On July 29, a Reimagining Agility workshop took place immediately following PMI Agile 2026. More than 90 enthusiastic participants joined the in-person session, bringing energy, passion, commitment, and plenty of actionable ideas.
The workshop, part of an Agile Alliance Board initiative, was led by board members David Luke, Margareth Carneiro, Apeksha Patel, and Darci Dutcher. Agile Alliance Managing Director Denise Jarvie opened the session and welcomed the participants.
The Reimagining Agility initiative is envisioned as the ears (listening closely to our community), the legs (reaching communities across the globe), and the arms and hands (putting forward concrete actions). This was the latest in-person workshop in the series, with more to come.
The workshop provided a space for Agile practitioners and leaders to sit with complexity and learn in public. Over the four hours, board facilitators and participants worked in small, self-directed groups to explore and select the “wicked problems” each group would focus on. Wicked problems are those that don’t have clear owners or clean solutions—the tensions many of us are already living with but rarely get time to explore together.
Some Common threads
The workshop participants broke into five working groups, each focusing on some of the Agile community’s biggest current challenges. These three threads ran through each working group’s findings:
AI with responsibility
The community needs ethics, guardrails, playbooks, and a maturity model to adopt AI while ensuring people remain at the center of decision-making and value creation (human in the loop, ADKAR, new roles, and upskilling).
Hybrid, with data and trust
Rather than pitting Agile against Waterfall, we should create delivery systems that balance predictability, adaptability, and value delivery, and prove the results with data rather than labels. Metrics should build trust and context, not fear. Psychological safety should be a precondition.
Role clarity and evangelization
Agile roles need definition, a skills/value matrix, and career paths that make sense outside of IT. Facilitation and Agile success stories need to be published, distributed, and evangelized.
The Five Wicked Problems
Here is a rundown of each of the workshop breakout groups and the wicked problems that they focused on.
Wicked Problem 1: Ethics and AI Adoption
This group organized its problem into three component parts – all anchored in the values of the Agile Manifesto.
Ethics – what does it mean here, who controls the AI, how is its use disclosed, and who is accountable when it fails — with copyright, job loss, and “maintaining human primacy” all also on the table.
Interactions – roles are changing, and we haven’t defined the boundaries between humans, robots, and agents. The group flagged over-delegation (“trust and abdication”) as a real risk, alongside losing the human connection that makes collaboration work.
AI Adoption – There are different paces of AI adoption; output is fast, but review isn’t. Is the output valuable? Are skills keeping pace? Are teams drifting into “electronic groupthink”? And who owns the risk when an agent gets it wrong? Many of these challenges reflect a broader reality facing organizations today: success with AI depends not only on technology, but also on the ability of people, teams, and organizations to adapt.
Some Possible Solutions
Create a charter that covers the disclosure of AI use, intellectual property (IP), accountability, and data. Write a playbook that considers the human (ADKAR model), identifies new roles, and helps upskill and migrate people. Produce a maturity model playbook for determining how to measure success. This playbook would detail the AI adoption levels (generative, agentic, and agents), with content distributed into chapters, including sustainability, maintainability, scalability, observability, and compliance.
Into the world
The charter, playbooks, and maturity model are meant to be published artifacts — things a practitioner can pick up and use, not position statements.
Wicked Problem 2: A hybrid delivery system: predictability + flexibility
Most real environments are already hybrid. The question isn’t whether to blend Agile and traditional approaches — it’s how to make the blend work, so you get the benefits of both instead of the frustrations of each. The group’s stated goal: create a delivery system that provides predictability and flexibility.
What the group proposed
- Agile teams inside traditional gates. Attach Agile events to required milestones, run mini-gate reviews mid-sprint so feedback lands in the retro. And shorten sprints where customer deadlines demand it.
- Show leadership, don’t tell them. Use empirical data to demonstrate the advantage of Agile approaches. Practice it without insisting on the label — let flexibility improve predictability and let the results make the argument.
- Schedule Risk Analysis. Fold risks and mitigations into Monte Carlo-based forecasting, plan intentionality into the schedule, and gamify the data so people engage with it.
- Stop treating Agile and project management as career tribes. Build career paths that combine delivery leadership and project management, with shared language and shared education.
The group also sketched a decision flow for PMOs deciding how to run a given effort:
Into the world
Recommendations from the group include publishing data-rich case studies, guidelines, and white papers aligned to Agile Alliance training; building a RAG-based assistant over a shared knowledge base; and collecting success stories and feeding them back through blogs and workgroups. The group’s rallying line was: Change your life. Change your org. Change the world.
Wicked Problem 3: Metrics, Trust, and Team Health
Problems and roadblocks
Metrics get weaponized. Leaders compare teams against each other, the C-suite competes on numbers, and teams respond by hiding problems in creative ways. A leader simply checking a metric is read as “something is wrong.” Add the difficulty of quantifying team health, the unanswered question of who defines business value, and how personally people tie themselves to their numbers, and you have a measurement system that erodes the trust it’s supposed to support.
What the group proposed
The group’s answer was to prioritize context before numbers — and they framed it as three user stories:
As a team member, I want to understand the “why” so I can contribute to business value. If I don’t feel safe sharing my ebbs and flows for fear of retaliation, psychological safety needs to be built into the culture.
As an executive, I need data to ensure benefits are realized. If the messaging isn’t landing, the fix is common knowledge, common language, transparency, and standardization.
As a manager, I want to honor both my team’s “why” and my executives’ “why” so that business value is realized. The problem: unbalanced whys — do I choose my team’s health or my exec’s happiness? The group left that one open on the chart, deliberately.
Around those stories, the group proposed the following: Define a clear North Star tied to customer, business, and organizational outcomes; invest in skills regardless of what the metrics say this quarter; make metrics more visual and transparent to lower anxiety; and train managers, team members, and executives on how metrics connect to business value.
Into the world
It all starts with us – effective leadership messaging, psychological safety resources, and change management training are all important items to consider.
Wicked Problem 4: Agile Roles, Careers, and Recruiting
The problem
The group traced a chain of consequences. Agile roles and adaptive leadership capabilities are often ambiguous inside and outside IT, the organization, and the industry. That makes them hard to recruit for and fill well. Under-filled roles cause problems on teams, so work gets delayed, and the conclusion is what it often is: “Agile doesn’t work.”
There are, of course, underlying causes. Agile titles don’t map to traditional org charts, aren’t understood outside tech, and are often company-specific in ways that hurt candidates when they move. Leadership makes decisions without giving teams the guidance to execute them. And scaling tends to strip away the autonomy that made the roles valuable in the first place.
What the group proposed
- A generic Agile capabilities/skills/value matrix and org chart, with job titles for each rung of the career ladder (junior through senior), focused on skills, capabilities, and value delivered rather than tasks. Keep it simple and generic enough to travel.
- Crowdsource the data from the community on titles, roles, responsibilities, and skills, then use AI to analyze it and build the matrix.
- A library of transferable skills mapped across projects and verticals and extended to the AI roles currently emerging, plus a way to describe what Agile teams deliver in traditional business terms.
- Engage academics to research which titles and structures best fit emerging roles.
Into the world
Publish and distribute widely to practitioners, leaders, recruiters, and educators.
Wicked Problem 5: Collaboration in Complex Contexts (Group Facilitation)
The problem
Our systems theory of collaboration, its practices, and tools are out of date. This group values the craft of group facilitation and its continuous improvement (by doing it and helping others do it), and sees focus, attention, and funding as the main barriers keeping others from developing it. The good news: facilitation transfers. These are capabilities, not a role.
What the group proposed
Evangelize by bringing data (for example, from BAI) and producing content like games, a community of practice, bite-sized videos, facilitation templates that go beyond ceremonies, a “phone a friend” network, and an honest list of what not to do. And demonstrate the financial value in dollars, not sentiment.
Into the world
The group’s ask: run experiments with data and results, leverage Agile Alliance and local chapters, launch marketing campaigns with an iterative improvement loop, and coordinate through a shared Slack channel to communicate what and when to boost social posts.
One Common Theme?
While the group discussions ranged from AI and metrics to delivery models, careers, and collaboration, a common theme emerged: organizations are searching for better ways to adapt, learn, and deliver value in increasingly complex environments. The many challenges explored during this Reimagining Agility workshop reinforce the importance of developing both organizational agility and the capacity to navigate continuous change.
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