Artificial intelligence (AI) is a fast-moving target, and the conversation surrounding AI isn’t slowing down. New tools, new opinions, and a never-ending urgency to ‘figure it out’ pervade our everyday lives.
What’s harder than ‘figuring out’ something that’s constantly changing? Finding the space to practice and learn – taking the thoughtful, intentional time to ask questions and compare notes with people who are navigating that same uncertainty.
It’s this space that Jesslyn, a Manager in Siegfried’s Washington, D.C. office, set out to create by hosting an internal gathering that she called “The Smart Table.” Part connection event and part hands-on working session, The Smart Table gave Jesslyn and her Siegfried colleagues exactly what they needed to better navigate the fast-paced, ever-changing digital landscape – the chance to explore AI in a low-pressure, collaborative environment.
Taking a community-first approach
After wrapping up a client project, Jesslyn was looking forward to reconnecting with her Siegfried colleagues. Around the same time, she had been energized and inspired by a MY Journey® event that introduced practical ways of thinking about AI – seeing AI as not just a ‘buzzword’ but a strategic and valuable tool.
“Community is very important to me, and I wanted to be more involved,” Jesslyn said. “I wanted to connect with my Siegfried D.C. colleagues and find a way to do something meaningful with what we were hearing about AI.”
Jesslyn tapped into a personal passion of hers – event planning – and the idea for a gathering that blended AI curiosity with genuine connection took off. Soon enough, Jesslyn was crafting a unique experience – preparing AI exploration activities, transforming a Siegfried conference room into the perfect space for dinner and conversation, and welcoming 12 of her colleagues to The Smart Table.
“I aimed to balance a tactical and focused learning experience with a sense of community and fun, while also incorporating my own dedication to the details,” shared Jesslyn. “I wanted to create a space for attendees to explore how AI could elevate daily work, collaboration, culture, competitive edge, and human judgement – all while savoring delicious food and bold new ideas.”
A table designed for brainstorming and collaboration
On the night of The Smart Table, walking into the Siegfried conference room didn’t feel like entering a meeting. Brown paper canvases covered the table, ready for guests to take notes and make sketches. Printed menus lined each place setting. Blue cards with AI prompts were positioned face down, waiting to be flipped. Quiet background sounds lent a calm and fresh ambiance to the familiar space.
Jesslyn’s goal was simple: lower the stakes.
“AI can feel intimidating if you think you have to ‘get it right,’” she said. “The goal of The Smart Table was to feel like a conversation – to create a space where my Siegfried colleagues could try new things, laugh when they don’t work, and learn from each other.”
A format anyone could repeat
The Smart Table followed a structure that was deliberately replicable. “Just as AI powered the evening’s interactive challenges, it also powered the materials, meeting recordings, and even the recap assets, making The Smart Table a fully AI-augmented and easily repeatable event. An experience like this could be helpful for a lot of different people, across the Firm and beyond,” Jesslyn explained.
The Smart Table program
- 6:00-6:25 PM – Icebreakers
- 6:25-6:30 PM – Pre-Work Results
- 6:30-8:15 PM – Dinner and AI Prompts
- 8:15-8:45 PM – AI Speakers
Much like a typical dinner experience at a restaurant, The Smart Table featured a starter, main course, and dessert, in the form of both food and activities. “I had the full encouragement and support of the Siegfried D.C. leadership team to curate something unique.”
Ahead of time, attendees completed a short pre-work survey. It asked a few AI-focused questions around comfort level, areas of interest, and experience that the group had using AI thus far. The responses shaped the course of the evening and revealed an important truth: most people were curious about AI, but very few felt fully confident about leveraging it.
“The group’s insights informed my pre-planned themes and encouraged a thoughtful dialogue, making the night more interactive and grounded in participant perspectives,” described Jesslyn.
The Smart Table’s first activity, or ‘appetizer,’ was an icebreaker that Jesslyn called “CRIT & Cookies.” Based on a simple prompting framework she’d learned at MY Journey® from Geoff Woods, Jesslyn asked participants to share:
- Context from their work, where AI led them to feel stuck or inspired.
- A Role they’d assign to AI to help them.
- An Interview-style question they’d want AI to ask them.
- A Task they’d delegate to AI.
Within minutes, the table was buzzing.
“By incorporating a way we’d all been exposed to AI – through Geoff Woods at MY Journey® – I set the tone for collaboration and sharing. It was a non-edible, digestible start to the evening,” Jesslyn joked.
From there, the ‘main course’ was served. Participants split into pairs and flipped over their AI prompts, assigned by the blue cards on the table. Each pair tackled a different scenario, considering AI as it relates to collaboration, human judgement, competitive advantage, innovation, culture, and daily use. The six pairs used AI tools of their choice to brainstorm use cases and prepare a short presentation for the group at large.
Practicing AI responsibly and creatively
One prompt, nicknamed “The Invisible Assistant,” asked the assigned pair to imagine an AI tool that quietly supports their day-to-day without being asked. Similar to a task manager, it would summarize priorities, give gentle reminders, and reduce mental clutter. The pair sketched out dashboards, workflows, and even a concept for a personalized daily briefing.
Another prompt called “The Judgement Call” explored an important consideration when it comes to AI in financial reporting: where AI helps and where human judgment must stay firmly in control. Using real work scenarios, participants talked through what AI could reasonably support and when professional responsibility and accountability belong with people.
“Some guests were very comfortable experimenting,” Jesslyn said. “Others were more cautious and thoughtful about context. The contrast was the best part.”
Around the table, participants enjoyed great dinner conversation and shared how they approached AI depending on the situation or environment they were in. They asked each other questions, and, in some cases, suggested alternatives. The result wasn’t total agreement: it was learning.
“There was this shared understanding that you don’t have to have all the answers,” reflected Jesslyn. “You just have to be willing to listen and ask better questions.”
The final portion of the event was the sweetest – dessert! As baklava was passed around, two Siegfried professionals shared their real-world encounters using AI. “It was incredibly compelling for participants to learn from Jordan and Johnny as they shared where their Siegfried projects required them to think on their feet and use AI for creating quality work products. Their stories made the dinner practice prompts feel practical.”
Leadership without a title
For Jesslyn, the biggest takeaway wasn’t a specific tool or output. It was what happens when people are given room to lead.
“One of the many things I’ve learned at Siegfried is that you don’t need a formal leadership role or title to lead meaningfully,” she said. “You just need to care about the people around you and be willing to try.”
“The Smart Table wasn’t just a dinner; it was a shared moment of discovery, where AI became less of a buzzword and more of a bridge between ideas, people, and possibilities. Guests left with fresh perspectives and a renewed sense of curiosity.”
The Smart Table also sparked ideas about what could come next, for those at the table and in other areas of the Firm. At the end of the night, Jesslyn had achieved what she was searching for: momentum, community, and a way to set herself and her colleagues apart through AI curiosity and individual leadership.
Learning in layers
At Siegfried, we want our professionals to grow, not only through formal training but through shared experiences and individual interest. We know that AI capability doesn’t come from a single workshop. Instead, it’s built in layers: maintaining curiosity, engaging in practice-based learning, sharing personal use cases, and more.
The Smart Table is just one example of how we encourage Siegfried professionals to interact with themselves and those around them – specifically, remaining curious, making the space for learning, and building confidence through leadership.
If you’re a finance or accounting professional who’s curious about AI and motivated to learn, we’re looking for people like you. Explore careers at Siegfried.
Siegfried is committed to remaining at the forefront of artificial intelligence (AI) innovation, delivering AI-enhanced business solutions both internally at the Firm and externally for our clients. We support our professionals in continually upskilling, enhancing our collective approach to technologies like Generative AI and exploring emerging AI opportunities and business applications. This approach allows us to transform with the landscape around us, bolstering our ability to provide talent delivery, leadership advisory, and financial advisory support services to Fortune 1000 and other dynamic companies.
