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August 13, 2019

8 Questions to Explore Before Embarking on an Agile Transformation

9 mins read

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Written by

Marissa Bornholdt

Enterprise Transformation Coach

Considering bringing Agile into your organization? Great! You’re about to start out on a challenging but rewarding journey, and if you stick with it, you’ll realize some of those highly-touted benefits like flexibility to adapt to market changes more quickly, better visibility and alignment between the business and IT, and higher team morale. But this is no small undertaking and you must ask yourself the right questions about your Agile Transformation strategy! At the beginning of an Agile effort, most organizations haven’t realized that they’re not only introducing a new IT initiative but also fundamentally changing the way they do business.

As an Agile Coach, I’ve seen and been part of many Agile transformations. Nowadays, when my fellow coaches and I get together, we often find ourselves wishing that more companies were better prepared before embarking on their Agile journey. I started thinking, if I was a member of the C-suite and I was going to introduce Agile to my organization, what questions would I want to answer in order to give us the greatest chance for success? If you can answer these, I’m confident you will be well on the way to crafting your own transformation strategy.

Strategic Questions for Agile Transformation Success

1.  Start with “Why?” 

Agile is a significant change, both how work is done and company culture. Significant change is very challenging, especially without a clear and compelling vision to rally around. So, it’s best to start with asking questions about your Agile transformation, like, “Why are we doing this?”

As you answer that question, here are some related questions to consider:

  • What benefit is the organization seeking from this effort?
  • What is the “burning reason” why the company is doing this now?
  • What challenge/pain point/weakness are we seeking to avoid?
  • What will anchor this effort when things get difficult?

2. What lengths are we willing to go to as an organization? 

Agile often starts in the IT department and then spreads. It might move to finance if the budgeting process needs to adjust to the emergent nature of Agile culture. It might spread to HR if we discover that our corporate titles and job families don’t align with Agile roles and how we need to recruit for them.

It’s helpful to consider what degree of organizational change we’re willing to implement before other departments get involved. This leads to a series of questions:

  • Are we willing to restructure? What structure will be needed to support our effort?
  • Are we willing to transition from siloes/matrixed divisions/departments to a flatter organization?
  • What should our leadership structure look like and are we willing to transition from resource managers to servant-leaders?
  • Are we configured to support the persistent teams necessary to make Agile successful?
  • What is our vendor-partner strategy and how does our staffing strategy incorporate vendor support for persistent teams?
  • How much of a cultural change are we willing to embrace?
  • Have we honestly assessed our culture to date?
  • Are we prepared for the transparency and fail-fast mindset Agile relies upon?
  • What cultural challenges will adapting to an Agile way of working bring to those outside of IT?
  • What is our talent development strategy? How does it affect current teams?  What Agile skillsets do we have and which ones do we lack?

3. What is our communications strategy? 

Clear messaging is essential both internally and externally. Here are some communications opportunities to consider:

  • Who is championing the effort and what will they do to demonstrate and communicate the organization’s commitment?
  • What level of buy-in/support do we have from executive leadership? Middle management? Our colleagues on the teams?
  • What steps will we take to socialize the purpose of this transformation?
  • What might we need to communicate to external partners/vendors/regulatory units along the way?

Tactical Questions for Agile Transformation Success

4. What Agile frameworks will we use?   

There are many approaches under the Agile umbrella. Most organizations find that a mix of frameworks, where teams have choices, works best. However, that can introduce challenges when trying to get a cohesive view across the organization. Some questions to consider include:

  • What degree of flexibility do we want to encourage? Antipatterns can emerge if teams lack sufficient understanding of underlying principles. There is often a tradeoff between flexibility, conformity, and effectiveness.
  • What tools might we need to provide to the teams (e.g. physical and/or virtual Scrum or Kanban boards)? What internal support might we need for these tools?

5. Do we have the right skills to be successful?   

Agile and DevOps go hand in hand. When an organization starts out down the Agile path, it’s also a good idea to incorporate DevOps practices, especially Continuous Integration (CI) and Continuous Deployment (CD). The following questions are important to consider when introducing these practices in your Agile Transformation:

  • What skills do we need?
    • What tech stack will we be using? What tools will we need? Do we have the hardware, software, and licenses to support this approach?
    • What will our standards be? How will we ensure the right level of consistency across teams/programs/business units/the enterprise?
    • What development languages will we use? How will we integrate new ones? What is our strategy for adaptability and maintainability over time as languages evolve and new ones emerge?
    • If we don’t have the right skillsets today, how will we bring them into the organization?
  • How much experience does the team/program/organization have with these technologies?
  • What experience do we have with lean budgeting/Agile finance? Agile performance management/HR? Business Agility?

6.) Do we have the correct people in each role? 

Agile roles differ from traditional ones. Organizations often begin an Agile initiative by placing people in roles that appear to map to pre-existing ones, but often the mindset needed is lacking.

This is a list of common Agile roles and a few questions to help you determine whether the person you have in mind embodies the necessary characteristics:

  • Product Owner: Is this person a representative from the business? Is s/he an authorized, empowered, and knowledgeable business expert? Does s/he own the vision and direction of the product?
  • ScrumMaster: Is this person an Agile expert with prior experience working on an Agile team? Does s/he have a servant-leader mindset and empower colleagues? Does s/he have experience facilitating team events and conversations?
  • Development Team Member: Does this person have a broad range of expertise across various technologies? As a group, does the team have a mix of senior, mid, and junior technologists? Is the team able to complete their work without outside assistance and deliver autonomously?

Is your organization looking to integrate teams together and adopt a scaling approach? If so, the following roles may also be needed:

  • Chief Product Owner: Is this person a senior leader from the business? Does s/he have extensive product owner or product manager experience? Does s/he exhibit a servant-leader mindset? Does s/he have the political savvy to exert influence across the organization?
  • Release Train Engineer: Is this person a senior Agile expert with extensive ScrumMaster experience? Does s/he exhibit exemplary servant-leader behavior, and can s/he teach others to be servant leaders? Does this person have experience working across teams and programs to facilitate large scale coordination and planning?

Is your organization new to Agile or finding it challenging to adopt? Bringing an Agile Coach on board can accelerate adoption and help teams work through their challenges.

  • Agile Coach: Does this person demonstrate a high-degree of Agile expertise with extensive experience across a range of roles, initiatives, and organizational environments? Is s/he someone who empowers teams, programs, business units, and companies to work through challenges and become high-performing?  What mix of internal and external coaches will provide the best solution for your organization, leveraging the strengths and benefits both types provide to encompass the right amount of coverage for the size of your organization and its challenges?

7. What will we do to educate the entire organization? 

Agile is a different way of working and the organizations who invest in training up front tend to have a smoother path towards adoption. Consider what mix of the following activities might work best:

  • Multi-Day/Multi-Track Agile Fundamentals Training Sessions
  • Role-Based Training (e.g. ScrumMaster, Product Owner)
  • Brown Bag Sessions to deep dive on specific topics
  • Create Role-Based Communities of Practice/Excellence (aka CoPs or CoEs)
  • Coaching Office Hours/Coaches Corner/Ask A Coach
  • Town Halls to share strategic messaging with the entire organization at once
  • Road Shows to visit each work location in person
  • Webinars to provide on demand learning content
  • Podcasts to provide experiential stories from teams/programs/divisions
  • Gemba walks to give new teams a way to observe exemplary teams in action, ask questions, and learn from their peers

8. How will we measure progress? 

Metrics can be powerful tools to gain insight into how the transformation is going and answer questions about Agile progress, but, if constructed poorly, can create confusion. When deciding what metrics to gather, be sure to measure what matters, and leave space to evolve over time as the organization advances. Here are a few questions to consider:

  • What are we looking to accomplish and how will we measure progress? Based on the benefits we’re looking to achieve and the challenges we’re looking to address, what metrics will help us determine whether we’re meeting our goals? Are they different at different levels (programs, teams, etc.)?
  • What misperceptions and challenges might we seek to avoid while gathering these metrics? How might we empower the people closest to the work to determine which metrics are best and provide meaningful interpretations?
  • What will we do to evolve our metrics over time as teams, programs, and the enterprise improve?

And that’s it!  If you’ve taken the time to work through these questions, you’re way ahead of the game. It’s time to get started! Don’t worry if you don’t have all the answers upfront, or if you feel you need some help along the way. We’ve accumulated a lot of experience helping our clients and are there if you need us. Go ahead, take the leap, and have fun – let the journey begin!

Are you ready to take the first step in your Agile adoption journey? Download our ebook "A Guide to Making Your Agile Adoption Work for You" and get started!

Download My Free Copy

Marissa Bornholdt

Enterprise Transformation Coach

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