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How to Have a Complicated Conversation

Issue 47: March 17, 2022

How many recent conversations at work or in your personal life have been complicated?

Everyone is anxious about the war in Ukraine, the unjust actions on its people and the unprovoked war’s effects on our country and the world. This new source of anxiety adds to our stress levels in navigating a return to some level of what was normal pre-pandemic. The global situation has also thrust us into having complicated conversations as the world around us seemingly changes and we don’t have a concrete way to understand what the future will bring. It’s a potential minefield out there to address conversationally and express ourselves.

Why Conversation Matters

This week, we want to dive into the topic having complicated conversations and offer some thoughts and approaches for your interactions with individuals and groups. Why? Leaders, managers and really any individual, in professional and personal lives, need to be prepared to have complicated conversations that provide an open forum to have results-driven discussions on any issue from the global level to the office and across our personal lives.

In our 2040 newsletters focused on leading with courage, active listening, shared knowledge, individual biases and critical thinking, we brought forward the necessity to step back from ourselves, embrace humility, and recognize those that we are interacting with. And above all, we advocate structuring our communications and conversations for positive outcomes. We invite you to check them out for more strategies on leading with purpose, humility and empathy.

Stepping back and preparing for a complicated conversation takes mental energy. Human survival has ensured that we are programmed to conserve energy, not expend it, and therefore we often approach our interactions and complicated conversations by winging it. In your own experience, have those spontaneous conversations resulted as you intended?

We don’t have all the answers but suggest that preparation, self-awareness and engaging with those with whom we seek to have a conversation is key to ensuring a complicated conversation — regardless of topic or intent — is meaningful and productive.

It’s also important to know in context of complicated conversations that by human nature we are programmed to expend as little energy as possible, and therefore our unconscious mind drives us to get to the point, take what we need from the conversation, and move on with intended objectives. This can derail a productive conversation, prevent an active exchange and erode trust.

What Is a Complicated Conversation?

According to Thaler Pekar, an internationally recognized pioneer of organizational narrative and persuasive communication, “A complicated conversation is one in which you desire an outcome that is not shared at the outset. Or a conversation with high emotional content. Complicated conversations are accepting of human paradox, and therefore of contrast. That’s the complication: accepting the messiness of the middle, not staking out poles of right and wrong. Complicated conversations can be delightful and fulfilling conversations if one stays open to contrasting options and seeking contrasting opinions in pursuit of insight. Like in photography, contrast enables us to see the depth and complementary details. They are complicated because they take a lot of cognitive energy to remain present and open and refraining from judgment and presumption.”

We have all had complicated conversations that spark disagreement, controversy, ambiguity, consensus, and have unintended consequences given our beliefs and biases. This scenario is typically the result when we don’t actively listen to those we are seeking to engage in a conversation. Speaking, including our choice of words and what information we convey or decide to omit, can lead to being misunderstood. Our listening and internalizing the responses are often filtered through our personal defaults believing that we are the center of the universe, and all solutions center on us.

A complicated conversation forces us to be critically aware and get out of our intrinsic self-centeredness way, recognizing and removing our own biases and judgments, to actively listen to others. It requires paying attention and having an open mind to manage the discourse and respect those engaged in the conversation. In a world tinted by degraded discourse, the need for preparing ourselves, leveraging deep and critical thinking, and respecting others help us have complicated conversations.

Pekar, advises, “In a complex conversation what you say doesn’t matter as much as what the other person hears. The meaning of your words is actually determined by the listener, so we can only understand the issues by listening to them.” She adds you have the responsibility to listen and need to take the time to actively listen. Ultimately, you need to balance the need to be heard with hearing. Most people speak without listening, which Pekar refers to as premature articulation. She adds that we have a tendency to speak too soon – to move the conversation forward, push for consensus, reduce tension. But when we do this, we bring all our own biases to the table: “I only want to hear what I want to hear,” adds Pekar, “The benefit of listening better is the ability to speak better.

Managing a Complicated Conversation

The way into any complicated conversation is to start with the first honest word, which is different than discovering “absolute truth,” according to Maria Seddio, founder of CorpTalk and an executive coach. She adds, “That first honest word becomes the basis for going forward and earns you the right to authentically engage in the conversation. It sounds easier than it is though because we lie to ourselves all the time. And with good reason. Who wants to face loss or do the grief work that might be involved in negotiating a disappointment or risking a relationship?” It takes time, mental energy and courageous self-reflection to launch into a complicated conversation. The results can be significantly affirming if we prepare and keep ourselves open to how the conversation unfolds and concludes, even if it is not to our desired outcome. Seddio says, “Conversation is the cure — nothing gets resolved if we aren’t willing to talk about it. And change is a conversation — it does not happen in a vacuum.”

Having a Complicated Conversation

There are some practical guidelines individuals can leverage in preparing and having complicated conversations:

  • Expectations

All communications generally lead to an end goal (unless they are bloviations, filling air space for trivial reasons). Organize the conversation by setting an intention for the dialogue and ending with a call to action. Pekar maintains that people can only relate to things they already know, so the job of a communicator is to think about the overall experience of the conversation. Recognizing what another individual knows and accepting there is limited shared knowledge and experience with another sets up the challenge of understanding the other participant(s) in the conversation. Pekar further states it’s important to set a framework, then deliver the facts and information, and remember the intent of the conversation.

The important question to ask yourself is:
What do you want to leave in the hands of the listener?

  • The Sandwich

When giving difficult feedback to someone, many managers sandwich in something positive before ending with a negative conclusion. There is a risk to using this technique often; people will anticipate the negative after a sandwiched compliment and instead of listening will wait for the other shoe to drop. The sandwich sets up an expectation to fear what comes next. We inherently take the sandwich approach as we are often reluctant to engage in direct confrontation. We also by default want to preserve the perception by others that we are not a “bad” person. On many levels want to soften the blow and ensure the participant maintains emotional stability throughout the conversation. A sandwich approach should end with an unequivocal balance of positive and constructive criticism.

  • Clarity

It helps to know what individuals want from you in a complicated conversation. Are they looking for brainstorming, feedback, venting, help? Do they need you to go to battle for them? If you are clear about what they want, you can listen in an appropriate frame of mind. The goal is to stay on the same page and avoid talking at cross purposes. Clarity requires you to stay inactive listening mode, removing your own biases and perhaps personal objectives, attending to what is needed and responding accordingly. Clarity does not require you to meet the participant’s objectives if they are out of your realm of comfort or span of influence. Clarity does require you to objectively hear the participant.

  • Empathy

Thaler describes a conversation as a partnership. That requires the speaker to get off his or her throne and sit beside the listener. Context is everything and you need to be sensitive to all the small signals during a conversation to prevent them from building up into something dramatic. Read the room and the participants. Be aware that not everyone is going to be alike, resonate with what you are communicating or agree with what you are sharing. Understand where you are aligning with the listener and where you need to align. A complicated conversation is not a popularity contest.

  • Power Dynamics

Complicated conversations, especially in groups, are influenced by power dynamics. Not everyone processes information or responds at the same speed. Meetings are typically dominated by quick processers who get it fast. The extroverts are also the first to contribute ideas and fast forward to solutions. Yet the slower processors and the introverts have valuable contributions as well if given a voice. Setting up a structure and establishing a safe framework is more inclusive with a diverse group of people. Most individuals want choice, and they want to have their voices heard, even if they are shy or timid. Often in a group, some may be multitasking, daydreaming or simply disengaged as they don’t see the conversation as relevant to them. The meeting leader or facilitator needs to practice compassionate curiosity, according to Pekar. There is power in who gets to engage in the conversation. She adds, being is a position of power isn’t about personal power, it is about empowering others. Many people do not have the opportunity to be heard. Give them the dignity and respect they deserve to build trust, she advises.

  • Goal Posts

The mission of a complicated conversation is not to win every argument or convert others to your point of view. It is not expending inefficient mental energy and being invested in having the last word. Set boundaries for the conversation with limits that prevent breakdowns and degradation of the discourse. Let people feel they have a choice to share, but don’t neglect them because they are quiet. As Pekar says, don’t ignore the corners. The bystanders of a conversation have roles as well. That being said, set up the conversation with high-gain responses avoiding one-word answers. And leaders will be successful in eliciting information from the entire group only if they are sincere.

  • Defusing a Conversation

Complicated conversations are fraught with conflict. Individuals may well have to step in to defuse a situation, change the subject or infuse humor. If you can’t pivot, take a breather. Or create a distraction that changes the flow and buys time especially if someone is being bullied. Pekar uses a simple tactic of tipping over a glass or water (or an equivalent) to enforce a pause. How do you exit a difficult conversation? Ask for a summary. Use the language, “As I understand it.” If the outcome is unclear, simply ask, “Help me understand.” Pekar also warns about radical candor and brutal honesty. “If you are going to tell the brutal truth, add what can be done about the situation. Otherwise, it is a dead-end conversation. You want to progress, not payback.”

  • Personal Bias

Any conversation can become unproductive if both the speaker and listener are operating from their own personal biases. What has been appropriated into a cliché, “Before you judge a man, walk a mile in his moccasins” is actually pretty good advice. But most of us don’t follow this simple Native American philosophy. A complicated conversation should enable “a democracy of equal audibility,” states author Rebecca Solnit. The tipoff that your biases may be interrupting the conversation is when you feel fear, rage or are defensive. Pekar advises to sit with it. If it strings, there is probably truth to it. Self-awareness is the key to unlocking what the sting is activating.

Ending the Conversation

At 2040, we coach clients on the skills and benefits of mastering complicated conversations. We stress the importance of being aware of what knowledge others have and how that will affect their responses. We work on word choices and whether they have the same meaning to a participant.

Explore our other articles on the art of leading. TheThe human element remains are the greatest asset in today’s society and working to clearly understand each other and being open to complicated conversations allows us shared clarity to meet today’s problems and challenges.

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