Agile Transformation Checklist for Success

Agile Transformation Checklist

A checklist cannot fly a plane. Instead, they provide reminders of only the most critical and important steps–the ones that even the highly skilled professional using them could miss’ – by Atul Gawande

In the past two decades, ‘Agile’ has become the talk of the town. It might be the rarest of the rare trend in any kind of industry where the culture and mindset that has been first applied at the lowest level of hierarchy (the development teams) has become so much popular that the leaders or the senior management got inspired by it and want to adopt. The leadership called it ‘business agility’. Actually, agile ways of working is adopted to address the common challenges –

  • Frequently changing customer demands
  • Evolving market trends
  • Budding competitions
  • Technology advancements
  • Faster delivery with utmost quality

Many organizations start on their own and few also reach out to agile business consulting firms. There has been a spike in the demand of agile transformation services and stories surrounding such agile transformations. Most were failure stories and still they are in abundance when compared to successful implementation of agile transformation strategy. Why does this happen? Mostly because there is no standard way to implement the agile transformation checklist template, the journey has to be contextual and culture & mindset driven rather than following frameworks.

Organization should start preparing their own agile checklist for transformation asking a few critical questions –

  • Do we have a clarity of our vision or goals before kickstarting our agile transformation initiatives?
  • Do we have the right plan to execute our agile transformation roadmap?
  • Have we taken the actions that are aligned with our plan which rolls up to our vision and goals?

The gaps in all the questions could be addressed by having an effective agile transformation checklist in place. This checklist could also be referred to as agile transformation checkpoints.

What is a checklist for agile transformation?

‘A goal without a plan is just a wish’. by Antoine de Saint-Exupéry

‘A plan without action is just a dream’. by Joel Arthur Barker

This checklist is one of the essential tool of Benzne Transformation Agile Services which enable us to successfully understand the problems or challenges that our customer is going through, curating a tailored agile transformation strategy, target low hanging, immediate next state which we call as ‘first success’ and continuous growth by scaling and continuous improvements.

Agile business consulting is not a one size fits all but that doesn’t mean that you need to create a completely separate checklist for all clients. The Agile Transformation checklist template are the reminders that help you as ready-reckoners to course-correct or reference when lost.

Checklist for successful agile transformation

Change is inevitable, but transformation is by conscious choice.” by Heather Ash Amara

Transformation of any type confirms that you are not happy or satisfied with what is going on now or you might be happy but concerned that if we won’t transform today then we may land up in a future which will be concerning. In today’s VUCA world, there is no such organization or team that could stay in complacency. Change is indeed inevitable and we at Benzne curated this checklist as the result of dozens of successful agile transformations we did across years. Definitely, a checklist can not be guaranteed but we are confident that it will help you in tapping into those details that you might have either missed or need reassurance.

You can also reach out to us at for a more detailed Agile Transformation checklist ppt and implementation strategies. We can also share a standard template for agile transformation checklist download for your reference.

  1. A week of hiking on ‘WHY?’ mountain
  2. A houseful premier release of ‘How Might We?’ movie
  3. Mutual agreement on the First Course Meal i.e. ‘MVP’
  4. Recruit & form A-team to drive agile transformation
  5. Iterate (Observe -> Investigate -> Act -> Evaluate)
  6. Timely ‘assess the right direction’ using Transformation Compass
  7. Identify opportunities to ‘Scale’ & hence the expedition continues
Checklist For Successful Agile Transformation

1. A Week of Hiking On ‘WHY?’ Mountain

Einstein is quoted as having said, “If I had an hour to solve a problem I’d spend 55 minutes thinking about the problem and five minutes thinking about solutions.”

Many times we are contacted by customers who tell us that they want agile coaches for their agile transformation initiatives and we gracefully reply back saying that we are not a recruitment agency. It has been observed that organizations often rush to understand the problem they want to solve and believe that the transformation is all about changing their practices and using popular frameworks. To overcome this, we follow the below checklist for probing the stakeholders to understand the problem –

  1. Why are we not able to achieve our goals?
  2. What are the symptoms that we are seeing today that tells us that things are not going well?
  3. Do we know the problems that are causing those symptoms?
  4. What have we tried so far to solve those problems? What worked and what didn’t?
  5. Why do we think that doing agile transformation is going to solve the problems?
  6. Can we support our hypothesis with data for both qualitative and quantitative measure?
  7. Do we have sufficient buy-in to solve the problems?

Once you understand ‘why?’ and the ‘what?’ part of the problem then it is time for us to explore the possibility of solutions to explore the ‘How?’ part of the problem.

2. A houseful premier release of ‘How Might We?’ movie

Any assessment that we conduct it has two parts –

  • As-Is: here we share the findings
  • To-Be: here we talk about the next steps that we could take to reach at the ‘better’ place

Identifying the To-be state is not a rushed job but a well-orchestrated activity done along with the cross-functional people who bring their perspectives together, firstly to diverge and collate different dimensions of thoughts and, then converge to bring alignment in the order of priority. This helps us in knowing various things like –

  • What should be the first problem that we should resolve?
  • Definitely that will provide business the maximum value
  • Instead of giving up on possibilities, we put effort in figuring out ways that could make us move forward
  • Usage of voting techniques to focus on critical problems & their potential solutions

Once this is explored, then it’s time to dig in further and get into much more actionable details.

3. Mutual agreement on the First Course Meal i.e. ‘MVP’

The biggest point of failure with most of the agile transformation journeys are their very nature of not being agile in its own form. They are sequential and too BIG and it ends up letting the late realization of value by the organization. W,  at Benzne, always insist our customers to focus on piloting the transformation and then gradually scaling the scope by continuously replicating the success stories.

Following is our transformation checklist with agile that help us in focusing on just-enough instead of boiling the entire ocean –

  • Find out the most critical point that the organization is struggling to solve
  • Believe in pareto’s law, it’s 20% of things that create the 80% of the problems, hence conduct the root cause analysis to identify the root
  • Curate the focused training for onboarding the team/s
  • Apply needful practices that could help us in imbibing the falling essential traits for agility –
    • Fail faster
    • Shorter the feedback loop
    • Stop starting and start finishing
    • Simple but impactful metrics to check the execution certainty
    • Just-enough plan over exhaustive & extensive plan
  • Identify feedback loops with internal and external stakeholders supported by reports and metrics
  • Create psychological safety
  • Continuously coach leaders to support teams and do not micro-manage, instead focus on inspiring them by creating healthy environment for experimentation and continuous evolution

All in all, the problem with the big plans in it is a coin-toss, it may either succeed or fail and most of the time, it fails. The best part of the MVP approach is, you embrace failure to happen in early stages so that we won’t repeat later and can continuously improve and pivot.

4. Recruit & form A-team to drive agile transformation

It is important to form a team of focused people who are responsible for driving the agenda of the transformation. These people should be experienced and have had such experience before in the past. It might happen that the internal people may not have such experience and the organization should bring in industry experts from external agencies or firms that have already been to such complex engagements before and successfully helped their customers with meeting their goals.

Following is the checklist to consider when we identify Agile transformation agents and form this cohort –

  • Everyone should be aware of the organization objectives and work as one-team instead of following their personal agenda
  • Together they know everyone who is going to be impacted by this transformation
  • They are united by the goals but separated by responsibilities for different focus areas
    • Portfolio or business level agility
    • Program level agility
    • Team level agility
    • Product or specific group level agility
  • They also should have different competencies to drive such critical initiatives like –
    • Training on various agile related topics
    • Coaching traits to cultivate the one-team mindset and bring alignment in culture to strengthen the organization fabric
    • Facilitators to drive important events like problem solving workshops, cadence based planning, bringing metrics and reports, adept in tools that are required to manage the work and many more
  • Competent enough to create interest groups or guilds to create self-organizing environments
  • Learnabilty to upskill their own self

It is important to take time in forming such an A-team. We should not add too many members upfront, instead we should start with few who are passionate and eligible to drive such change and over time we should keep checking the necessity of expanding it.

5. Iterate (Observe -> Investigate -> Act -> Evaluate)

Naval Ravikant has rightly said, “It isn’t 10,000 hours that creates outliers, it’s 10,000 iterations.”

The A-team shouldn’t just preach others to change their ways of thinking and working but themselves should lead by example. We may also have anticipations on what could and should be working but that may not be the case as the dynamics vary based on change in people, process, product, customer and technology needs. Henceforth, this is what we recommend –

  • It is important to be an Observant. There could be many possibilities to cause a certain behavior and it is our responsibility to depict what might be that root cause that is making it all wrong or also right. It’s an art called ethnography and for any successful agile transformation, it is a must-have.
  • Once we observe, it is important to not be biased and rush to come up to a conclusion. We should learn to investigate continuously so as to sit on a problem for a longer time to find the solution that could be impactful and acceptable by all.
  • Once, we identified the possible reasons and also the solution, the next big thing is to determine the approach to put that in action.
  • Throughout this activity, we have been applying the lean startup mindset. For any approach that we want to try, we should be mindful to identify the data-based indicators to measure the progress. One such approach is OKR. And there are various such metrics that help us in evaluating the leading and lagging indicators to see if we are going to fulfill the benefit hypothesis of any approach so that we could solve that problem statement.

6. Timely ‘assess the right direction’ using Transformation Compass

‘If you can measure it, you can’t change it’ – by Peter Drucker

There are many ways we can measure the agile transformation implementation. Following are the few popular approaches –

  • Business Agility Health Assessment
  • Portfolio & Program Agility Health Assessment
  • Project level health assessment
  • Individual level assessments

But what matters the most are the business indicators that matters more to the organization like Increase in Revenue, Decrease in operational costs, Reduction in lead & cycle time (ie. faster delivery), Customer Satisfaction Index, Customer Retention Rate, Key certifications and accreditations, NPS Score and many more.

To perform so, we need to continuously organize and facilitate events to Plan & Review the health of strategic initiatives.

The effectivity of such assessments could happen if you ensure the following –

  • Anonymity, if that could help in getting the unbiased views and results
  • Transparency, to ensure that the results be shared with the participants and also the action items
  • Empowerment, people at all levels should be encouraged to share their opinion to suggest betterment ideas
  • Actions on identified areas of improvement & follow-ups

Assessments are good to have till they are fair and provide the true results. It shouldn’t be manipulated and it should definitely be one input for deciding the future decisions.

7. Identify opportunities to ‘Scale’ & hence the expedition continues

The journey of a thousand miles begins with one step.” – Lao Tzu

It is important to create success stories at the grassroots level before going for bigger landscapes. Once the traits of agility are visible and organization has already started experiencing success in small pockets, then with no further delay we should identify the next possible MVP that we could start with. We may need to scale up the A-team also to meet that need. Following is what we suggest –

  • Be mindful of above 7 steps – they will support you surely in your scaling
  • Ensure that big job comes with bigger responsibilities henceforth scale only that much what you could assure your full commitment with
  • The new accounts will definitely be interested in knowing the report-card of your earlier success so ensure that your case-studies, metrics and needful reports are in place
  • Always keep your cheer-leaders with you and request them for references so that they could help you with onboarding the stakeholders of unexplored territories
  • Remember, it all starts with knowing the problem first and the challenges that the business is facing due to them
    • Do not rush to know them
    • Include everyone who are crucial
    • Conduct or facilitate events that can help in learning more about them
    • The solution shouldn’t be long-timed but definitely an MVP
    • Find your new buddies who could be part of A-team
    • Iterate, Iterate and keep doing it till you succeed
    • Onboard them instead of convincing
  • Agile practices are good to know and implement but if they do not solve the problem then there is something wrong. You might be imposing your ideas which are baseless. Better, learn the new ways that are effective and more relevant to their needs.
  • Goal is always to help business achieve its objectives and not to put agile practices in place.So your approach should always be aligned with them.

Recommended Read

Agile Transformation Challenges Surprising Downside Of Agile What Is Business Agility
Agile Transformation Journey Establishing First Agile Release Train What Is PI Planning In Agile
Agile Transformation Metrics How to scale agile using SAFe What is SAFe Transformation
Agile Transformation Strategies Scrum Master Do’S And Don’Ts Agile Metrics For Leadership
How to Plan Agile Training for your team Effective Sprint Planning with Steps Agile Project Management Tools


We believe that using the above Transformation checklist with agile will help any organization or consultants whom they hire to stay focused towards the agile transformation goals. We, at Benzne, curate our agile transformation services aligned with customer needs and believe that the undivided attention and relentless commitment lead us to help our customers in being their truest expression. Agile transformation checklist serves its purpose to keep you guided but the secret sauce is to be vigilant about the know-abouts of your need, continuously experiment and pivot.

There is no one-size-fits-all approach to success when it comes to agile transformation but these agile transformation checkpoints are generic enough to guide you and your organization to success. All the best!


  1. What should I consider for agile transformation?
  2. What is the first step to take to kickstart an agile transformation journey?
  3. How to know during the agile transformation journey if we are on the right path?
  4. Is there any step-by-step guide to bring agile transformation in an organization and assure success?

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