So the move to agile needs to be agile itself.
Each organization is different, there are various characteristics make or break agile adoption at an organization, but those that successfully transition to being agiler probably share similar characteristics. What are the best indicator of business readiness to be agiler?
C-level support affects many aspects. Awareness of agile (or lack of it) at the top does matter a lot. No matter what happens or desire at other levels, without C-level blessings, any attempt at aligning the projects with agile values turns out to be a waste of time and resources. Being Agile can't happen in isolation of other corporate processes (funding & financial, HR hiring, talent and & performance management; etc.). And it's likely the legacy processes don't support doing work differently and have to be addressed. Changes to the legacy processes need C-level support, otherwise, teams feel like they're running into bureaucratic obstacles and get discouraged because being Agile appears too difficult. And, the recognition C-level executives give for great results related to being Agile really fuel the teams and organizations! The ability for upper management/executives to clearly state what they believe agile will do for an organization and deciding how they will measure its success. Unfortunately, much upper management doesn't even have a proper understanding of what an "agile" environment means to them other than getting things done faster!
Communication is at the heart of building a better, more trusting relationship. Without it, it's hard to see how teams could be successful. If management doesn't trust the people they hired to come up with solutions and do the job right, then management shouldn't have hired them. If management does trust its employees, then let them do their jobs. There shouldn't be much need to "manage" people. The main goal of Agile is to manage changes, and the best way to do that is to improve the communication. All others points of Agile are great improvements, but this is the principle. Managers and executives have to serve and lead, and the traditional management paradigm needs to shift 180 degrees; leadership teams have to trust and support teams and remove organizational impediments. They need to empower teams and individuals that are closest to the 'problem' to make the right decisions, and ensure that those decision makers have everything they need to implement. The truly trusting relationship can overcome the fears:
-Fear of making an estimate and having it turned into a commitment.
-Fear of pursuing a solution and finding out it doesn’t work.
-Fear of starting something without having all the facts.
-Fear that mistakes are punished.
-Fear that discoveries will be treated as failures to foresee events.
-Fear that all the work will not get done if you don’t force it into the current release.
Clearly a strong IT / business relationship matters. So, if the IT teams are really interested in being Agile, then the grassroots desire is the most important attribute to drive Agile acceptance. As IT works on projects, it can start to implement Agile practices: getting more frequent communication with the business during discovery and development, daily standups, frequent releases of high-value features, etc. As the business realizes they are getting valuable features from IT at a faster pace, and those features are exactly what they wanted (since they are more touchpoints during development), they will come to see the value of Agile and support it more.
The crisis is a catalyst for change. Complacency with the status quo and statements like 'it's not broken so don't try to fix," it'll signal roadblocks ahead for trying to implement new ways of working. If it is acknowledged at board level that the existing delivery mechanism is considered to be fundamentally broken or there has been a major delivery disaster (or more often - no delivery at all), then the organization may be ready to consider a major change. Without this 'crisis' there is often not the urgency or commitment for change. However, a crisis can imply an expectation of a quick fix to alleviate the crisis rather than a careful evaluation of why existing processes don't support growth. Implementing Agile in a "crisis mode" is probably a formula for failure. Instead, consider positioning agile as a way of helping the business meet its objectives. Every business wants to increase sales, revenue, etc. Show how implementing Agile will help meet those long-term business goals by providing valuable features faster than current processes.
So the move to agile needs to be agile itself. Simply because every organization is different, it has different challenges and has a different ability to absorb learning and change and different resistors. The organization needs to be willing to invest in learning from failure, as at times things will progress. The ability to clearly state what you believe agile will do for your organization and deciding how you will measure its success. Moving to Agile should be business driven. It is organizational change and organizational change has low success rate and needs a strategy and close inspection and adaptation.
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