Practicing Unpreparedness: Extensive Research May Not Be the Best Way to Prepare for Your Next Client Meeting

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Before a meeting at Paradise Bakery with a client, I had studied this guy inside and out. I knew his background and education. I’d read every article he’d written or had written about him. I was ready to wow him.

But then something magical happened — I met a real human being. The person in front of me was this funny, kind, and contradictory character I could hardly keep up with because I was trying so hard to match him with the person I had researched. I was so thrown off trying to know everything about this person in advance that I missed the true value of our potential connection.

This was an early moment in my career, but it was pivotal; it marked the first time I recognized an important tenet of relationship-building. I learned that the most indispensable part of preparing for any meeting isn’t research or committing facts about someone to memory — it’s approaching each meeting with an open mind to connect with someone without preconceived notions.

Let Go of Preparation Perfection

A present and open mind, rather than a distracted one, can help you get the most out of any meeting. This is a philosophy I try to embody personally, inspire in my team, and seek in partners and colleagues.

I am reminded of a story an acquaintance of mine told me about a particularly fruitful encounter. While at a partner’s office, my colleague noticed the names of companies written on a whiteboard. She knew the leaders at some of these companies and offered to make a few connections. This gesture cost her nothing, but it created a bond with this new partner that led to an exchange of further introductions and interactions. Best of all, it wasn’t an act prompted by a bulleted item on some agenda. It was an organic connection triggered by a genuine interest between two people.

Anyone can build this kind of rapport with the right plan. Here are five ways to practice intentional unpreparedness and genuinely connect with everyone you meet:

1. Listen Without an Agenda

When meeting new people — or even people you might have met previously — prepare to also greet their baggage, their background, and their stories. Be intensely interested in them as people rather than as potential clients or referral partners. Listen closely without ulterior motives to get a clear picture of each person’s history and interests, which will help you understand how to relate to them.

That said, don’t listen to people’s personal stories solely to find similar interests or points of connection. That sort of cheesy salesmanship rarely works. I’ve seen many meetings go awry when people try to force connections by excitedly stating that they also happen to love waterskiing after someone mentions a passion for water sports. Be genuinely interested in people; listen with an open mind and without neediness.

2. Practice Calm Presence

Preparing to the nth degree for your meeting may hinder your ability to sit and listen openly to the other person. Preoccupation with your notes or agenda can also cause you to practice bad listening, which can make the conversation shallow and disappointing.

Do whatever preparation you need to feel relaxed, and then focus on simply being present in the moment. Go into the meeting with the mindset that this human is the most interesting person in the world right now. Learn as much as possible about what makes this individual tick during the meeting, not from facts you’ve gathered or your preconceived expectations.

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3. Ask Questions to Dig Deep

An important part of being present during any meeting is opening the conversation up to tangents and depths you didn’t expect. You can do this by asking open-ended questions that make the speaker feel their opinions and experiences matter.

Invite the other person to simply tell their story, and then look for opportunities to delve deeper. Pick out a detail or a feeling and respond in a way that encourages elaboration. If someone mentions a divorce, for example, you could say something like: “Wow, that had to be painful. How did you get through that?” These kinds of penetrating questions — not the ones you jotted down in preparation — elicit the insights that build a real connection.

4. Bring Zero Judgment to the Room

Overpreparation often leads to getting caught up in expectations and prejudices about how you assume someone will appear or act. These preconceived notions can inhibit a natural relationship from forming and can leave the other person feeling boxed in.

The more you enter a room judging others, the more you’ll limit your own self-knowledge and growth. If you enter from a standpoint of openness — not harboring biases about people or their beliefs — you position yourself as a listener who can be of service.

5. Ask How You Can Serve People

Preparation is often self-serving. We want to be prepared to present our own needs and our own personalities to get the most we can from other people. One of the best ways to be present and form an authentic connection with someone is to go into a meeting focused entirely on how you can offer help instead.

Start building selflessness into the way you interact with others. Practice looking for ways you could be of service. Could you make an introduction or offer advice? Do you have a skill that someone needs? Let service be the ties that bind you to new acquaintances.

It may feel strange at first to go into a meeting without an agenda. You’re likely used to approaching meetings with the same dedication you bring to everything else in your life. However, if you learn to step back from the idea of perfection, you could find yourself making deep, meaningful connections that lead to long-term relationships.

Jonathan Keyser is the founder of KEYSER.

By Jonathan Keyser