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Digital Transformation: the Agile journey continues

The second installment of a blog trilogy to guide you on your Agile journey towards Digital Transformation.

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Continuing with our trilogy on your organisation’s Agile journey towards Digital Transformation, let’s take a look at the next two levels of agility, and what challenges you may face. If you missed the first two levels, you can read these here.

Your next stage may look something like this:

Level 3: Agile Adventurers

  • Your organisation is interested in Agile adoption across the board as they have seen your success
  • You have the permission of your organisation to use an Agile methodology, such as Scrum, and you can set your project up with the development team you need
  • You are typically building web applications that need to get to market quickly, but are usually of low risk to the business
  • You may have new people in your organisation who have worked in this way before and are driving this change more broadly
  • You have an assigned Scrum Master for your team, and maybe a Project Manager as well, who manages the budgets and milestones
  • You have someone to assign the Product Owner role, but they may have never done this before
  • Your project has fewer constraints around how you can run the project, and you are likely sitting together in a team
  • You are all allocated to work on projects with your team at least 80% of the time.


You really are going to do this thing now. You have been given the power at a team level to structure this in the best way it can be, so now is your opportunity to really get stuck in!

You have your Product Owner on board (they may find it useful to have this guide to great Product Ownership); you have your team ready for the work, and they have worked together before. Your Scrum Master (or the person who will wear this hat in your team) knows enough to get things up and running quickly for the team, and can work with the Product Owner to establish a prioritised backlog of work. The team needs to come together to refine this backlog, so everyone knows what their stories are about. Once these are in a good state, enough for the first sprint, it’s time to begin your regular cadence, and stick to it! Discipline is a very important part of this stage. You have already tried it—it is no longer an experiment; it is a professional practice.

For people in management roles who are working in a project in an Agile way, it is important that you are attending things like sprint demos, and showing management the progress the team are making in real time, especially the first few sprints. This shows evidence that things are able to be delivered quickly, as it’s very hard to argue with working software. Part of your role is to evangelise for the team, and help them remove any potential blockers within the organisation to them doing their best work. You need to review processes pragmatically, and ask whether the process adds to the direction you need to go, or directly holds it back. If it clearly adds time and energy for little value, ask whether it is a process that is a ‘real constraint’ rather than a ‘perceived constraint’. Real constraints may be compliance for government or legally mandated practices, whereas perceived constraints are often long-established practices that ‘have always been done this way’ but may no longer need to be continued or that if stopped, no one would notice. The fewer constraints an organisation has, the faster and more adaptive to change they can be.

Many organisations spend a long time at the Level 3 stage, and although this is a lot better than before they began with Agile practices, the journey is far from over. Once you have mastered the rules, it’s nearly time to break them! 

Level 4: Agile Game Changers

You are now Zen Masters of the Art of Agile, and it’s now time to level up. Your organisation may now have these traits:

  • You team has delivered multiple projects using an Agile methodology and you now have it down pat
  • Other teams are trying it your way with good results
  • There is a ‘Community of Practice’ for your Agile roles, like a Scrum Master guild, Product Owner or UX guild
  • Your team is seen as the ‘ones to watch’ due to your quick delivery to market, and your successful projects coming in on time and within budget
  • Your organisation has seen the benefit of this quick delivery and are making ground on their competitors
  • Other areas of your organisation, such as Testing services and Marketing are making steps to support your processes, and are adopting Agile practices within their own teams
  • Management have changed some key areas that had previously blocked you, such as reporting structures, sign-off of certain decisions, your ability to easily get the right tools to help you deliver, and potentially how your projects get funded
  • There is no longer the aversion to change that used to be prevalent in your organisation, and people are happy that things are moving forward at pace, even if it means failure
  • Thins are a lot more visible across the organisation, and Management are responding to any areas of constraint that are holding things back.


It feels like you are now working in a really fast moving, proactive space, with lots of camaraderie and trust across the organisation. You really can be heard by higher-ups, as mechanisms are now in place to give feedback and raise new ideas without fear. It’s a great feeling, and the energy is addictive!

Although there are a few areas within your organisation, typically in process heavy departments at earlier levels of their Agile journey, there is at least visibility of their issues and a leadership drive to move them forward too.

If you are part of a highly functioning team that are pros, you may think there is nothing more to be done—you are just so awesome! But there is always something more to be done. Have you thought of offering training to other teams? Are you sharing your lessons learnt broadly within your organisation and helping the organisation learn from everyone’s experience? Have you thought of ‘squadification’ to mix things up a bit? Are you thinking ‘what’s next’? Running regular ‘Lunch and Learns’ or starting your own Meetup? This will help solidify your practice and help others outside your organisation begin their own journey.

As a manager, have you been readily resolving the structural and strategic blockers? Does your incentive model support the behaviour you are looking for? Are you proactive in seeking a broad range of opinions across your organisation? Have you truly broken down the silos? Are your people digitally competent enough to really break through to new ideas and ways of working? Have you begun working with other organisations and seeing what can be learnt from their own journey? Are you really using data from your users to support your decision-making rather than listening to the HiPPOS (Highest Paid Person’s Opinion)?

The goal should never be 'to do something that has always been done in a certain way but "more efficiently"', even though anything that improves efficiency is definitely beneficial. But now it’s time to move up another level, to a really innovative and truly transformative stage that puts you in the realm of disruption and potentially could completely change your business model. Pat yourselves on the back first and foremost, because reaching level 4 is quite a feat and not for the faint of heart! Your resilience and persistence has paid off greatly, and you should be very proud of what you have achieved.

Have a quick rest, hydrate, and put your ‘big boy pants’ on, because you will need everything you’ve got for the next level…

Stay tuned for the final installment of this trilogy—Level 5: Organisational Transformation Champions—where we will discuss why transforming is so important in this age, how you can really push out, no matter what role you have, and why it’s essential to begin now.

If you want to have a specific conversation on how SilverStripe can help you at any of these levels, contact us—we are Digital Transformation ninjas!

To find out more about how you can make your workplace Agile, download the free Agile Mojo Booster below!


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About the author
Diana Hennessy

Diana heads up the Channel Excellence team at SilverStripe, ensuring clients and partner agencies deliver amazing customer experiences through the web, every time, with the best tools and practices. Diana believes coaching executive level leaders in Agile practices and focusing on practical execution of Digital Transformation strategies is essential in delivering large scale transformations in both government and commercial organisations.

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  • Hi ASG,
    Glad to hear you are interested how Agile works in the different departments around SilverStripe. A request has been put in for a blog on this topic. :)
    If you want to see a blog on a similar topic, take a look at this blog about the Agile transformation journey in the accounts team:

    Posted by Silverstripe, 23/02/2018 3:25pm (6 years ago)

  • How does the HR department play a role in the Agile transformation process. What is their role and what changes for the in an Agile transformation? Also how do employees get reviewed on their performances in an Agile environment. I would like to know or read more about these topics please.

    Posted by Agile Scrum Group, 15/02/2018 5:13am (6 years ago)

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