Conversations That Matter with Daniel Stillman

If you were to boil down the purpose of leadership into two words, you might say that leaders inspire. They must help their teams align in terms of vision, deal with complex issues in a unified manner and help build a creative and inclusive culture. All of these activities require well-structured conversations.

In our workshop with Daniel Stillman, founder of the Conversation Factory, we gained insight into his step-by-step framework for inspiring teams and design impactful conversations.

Stillman begins by explaining why its vital to structure better conversations. With a background in industrial design, Stillman sees design in every man-made object we use. Why should conversations be any different? In terms of the facilities that we use for holding conversations (Zoom, board rooms etc.), those too are designed. And if we don’t design our own conversations, we’ll inevitably fall into common patterns created by someone else.

STEP ONE: How to See the Structure of Conversations

First, you must ground yourself. Know what your best- and worst-case scenarios are in a difficult conversation and be prepared to walk away. Prepare for each eventuality, while realizing that it’s likely the real conversation will lie somewhere in the middle.

It’s also important to observe what happens in the silence – reactions, body language and more.  A 200-millisecond pause is the average expected time for a response. Longer and we assume they are overthinking. However, studies have also shown that it takes around 600 milliseconds to come up with a reasoned response. To reply quicker you’re either giving a junk response or considering your reply before your interlocutor stops speaking.

To buy time you can respond with a placeholder like “that’s an interesting question” or “let me think about that”, giving you time to design a better response. The average speaker can talk at 125 words per minute but think at around 4000 words per minute, so slowing down a conversation is a helpful technique.

STEP TWO: Know your Conversational OS

There are a range of questions to ask to find out what the rules of engagement are.  Who’s invited to speak first? Where is the conversation taking place? What do you do when someone misspeaks?

Stillman has identified nine elements you can control to define how you’ll conduct a conversation, including turn-taking, cadence, goals, and error-repair. These are the parameters of your conversational OS, and it pays to think them through. You can be innovative and experiment – giving people smaller sticky notes so they can only post short concrete thoughts or using drawing in addition to speech.

For example, within Stillman’s error and repair strategy, consider apologies. The Greater Good in Action project from Berkley did a psychological study of apologizing, identifying four essential components. These included showing remorse, acknowledging the offence, and making amends. “I’m sorry you’re upset” is no kind of apology.

Conversational threading is an important concept – the idea that when a good speaker is talking to a good listener, he or she can weave a complex tapestry and always come back to the main thread of the topic. It also refers to the way two good friends can pick up the threads of their ongoing conversation even after a long period of not speaking.

We even say “I’ve lost the thread” – it literally means the listener has lost their way in what’s being said, often due to the speaker not structuring their narrative well enough.

STEP THREE: Define your Conversational Range

The conversation changes significantly depending on how many people are involved. For some people, one on one is most comfortable, whereas others find that combination too intense and prefer to talk in groups.

We even must consider the conversations we have with ourselves – our inner monologues. Sometimes those inner conversations are the hardest of all to resolve, and we should probably start there. To quieten those inner voices of doubt, learning to meditate can help.

Somatic work can be helpful – identifying the physical sensations which accompany emotions. This helps you become more present in the moment.

Look at the ABCDE Process for working through difficult emotions:

Adversity – What’s happening to me?

Belief- What beliefs is it leading to?

Consequence – What are the consequences of those beliefs?

Disputation – Talking through the contradictory feelings with a coach

Energy – Which belief brings the most energy? Invite yourself to hold this belief.

STEP FOUR: Designing a Better Conversation

Start with empathy – think about what all the parties in the conversation need. Consider where you are happiest in the command/engagement framework (IAP2). For the type of conversation must you be a top-down leader, informing others that things must be a certain way? Alternatively, the situation might suit a highly collaborative, egalitarian approach.

Learning to be flexible in terms of how you approach a conversation will make those conversations more productive.

When you need to push for a sale, it’s okay to ask explicitly what’s causing the hesitation. If they won’t decide there and then, you can ask when it might be okay to follow up. You can talk around the issue and find out what they really want from you by considering a purchase – what problem are they trying to solve.

How to Have Difficult Conversations

Stillman believes in writing down the basic shape of a difficult conversation, but then reading it, and throwing it away. You want to have a plan but still build room for spontaneity.

If you have to part ways with an employee, that’s a very charged conversation. However, research has shown that people prefer to hear bad news before good. However, most people when delivering bad news prefer to soften the blow. Give the news to people straight if you can.

Miscellaneous Tips for Better Conversations

You can use sticky notes to remind yourself of your priorities in a conversation, especially over the phone or via Zoom i.e., “Remember to be Generous.”

Become aware of your tone, much of which can come from your body posture, how you use your body and how you feel physically as you speak.

Using work metaphors can be helpful to convey structured ideas – the four seasons is an especially good one.

Don’t be afraid of small talk – it may seem inconsequential but it’s how we connect as humans and it’s our on-ramp to big talk.

A go-to strategy at all times is to maintain empathy and mindful awareness of how the conversation is going, and to be willing to change gear if it’s not working.