Business conversations can be challenging at the best of times, especially when they are addressing sensitive topics. During economic downturns, they become even more fraught due to financial pressure and job insecurity. This leads to increasingly charged questioning from employees and clients alike. Arnnon Geshuri, the chief people officer at Teladoc, takes a proactive approach to difficult workplace talks. “It is important to be present and welcome hard conversations,” he says. “Many people avoid tough topics and either allow issues to fester or view the interaction itself as a source of stress. Rather, one should embrace issues even in the most challenging of situations.”
A big component of my job running a communications firm is to coach executives on how to deliver information in a relatable, trustworthy, and authentic way—especially true when there’s trouble in the water. Sounds easy enough, right? Well, time and again I’ve witnessed experts fumble questions that were asked unexpectedly, or were onerous by nature. This doesn’t have to be the case.
Difficult conversations emphasize the need for both preparation and understanding. While leaders never know exactly what someone will ask or what tricky dialogues they will encounter, here are three frameworks to compose—and deliver—genuine commentary during challenging situations.
Enact Radical Preparation
When comedians effortlessly deliver improvisational jokes or politicians take pressing questions in stride, there’s one key underlying force at play—preparation. This level of practice is paramount for leaders when delivering information, and especially true when there’s problematic content to share. At my firm, I work with companies to build out foundational “Home Base” points, which are the four main points they need to articulate in any exchange. Not only must they have these memorized to tell their story, but executives use this as a lighthouse to exit murky topics and stay aligned with what they’d like to discuss.
In addition to being so well practiced with fundamental messaging, it’s imperative to anticipate questions that may be asked. To keep leaders on their toes, put them through what my firm calls “Red Line” drills. Here, we repeatedly pepper executives with thorny questions to build up stamina and not get thrown off course in any conversation. It helps battle test them for when they are speaking on CNBC, in front of board members, or addressing their company. The rigor associated with this exercise helps remove the ego around an individual’s knowledge of a topic, and instead hones in on their ability to deliver it well.
Take Extreme Ownership
Former retired Navy SEAL officer Jocko Willink implores leaders in his now infamous TEDx Talk to take “extreme ownership” in every situation, especially when addressing a team during challenging moments. When tackling a difficult issue, it can be helpful to use “I” statements to express feelings and perspective. For example, Willink took full responsibility for failed battlefield actions, and then offered solutions to ensure they never failed that way again. It created even more confidence from his command cadre, as well as trust from his team. Similarly, using “I” statements at work can help leaders de-escalate situations, making it more likely that other people will feel engaged to listen and work towards durable solutions.
By respectfully approaching topics from one’s own perspective, someone can show the other person that they are genuinely trying to understand their thoughts. This mutual understanding creates a critical foundation to foster productive debate, an idea that Geshuri believes is important in healthy workplace culture. “To deliver sensitive topics, one should create an atmosphere for constructive discourse where everyone feels comfortable to challenge each other. Creating a space that is psychologically safe and empowers each person to openly debate ideas can be constructive for all parties and will unify the team towards achieving business goals.”
Embrace Technology
While little can replace a leader’s experience, technology can meaningfully augment their expertise to better handle difficult times. Today, executives can use AI tools at nearly every step of their information preparation and dissemination process—thus ensuring tough messages are well-crafted as well as most appropriately delivered.
By scraping sites like Quora, Queue.ai proficiently identifies high-value questions that are pertinent to the issue at hand, and then uses AI to supplement leaders’ own answers pertaining to these insights. Generative AI programs are also particularly suited for helping address tough talks. OpenAI’s ChatGPT is deft at churning out content in conversational tone from a simple text prompt. This model can help executives organize and formulate their thoughts, as well as create difficult questions for “Red Line” drills to test their delivery ability. Microsoft’s recent announcement to integrate ChatGPT into their Office suite will foster a more seamless workflow to rapidly generate content. Other unique gen-AI tools include Longshot’s FactGPT, which can also provide text-prompted material that includes source citations, Forethought to assist in customer support messaging, and Writer to streamline information dissemination.
While these emerging tools can help the difficult conversations process, leadership teams should ultimately be responsible for the final curation and dispatch.
Peter Weltman is a storytelling entrepreneur who used to report about wine regions in conflict zones, and now runs his own media firm, Man of the World Media. He also runs a social impact wine business, Borderless Wine, where he amplifies winemaking voices from Lebanon, South Africa, Israel, and more.
Recognize your brand’s excellence by applying to this year’s Brands That Matter Awards before the early-rate deadline, May 3.
