Note: this discussion is closely related to What Are The Changes in Culture That Need To Happen with Agile?

One problem that is often encountered when going to an agile approach is that management believes the transformation is “about development” or “about IT” and has no effect on an organization or, more importantly, what management does. This thinking creates a problem for the transformation. The agile approach was developed to allow organizations to produce software better, faster, cheaper (and with more fun). But if the organization insists on old thinking processes then it will not be able to reap the benefits of an agile approach. For example, many organizations say What Does a Scrum Master Do All Day? and decide that they do not need this to be a full time role. The problem is that this role is created to allow the system to produce better, faster, cheaper so saying “we don't need this” is pretty much akin to saying we don't want better, faster, cheaper. I understand that you may be skeptical about some of the ideas, but they are proven ideas, and you owe it to your organization to try them before dismissing them out of hand.

The core changes in mindset that we need to make are changing to approach of leadership (see Jim Highsmith's excellent Adaptive Leadership for a longer discussion):

• Adapting: Since change is inevitable, the mindset must be set to be resilient in the face of change. We need an approach more open to leveraging change, sometimes creating change through experimentation. This is different from the traditional approach which treats change as “the enemy”. As Jim Highsmith says “A traditional manager focuses on following the plan with minimal changes, whereas an agile leader focuses on adapting successfully to inevitable changes.”
• Exploring: Similar to adapting but focussed more on how to response to change. The problem is that traditional thinking forces the development of an idea through a big upfront effort. Agile approaches support the development of an idea through gradual evolution rather. Leaders need to support the use an Envision-Evolve process rather than a Plan-Do process. This is a hard change both for leadership as well as the people involved and effects many aspects of the thinking process (for example, think about forecasting a release date with this approach.)
• Facilitating: Instead of telling people what to do, managers and leaders need to create an environment where the self-organizing, self-developing team can develop. “Adaptive leaders lead teams, non-adaptive ones manage tasks.” Facilitation does not mean “don't do anything”. Part of it is also to bringing clarity to ambiguous situations. “Adaptive leaders have the ability to cleave through this ambiguity, to focus on a decision when everyone else is floundering, to clarify direction when everyone else sees confusion.”
• Riding Paradox: Most of the pressing issues facing leadership seem contradictory. Adaptive leadership strives to treat issues in an “and” way, rather than an “or” way. In other words, the idea is to see if we can leverage both issues and come up with a great solution, rather than having an or result where one or the other approaches loses. An example paradox - “we need predictable dates” and “we need to change direction”. In many situations management this apparent paradox plays out as “lip service” where the words might be “we need to change direction” while the actions clearly indicate “a predictable plan” and leadership has not helped to address this apparent paradox (note: agile approach allows for predictability and the ability to change direction, but it requires a thinking process that understands how to apply this approach, not one just based on demanding “we want to do both”).

Key questions that an executive can use to drive the required changes include (see Alistair Cockburn's "The Heart of Agile"):

1. Independent of anything else going on, how will you increase collaboration?
2. Accounting for everything else going on, how will you increase trial and actual deliveries to customers?
3. How will you get people to pause and reflect on what’s happening to and around them?
4. What experiments will your people do at different levels in the organization to make a small improvement?

The role of management changes as well (for more see Jeff Sutherland's discussion on how management needs to change):

• Provide challenging goals for the teams - something focussed, exciting, engaging.
• Create a business plan that works - based on reality of what you are seeing
• Eliminate organizational debt - such as structures that require working dependencies for every item of value we need to deliver to customers Why Should We Work Harder to Eliminate the Effect of Dependencies?
• Provide all resources a team needs - hardware, capability, training, tools.
• Identify and remove impediments for the teams - and make sure you are seeing these impediments, that they are not being hidden.
• Know velocity (capacity) of the teams - so you can understand the true capacity of your organization to deliver value and do not push too much work-in-progress (WIP)
• Remove waste – eliminate technical debt
• Hold product owners accountable for value delivered (for example, per point) - which means they also need to be concerned about technical debt.
• Hold scrum master accountable for process improvement and team happiness - which means we have engaged teams.