The most popular and proven method of kick starting your adoption of Agile into your organisation is to start with a pilot project, see how it works for you (and where it doesn't), and to then scale out from there. This is an approach we recommend to most of our clients because:
Best way to learn is to do: No one really gets what Agile means until they are doing it. A single pilot project is an easy way to start doing it.
Focus your support: It allows an organisation to fully focus on making the Agile project successful (as opposed to doing Agile for 10 simultaneous projects where your senior supporters will not have enough time to provide that early tender loving care). As much we talk about fail-fast being a good thing, you don't want to fail fast with your first Agile project as you first need to silence the skeptics and build confidence.
Flush out blockers in controlled way: The pilot enables you to unearth where the blockers to Agile adoption are. This will then influence your choice of future Agile projects as you will better appreciate which initiatives will best suit Agile and your organisation. You can also setup a task force which targets these blockers so that as you scale out your use of Agile there blockers are being removed.
So, start with a pilot and then scale out. Simple right? Not quite. Scaling out Agile is not simple. People often take the view that having proven Agile works in their pilot project they are now ready to scale out. The answer to this is NO NO NO!
The pilot project allows the organisation to understand Agile better, but it doesn't equip the organisation to immediately scale out Agile. The pilot will most likely have been given special leeway in terms of governance and funding, and also is likely to have been staffed with heavy hitters. So it will not have addressed wider questions which need to be answered at the enterprise level, such as:
Skills availability: Agile requires not just a difference mindset, but also different skills. Just ask any organisation which has been through the challenge of retraining Project Managers, BAs and other roles into Scrum Masters and Product Owners. To scale out Agile successfully an organisation needs a resource pool of Agile practitioners - people who know how to operate in this way, and who have the skills to perform specific Agile roles. This is a recruitment, training and organisation design question, and will not have been answered by the pilot project.
Governance: Most pilot projects I've been involved in have been allowed to operate outside of the standard project delivery framework (for the most part). The pilot comes up with its own governance structure and assuming this gives the right level of confidence to the stakeholders involved then that is good enough. However, the approach used for the pilot is rarely suitable for using on other Agile projects. An enterprise level governance approach is needed for Agile projects, especially in highly regulated industry sectors where audibility and security are key considerations.
Business availability: For me, the number one challenge to scaling out the use of Agile is the availability of the business to truly be part of the Agile team. You might easily find a business area up for providing the time and commitment for making a pilot project successful, but as you scale out Agile you'll quickly realise that most business units don't have that kind of spare capacity. This could mean your aspirations for doing Agile may need to be lowered, or much broader conversation needs to be had around digital transformation
Out approach to dealing with this challenge is to have an Agile Coach working alongside the pilot project and defining the scale out roadmap. This is a transformative piece - the coach is looking at how to ready the organisation to adopt Agile more broadly. Much of the input will come from the pilot project, but there will also be input from reviewing the wider enterprise and looking at the questions noted above (among others!).
So our approach is this:
Pilot Agile to learn and prove how it can work
At the same time, kick off your transformation planning for how you can adopt Agile more broadly - the key is to create your transformation roadmap which everyone buys into
Once you have learnt enough from the pilot, seek opportunities to expand Agile to other projects/products, ensuring this ties in to the transformation roadmap
Kickoff a working group/ initiative to deliver the wider transformation changes noted in your transformation roadmap. This initiative will target changes which you cannot deliver simply by delivering the individual Agile projects e.g. rolling our Scrum Master training to your all staff, changing your office environment to be more collaborative, procuring enterprise dev tools which are Agile friendly