Coaching the Challenge Strategist

Coaching the Challenge Strategist

The way the Challenge Strategist interacts with the Team Leader and the Team is critical for the experience of the team and their success. 

The Role of the Challenge Strategist

The Challenge Strategist will provide the inspiration and energy to bring 100-Day Challenges into existence, and will put them on the proper track to run their race. The Challenge Strategist will also cheer the team along during their 100-Day race. In short, it is a very critical role.

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.

Tips You Can Offer the Challenge Strategist

Here are some tips you can offer the Challenge Strategist during the 100-Day Challenge. Ideally, you can offer these tips in response to specific situations they describe or guidance they seek.  You can also offer these in anticipation of situations.

Offer support and avoid offering solutions

Once the team decides on a course of action, ask: “What support do you need?” It’s important to be honest about what you can and cannot do, and don’t be afraid to say, “I don’t know but I will find out.” Then do so quickly!

Praise the 75% that is right, rather than point out the 25% that is wrong

It is more impactful to praise an idea’s positive aspects and ask the team to build on them than to focus on its negative aspects. Instead of being the place where ideas get buried, the Challenge Strategist can become the person the team comes to to bounce ideas off.

"How can I help?"

This is among the most powerful combinations of 4 words in the English language. Challenge Strategists can use it in their informal weekly or bi-weekly check-in calls or emails with team leaders. Along with another powerful phrase: “how are things going?” If this does not open the conversation up, mentors can use some of the follow up questions in the Coaching tool.

Why the Role of the Challenge Strategist

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.