Leadership Conversations — How to avoid digital chocolate conversations.

January 18, 2023
9 min read
Photo by Aarón Blanco Tejedor on Unsplash
“Leadership happens in the conversation.”
— Rose Fass

When you hear the word "chocolate," what comes to mind? 

We ask our clients this all the time. Some say "candy," some say "cake," and some say "labs" (as in the dog). Now think about words like "strategy," "pivot," or "hybrid work," and think about how many different directions you can go. Discuss these words with your colleagues, and the possibilities become endless. 

In 2013, fassforward co-founder and CEO Rose Fass released her first book, "The Chocolate Conversation: Lead Bittersweet Change, Transform your  Business.” ¹

It was based on a concept that Rose and co-founder Gavin McMahon developed since they opened the doors to fassforward in 2001, that: "everything regarding leadership, the market leadership of your company, followership, and change happens in the conversation.” ²

Chocolate conversations occur when colleagues talk past each other, but think they are on the same page.

Rose has just released her 2nd book, The Leadership Conversation: Make Bold Change One Conversation at a Time. And the timing is perfect. With the increased complexity of this new hybrid world and the significant changes in the way we communicate, chocolate conversations are more rampant than ever. 

Digital Communications hit Warp Speed

In the 90s, we communicated in person or on the phone; pagers were cutting edge, while email was still in its infancy. Phone booths blanketed every city block. 

In 2013, when “The Chocolate Conversation” was published, Apple introduced the iPhone 5, and for the first time, more than half of American adults owned a smartphone³.  Our in-person conversations declined as communications via smartphone, email and text increased. Phone booths started to disappear. 

Businesses adapted to customers' preferences for digital communications. A 2013 survey showed that live chat registered the highest satisfaction levels for any customer service channel at 73%, compared with 61% for email and 44% for phone.⁴ 

By January 2020, digital dominated our communication. Out of a global population of 7.7 billion people, 5.19 billion people were using mobile phones, 4.5 billion people were using the internet, and 3.8 billion people were using social media. ⁵

Then COVID happened. 

The trend toward digital communications accelerated to warp speed. Work meetings, family get-togethers, birthday parties, and even funerals took place digitally. As our digital communications exploded, so too did the number of chocolate conversations.

Chocolate Conversations go Digital

The three main ingredients of chocolate conversations are worldviews, standards, and concerns: 

  • A worldview is a series of images, assumptions, and beliefs we hold about ourselves, others, and the world, based on our experiences. These perceptions shape our picture of reality. 
  • Standards are rules, codes, and guidelines that direct our actions in different situations. Like our worldview, our standards develop through our interactions. 
  • Concerns are our unmet needs that arise from information filtered through our worldviews and our standards. 

Chocolate conversations usually occur when we are unaware of these three ingredients.

Back-to-back meetings are now the norm with little, if any, break in between. As a result, we usually jump right into the subject at hand, which we refer to as "managing the work." Rarely do we allow time to share our worldview or talk about standards. Concerns rarely surface in these meetings; when they do, people seldom step back and ask what's behind the concern.  

Two-way conversations, whether in-person, on video, or the phone, provide the best opportunities to unwrap a chocolate conversation.

We can ask real-time questions about a point of view and better understand worldviews. Standards can be defined and concerns can be raised. We are more likely to provide context and background when having a two-way conversation. The best discussions always leave time for questions. Back-and-forth interactions that offer the opportunity to dig deeper are the best ways to avoid chocolate conversations.  

These opportunities disappear when we communicate via email, text, or IM. 

Emails: the Pathway to Passive-Aggressiveness

Like meetings, the messages in our inboxes seem to multiply daily. 

The time required to read and respond to emails feels like an additional full-time job. In a recent survey of 1500 professionals, 16% claimed they consistently fail to keep on top of their emails. 30% meanwhile, claim they lose sleep because of the number of emails they receive each day, with an average of 651 unread messages waiting in their inbox. ⁶

Emails quickly lead to passive-aggressive, judgmental, and dismissive behaviors. It's easier to express anger or frustration when hiding behind our keyboards. If you can't have a conversation and need to resort to email, ask yourself: would I say this if I was looking someone in the eyes and getting a real-time response? Or my favorite from my wall street days: would I be comfortable if the Wall Street Journal published this email?

A client recently sent me an email chain between her head of engineering and head of sales that consisted of 26 back and forths over three days. The exchange escalated to unprintable words. It was a classic chocolate conversation, and it permanently scarred their relationship. A phone call or video chat on day 1 would have saved them time, anguish, and their relationship.   

Texting/IMing: Speed and Brevity over Clarity

How often do we call someone, get their voicemail, hang up, and then send a text?

Ever stop to think how inefficient that is? But the reality is that people check their text messages much more frequently than voicemails. For Millennials and Gen Z’ers, it has been their primary form of communication since they received their first cell phone (which, on average, is age 10). A recent survey revealed that 74% of Millennials prefer communicating digitally.⁷

This hit home for me when I hired a young analyst in my last job on wall street. 

We had an open trading desk, and in the interest of mentoring him, I positioned him at a desk across from mine. The only thing separating us was our four large computer screens. His first day on the job, I welcomed him and said if he had any questions, just ask. About 20 minutes later, he had a question, but rather than asking, he IM’ed me. 

Texting, like emails, exacerbates passive-aggressive behavior, limits emotion, and emphasizes speed and brevity over clarity.  

All of these factors create digital chocolate conversations. 

Touch: Human Connection is our Lifeblood

The great news is that we only need to connect on a human level. 

Pick up the phone, set up a video chat, or ideally, have an in-person conversation. 

We all need human interaction or what we call “touch.” We just need it to different degrees, as my colleague Frank Mazza explains. Touch is at the core of who we are as human beings; it creates bonds and connectivity that digital interactions cannot. It allows us to understand each other in more profound ways. 

A few years ago, HotBlack Coffee in Toronto defied the growing trend of coffee shops and celebrated NOT offering Wi-Fi service. Jimson Bienenstock, CEO of HotBlack, explained, "It's about creating a social vibe. We're a vehicle for human interaction, otherwise, it's just a commodity." 

Mr. Bienenstock understood what a 1965 study of 7,000 men and women in California showed. "People who were disconnected from others were roughly three times more likely to die during the nine-year study than people with strong social ties," John Robbins explained in his book on health and longevity, “Healthy at 100.”⁸

The notable takeaway from the book is that social connectedness was the primary factor in survival. Connection exceeded other factors like people's age, gender, health practices, or physical health status. The study found that "those with close social ties and unhealthful lifestyles (such as smoking, obesity and lack of exercise) lived longer than those with poor social ties but more healthful living habits." However, not surprisingly, "people with both healthful lifestyles and close social ties lived the longest of all."

How to Avoid Digital Chocolate Conversations

The social connection that helps us live longer also helps us to avoid digital chocolate conversations. When we have one-on-one conversations and connect personally, we are more likely to share our worldviews, standards, and concerns. 

Here are six ways to avoid digital chocolate conversations:

#1 Have one-on-one conversations

In this new world of hybrid work, human connection has never been more important. We need to make extra effort to replace the old water cooler/hallway conversations. Schedule regular one-on-one conversations with team members weekly, bi-weekly or at the least monthly, and schedule quarterly one-on-ones with different colleagues in other areas.

#2  Take it Offline

When an email you are writing, or an email chain you are on, is getting too long, pick up the phone. If an in-person conversation or video call is possible, even better. Two-way communication enables context for worldviews and standards to be understood, and concerns to be raised. Questions can be asked and confusion addressed real time. 

#3 Connect Personally

When you start a meeting, take time to connect personally, rather than diving right into the work. Start conversations by asking your colleague, "how are you/your family doing?", "Did you have a good weekend?", "I know your dog had surgery. Is she doing all right?"  When we connect personally, we better understand how people see the world, their standards, and what causes them concern. 

#4 Provide Context 

After taking time to connect personally, provide context for the subject that you want to discuss. Take time to explain how your worldview shaped your perspective on the subject. Give some background about other meetings/conversations you have had that pertain to this work. 

#5 Encourage Questions and Concerns

At the start of the meeting, encourage colleagues to offer questions, concerns, and what needs clarification. Too often, we only leave time to explain whatever we need to explain (the solution we are trying to solve, the task we need accomplished, the problem we are trying to address). Before the meeting ends, make sure everyone feels heard. 

#6 Devices Down

Finally, there is no better way to ruin a conversation than by being on a device while talking to someone. This has become much more prevalent on video calls. When you think you are subtly checking email or texts on a video call, it is obvious to everyone. Give the person your undivided attention, and give yourself a break from your emails and texts. 

Connecting in this new hybrid world

The advent of the internet, email, texting, and social media introduced a new opportunity for misinterpretation and misunderstanding. COVID-19 accelerated the trend towards these digital forms of communication, which in turn, increased the number of chocolate conversations. 

Chocolate conversations are detrimental to our relationships, personal well-being, productivity, and success. The great thing is that returning to our roots of human connection is the key to  addressing this challenge.

In this new hybrid world, we will all benefit by taking the time to connect and understand each other's worldviews, standards, and concerns.

Hungry for more? Order your copy of The Leadership Conversation on Amazon or read more about Rose and her new book on the leadershipconversationbook.com.

You can also snag a copy of her first book, The Chocolate Conversation.

David Frost is fassforward’s Head of Executive Coaching and Managing Director. He strives to do good work for good people. He also focuses on business development and operational improvement. David previously spent 20 years on Wall Street. He received his A.B., magna cum laude from Princeton University.

Eugene Yoon is a graphic designer and illustrator at fassforward. She is a crafter of Visual Logic. Eugene is multifaceted and works on various types of projects, including but not limited to product design, UX and web design, data visualization, print design, advertising, and presentation design.

¹ Fass, Rose “The Chocolate Conversation” Bibliomotion, 2013
² Fass, Rose “The Chocolate Conversation” Bibliomotion, 2013 pg 19
³ Pew Center for Research, “Smartphone Ownership 2013” 2013
⁴ eDigital’s Customer Service Benchmark, https://econsultancy.com/consumers-prefer-live-chat-for-customer-service-stats/, November, 2013
⁵ The Next Web, “Digital Trends 2020” January, 2020
Pure Commercial Finance “The Average Worker Has 651 Unread Emails in Their Inbox”
⁷ Stacey Hanke, https://thriveglobal.com/stories/how-social-media-affects-our-ability-to-communicate/
⁸ John Robbins, “Healthy at 100” Random House, 2006

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