Multiple Hats the Challenge Strategist

Multiple Hats of the Challenge Strategist

Challenge Strategists wear multiple hats during the 100-Day Challenge – alongside the role of the overall strategist of the Challenge (what to focus the Challenge and who to deploy to tackle it). These four additional roles are outlined below, with some guidance on each. 

Curator of the experience of the Team during the 100 days, creating the enabling environment for Team members

Coach & role model for the Team Coach and Team Leader, helping them reinforce the enabling environment for the Team

Custodian of the Challenge: Ensuring that the Team operates within the framework set out by the leadership stakeholders in the Challenge Note

Connector of the Team with other leaders and stakeholders, and mobilising support as needed.

Let’s examine each of the above ‘C’s and offer tips on indicators you can use to assess your success in that particular role. 

Curator
of the experience of the Team during the 100 days

  • Blocks interference and meddling from other leaders.
  • Encourages risk-taking and experimentation.
  • Shows curiosity and appreciation for the work of the Team.

Positive indicators

  • Team members take initiative and try out new ideas.
  • Team members from different organisations/departments work together seamlessly.
  • Team members hold each other accountable for the commitments they make.

Worrisome Signs

  • The Team Leader frequently reaches out to you to ask permission to do things.
  • Other leaders  jump in to give directions to the Team.

Coach and role model
to the Team Leader

Positive indicators

  • Team Leader reaches out to you for advice and guidance.
  • Team Leader expresses appreciation for the role you are playing.
  • Team Leader is growing and developing as a leader who empowers others on the Team.
  • Team Leader asks you for feedback after meetings you participate in.

Worrisome Signs

  • Team Leader does not feel comfortable sharing with you issues and difficulties. Their answer is always: “All is fine”.
  • Checking in with the Team Leader is a chore that you dread. It is filled with awkward silences.

Custodian
of the Challenge

Positive indicators

  • Team Leader refers back to the Challenge Note during the 100 day sprint. 
  • Team is tracking and reporting not only on the performance indicator in the 100-Day Goal but on other things that could be adversely affected by the intense focus on the Goal.
  • Team members are beginning to think about how the work will be sustained beyond the 100 days.

Worrisome Signs

  • Other departments and/or organisations are complaining that their issues  are not getting enough attention, and that all the resources are being diverted to the areas the Team is focused on.

Connector
of the Team with other leaders and resources

Positive indicators

  • Other leaders are showing interest in the 100-Day Challenge and reaching out to you for updates and offers to help.
  • Team members are getting positive feedback from their managers/leaders about participating in the 100-Day Challenge.

Worrisome Signs

  • Team members are being pulled away from their 100-Day Challenge commitments by their managers/leaders.
  • You are the only advocate for the 100-Day Challenge in leadership forums.  

Role of Challenge Strategist vs. Role of Team Coach

The 100-Day Team operates outside the existing organisational accountability structures. It is commissioned by a group of leaders who typically represent multiple organisations. So, the 100-Day Team is accountable to this group of leaders. 

But we all know how hard it is to have multiple people to be accountable to. This is why, in 100-Day Challenges, the group of leaders that commissioned the 100-Day Team ask the Challenge Strategist to represent them vis-a- vis the Team. So the Team has a single point of accountability.

The Coaches, by contrast, are designated b the Challenge Strategist to guide the Team through the 100-Day Challenge race. 

The Coach does not represent the Challenge Strategist or the other leadership stakeholders. Their role is to guide and support the 100-Day Team and to advise the Challenge Strategist about their role during the 100-Day race. 

So there is an accountability relationship between the 100-Day Team and Challenge Strategist. The Team, or the Team Leader, “reports” to the Challenge Strategist. 

However, it is important to note that one of the reasons that 100-Day Challenges are so impactful is that they involve a very unique way to handle power within and between organisations. So even though the Challenge Strategist is in a position of power vis-a-vis the Team, the 100-Day Challenge is an opportunity for the Challenge Strategist to practice “power with” and “power through” the Team versus “power over” the Team. 

This is what we refer to as leading from a place of “confident humility”. 

So the two roles are different, and both are important and needed. More often than not, both Coaches and Challenge Strategists provide support to the Team (and especially the Team Leader). 

At times, the Coach will advise the Challenge Strategist to play a heavy-handed role with the Team if, for example, Team members start drifting away from their 100-Day Goal. This heavy-handed role cannot be played by the Team Coach, as the Team does not report to the Coach. 

Thought starter reflection questions

Jot down thoughts on these questions – to the extent they are relevant to your experience at the session:
  • When did the mood in the event shift from “why are we here?” to “this could be interesting – I am excited to be part of this.” What triggered this shift? 
  • When did you have to go “off script” on the agenda or to change the agenda? What triggered this? What did you adjust? How did it go?
  • What was most surprising to you at the event?
  • What new insights did you gain about the issue at hand, and about the way leaders in the system interacted with each other?
  • Where did the conversation get stuck? What got it unstuck?
  • How would you characterise the level of trust among participants in the meeting? To what extent did this shift as the meeting progressed? To what do you attribute this shift, if indeed it happened?

Thought starter...

Reflection Questions 

Jot down thoughts on these questions – to the extent they are relevant to your experience at the session:

  • When did the mood in the event shift from “why are we here?” to “this could be interesting – I am excited to be part of this.” What triggered this shift? 
  • When did you have to go “off script” on the agenda or to change the agenda? What triggered this? What did you adjust? How did it go?
  • What was most surprising to you at the event?
  • What new insights did you gain about the issue at hand, and about the way leaders in the system interacted with each other?
  • Where did the conversation get stuck? What got it unstuck?
These are 100-Day Challenge Mentors. 

They did some work before you received the Challenge Note. This included:

  • Writing the Challenge Note, and making sure that the leaders of all the organisations represented on the team are comfortable with it – and committed to supporting the work of the team
  • Helping the leaders of these organisation recruit you and your colleagues to the team
  • Gathering some baseline data and other information that will help you and your teammates set your 100-Day goal and develop your plan.
  • Making sure all the preparations are made for a successful Lift-Off workshop, when you and your teammates will meet and get your 100-Day Challenge started. This includes venue, facilitation support, food, swags, comms, travel arrangements and whatever else is needed.

 

Mentors will participate in all or part of the Lift-Off Workshop, mostly at the start to provide context and answer questions, and at the end to give you and your teammates feedback about the goal and plan you develop.

During the 100 days following the Lift-Off Workshop, here’s what the Mentors will do:  

  • They will check in every two weeks with the team leaders to see how the team is doing and what support they and the team need.
  • They will keep other organisational leaders informed and engaged during the 100 days, and pull them in to help as needed.
  • They will participate in the last part of the Refuelling Workshop, halfway through the 100 days, to see what additional support the team needs, and to begin to plan with the team for sustainability and scale-up.
  • They will work with the team at the Sustainability Workshop to finalise recommendations on sustaining the results and building on the work of the team.