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Digital Transformation: where are you at on your Agile journey?

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

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Many organisations have asked us at SilverStripe where they should begin their Agile practices, and how they would move their organisations out of traditional methodologies into a more Agile mindset on their Digital Transformation journey.

It really is a journey of discovery. Luckily, many organisations have done this before, and have been very successful at it. There are typically five stages of this transformation, and some well-oiled ‘lessons learnt’ at each stage that we can share with you. I hope you can recognise your own organisation somewhere along this journey, and gather some next steps to help push up a level.

In this blog series, we will go over each level, map out some options for ‘where to next’, and some general thoughts and ideas of the challenges you could face.

The levels are:

  • Level 1: Absolute Beginner
  • Level 2: Starter for 10—
  • Level 3: Agile Adventurers
  • Level 4: Agile Game Changers
  • Level 5: Digital Transformation Champions

Ideally, we all want to end up at Level 5 where your organisation has transformed into a digitally led, customer driven, business model challenging force to be reckoned with! We will discuss why that’s important over this series, but today, let’s address Level 1 and Level 2 where many begin this great evolution.

Level 1: Absolute Beginner

At level 1, you may find some of these familiar:

  • You have heard a lot of good things about Agile and have seen other organisations succeed and deliver quickly to market
  • You think your organisation needs this too, but have no idea what that would entail
  • Your organisation currently runs development projects in the classic project management way by having phases of conception, initiation, analysis, design, development, testing, production/implementation and maintenance
  • Your organisation is likely to have a hierarchical management and reporting structure
  • There may have been something happening in your industry that has made your organisation worry, and feel the need to respond faster

So many good ideas, but where to begin? And yes, you are definitely on the right track!

At this stage, you are unlikely to be able to walk into your CEO or CTO’s office and just say ‘Let’s change EVERYTHING’, so let’s look at things you can begin trying to further prove your case.

Firstly, identifying things you have influence in changing is a good start. No matter what role you have, you can change something to become more agile immediately. You don’t need to wait for an ‘Agile Expert’ to begin.

Some ideas:

  • Research what makes Agile methodologies work, and how they differ from what you currently do. There is a lot of online information about Agile practices, and when best to use something like Scrum or Kanban. Do a brief analysis as to whether it would work for you in your situation. It’s not for everyone.
  • Read about the Agile Principles. These are actually very important, as it is less about a defined process, but more about the underlying principles. If you could only ever get to the point of using the Agile Values in your project decision making, you would be much better off.
  • If you are typically in project teams, talk to someone who has visibility of upcoming work, and see if there is a candidate project that you could try some of the key practices out on. This doesn’t have to be a fully Agile project, but it could be that you try sitting the team together in one area, and start having daily stand-ups to review progress, and planning your work in smaller pieces.
  • If you are in a role where resourcing of work and planning of teams are part of your remit, look for a candidate project, and ask around to see if any developers are keen to give some of this a try. You can try to ring fence this group of people to work 100% on this one thing, and make them as self-reliant as possible—that really helps!
  • See if you can get someone from Testing involved early, even if it is in exploratory testing only. Don’t be disheartened if they don’t. Testing Services typically have the most defined processes and procedures to follow, so they are often the last to make the change to Agile. The main thing to achieve at level 1 is to get people to start thinking about whether something is working or not, and if not, changing it to work better. Even just doing this you will get a better outcome for your organisation.
  • Most of all, start talking to people around the office. Get other people curious as to what it’s all about, and help them find some information to help them in their role too. You need to create more voices that get the word out there. Become a virus for change!

If something serious has triggered higher-ups to look for ways to gain competitive advantage, head straight to Level 2!

Level 2: Starter for Ten

Now Level 2 is where many organisations currently are:

  • One development team in your organisation has tried an Agile methodology for a project.
  • Some of your teams use ‘stand-ups’ as a daily check-in, and work together as a team.
  • Work comes in, already planned and designed for you to begin development with. There is no ability to change scope.
  • Once development is finished, a different testing team tests the deliverables and your team may fix bugs long after the work has finished.
  • Projects work a little better but still have a lot of constraints and paperwork like high-levelspecification documents and gantt chart project plans.


You have made a good start, and people are feeling positive about how good it is to get more visibility, and being more of a team member than a ‘resource’.

But you know it is only the beginning, and you are looking at taking it to the next level. This is where a lot of Agile projects get a bad name—Agile practices done poorly are harder to combat than other methodologies like Waterfall. An Agile methodology like Scrum takes discipline!

Some ideas:

  • Get more visibility within your organisation about what you have tried before, and what you’d like to try next. Try to hold a ‘Lunch and Learn’, or create a slide set to show the higher-ups.
  • Identify someone who can fulfill the role of ‘Scrum Master’ (if you are thinking of using Scrum) in your project. It doesn’t have to be a new person, but make sure they understand what a Scrum Master does, so they can begin using some of the key techniques.
  • For Kanban and Scrum projects, a physical board is helpful in arranging and planning your team workload, so this is a typical next step. Investigate what a good board looks like, and the process to set up and manage the board. Ask the team if they like the idea, find a whiteboard and get started!
  • Look for who is mostly responsible for the upcoming work, and ask if they would like to play the Product Owner role in your next project and get them to research what that entails. You may not necessarily action this right now, but it’s good to have someone earmarked—this role is vital to a great product at the end for your users!
  • If trialing Scrum, have the Scrum Master set up the regular cadences of a typical ‘sprint’ cycle. This would involve activities like Planning, Stand-Ups (if not already in place), Demos and Retrospective. Try it out for a two-week period, then talk about whether it improved things or not.
  • Look for what constraints surround the team, and see if they are real constraints or have ‘always just been done this way’. It is unlikely that you can remove larger constraints that affect large groups of people outside of the team, but smaller ones like reporting, testing processes, bringing work onto your board, deciding tools you need, and whether you remain together as a team ongoing instead of being reassigned may be good options.

The main goal in this stage is to begin and mean it. Agile methodologies have the impression of being a ’no rules’ way of working. It couldn’t be further from the truth. It takes discipline to stick to the plan, have ownership of the outcome, and be consistent. This is where you need to keep ‘inspecting and adapting’ so you can incrementally improve. This can take a while in any new team, so don’t be worried if after two or three sprints you are not amazing at it. It can take a few projects with the same people to really be highly functioning. This is really putting your toe in the water of doing this for real, and it may even be done under the radar of your higher-ups at this stage.

The other most important thing in this phase is to enable trust within the team. When a team trusts and respects one another, it often doesn’t matter what methodology you use. Put yourselves in scenarios where you can grow this trust.

In the second installment of this blog trilogy, we move into Level 3 and 4. Let us know if you have any thoughts on these stages in the comments below.

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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