DC72: Part 5: AI Collaboration
Case Studies & Real-World Scenarios
“I think what makes AI different from other technologies is that it’s going to bring humans and machines closer together. AI is sometimes incorrectly framed as machines replacing humans. It’s not about machines replacing humans, but machines augmenting human collaboration.”
— Robin Bordoli
In this chapter, we explore four real-world scenarios that represent the kinds of complex, adaptive challenges strategic leaders face. These aren’t theoretical examples, they’re the same case problems used in our in-person meetup and AI Collaboration Course. Each one comes from the problems we help to solve in our consultancy, and what our soon-to-be-released Deeper Change AI Bot is designed to help teams solve together.
AI isn’t the hero in these stories; collaboration is. But AI plays a powerful supporting role, helping people clarify, align, experiment, and decide.
1. Disjointed Transformation
A company’s leadership team has launched a major transformation, but something isn’t landing. Tooling is inconsistent, communication feels top-down, and the delivery teams don’t feel heard.
Your challenge: Use AI to cut through confusion, analyse mixed messages, and surface the real blockers. Then, synthesise recommendations that help rebuild clarity and coherence across the organisation.
You’ll receive: a transformation overview, real bios, meeting notes, and pain points from both leadership and team levels.
This is the first case study we tackle together in the course; learning the tools, hacks, and team collaboration patterns as we go.
2. Designing Learning That Lands
You’ve been asked to design a high-impact leadership development journey, on a short timeline and with diverse learner needs.
Your challenge: Use AI as your design partner. Work with your team to turn fuzzy strategic goals into a clear learning experience. Co-develop modules, generate inclusive exercises, and iterate based on participant personas.
AI will support the design process, but it’s your collaboration and critique that makes the learning meaningful.
3. Resistance Behind the Silence
A department is quiet. Too quiet. Engagement survey results are flat, town halls feel performative, and no one is raising concerns directly.
Your challenge: Work with AI to simulate stakeholder conversations, uncover hidden resistance, and frame coaching questions that surface unspoken dynamics.
Then, use those insights to shape a re-engagement plan that meets people where they are, not where leaders wish they were.
4. Choosing the Right Strategic Future
The board is split. Some want to consolidate, others to expand into adjacent markets, and a bold few argue for disruption.
Your challenge: Use AI to stress-test each scenario. Build comparisons, risk models, and stakeholder narratives. Help leaders move from opinion-based debate to values-based decision-making.
This scenario trains teams to use AI not as a decision-maker, but as a lens to explore implications, clarify values, and guide discussion.
Conclusion: Working with Complexity in Real Time
The scenarios in this chapter aren’t puzzles to be solved once, they’re doorways into the kind of messy, shifting challenges that leaders face every day. These are complex and adaptive issues, where solving one part often disrupts another. The very nature of systemic change means unintended consequences will arise. This is where collaborative AI becomes invaluable.
Rather than trying to control complexity, teams can use AI to engage with it, rapidly exploring perspectives, simulating interventions, and surfacing implications. Wicked problems may remain sticky, but AI allows us to analyse faster and make sense of live data in context.
As new dynamics emerge, they can be fed back into team-based AI sessions. This creates a learning loop where people aren’t waiting on consultants or quarterly reviews, they’re adapting in near real time.
Just as agile ways of working helped product teams iterate faster, collaborative AI equips strategists, change agents, and managers to do the same across whole systems. It deepens understanding and speeds up strategic sensemaking, helping groups move forward together with more clarity and less drag.
I am currently looking for some contract work where I can help your organisation be even better.
Please get in contact if you would like to discuss whether I would be suitable or not.
Subscribing
Please create a paid subscription if you want to comment on this article or support the writing of these articles.
A subscription costs the same as buying one book per year.
Sharing and liking
I would appreciate it if you shared this article with your network if you think they would be interested. Please like this article if you find it valuable.
Thank you.