollywood

When I moved from Columbus, Ohio, to Los Angeles, California, I lived in Hollywood. Every day, drug dealers and other ne‘er-do-wells stopped me on the street to try to sell me something. Their pitch offered me cocaine and other drugs. When that didn’t work, they tried to sell me other things I didn’t want. Fortunately, I soon found an apartment in Brentwood far away from Hollywood.

Why the “Pitch First” Sales Model Is Broken

The most common pitch I get from people suggests they can get me two to four new clients every month—and if they don’t, I won’t have to pay them. There are many problems with this approach, but the biggest is that these people know nothing about my business. They don’t know me, nor do they know what a good client is in my world. Most of these pitchers believe I want individuals as clients. They don’t realize that I work with large B2B clients.

But just being in the right industry isn’t enough for me. I also look for clients who share values with me, and have an approach and perspective that is likely to align with the content of my training and development materials.

Strategic Sales Conversations over Transactional Tactics

There is a time to pitch, but it isn’t the first conversation. The low-skilled salespeople who believe the pitch is how to win a client’s relationship and their business get sales completely backward. People love to buy, but they hate to be sold. We call the folks who pitch before they should peddlers. Their approach is lazy. They are simply looking for a transaction that puts money in their pocket. They don’t care about the relationship or helping their clients succeed.

How to Convert Prospects Without Pitching

If you want to acquire a client, the best strategy to win a deal begins with a strategic conversation. This should help you share key insights with your prospective clients, including the challenges and opportunities you’ve noticed in the industry based on your experience. It also allows you to ask your clients questions that can help you both better understand the client’s strategic goals, the root causes of their problems, and the impact of a solution. A pitch will not make a prospect buy from you. Without the conversation, you know too little about what the prospect values and what they want or need.

Sales Training for Enterprise Clients Starts with Discovery

There is a time to pitch after you have had the conversations that allow you to learn about your prospect. Your contacts are trying to improve some result that they value enough to give you their time and attention. In exchange, you must take the time to recognize the outcomes they are seeking and craft your proposed solution around that. The Lost Art of Closing: Winning the 10 Commitments That Drive Sales can help you identify the commitments you must secure in your conversations with decision-makers and their stakeholders.

Why Discovery Must Precede Any Sales Pitch

A strategic conversation is one where the salesperson helps their client learn what they need to be prepared to make a decision that will ensure they get the necessary results. It is a conversation where you build trust and establish yourself as an expert. Your contact also gets a lot out of it in the form of key information and a better understanding of their problem and its context. This is not possible in a pitch.

Pitches drive prospects away. That is why we start with discovery. Only with effective discovery can you make a credible pitch. Discovery is your opportunity to show the prospective client the depth of your knowledge. It’s your chance to ask them open-ended questions that get to the heart of their problem and help them understand what has to change to get the results they need. This is how you develop relationships, which are the foundation of effective sales strategy.

For individuals who want to master strategic sales conversations: Start here

For companies that need sales training for enterprise clients: Visit the Sales Accelerator