The Future of Speaking

Part 1 · Why we gathered

Your voice is the neck of the bottle

Marc Williams, SSA co-founder and former high school English teacher, opened the roundtable with a story about a college professor who stood in front of his class and shook a bottle of soda until the students in the front row flinched. He never opened it. His point was that the bottle can be full of brilliant, creative, fizzing ideas, and none of them get out until the cap comes off.

“It doesn't matter how brilliant the ideas inside you are. If you don't open your mouth and speak up, speak to, and speak with, nothing happens.”

Marc Williams, Co-founder, SSA

That cap is getting tighter, and Marc pointed to new research showing that we are simply talking less than we used to.

The room named the likely causes: texting instead of calling, a hybrid world that has quietly become a siloed one, conflict that makes it harder to trust each other, and AI doing more of our thinking and talking for us. Whatever the mix of causes, the consequence is the same. A community can't move forward when its people stop speaking up for each other, to each other and with each other.

The goal for the day was to get better at this before it gets worse, trusting that the best answers were already sitting in the room.

Part 2 · How the room worked

A roundtable built on reps, not panels

True to the Skills Drills™ approach that SSA is known for, nobody delivered a keynote. Every segment sent participants into small breakout groups and then brought their best thinking back to the full room, and each format is a tool any leader can take back to their own team.

Part 3 · Living Room Conversation

Is AI helping us build trust faster, or letting us skip the part where trust gets earned?

Teresa brought this question from 2 very different chapters of her career: facilitating a community coalition tackling youth substance abuse, and helping build the national data standards that now connect electronic health records across the country. Both taught her the same lesson.

“Change really does move at the speed of trust. AI is moving at the speed of compute.”

Teresa, Roundtable participant

Cathey Armillas added that we only get the best out of technology when we put our best human thinking into it. AI can be a great thinking and creative partner, but too many people are using it to skip the thinking altogether and jump straight to the finished product.

What the breakout rooms said

• Real conversation can matter more than the right answer. When we stop hunting for the answer and simply talk, we discover the information and each other at the same time.
• Imperfection is believable. Gina records her LinkedIn videos from a few bullet points with no rehearsal and no editing, and she believes that unpolished honesty is exactly why her audience trusts her.
• AI-sounding content costs the person, not the tool. When a post reads like a robot wrote it, readers don't just dislike the post. They begin to wonder whether they trust the person who shared it, which makes authenticity the real source of legitimacy.

Rose raised one more tension worth sitting with. People change slowly, even when the change is good for them, while the tools change overnight, and the gap between how fast trust is built and how fast we adopt new technology may become one of the defining communication challenges ahead.

Part 4 · Living Room Conversation

If technology can do it faster, what human skill should we double down on?

Cathey asked this question as both a speaker and a coach who trains teams, and she framed it for ourselves and for the people we lead: which skill is worth practicing harder now that machines can do so much of the rest?

Marc's answer surprised the room, because it was handwriting. After catching himself letting AI build a workshop for him, he decided to put a notebook and pen back on his desk so he could step away, form the idea himself and only then bring the tool in to help refine it. His second answer was the human skill of opening a conversation with a question, especially as more young people turn to technology for the advice they once got from each other.

“After presenting it, I didn't feel good, because it didn't feel like me. Even though it may have been better written.”

Colleen, on giving an AI-polished talk

Colleen, a technical writer who writes for executives, described running her own company talk through an AI tool that tidied up her structure. The content was solid, but she hadn't left herself time to merge it back with her own voice and energy, and she could feel the difference on stage.

Rose had seen the same thing at a live event the night before. A strong panel held the room for most of the evening, and then a sponsor stepped up and read what was clearly an AI script. The stage and the microphone were the same, yet the energy in the room dropped the moment the words stopped sounding human.

The case for “yes, and”

The room didn't land on a simple verdict that AI is bad and pens are good. Marc admitted that his first AI experiment happened when someone needed a message sent 5 minutes before he left the office, and speed won. One participant said an AI note taker made her a more present listener once she broke the habit of scribbling, while Amy, drawing on 32 years of coaching, pointed out that writing by hand is a proven part of how we remember, even if we never reread the notes. Cathey described writing while a client talks because that is when her best coaching ideas surface. The common thread was intention: choose the tool on purpose, and then add the human layer the tool can't provide.

Part 5 · Case Lab

2 workplace problems, solved by strangers

Case 1: Nobody speaks up

A company is desperate for honest feedback and keeps launching new tools to collect it, yet nobody uses them. Alexina reported her group's diagnosis, which was refreshingly blunt: the company is substituting tools for trust. Here is the playbook the group built.

• Check the foundation firstLook at whether your values or mission even mention openness and trust, because if they don't, that is your starting point.
• Ask better questionsPeople may be willing to give feedback, just not to the questions you are asking, so ask whether your stated values match what they experience day to day.
• Audit psychological safety at the topPay attention to how senior leaders behave, how they handle bad news and how openly they explain decisions, since a loud rumor mill is usually a signal.
• Say it, do it, then say it againShow people that you have their growth in mind, and then remind them that you followed through.
• Close the loop out loudThe gap between hearing a concern and delivering a fix can stretch from 6 months to 1 year, so keep telling people what you heard and what changed.
• Train line managers to listenTeach managers which questions to ask and how to respond when someone brings a concern, and remind them that you have to give trust before you can expect it back.
• Build 2-way time into the calendarTeresa suggested deliberately scheduling time for information to travel up the chain and back down again.

The group also named an uncomfortable root cause. Some leaders don't want to hear about problems because they are short on time, short on people skills or quick to hear criticism as a personal failure, and spotting that pattern is the first step toward working on it.

Case 2: The AI-powered executive

A CEO is sending communications faster than ever with AI help, and employees say the messages feel hollow. Rose, George and Amy agreed that most of us have been on the receiving end of that feeling.

“Bring the HI, the human intelligence, back into the AI group chat.”

Rose, Roundtable participant

Their fixes were practical. Treat an AI draft the way executives once treated a speechwriter's draft, with a real review for anything that doesn't sound like you, and put your own eyes on every message before it goes out under your name, because sending more messages doesn't matter if the message isn't landing. George shared that his doctoral cohort wrote its own ground rules for AI use, including raising hands on Zoom so nobody quietly pastes in a chatbot's answer as their own thought, and Rose encouraged every team to write rules of its own.

Leave room for questions

Marc closed the Case Lab with a confession from his teaching days. When he led tours of his school, he took pride in finishing with zero questions because it meant he had covered everything, and he now sees that as a missed opportunity. AI makes it easy to cover everything, and if that crowds out the space for questions and conversation, we lose the part that makes people feel connected. As Cathey has long coached him, it is better to give people just enough to make them want more.

Part 6 · Open Space Protocol

3 topics the room chose for itself

Preserving the human connection

Alexina proposed this topic, and Amy, a business owner, shared how she creates deliberate occasions for her team and clients to come together. Many of them are built around service, so everyone has a role and real relationships form outside the usual work. The group also made a strong case for dogs in the office, since it is hard not to be human around animals, and the room happily named it creature connection.

Communicating across generations

Colleen asked whether leaders should stop assuming that people in their 20s and 30s want the same communication skills and training that earlier generations did. Marc noted that the New York City public school system now has 5 generations working side by side. One approach that works is to give mixed-generation teams the same workplace scenario, such as how to tell your manager you are running late, and compare their answers so the goal becomes understanding rather than agreement.

“I still wouldn't do it, but at least I understand why you do it.”

Marc Williams, on cross-generational scenario work

Prompt literacy and the evolution of language

George proposed this topic, and the room questioned whether elaborate prompt engineering is worth the effort. Teresa's view was to keep it simple, and Cathey noted that today's tools increasingly decode messy, misspelled requests on their own. The deeper question was how to keep an authentic voice when a machine is helping you find the words.

Part 7 · Closing Skills Drill

Debate to Connect: ask before you answer

Cathey closed the day with a short version of one of SSA's most popular sessions. The idea is that when someone says something you disagree with, connection doesn't come from taking the floor. It comes from asking questions that help you understand where they are coming from, starting at the surface and working your way deeper. These are the questions the room built together in real time.

The most honest moment of the drill came when Gina admitted that the last example was hard, because every question she reached for carried a little of her own judgment. That is exactly why it is a drill: getting curious without getting judgy takes reps.

Part 8 · What leaders can do now

The future of speaking might be a question

Marc closed with a thought that stayed with everyone. Children ask hundreds of questions a day, but by adulthood that number drops to about 6, because grown-ups are expected to have the answers. The future of speaking may depend less on making better statements and more on asking better questions.

• Draft human firstForm the idea yourself, on paper if you can, and then invite AI in to refine anything that will carry your name.
• Protect your imperfectionsA stumble or an unpolished sentence is proof that a real person is talking, so resist the urge to edit out the evidence.
• Stop buying tools to fix trustFeedback follows safety, so fix how leaders listen and respond, and then close the loop out loud.
• Write your team's AI ground rulesDecide together when the tools help and when a human voice is required.
• Leave room on purposeCover a little less and leave space for questions, because that is where people connect.
• Let your team pick the topicsRun an open space session and find out what people actually want to talk about.
• Practice like an athleteSpeaking, listening and curious questioning are skills that get better with reps, not with reading about them.