Why impressive people lose deals

What you need to know:

  • The next time you prepare a pitch, remember that your audience is probably not wondering how impressive you are. They are wondering whether you understand what is making their job harder and if you can make a difficult situation easier.

A few years ago, I walked into a client meeting convinced I needed to impress him. I had the full "Impress the Client Starter Pack": case studies, glowing referrals, a polished portfolio, and rehearsed answers to questions he hadn't even asked yet.

In my mind, this wasn't a pitch, it was the thin line between financial stress and financial flexibility. I'd already spent the money mentally, I was ready to join the soft life and end my social media posts with “#NaEnjoyment”.  

When the day arrived, I was ready to explain my process, experience, and services, and convince him that hiring me was the smartest business decision he'd make all year. Then, 12 minutes into the conversation my carefully rehearsed talking points felt completely irrelevant. The client started talking about his pain points and what was frustrating him. I had spent so much time preparing to talk about myself that I hadn't spent nearly enough time preparing to understand his business needs.

I did not get the project. 

My imaginary brunches were postponed and my soft life era was immediately downgraded to "character-building season." I took the news particularly hard, but the experience taught me that pitches are not just about proving how impressive you are but rather about helping people feel understood.

Fast forward to five years later, and I’ve landed a very similar project. This time I approached the pitch with the mentality of building trust and understanding the business needs first, rather than proving myself.  

Communication experts often refer to a concept called WIIFM, which stands for "What's In It For Me?" Whether we are pitching a client, investor, employer, or business partner, people naturally view opportunities through the lens of their own needs and challenges. They are not primarily interested in how clever our solution is. They are interested in how it improves their situation.

The mistake I made and others still do when pitching is believing their product needs to sound revolutionary. As a result, they spend most of their time talking about features, credentials, and capabilities. Meanwhile, the person sitting across from them is silently asking a different set of questions. Will this solve my problem? Can I trust you? What could go wrong? Why should I choose you instead of someone else?

Research in communication psychology consistently shows that people are more likely to be persuaded by individuals they perceive as credible, competent, and genuinely interested in helping them. This principle is reflected in what many professionals call the Trust Equation. While there are several versions, the underlying idea is simple: trust increases when expertise and reliability are combined with genuine understanding.

I learnt this lesson the hard way. Early in my career, I thought my job was to impress people with everything I knew. Over time, I discovered that the most successful conversations happened when I spent less time explaining and more time listening.

The next time you prepare a pitch, remember that your audience is probably not wondering how impressive you are. They are wondering whether you understand what is making their job harder and if you can make a difficult situation easier.

The most effective pitches do not sell services. They sell a future where the problem is smaller, the risk is lower, and the path forward is clearer.

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