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Questions to initiate meaningful conversation about change

The questions below can be leveraged as both a self-check tool to assess the depth of your business case and to help you orchestrate a meaningful conversation about change as you seek buy-in and sponsorship from key stakeholders. We got these extracted from Change in a Successful Organization: Avoid Complacency by Making a Case for Continuous Improvement Copyright © 2020 by IT Revolution


  • Why do we want to (or should we want to) undertake this change (e.g., vision, business case, benefits, WIIFM, etc.)?

  • What business challenge(s) are we looking to solve?

  • What is the negative impact of those now?

  • What is the potential negative impact of those in the future?

  • As a result of our change efforts, what do we expect people to be doing/saying differently?

  • How would this mitigate negative impacts in the short term?

  • How would this mitigate negative impacts in the long term?

  • What positive results could this yield?

  • How would stakeholders/stockholders respond to those positives?


  • Who may be willing and able (have the authority) to go to the lengths needed to inform, engage, communicate, and model leadership for, and during, change (e.g., visible sponsorship, remove barriers/impediments, etc.)?

  • Who must be willing and able to sponsor this change? (Note: Sponsorship is not support. Sponsorship is visible, active, and vocal.)

  • Do we agree on the product/feature priorities for the change effort?

  • Do we understand who, how, and where our work comes from?

  • Would multiple divisions be needed to implement and adopt this change (e.g., Business and Technology) to gain the highest value? If so, do we know key people in all spaces?

  • Do we have an initial understanding of who will be impacted (e.g., team members, foundational partners, dependents, SMEs, customers, etc.)?

  • Do the leaders typically agree on governance and performance objectives?


  • Do we understand and agree on the potential and /or prioritized scope of the work? Size and complexity?

  • What group(s) will be involved?

  • What products/features?

  • What tools will we use?

  • Do we understand and agree on what “readiness” means for the organization and for people as we look to start this change?

  • Do we understand the people and resources required?

  • Do we understand the time commitment and trade-offs needed?

  • Are the people in place? If not, do we understand what skills need to be sourced?

  • Do we know the framework we will utilize to prepare for, build, and launch this change (e.g., waterfall, Agile, other)?


  • Can we agree on a realistic/reasonable timeframe to create the needed team(s) who will do the work?

  • Can we allocate the time necessary to enable the team members to make the transition from current duties, work frameworks, and/or behaviors?

  • Can we agree on realistic timeframes and benchmarks for team delivery measurements/ metrics?


  • Do we understand how to effectively support the people through the change, including effectively communicating the changes and keeping the teams engaged and informed?

  • Are we willing to:

  • » Restructure?

  • » Lead by example? (Do we understand how this change may affect how all others work and what behaviors or skills they will need to learn and adopt?)

  • » Be a servant leader (i.e., empower those involved to self-organize by providing vision and removing impediments instead of taking control)?

  • » Intentionally change the culture (focus on moving to the future, rather than holding the past)? New principles, behaviors, and leadership.

  • » Go through the J-curve, in which performance initially decreases during the change and learning phase and ultimately rebounds following the change?

  • » Develop talent or hire the talent needed?

  • » Provide the learning / education needed for all team members to support this change?

  • » Identify minimal viable product (MVP), then minimum marketable features (MMF), so we can inspect and adapt along the way?

  • » Start small and expand to help grow understanding and gain advocates?

• Do we understand and agree on what measurements/metrics we will use to determine success? (OKRs, KPIs, ROI.)

  • » If yes, are they documented so we can socialize and track?

  • » If no, what must happen to establish and align?

Ref: Change in a Successful Organization: Avoid Complacency by Making a Case for Continuous Improvement Copyright © 2020 by IT Revolution

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