Driving a conversation

Abracadabra
6 min readAug 22, 2021

Introduction

At work and family, most of us influence the world mainly from conversations. For years, this communication channel had been ineffective for me. I constantly felt that others were not listening or were too ignorant to understand what I said. I tried hard to be more patient and polite. I made my messages simple, clear, and hard to misunderstand. Sadly, my improvements in techniques and behaviors didn’t help much.

I missed a vital perspective towards conversation: It’s not about being insightful, knowledgeable, logical, or concise; it’s about getting the other person into an open and receptive state. I’ve categorized people’s states as

  • Resistance
  • Defensive
  • Talking
  • Listening
  • Influenced(our goal)

In 95% of the conversation, both parties start in the talking state and will stay there until the end. Sometimes, such conversations turned into a debate, then a quarrel. Other times, they politely adjourn while believing the counterpart is unreasonable, short-sighted, or stupid.

The skill of driving a conversation is to navigate through the states, depending on various factors, before reaching the goal of influence.

From Talking to Listening

At work, you enter a meeting ready to talk, present, and persuade. You are either talking or preparing to talk. Chances are you will leave the meeting frustrated. Your counterpart will hear your voice but won’t listen to a word you said. It’s because they are in the Talking state, too; no one will listen when in that state.

“Why won’t anyone listen to me?”, it’s because you didn’t listen to them either!

In such situations, your only correct action is to transit your counterpart into the listening state via empathetic listening. The goal is to truly understand the other person, even with lots of effort. The techniques of empathetic listening, as illustrated in Never Split The Difference by Chris Voss, are mirroring and labeling.

  • Mirroring: Repeating the last phrase the other person just said
  • Labeling: Rephrase whatever the other person said with your expression

Through mirroring and labeling, the counterpart will see you as someone who understands, rare in humankind. So they will treasure the moment with you and be open to hearing whatever you want to say. Only at this point, your prepared logic and facts may come into play, but they are still weak choices as you will find in the next section.

While mirroring and labeling work magically well, you can’t get very far by techniques only in any long-term relationships — unless you genuinely hope to understand the other person’s perspective and concerns. In the long run, all behavioral techniques will be found out as what they are.

What if they keep on talking forever?

Interruption is for efficiency; keep listening is for building trust. So it depends on your goal in the conversation. I wish I had never interrupted anyone, but regretfully I still interrupt when I believe, at least subconsciously, that gathering information is more valuable than trust. One example is during the phone call with customer service, and they were not solving my problem.

In hindsight, I interrupted more than my fair share.

Driving by calibrated questions when the other is listening

Here comes the more active part of driving. After enough empathetic listening, the counterparts will feel being understood and respected, a rare feeling in their lives. In exchange, they will be open to learning our perspectives, opinion, and concerns. They will seek our advice and guidance. How to influence through this newly established channel?

The most common, and wrong, way is autobiographically mapping their situation to our experience and giving advice and interpretation based on that. People poor at conversation do this even when the other side is in the Talking state. This method is almost always bad — it’s usually patronizing and the others usually won’t resonate.

The best approach is asking calibrated questions. For example, ‘You seem to be frustrated by being overweight; how do you plan to improve it?’ ‘I see you feel stuck at your current job. What have you tried to unblock your growth?’ ‘You are passionate about earning one million dollars. What do you think is your deeper motives behind it?’. Notice good calibrated questions start with how and what; very few of them can be answered by yes or no; why should be used very cautiously because it is a weak hint of disagreement.

I see mirroring, labeling, and calibrated questions as a progressive order of understanding. Calibrated questions build on the output from empathetic listening — the trust and the understanding to see through other’s perspectives. It gave the counterpart a chance to dig deeper into their heart with your accompany, and when appropriate, guidance.

Self-defense

Sometimes, Empathetic listening and calibrated questions take us to the deep mental world of others. It can be a hazardous environment. The influence is a two-way street. Without strong values and principles, one can lose herself. Harley Quinn is one such example. After entering the Joker’s mental world, instead of curing the Joker’s mental disease, she was attracted to it and became a villain herself.

Continue monitoring

You need to continuously evaluate what state the counterpart is in and react accordingly. People can drift from the Listening state to the Defensive state, especially when you try to promote some ideas instead of asking calibrated questions. When that happened, you must adjust your strategy and go back to empathetic listening.

I feel the constant monitoring and rebalance is like walking on a tightrope.

Resistance

People will be in the Resistance state when the trust level is too low or not confident expressing. Labeling is the best technique in this case. We usually need to get them into the Talking state.

Summary

This post put In one sentence: listen when trust is low, ask how and what when trust is high, constantly rebalance. The table below summarized the best practices and anti-patterns in driving a conversation aiming to influence.

The Caveat

Can empathetic listening, or any influence skills, build trust in all circumstances? Of course not. In Promised Land, President Obama told his failure to win trust from Republicans who determined to undermine his presidency, regardless of how much effort he and his team spent listening and how much compromise his administration was willing to make.

Not reaching a deal is the second-best option when a win-win is impossible. Facing people with who I can’t build trust, I used to switch gears and treat them as problems rather than humans; then, I try to solve them analytically with the first principle. Or simply put: To fight and compete.

Later on, I found that’s a much weaker strategy than avoiding them and go for no deal. Because fighting them forces me to violate my principles on synergy — always striving for win-win. One exception will break the consistency and jeopardize the whole system. Dag Hammarskjöld expressed this idea clearer than anyone else:

“You cannot play with the animal in you without becoming wholly animal, play with falsehood without forfeiting your right to truth, play with cruelty without losing your sensitivity of mind. He who wants to keep his garden tidy doesn’t reserve a plot for weeds.”

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