Preparing Your Organization for Transformation

We often have clients ask us about work they can do before a business transformation program gets underway, given how complex, cross-functional, and time-consuming major changes can be.

In response, we’ve compiled a transformation preparation playbook, including the various facets that are helpful to think through in advance of starting an operational or technology transformation. These include:

Phase 1: Preparing your organization

  • Decision-making and prioritization

  • Work management

  • Structures and processes

  • People and roles

  • Communication and alignment

  • Capacity and expertise

Phase 2: Defining the transformation

  • Customers and success criteria

  • Strategy and goals

  • Value stream / customer journey mapping

  • Financials and risk management

  • Transformation roadmap

Phase 3: Planning the transformation

  • Program structures and practices

  • Transformation teams and cadences

  • Key enabler readiness

  • Testing approach and defect management

  • Training approach and change management

  • Implementation approach

Today’s blog addresses the first phase: preparing your organization.

It includes questions to ask in each of these areas. Since every organization and every business transformation is different, there is no one-size-fits-all answer. It’s more about getting on the same page throughout your organization. We’ve included guidance where we can, and we’ve included real-world examples to illustrate how this can look.

The transformation preparation groupings build on each other, so it’s typically most effective to address them in the order listed. If needed for timing or buy-in, Phase 1 and Phase 2 can be tackled in parallel.


Decision-Making and Prioritization

Teams need to work productively together in a transformation program. Information is often in short supply, options may not seem clear, and disagreements can bubble up. Here are audit questions and guidance to succeed in decision-making, prioritization, and conflict resolution.

Decision-making audit questions:

  • Is it clear who makes decisions and how?

  • Are you confident that follow-up items will be taken forward?

  • When you reach a critical moment in a discussion where someone needs to make a path forward, is it clear who everyone turns to?

Decision-making guidance and examples:

  • We love using the GRPI (Goals, Roles, Processes, & Interpersonal Relationships) framework to strengthen any type of team.

  • We're partial to the DARE (Deciders, Advisors, Recommenders, and Execution Stakeholders) tool for projects and programs.

  • And, when in doubt, create a lightweight charter for standing groups/meetings, describing the expectations for each role.

Prioritization audit questions:

  • Is it clear how we prioritize what gets done now, and later?

  • Do priorities stay relatively stable through the month? quarter?

  • Can you point to a widely accessible artifact that illustrates top priorities for your company? department? team?

Prioritization guidance and examples:

  • If goals are set but not easily accessible, publish them and refer to them often in all-company channels.

  • If a team is using a goal-setting framework successfully, have them help roll it out company-wide.

  • If you're looking for a new prioritization method, we're fans of OKRs (Objectives and Key Results), defined for the enterprise and cascaded to departments and teams.

Conflict resolution audit questions:

  • When we have conflict, do we have a consistent track record of seeking productive resolution?

  • Can we separate conflict on the content of our work from conflict with coworkers?

  • Do we have the real conversation in the meeting, rather than in the meeting after the meeting?

Conflict resolution guidance and examples:

  • This starts from company guiding principles and culture. Make sure every employee has easy access to observable behaviors that are and aren't okay.

  • Facilitate a ground rule definition exercise in recurring meetings, and empower facilitators and participants to call out deviations from what was agreed upon.

  • Work with your HR/people ops team to invest in courage- and trust-building capabilities.

To get you thinking about the next phase, defining the transformation, we’ll need to answer the big question: What business purpose does the transformation propose to solve? Whose perspectives will we need to determine this? How will we prioritize among competing interests? Who will act as tiebreaker?


 On one project we were brought in to facilitate two corporations during their merger. One company’s customer data and operations needed to be migrated into another’s without the end-customer experiencing an outage in service. During gap sessions at the beginning of the project, both sides were able to outline what was needed to maintain service while a customer’s service was being migrated. Known differences between systems were documented, and conversion planning could begin in earnest.


Work Management

Transformations typically include lots of cross-team work, shifting expectations around team roles and coverage, and delivering day in and day out. Here are audit questions and guidance to succeed in work management, team coverage, and working rhythms.

Work management audit questions:

  • Do you have a clear way to divvy up work, particularly across teams?

  • Do you know if work you've requested of another team is in the queue? Completed?

  • What if one person has too much to do and another has too little: do we have visibility? Are there ways to adjust?

Work management guidance and examples:

  • Create a lightweight shared board that includes requests and tasks crossing teams. This can be a spreadsheet, task list, Kanban board: just something to provide visibility.

  • Define practices of picking up work with spare capacity; have team leaders keep an eye out for people being overloaded via 1:1 sessions and tools like time reporting.

Team coverage audit questions:

  • Have you identified strategic roles – those that are critical to success – for each department, function, and team?

  • Are each team's strategic roles filled with top talent?

  • Have you created job success profiles for any openings? These should include:

    • Key success factors and performance factors

    • Essential traits and exceptional skills

    • Experience and education requirements

Team coverage guidance and examples:

  • Segment roles, prioritizing teams with vacancies, into:

    • Strategic: vital to success, holes compromise future success, and evolving with strategy

    • Core: important for operational success, holes risk goal achievement, and aiming for constant coverage

    • Supporting: keep operations running smoothly

  • Create job success profiles for strategic and core roles.

  • Map out coverage by role segment.

Working rhythms audit questions:

  • Do you have a consistent, reliable way to understand plans, progress, blockers, and issues from your team?

  • Are you happy with how visioning, planning, and retrospectives take place across teams?

  • Do you and your team have adequate time to do the work, not just talk about doing it?

Working rhythms guidance and examples:

  • Add or update regular stand-ups with your team, timeboxing responses.

  • Work with other team leaders to design planning sessions across teams, with candid discussion around goals, plans, dependencies, and challenges.

  • Incorporate retrospectives on both what was done and how it was done. Make space to experiment with new ways of working.

We’ve included several different practical examples, but these don’t need to be overly complex or administrative-heavy. The idea is to create an efficient process, and cadence for that process, that keeps stakeholders in the loop.


Structures and Processes

  • Do you have a well-defined operating model for how you get work done?

  • Does your organizational structure align with your strategy (for now, at least)?

  • Do you have the right roles?

    • Which ones need to change?

    • Which ones need to go away?

    • Which ones are you missing?

  • Are you organized the right way to drive results and accountability?

  • Are you organized the right way to ensure effective people management, performance management, and career development?

  • Are you organized in a way that makes it easy for customers (internal & external) to communicate with us?

  • Do you have the right processes and tools in place to be successful?


We had one client that hadn’t run a data transformation before, and in their (understandable) desire to get the project kicked off, inundated team members with so many redundant meetings, very little actual progress was getting made toward the project goals. We were able to sit down with stakeholders, eliminate redundant meetings, and create an attainable project schedule for everyone involved.


People and Roles

  • Once you’ve aligned on the structure and roles, do you have the right people with the right skill set and attitude in each role?

  • Are you investing in high-potentials with stretch roles and coaching?

  • Are you putting your “aces” in the right “places” (i.e., are your best people working on the most important strategic priorities)?

  • Is there low-value work you should be offloading, automating, or offshoring?


Communication and Alignment

  • Are you telling your story effectively internally and externally?

  • Where do you have communication blind spots and how can you solve them?

  • Are your leadership team/board/owners aligned on your vision and approach?

  • Are your team members aligned on the vision?

  • Are your customers aligned on where you’re going, and do they see value in the path forward?


 If a discussion is getting hung up on one particular topic, a good trick can be to get the other side of the conversation to repeat their understanding of the conversation back to you. Sometimes you’ll find both sides are talking past one another, and neither side realizes it until the conversation is flipped around.


Capacity and Expertise

  • If half the delivery team was suddenly unavailable, do you have an idea of how you'd adapt?

  • If twice as much work came into the pipeline, do you have a first and second step to address it?

  • Do you have a short- and medium-term talent acquisition plan, potentially in addition to typical recruiting channels?

  • If you encountered a brand new, ambiguous, or strategic challenge, do you know who you would call?

  • To preview upcoming steps in transformation prep: How do you plan to staff the transformation effort?  Is there enough capacity on the team to just add this to their current jobs or should you consider backfilling the day-to-day duties with contractors? How will you onboard them and ramp them up?

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Defining the Transformation

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Applying the Hero’s Journey Restorying Intervention