As I wrote this book, I was working on my doctorate in leadership and working as the CIO at a technical college. As a consequence, I thought a lot about leadership and how senior leaders can influence the success or failure of agile within an organization. Aside from the various tactical challenges noted elsewhere in this book, the biggest causes of failed or muted agile are failures at the senior leadership level. These failures can manifest as failure to provide the appropriate support to the teams and the organization as they work to try agile or improve on it. The other way that senior leaders fail their teams and organizations is by failing to prioritize in the way that organizations, regardless of methodology, must do in order to run their project deliveries effectively and for maximum benefit to the organization.
The executive leader has a critical role in the adoption and implementation of agile practice within their organization. Like any change, the sustained and unequivocal support of leadership is among the most crucial success factors to an organization’s attempts to adopt and use an agile framework to deliver projects and other work. For this reason, it is also critical for leaders to understand not only the necessity of their support for the overall adoption of agile but also how the decisions made by leaders become even more impactful given the reliance of agile on rapid decision-making to deliver value rapidly and continuously to their organization.
Executive leaders must recognize how their understanding of agile influences their decision-making and the impact their decisions and leadership have on the organization’s ability to successfully leverage agile methods. An agile executive must understand how agile practices fit in organizational culture and structure and with other project management methods used in the organization. Recognition of misconceptions about agile, the need for rapid decisions, effective governance, removal of organizational impediments, and servant-leadership at the executive level will help the executive leader perform effectively in agile environments and ensure organizations maximize the potential benefits of agile.
Leadership Misconceptions of Agile
When executives learn about agile, it is not uncommon to learn about only the possible benefits of agile and misunderstand how these possible benefits are truly realized. These misconceptions happen when executives gain only a superficial understanding of agile methodologies and practices. The most common misconception is that agile equates to “faster,” and that choosing to use agile on a specific project or as an approach to project management will automatically make projects complete faster than previously seen.
Other misconceptions include the assumption that agile project management will reduce the amount of planning necessary for successful projects or that projects could go faster because less documentation or measurement will be needed to be successful. It is also a misconception that agile project management is somehow less disciplined than traditional project management approaches.
Recognizing the common misconceptions helps the savvy executive recognize when their misconceptions of agile are affecting their leadership decisions while there is still time to correct the decision. One example of this misconception is assuming that the initial release plan generated by an agile team will be the plan followed throughout the duration of that project vs. recognizing that each sprint will result in some adjustment to the plan.
Leadership Mistakes with Agile
I’ve seen executives with only basic knowledge of agile methodologies and practices make assumptions about agile practices and misapply them. When this happens, the benefits of agile may not be realized, and the use of agile in the organization may be diminished or even fail. It is not uncommon for executives to assume that using agile means a project will be completed faster, or that less planning and discipline will be necessary. Executives may also misunderstand some metrics used with agile to the overall detriment of specific projects or the successful adoption and usage of the practices within their organizations.
While consulting for a health insurance company, I was in a project steering meeting and heard the CIO propose an agile approach for a project expecting that this would automatically shorten the overall projected duration of the project. I knew that the CIO’s familiarity with agile practices was very basic, and that agile was not the best approach to use with the project in question. I also knew that this meeting was not the place to expose the CIO’s basic understanding of agile. After the meeting, I met with the PMO leader (he was also in the meeting) to discuss and to propose a conversation with the CIO. The PMO leader met with the CIO to explain how agile does not equate to “faster” when looking at the overall duration of a project.
A vice president adding work from another project that was behind schedule into the backlog of an agile project and team in hopes that it would get done faster.
Business and IT leadership forcing a team to co-locate into a “team room” in hopes that forced collaboration would “motivate” the team to complete their work sooner.
A senior director at a client on one of my CloudCraze implementation projects asked the project team to add a second daily stand-up to their routine to review and report on bug status – resulting in less time each day to work on the bugs (on this one, the lead architect called me nearly in tears to ask me to talk the client out of this – I did).
Early days of CloudCraze – Working with a vice president of product management who was not versed in the need to maintain a prioritized backlog of work, which caused sprint planning to be ineffective and the sprints to start late and underplanned.
All too common – Spreading resources across multiple projects in an effort to make incremental progress on these projects.
When senior leaders believe or assume that “agile” means “faster,” or that using agile practices will quickly fix long-standing system problems with project delivery, it often results in ineffective or failed agile projects and practices. Smart executives will seek education in agile methodologies to avoid these misconceptions. This education can help leaders avoid common mistakes and leadership failures that can have short- and long-term impacts within their organizations and result in diminished returns from the organization’s investment in adoption of agile methodologies and practices.
How Executive Leadership Can Influence Agile’s Benefits
Executive leaders in organizations that are using agile practices must understand how their leadership and decisions influence the outcomes. A savvy executive will recognize how timely decision-making and accountability can ensure that agile projects and teams in their purview maintain a high pace of output and high-quality deliverables. Executives who don’t understand how their leadership could help maximize agile benefits put their organizations at risk of their agile teams and projects missing out the potential benefits of agile practices.
An organization, its projects, and employees realize the complete benefits of agile when agile practices are fully implemented and leveraged within an organization. As noted earlier – with any change or process improvement, the most critical success factor is executive buy-in and support. It’s also key for executives to recognize how their decisions help to focus their organizations on projects that deliver the highest value to their customers. They in turn must hold their product owners, scrum masters, and project teams accountable for value creation while holding themselves accountable for providing timely guidance and governance.
Executives have a different type of responsibility in agile environments. They set an example by holding themselves and their peers accountable for the same behaviors that help agile teams function. Leadership teams get pulled in many directions each day, but they can support their agile teams and projects by meeting daily to make decisions needed to keep the teams and projects moving and then communicating these decisions quickly.
Don’t Create Impediments – Remove Them
Leaders in agile environments best serve the organization when they are removing impediments, but sometimes the executives are an impediment. Avoiding situations where executives slow down agile teams is critical. Conversely, being attuned to impediment removal is also critical. Jeff Sutherland once said, “For Scrum to really take off, someone in senior management needs to understand in his bones that impediments are nearly criminal. The effect of eliminating waste is dramatic, but people often don't do it, because it requires being honest with themselves and with other.”
Earlier, I noted how a senior director created an impediment by asking for a second daily stand-up focused on bug status – major impediment. Another impediment that senior leaders sometimes create is by insisting on showing up at team’s daily stand-ups. Even if they manage to remain silent, they still create an impediment for the team just by being present. The muting effect that senior leaders have on their team’s ability to communicate candidly with each other cannot be underestimated.
One of the most important contributions of an executive in an agile environment is to remove impediments that a team cannot remove because it lacks authority. The impediment could involve a spend approval or an organizational change that the executive would need to sponsor and approve. For example – at CloudCraze, as the breadth and complexity of the overall product expanded, it became increasingly clear that the development organization’s ability to rapidly and thoroughly test the software due to lack of automated testing tools was severely limiting the team’s capacity in sprints and releases.
The QA manager regularly brought this to my attention, and I stepped up the pressure on our new owners to approve the funding necessary to acquire these tools. I recall one of the tipping points being my use of a well-placed F-bomb to describe our lack of automated testing as “f***ing embarrassing.” Given that I rarely curse (at least in professional settings), this helped to convey the seriousness of the situation and the urgency of remedying it as quickly as possible.
My agile coach/scrum master and I removed another impediment when we made the decision to split our single large development team into two smaller teams. Over time, the team had grown to the point that sprint planning and daily stand-ups (performed virtually through conference calls) were becoming inefficient. The team had not wanted to make this change; however, the scrum master/agile coach and I knew it was the right move. I had to own and make this tough decision.
When agile leaders act and are accountable to each other and their teams to help realize these benefits through actions such as timely decision-making, it maximizes these benefits for the whole organization. Executives must be aware of scenarios where their actions or failure to act could actually impede agile teams and projects and learn how to avoid those situations. An executive should remove organizational impediments allowing the teams to work more efficiently and maximize value creation.
Ruthless Prioritization
One of the soapboxes I’ve chosen to stand on throughout my career is the importance of prioritization in project management. I’ve seen otherwise respected and successful organizations struggle with projects because they could not or chose not to do the hard work of prioritization. In environments where everything is top priority, nothing is top priority. A key responsibility of senior leadership is ruthless prioritization, leaving no doubt as to the organization’s top projects.
There are four common scenarios where failure to ruthlessly prioritize impedes project execution. While these scenarios transcend any project management approach, they are even more impactful when an organization is using agile practices.
The compromise – The compromise scenario comes from fear of slowing some “important” projects in favor of other projects and pushes leaders to a poor compromise. No tough decisions are made, no projects are paused or deprived of resources, and all projects continue. Resources are diluted and spread thinly across these projects, reducing progress to a crawl.
By prioritizing too many things, the organization makes minimal progress on many projects, but makes no value-creating progress on any. Compromising on prioritization also compromises competitive advantage.
Do it all – This scenario asks teams and resources to work 80-hour weeks to make measurable progress on multiple “priority” projects. Sometimes this is necessary in early phases of startups, and rare “bet the company” scenarios where this approach is warranted for a short, intense time.
Too often, the 80-hour-week solution is senior leaders’ failure to prioritize vital few projects, combined with willingness to place the burden of failure to prioritize on their teams and resources. In the short term, this tactic can yield results. Beyond a few months, any accelerated value delivery is unsustainable. Long term, this tactic burns out teams, creates toxic workplaces, and causes turnover.
Analysis paralysis – Slightly less destructive is the analysis paralysis scenario. This emerges when the organization’s senior leaders have low urgency to prioritize and direct project teams and resources accordingly. Instead, their repeated requests for “what-ifs” burn cycles from key resources, create zero value, and create a false impression of careful consideration while concealing indecisiveness.
Organizations afflicted with analysis paralysis can’t advance their key projects. Team morale suffers as they perform low-value work while developing scenarios for consideration at the next project review meeting. When a decision is finally made, too much time has been lost and effort wasted that could have been saved by decisive leadership through ruthless prioritization.
All projects are high priority – Worst-case scenario: senior leaders telling subordinates to treat everything as top priority and “find a way.” Prioritization is not easy. Senior leaders put their reputation, credibility, and even their career on the line with these decisions. This partially justifies their compensation and perqs. The expectation is leaders know their business, strategy, and teams and therefore can make these tough calls. That is why it is unacceptable to pass tough priority decisions and consequences to subordinates when senior leaders are literally paid to prioritize.
Avoiding these problem scenarios requires a regular and ruthless prioritization process for projects. This seems obvious, but many organizations lack this or the ability to execute it at critical times. Like security or disaster planning, ruthless and rigorous prioritization cannot be reactive or situational. It must be become as routine and natural as coming to work and becomes easier to sustain over time. In organizations where this is the norm, any pause or deviation from this cadence is impactful. The organization comes to rely on the process, even take it for granted. This is a good thing – it means everyone at all levels is bought in, the rhythm is there, and it is a natural business process.
The challenge is getting this in place. Like all change, it requires realization of the problem and the importance of fixing it. Once an organization follows through on the commitment to put a rigorous prioritization process in place, they must stick to it every week. From the CEO down, there must be an environment of accountability and rigor in assessing priorities and recognition of the critical role of constrained resources as engines of value creation. They can be driven hard, but selectively, and only when priorities support this, lest you burn them out.
Pulling resources off an important project and dealing with the fallout in order to execute on a more important project
Delaying or canceling “nice to have” projects that please some stakeholders but create little or no value or competitive advantage
Stopping some projects to take advantage of a window of opportunity and accept that a near-complete product release might slip
Appeasing an angry customer for one more sprint in order to ship a near-complete product release or – the exact opposite – delay the release to fix the angry customer situation
Finally, it means scrutinizing the project and product portfolio every two to four weeks without fail and revisiting decisions if new or changed conditions warrant. This requires a structured agile governance process. I’ve put this in place in some organizations and coached other organizations on how to stand it up and operate it. I do not claim this to be the best or most perfect approach to agile governance, but it’s worked for me.
Agile Governance
Executive leaders are responsible for governing projects, project portfolios, and products in their organizations. Executives are responsible for evaluating projects and new product development efforts before they are started to ensure they are a good fit for the organization and its objectives. They must evaluate results and metrics to ensure that the projects are progressing and will deliver expected value.
Agile requires a continuous focus on governance and decision-making from executives due in part to agile’s rapid iterative pace. Agile projects will stall or see their value delivery muted if executive leaders do not provide continuous input and timely decisions, particularly associated with prioritization.
The biggest difference between agile project governance and governance in plan-driven project environments is the pace and frequency at which governance input is needed. Executives accustomed to phase-based project environments may expect monthly steering committee meetings where project decisions are debated or deferred for further consideration. Environments and approaches like this will stifle agile projects and cause them to stall, fail, and ultimately prevent them from delivering value to the organization.
Using Metrics for Agile Governance
Executives operating in agile environments should expect to see frequent updates from various project, product, and value stream efforts within their organizations. The agile teams work from roadmaps defined by organizational strategies and objectives which are set by executive leadership. The path to progress toward these objectives is mapped out in release plans which are then executed by the various teams in their sprints.
The executive leadership team brings important information and perspectives to the governance process. Input from the executives representing sales, various customer-facing operations such as implementation or customer success, product support, and product management must all be considered and balanced to provide guidance to the agile teams and projects. Based on this input and the evaluation, the executive leadership team may adjust the overall objectives of the release plans and sprints to meet the evolving needs of the organization.
Making Leadership Decisions in Agile Environments
Executive leadership and project governance imply making decisions that are sometimes challenging or unpopular. In agile environments, these decisions must be made rapidly so that the agile teams are not waiting for direction or impediment removal.
Executives are called upon to guide projects and project teams based on the information they receive and the outcomes of the ongoing sprints and releases. They must consider the likelihood of completing committed features in a release along with the risks that technical or resource challenges are posing. Executives must provide guidance and decisions on whether at-risk features or deliverables should be dropped or deferred, or whether less-vital features should be dropped to focus on must-have features.
Leaders must also consider external factors such as customer requests, input from sales, movements in the competitive landscape, and important customer-facing projects or implementations that may be dependent on or influenced by the deliverables from ongoing agile projects. These external factors combined with the progress of projects and teams influence the guidance and decisions that executives are called upon to make to govern the projects or products and keep the overall flow of agile projects moving so that the organization regularly realizes value from them.
Executive Servant-Leadership in Agile
Servant-leadership is a core tenet of agile project management practices. At the project team level, scrum masters/agile project managers are expected to be effective servant-leaders. At the executive level, effective servant-leadership is even more important, because it sets the tone for the organization and ensures that leaders are focused on empowering their project teams, providing timely decisions, removing any impediments to their progress, and ensuring they have the resources they need to deliver value to the organization. This enables the organization to leverage the benefits of the agile methodologies.
Executives used to more formal or traditional management structures must recognize that in agile, the effective leader works in service to the people in the organization that can deliver value. An executive leader in the contemporary business environment embraces the evolution away from the bureaucratic, status-conscious hierarchical structure and toward the flatter, leaner organization focused on merit and value creation. An executive servant-leader recognizes that empowered teams working in agile environments need leaders who will protect them and do whatever must be done to enable them to work effectively with focus on the customer.
Impacts of Missing Servant-Leadership
Successful use of agile practices to deliver value requires that everyone in the organization be accountable to keep things moving. When executive leaders fail to do this, the processes break down. Agile teams cannot be effective without governance, prioritization, continuous feedback and strategic direction, and constant attention to removing organizational impediments.
Executives who are invested in hierarchy versus value creation will cause agile teams and projects to slow down, ultimately becoming impediments to value delivery. Executives who fail to hold themselves and their peers accountable to do whatever must be done to enable agile to work in the organization do a disservice to their customers and their teams. Agile leaders who don’t participate in sprint reviews and ask what they can do to help teams improve performance are not helping their people, teams, and organization become iteratively more productive through agile practices.
Executives who expect use of agile practices to “fix” projects, make projects “go faster,” or who somehow expect to reap the benefits of agile practices without investing in them, changing the culture, or changing their own behavior are ultimately responsible for failed agile projects and implementations. Executives who embody servant-leadership enable their organizations to leverage benefits of agile. An executive servant-leader should work to empower teams by providing necessary guidance and resources and also by removing obstacles that can hinder value delivery.
Summary
Executive leadership sets the tone for success or failure in agile environments. Creating a culture of accountability, timely decision-making, support for prioritization, and servant-leadership helps to foster environments where agile and agile hybrids have a higher chance for success. Executives who cannot or choose not to lead in this way are doing their organizations, their projects, and their people a serious disservice. Agile is all about value delivery, and the effective agile executive does everything possible to ensure that their leadership removes impediments and creates opportunities for rapid value realization through agile.
In the next chapter, we discuss approaches to implementing agile practices. We will discuss approaches and impediments to implementing agile as well as review questions that should be asked to determine if an organization is ready to start using agile or an agile hybrid.