Challenge Strategist’s Role at the Start-up Workshop
Challenge Strategist's Role at the Start-up Workshop
As a 100-Day Challenge Strategist, you are the architect of the enabling environment in which the 100-Day team operates. You need to steer away from “Business as Usual” management and toward a leadership style of Confident Humility.
Deep Dive Video
The 100-Day Challenge Strategist's Mindset
There are three core principles that guide the Challenge Strategist mindset:
Radical Experimentation
The Strategist gives the team explicit permission to fail. They need to tell the team: “Making mistakes is okay; we are here to learn and pivot, not wait for permission”.
Confident Humility
A strategist acknowledges that they don’t have all the answers. The message should be: “If we knew the solution, we would have fixed it already. We trust you to figure it out”.
The Power of Absence
The Strategist leaves the room after the opening session. This signals trust and allows the team to set SMURF goals without feeling the need to “please the boss”.
Managing the "Sandwich" Workshop Element
The Opening Session
The opening session is the Challenge Strategist’s opportunity to set the “Rules of the Race” and ignite the team’s momentum. The Coach helps the Strategist prepare talking points that move away from corporate updates and toward a high-stakes mission brief.
The "Why": Recapping the Focus Area
- The Strategic Context: Briefly recap the chosen focus area and its connection to the broader National Strategic Plan (NSP) on GBVF.
- The Rationale: Explain why this specific problem was prioritised now. Is there a persistent gap in local services or a critical data bottleneck that needs a 100-day sprint to resolve?
The "Who": Rationale for the Team
The Strategist must explain why this specific “multi-sectoral” group is in the room.
- Institutional Choice: Clarify why certain departments or organisations are represented, and others are not—focusing on who has the most influence over the targeted “impact indicator.”
- Individual Selection: Explain that these specific individuals were chosen for their expertise, proximity to the problem, and ability to innovate, rather than just their job titles or seniority.
The "What": Defining Expectations
- Experimentation over Planning: Clarify that the team is expected to move from “Business as Usual” to “Impact in Action”.
- The Deliverables: Explicitly state that by the end of the day, you expect a SMURF Goal and a 100-Day Plan centred on testing new ideas, not just creating more committees.
Handling the Q&A
Teams will naturally have questions about the Challenge Note.
- The Post-it Method: Instead of a standard Q&A, the Coach collects questions on Post-it notes during the briefing.
- Direct Answers: The Strategist should provide frank, honest answers to these questions before they transition to the “Team-only” part of the day.
Signalling Trust: The Strategic Exit
“By leaving the workshop after the opening session, the Challenge Strategist sends a powerful signal: she trusts the team to do the hard work of setting the 100-Day Goal and developing the Plan without ‘pleasing the boss’.”
- The Promise: Before exiting, the Strategist must promise to return at the end of the day to hear the final 100-Day Goal and Plan and provide their full “Leadership Blessing”.
Unlocking "Leadership Gifts"
The Coach can also help the Strategist prepare Leadership Gifts — tangible ways to remove roadblocks during the opening session.
Ideas for Leadership Gifts:
- Mission Control Centre: A dedicated physical or virtual space for tracking charts.
- Flexible Funding: A small “innovation fund” free from standard red tape.
- The “Fast Track”: A commitment to prioritise procurement or approvals for this specific team.
- Roadblock Removal: Pre-signing data-sharing agreements between departments so the team isn’t stalled by legal hurdles.
- Connectivity Enablers: Providing data cards or tablets to ensure instant communication.
The Closing Session - Securing the Blessing
The closing session is the second half of the “Sandwich” structure. After working in isolation to build their mission, the Team now welcomes the Challenge Strategist back to the room to present their vision and secure the leadership support needed to start the race on Day 1.
The Reveal: Presenting the Destination
The Team Coach officially welcomes the Strategist back into the workspace. The Team Leader then takes the lead, presenting the two core outputs of the day:
The 100-Day Goal: The Team reads their scarily ambitious SMURF Goal aloud.
The 100-Day Plan: The leader provides a high-level walkthrough of the “Swim Lanes” and immediate actions for the first 30 days.
The Four Pillars of the Presentation
To ensure the dialogue is productive, the Team Leader should structure their highlights around these four points:
- The Spark (Excitement): What innovative or “out of the box” ideas is the Team most eager to test?
- The Hurdle (Worries): What feels particularly unsettling or difficult about this goal?
- The Ask (Support): What specific resources or “Leadership Gifts” (e.g., funding, data access, or fast-tracked approvals) does the Team need to succeed?
- The Insight (Advice): What specific strategic advice does the Team want from the Strategist’s perspective?
The Leadership Response
The Leadership Response – Once the team has shared their plan, other members can “pitch in” with their perspectives if time permits. The Challenge Strategist then responds using these principles:
The Golden Rule of Feedback: Err on the side of being overwhelmingly positive. Focus on the innovation and commitment present in the plan rather than fixating on what is “missing”.
- Acknowledge the Ambition: Validate the “Unreasonable” nature of the goal as a sign of the Team’s commitment to the NSP.
- Commit to the Partnership: Confirm that the requested support will be provided, reinforcing the Strategist’s role as an “enabler”.
- The Blessing: Formally give the “green light” for the Team to begin their sprint the following morning.
Download a draft “script” of the Opening and Closing Session to help you.
