Strategic leadership questions to ask yourself

...before starting out on your change management initiative


Here are some good strategic leadership questions to ask yourself during the planning process.

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This list is not exhaustive but is intended as an aide memoire to kick start your thought processes and to help you avoid the 70% failure rate.

  • Have you thoroughly addressed the originating Strategic Review questions?

    • Where have we come from?
    • Where are we now?
    • Where do we want to be?

    In answering these questions, have you defined the cultural frameworks of your organisation – to show this is what we look like?

  • Where are the gaps between now and where you want to be?

    • Have you identified the areas of cultural dissonance?

    • Have you identified the positions of the key entities in your culture maps?







  • What steps are needed to close the gaps?

    • What are the implications of this?
    • Do you know the tasks / steps / processes to be undertaken to get from where we are now to where we want to be?

    • Have you identified for each step, the implications, issues and exposures that have to be addressed to progress to the next step?

  • How are you going to manage the transition?
    • How will you know how you’re doing?
    • Have you analysed, categorised and prioritised the issues arising across all functional areas impacted by the transition?
    • Are you using a structured Programme Management methodology?
    • If not, are you going to re-think this and take a strategic leadership decision to do so?
    • Do you have the skills in–house to do this properly?
    • Who is going to be the Programme Director with overall strategic leadership and ultimate accountability for the Programme [reporting to the board]?
    • Who is going to fulfill the role of Programme Manager with the responsibility for day-to-day management of the Programme, its risks, issues, conflicts, priorities, communications, and ensuring delivery of the new capabilities?
    • Who is going to fulfill the role of Business Change Manager(s) with responsibility for realising the benefits delivered by the change programme [ typically drawn from the areas of the organization affected by the changes and likely to be senior departmental management]?
    • Have these roles [and the names of those undertaking them] been communicated to staff?




  • Do you have a clear, defined and documented Blueprint?

    [A Blueprint that defines your changed organisation after completion of the Programme and the delivery of the benefits]

    • Is this Blueprint fully communicated to all staff?
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    • Is it going to be actively used in a structured manner to maintain focus throughout the duration of your Change Programme?

  • Do you have a definition and documentation for each Benefit?

    [Benefits are the whole raison d'etre for your Programme and are what usually don't get realised - as per the 70% failure rate!]

    • Have you documented what differences should be noticeable between now and the close of the change programme?
    • Do you have planned processes to put in place to ensure that these benefits are achieved?
    • Do you have a mechanism for measuring the improvements arising from the realisation of each benefit?
    • Are these benefits communicated to staff?

  • Do you have a Stakeholder Map?

    [A Stakeholder Map identifies all individual stakeholders and group of stakeholders and their particular interest in your Programme.]

    • Have you analysed the impact of the programme on their area of interest and the likely issues that will arise?

  • Do you have a two-way Communications Strategy?

    [The Communications Strategy for a programme defines how your stakeholders will be addressed. This is of strategic leadership importance to your programme. The greater the amount of change, the greater the need for clear communication about the reasons, the benefits, the plans and proposed effects of that change.]

    • What are the feedback mechanisms and processes that are actually going to make this a two-way communication process?

    • What are the processes that will ensure they are informed about the use of their feedback to influence the Programme?
    • What are the processes that will raise awareness of the benefits and impacts of the Blueprint?
    • What are the processes that will show that you are meeting the strategic requirements of the Programme sponsors [e.g. your board]?

  • Do you have an Issue and Risk Management Strategy?

    • What are the processes that will ensure that it is enacted effectively?
    • What are the processes that will ensure that it gives you early visibility of issues and risks?







Strategic leadership questions you should be asking yourself before starting out on your change initiative




Further resources

Vision and programme implementation




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