Removing Agile Roadblocks Brings Exponential Benefits

Posted March 24, 2021 in Business Agility & Software Engineering Excellence, Business Technology & Digital Transformation Strategies Cutter Business Technology Journal
In this issue:


As leaders, we naturally focus on the exciting, high-impact areas, which unfortunately leads to blind spots around the boring, "un-fun" areas. Cheryl Crupi shares six hygiene factors that can be crippling if not addressed. The factors highlight the need for a holistic approach to agility that integrates elements of digital, Agile, DevOps, and many other modern practices for companies that want to be successful in the digital age.


Speed, adaptability, and technical excellence are just a few reasons large enterprises are heavily investing in becoming Agile. Unfortunately, many forget the impact of deeply rooted historical processes and culture around enterprise controls, systems-of-record data, goal setting, funding, and change management. These roadblocks will not change without attention, and ignoring them will drain the momentum from your transformation, tarnishing Agile and DevOps with leaders and workforce alike.

This article examines these critical hidden hygiene factors as well as measures to remedy them. Removing these roadblocks is painstaking, tactical work. It doesn’t have the inherent fun and adrenaline of “going Agile.” However, investing time in making Agile easy will produce enormous benefits. In my experience … exponentially so.

Simplify Controls and Process

We know that controls and process ensure safety and quality. They evolved to support efficient operations at scale, coordinating the work of hundreds or thous­ands of people. But look closely at the processes of your organi­zation: procurement, legal, regulatory, audit/risk, architecture, and even new product devel­opment. You may be surprised to find they pose a series of waterfall phase gates. Sequential phase gates are a relic of an earlier time. Gates drive up batch size, reduce frequency of delivering to your customer, and impose costly delays and handoffs. A new product might pass through five or six of these waterfall processes before delivery to market. The aggregate wait time is staggering.

Sponsors, practitioners, and teams alike pale at the prospect of repeating enterprise processes on a sprint or quarterly cadence. Literally, it might be impossible to iteratively complete gates designed to be satisfied once in the lifetime of a project. Under the demands of a continuous product delivery model, these processes break down. Teams look to complete a gate once and not look back. Adjustments based on learning are sacri­ficed by lengthy change-control loops. In the worst case, a major change lands an initiative back at square one.

You must retool core bureaucratic processes and con­trols to achieve business agility. Incremental improve­ment is not fast enough. The authors of The DevOps Handbook tell us that “bureaucracies are incredibly resilient and are designed to survive adverse conditions — one can remove half the bureaucrats and the process will survive.”1 These processes accreted over years, even decades. Often, no one remembers the conditions or risks they were intended to guard against in the first place. The processes themselves are a source of division and blame between functions, undermining the collective ownership necessary for agility.

Instead of incrementally fixing these processes, stand up an alternative path for Agile. At first, this path will involve some countermeasures, a “skip the line” fast pass for Agile, and expert support. Make new processes simple and low friction. Minimize handoffs. Work carefully with enterprise control owners to ensure safeguards are intact. Employ Lean tools like the “Five whys” to figure out what you need and what you can throw away.

Build adaptability into your new process and controls. Eliminate, minimize, and automate repeatable activities, in that order. If you automate before eliminating and minimizing, you will rebuild the flaws of the old in the new. Guide your efforts with flow metrics. Validate and fix actual constraints instead of taking aim at commonly held scapegoats. Everyone may complain about funding approvals, but flow metrics may show server provision­ing is the real choke. Good telemetry, and a baseline to start, focuses everyone on the right problem and boosts morale.

As you retool controls and process, consider all the people being impacted. Remember that people are accustomed to using those things. Don’t assume they will share your relief at eliminating old process. Change, even good change, is stressful. Provide a clear vision, a roadmap, and a change plan. Help people understand the why, how, and when of change, as well as how they fit into the future. This transparency will dial down resistance and reduce distracting requests to improve legacy processes.

Ensure Actionable Data Fit to Steer

To truly be Agile, we must capture the right data and use it well. Much like enterprise process, data collection habits can perpetuate embedded waterfall thinking. I have witnessed organizations fall short of agility goals for years due to lack of actionable data fit to steer. Fitness relates both to the data you collect and the quality of that data.

Data tells a story about an organization. The data you collect reveals beliefs and frames the questions you can answer. Agile organizations optimize for predictability and outcomes, delivering on cadence and measuring business value. Waterfall organizations measure scope, schedule, and cost (and, sometimes, ROI). The iron triangle — scope, schedule, cost — is rooted in water­fall thinking. Inspect the executive dashboards in your organization. If top performance measures relate to scope, schedule, and cost, your organization is optimized for the wrong variables. Speed and adapt­ability are served by different meas­ures. Create a product-oriented scorecard that includes business outcomes, predictability, and end-to-end flow metrics in addition to financial and operational metrics.

To adapt is to steer, and to steer well requires quality source system data. Is your data trustworthy? How you, your colleagues, and company leaders talk about your data offers clues. Is the proficiency of people who create the data disparaged? How much time is spent validating and cross-checking? In meetings, do debates center on data reliability rather than what the data tells you? Do you make decisions to proceed or cancel based on data or despite it? 

If you spend a great deal of time cross-checking, dis­paraging, or debating reliability, you have some work to do on data quality. Consider dedicating a team to it. Give this team a clear charter and latitude to work proactively across your organization. Often, process complexity contributes to data quality issues. Process simplification can accelerate data improvement efforts. Also, invest in connecting data end-to-end along product lines. This will involve tracing work across enterprise systems, such as product development, funding, work management, and release.

Be clear on your vision to steer confidently with actionable data. As with legacy processes, apply the Five whys to legacy metrics. Eliminate those that reinforce waterfall thinking. Do not make the mistake of hanging onto legacy metrics too long; this sends the wrong message. Your workforce will march to what is measured instead of what is aspired. As part of your change roadmap, consider ceremonially retiring old metrics that do not align to new ways of working.

Empower Directional Change Without Guilt

Adaptability requires objective evaluation and the ability to pivot without guilt or blame. Fixed goals promote people (or teams) who predict and deliver over those that experiment and learn. Organizations can look Agile (hold stand-ups, retros, demos), but fail to achieve value because they cannot or will not pivot. Although not the topic of this article, psychological safety and culture change figure heavily here. Starting with practical hygiene factors, ensure HR goal setting, performance reviews, and rewards make explicit the permission to experiment without personal repercussions.

First, look for indicators of whether your company walks the walk of adaptability. When goals change or an initiative gets cancelled, does it negatively harm people? Does it impact compensation, limit growth potential, or result in people being exited from the company? Is there a culture of minimizing bad news or of watermelon initiatives (look green on the outside but are red on the inside)? Is the workforce resistant to new practices? If the pace of adopting Agile is slow, despite training and enablement, the workforce may not feel safe trying something new.

The inability to pivot has ramifications at every level. It prevents per­sonal and collective agility. It fatigues rapid learners, experimenters, and innovators. Dissonant empower­ment talk will eventually cost retention of top talent you dearly want to keep. Agile practices such as design thinking and customer centricity help evolve a “pivot without mercy” mindset and culture. While this thinking is taking hold, consider specific measures to reinforce adaptable goals and experimentation.

Experimentation, like anything else, requires time and practice. Leaders must model the basic tactics — the stance they take regarding their own experimentation really matters. They must be willing to learn and experiment in front of everyone else. Last year’s Harvard Business Review cover feature “Building a Culture of Experimentation” notes that “leaders have to live by the same rules as everyone else and subject their own ideas to tests.”2 When leaders use language that emphasizes “the right experiments” or praises “successful” experiments, they create an environment that is actually hostile to experimentation.

Good experiments are well framed and fact focused, and they produce learning regardless of whether they produce the desired outcome. Leaders sharing their experiments — and the results — establishes credibility for changing direction safely. Similarly, changing from annual performance rewards for hitting a goal set a year ago to adaptable objectives and key results (OKRs) makes it explicit that informed changes in direction are the new norm.

Town halls and internal social media are excellent forums to empower directional change without fear or guilt. Airtime in these forums is commonly reserved for success stories. Consider the impact of giving equal airtime to termination of product concepts found unlikely to produce profitable outcomes. This endorsement will promote experimentation. Excellence looks like running thousands of experiments, not tens or hundreds. When a team finds a line of experimen­tation unproductive, cancel the effort and assign exciting next challenges to that team. Also, frequently communicate strategies and OKRs, and provide guidance for new Agile performance and goals practices.

Accelerate Business Responsiveness Through Lean Strategy and Investment Funding

There is no question that iterative funding is a must-have for Agile. Lean Portfolio Management (LPM) dramatically speeds time to test top-priority ideas. Work is easy to cancel and thus easier to start. LPM is orders-of-magnitude better than protracted annual planning that locks in big bets for next year and beyond. Conventional annual planning kills speed and responsiveness by adding months, quarters, or years of lead time, and by locking in inflexible and unrealistic commitments with tens of approvals. In contrast, LPM offers speed, adaptability, and collective ownership.

Deciding what to fund is hard. The list of great ideas always outstrips the capacity to deliver. More effective funding mechanisms enable flow of work. However, it is not the only important factor. A better funding proc­ess will benefit your business only if you successfully pick top-value work. Look upstream from mechanics and ensure your strategy and alignment practices are working. Rather than focusing on funding alone, have alignment, scope, then fund be your goal.

Fixing the mechanics of funding is much easier than getting alignment on outcomes across top leadership. Value-stream alignment and clear commercial outcomes will help. If you haven’t done so, build product-aligned teams. In addition to simplifying the landscape, this provides an opportunity to reduce dependencies and boost predictably. It will also bring all stakeholders to the funding conversation — a tremendous game changer. In joint-funding discussions, I have seen years-long conflicts resolved with mutual understanding as a marketing leader and a technology leader realize building an automation capability is the top priority for both.

Keep an eye on cultural considerations. Going back to experimentation, consider tactics that promote curiosity instead of advocacy. In an advocacy environment, sponsors strive to convince others that their idea is best. Success looks like winning the debate. A context of curiosity supports keen conversation of alternatives. Success is arriving together at the best answer. Getting this right requires trust, a healthy forum for prioritiza­tion, and frank discussion about what your customer really needs. Practices like participatory budgeting offer a different way to facilitate these discussions.3

Partner with Sponsors

As you tackle Lean funding and investment strategy, you will surely encounter sticky questions about already-funded initiatives. Do you play through all committed work? Start fresh? The answer is neither. Rather, provide an outcome-oriented “on-ramp” that is empathetic to teams and sponsors.

Partnering early is essential. Sponsors may be excited about Agile, but the prospect of needing to rewin funding for a big multiyear investment could stop them in their tracks. Likely they have spent months, even years, securing funding. Any progress you have made on making Agile easy will help reduce concerns about onboarding in-flight work. Conversely, high-friction funding will garner resistance.

As with process and controls, build trust and confi­dence with countermeasures, “skip the line” fast pass for Agile, and expert support. Articulate the case for change in terms that matter to sponsors: maximizing business outcomes. Most organizations have too much work in progress to deliver with speed. Highlight the benefit of strategy alignment to make it easier to “set down some work” so the organization can focus on top-priority work.

Risk management is also compelling. Most sponsors have experienced big commitments gone bad in the form of slipped dates, jettisoned scope, and too many corners cut. No doubt, small, iterative deliverables are less risky. However, it can be hard to imagine big initiatives delivered in increments. It isn’t as simple as drawing two-week iterations on a Gannt chart. Offer expert facilitation to break big-bet initiatives into successive minimum viable deliveries (aka minimum viable products, or MVPs) that can be tested with customers.

Use these MVP discussions as field research for simplification work. Look carefully for impediments to breaking down work. The generally accepted “long poles” in the product pipeline might be processes you can work to simplify. Feedback from teams and sponsors offer terrific insights for streamlining. If these top constraints are external, talk with sponsors about ways to exploit these constraints to your advantage.

Bring the Workforce Along

In Dare to Lead, Brené Brown says, “We should all be held to be accountable for being both optimistic and realistic.”4 As change leaders, we must show a clear pathway to the future. This involves inspiring and empathizing. It requires an eye to practical consider­ations as well as aspirations. Keep in mind that at every level of your organization, there are people who advanced their careers through waterfall and conventional ways of working. Most have had no opportunity to work in an Agile team.

Agile change leaders are asking their organizations to take a leap of faith. Yes, we all want to be fast, high performing, and dynamic. But for those who have not worked in a thriving Agile environment, the path is not clear. Taking a page out of Switch: How to Change Things When Change Is Hard, “What looks like resistance is often a lack of clarity.”5 

It is normal to prefer habits (even bad ones) over change. Provide clarity as to why new habits are needed. Offer how-to guidance and job aids to make getting started easy for first-time Agilists. Get feedback from new adopters, and fix the things they don’t like. Most people prefer to learn from others. Provide a safety net through learning networks, job shadowing, and communities of practice. As noted, leaders must serve as exemplars. Set them up for success through one-on-one coaching and help in preparing for events like town halls and first demos.

In the course of “going Agile,” you will eliminate old processes, practices, and mindsets. Take care not to marginalize the people who are expert in the previous way of working. Success depends on everyone in your organization understanding the vision, the why, and the road to get there.


Achieving true business agility requires a solid foun­dation to go fast, with safety and focus. To do so, your organization must have simple processes, actionable data, the ability to pivot, alignment, a sponsor on-ramp, and a plan to bring your organization on the journey. Achieving these things involves grueling tactical work. This often-overlooked investment in basics is necessary for both Agile and DevOps to take root in your organi­zation. By fixing the hidden friction points addressed here, you’ll inject oxygen into your transforma­tion — breaking down hidden resistance, activating your workforce, and increasing speed. You will make Agile easy, and in doing so you’ll accelerate the switch to Agile and greatly amplify the benefits to be gained.


1Kim, Gene, et al. The DevOps Handbook. IT Revolution Press, 2016.

2Thomke, Stefan. “Building a Culture of Experimentation.” Harvard Business Review, March/April 2020.

3Participatory Budgeting.” Scaled Agile Framework (SAFe), Scaled Agile, accessed March 2021.

4Brown, Brené. Dare to Lead. Random House, 2018.

5Heath, Chip, and Dan Heath. Switch: How to Change Things When Change Is Hard. Broadway Books, 2010.

About The Author
Cheryl Crupi
Cheryl Crupi is the founder and principle of Crupi & Co., LLC, and an internationally recognized speaker, author and executive coach specializing in Lean-Agile change leadership. Cheryl is passionate about achieving the benefits of Agility, starting with the building blocks of team Agility, to the full span of enterprise business Agility. In over a decade as an enterprise Agile change champion in Fortune 500 companies, she has successfully… Read More