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Strategic Project

Alignment in
an Agile World
Managing projects that quickly deliver value
to customers while achieving strategic goals
and objectives
Table of Contents
Why we wrote this ebook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3

Project management—what’s the point? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4

Waterfall vs. Agile . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5

Agile in practice . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19

Agile roles and responsibilities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24

Events and artifacts . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31

Roadmaps and project plans in an Agile world . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 38

Agile and strategic planning . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 2


Why we wrote this ebook
Agile has been around for decades, but it is still a bit amorphous and of how software gets built. Project managers and product leaders can all
mysterious to the uninitiated. At its core, Agile removes the shackles from reap the benefits of Agile when they understand what it has to offer and how
product development. Instead of prescribing and specifying every last detail to structure projects and programs to get the desired results.
before work commences, engineers partner with the product team to deliver
functionality in quick, iterative bursts. Agile works to everyone’s benefit due to its strategic alignment—ensuring
that the goals and objectives are agreed upon and mutually understood
Forward-thinking senior managers obsess over Agile, which drives its use from the C-suite to entry-level QA staff. When everyone has the same,
in software development and engineering. As a result, those not directly shared purpose, Agile can supercharge the team and dramatically shorten
involved in writing code and shipping software can feel like outsiders. the time between ideation and delivery, giving the business more time to
learn and grow throughout the product’s lifecycle.
Agile and strategic planning might seem at odds to the uninitiated since
engineering autonomy and building software in two-week chunks can lead to
unexpected implementation decisions. Yet, with all the talk of rapid iteration, Agile can dramatically shorten the
learning on the fly, and “self-organizing teams” operating independently,
where is the space for long-range planning for complex initiatives?
time between ideation and delivery.
These two worlds shouldn’t be mutually exclusive and are, in many cases, The ebook will explain the practical elements of Agile and how those new
entirely complimentary. The ebook aims to demystify Agile and explain how to the methodology can prepare for and engage with the process. The
those in its orbit can extract maximum value from the Agile methodology goal isn’t to win over more passionate adherents but rather to point out the
while still staying true to company leadership’s overall vision and strategic critical need-to-know aspects of the methodology and the best position for
goals. Engineers, CTOs, and developers might spearhead Agile adherence organizations to thrive and succeed.
within the organization, but its benefits range far beyond the nuts and bolts

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 3


Project management—what’s the point?­
Planning out and managing complex projects is nothing new. Humans have requirements while (ideally) being completed on time and under budget.
done this type of work for millennia. Whether on a smaller scale, such as Steps must be broken down, completed in the correct order, supplies
building a shelter or on massive undertakings like the pyramids of Egypt. acquired and ready when needed. Construction sites, factories, and
kitchens are all modern-day examples where project management skills are

Almost any initiative requiring employed every day.

multiple steps, collaboration, When planning, designing, building, selling, delivering and supporting
products, project management is the only way those things all happen
resource planning, or a blueprint on time. Communication, assigning tasks, coordination, and monitoring

needs project management.


progress are essential parts of any successful delivery, and as products
become more complex, that need only grows greater.

Almost any initiative requiring multiple steps, collaboration, resource While there are many ways to approach this, most product development

planning, or a blueprint needs project management. Project managers organizations tend to use methods and processes that fall into one of two

provide oversight to ensure the result meets the expectations and camps: Waterfall or Agile.

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WATERFALL AGILE

Deliver results only at the end Deliver results early and


of project often, continuously

Perfect for long-term projects like Perfect for IT and software


construction or manufacturing projects, and marketing, too

Waterfall vs. Agile Change has to be managed


and controlled, lest it impacts
Enables change more easily
on projects
project negatively

The end product is defined and


Supports changing reqs, either in
fixed, regardless of changing
the market or technologies
market or technological needs

Delivering by tasks in succession


Delivering in sprints, supports
creates task and team
nimble product teams
dependencies, more fixed teams

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 5


Waterfall method

Product professionals think of Waterfall as the “original” methodology for 3. The user experience team creates design specifications and mock-
building software. It’s been around since the 1970s, although it didn’t get ups to show the development team how things will work from an
its official name until 1976. It was the only way anyone would try to build end-user perspective.
software for decades, unchallenged in its utility and cemented in place due
to its seemingly inarguable logical approach. 4. The product development team creates a functional specification that
specifies exactly how everything will be built and operated.
In a nutshell, waterfall product development is all about the order of
operations. Finish step one before starting step two, which always comes 5. The product development team may also create an architectural

before step three, and so on. overview of how different systems will communicate and the data flow.

6. The quality assurance team creates a test plan that expressly


confirms each requirement in the PRD works as specified in the
IN PRACTICE, IT TENDS TO LOOK SOMETHING LIKE THIS: functional specification.

1. Product marketing creates a Market Requirements Document


7. Product development team members are assigned explicit tasks to
(MRD) or Business Requirements Document (BRD), outlining the
build out the needs for each requirement.
opportunity and essential functions present to offer a viable solution to
the target market.
8. The product is tested by QA using the test plan.

2. Product management authors a Product Requirements Document


9. Operations prepare for the product launch and then deploy the
(PRD), spelling out precisely what functionality should be in the finished
finished product.
product, likely containing user cases and ranked priorities if there’s a
crunch for time or shortage of resources.

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A collaboration-friendly approach
REQUIREMENTS
Because everything is spelled out in advance, it’s easy to anticipate when
other teams will get involved in a waterfall process. Marketing prepares
for the launch by creating a launch marketing plan and then executing
PLAN
it. The sales team receives new or updated materials and training on the
product and its selling points. Customer service gets trained to support the
product when customers have issues or questions. And details like updating DESIGN
accounting systems, working out supply chain issues, engaging distribution
channels, and other essential tasks get handled by the appropriate teams.
DEVELOP

Even at a high level, there are still


a lot of steps and dependencies. TEST

This is where the project manager


RELEASE

comes in. Waterfall project management method

Even at a high level, there are still a lot of steps and dependencies. This is
where the project manager comes in.

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The project manager’s role in waterfall Transparency and visibility

Project managers create a schedule based on level of effort estimates and Waterfall allows for crystal clear visibility into who’s doing what, when
business-driven deadlines, often in the form of a Gantt chart. They’ll also it’s happening, and what comes next. A highly detailed schedule and
make a project plan breaking tasks down to granular levels and assigning extensively documented plan imbue a sense of control and clarity.
them along with each one’s specific timeline. And, of course, they’ll keep Stakeholders and contributors know what to expect, the responsible parties
track of how everything’s going, holding meetings, adjusting schedules and for each step, and a specific ETA early on in the project’s life.
assignments as needed to try and deliver the project on time.
Continual updates comparing the current status to the project plan give
stakeholders a sense of what’s on time, late, or early. Gantt charts and
Waterfall was—and still is in some cases—a popular and loved way similar tools provide visibility down to the individual task level to drive
to build products. However, numerous gates and checkpoints resourcing decisions and spot potential schedule slips and delays. While it’s
may stall the process. not quite 100% certainty, it’s as close as you can get, which makes anxious
stakeholders uninterested in surprises sleep better and focus on other
things. These detailed project plans also highlight how much time and
person-hours are spent on each item, so priorities get reshuffled if the ROI
isn’t there.

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The challenges with waterfall project management

Big, carefully specific projects with inflexible schedules, complex Waterfall creates a detailed playbook that thinks through all the details but
dependencies, and pervasive oversight sound like a great way to guarantee leaves almost no room for adjustments without change requests, schedule
success. But those same attributes make many push back against the adjustments, and other accounting for downstream impacts. Because
waterfall approach and prefer less linear and more flexible methods. the dynamic is structured to prevent deviation from the plans, many
organizations and concerned individuals won’t even try shaking things up.

While a product-led strategy Waterfall presumes the strategy’s assumptions are accurate, and the only
challenge is execution.

incorporates new feedback...


While a product-led strategy incorporates new feedback and sees which
waterfall essentially locks the directions users want to take the product and how to achieve those positive

product development team into outcomes, waterfall essentially locks the product development team into
plans that may last months or even years before a strategic review or reset. If

plans that may last months or years conditions change or new information comes to light, the team faces limited
opportunities to ensure the work will have the maximum impact and benefit.
before a strategic review or reset.
The team has less room for course corrections and pivots, nor is there much

Waterfall made sure you’ve dotted your I’s and crossed your T’s, but that’s freedom for innovation and inventiveness on the individuals building the

all keyed off of rigid requirements authored weeks, months, or even years actual product. The predetermined nature of waterfall stifles creativity and

beforehand. Specific resources mapped out months or even years in creates barriers to incorporate new learnings into projects already underway.

advance, informing headcount and staffing decisions for the leadership So instead, it’s a top-down, follow-your-orders approach that ensures

team. It all sounds great when the market or technological landscape hasn’t everyone is on the same page—even if it’s the wrong one.

changed at all since the original plans.

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Waterfall has maintained its hold on many product development activities THE WATERFALL PROCESS
for so long because it’s predictable and transparent. Things may slip, “This project has gotten so big, I’m not sure I’ ll be able to deliver it!”
problems may arise, and changes happen, but even those modifications are
tightly controlled and subject to approval. For the risk-averse stakeholder,
it’s tough to beat.

The project manager’s role in Agile

Waterfall does everything in order, which often leads to derailed and


delayed projects because of holdups or slowdowns in just one particular part
THE AGILE PROCESS
of the overall project. But, unfortunately, those same processes that make
waterfall so attractive are also its biggest weakness. “It’s so much better delivering this project in bite-sized sections.”

The Agile methodology and framework evolved in direct response to the


frustrations of product development experience in waterfall environments.
It requires a more nimble approach to project management, with
communication more critical than ever. Stakeholders need continual
alignment, and adjusting plans becomes a regular occurrence.

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A brief history of Agile AGILE VALUES

In 2000 and 2001, a group of software professionals assembled, with


the lofty ambition of creating something better. The Agile Manifesto Individuals and interactions
was developed with 4 values and 12 principles. The basic theme running over processes and tools
throughout these fundamental declarations boils down to a few main ideas:

• Things will change, so building out plans and sticking to them no matter
what is counterproductive. Working software over
comprehensive documentation
• Getting products into customers’ hands as quickly as possible is ideal
for delivering value sooner and learning directly from customers for the
future. Rapid iteration is superior to giant, spaced-out releases.
Customer collaboration over
• Developers and engineers know what they’re doing and don’t need to contract negotiation
be spoon-fed instructions. Just tell them the goal and let them figure it
out by themselves.

• Processes and tools are only helpful when they aid and assist versus Responding to change over
hinder and slow things down. Documentation and artifacts are following a plan
acceptable, but face-to-face interactions are superior.

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Agile principles

01 07
Our highest priority is to satisfy the customer through early and continuous Working software is the primary measure of progress.
delivery of valuable software.
08
02 Agile processes promote sustainable development. The sponsors,
Welcome changing requirements, even late in development. Agile developers, and users should be able to maintain a constant pace indefinitely.
processes harness change for the customer’s competitive advantage.
09
03 Continuous attention to technical excellence and good design
Deliver working software frequently, from a couple of weeks to a couple of enhances agility.
months, with a preference for the shorter timescale.
10
04 Simplicity—the art of maximizing the amount of work not done--is essential.
Business people and developers must work together daily throughout
the project. 11
The best architectures, requirements, and designs emerge from
05 self-organizing teams.
Build projects around motivated individuals, give them the environment
and support they need, and trust them to get the job done. 12
At regular intervals, the team reflects on becoming more effective, then
06 tunes and adjusts its behavior accordingly.
The most efficient and effective method of conveying information to and
within a development team is face-to-face conversation.

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For Agile’s practitioners—ideally, dynamic problem-solvers driven by It also distributes decision-making more widely across the organization.
customer delight and comfortable with a bit of ambiguity—it is freeing while Unlike in a waterfall setting, empowered small teams and even individual
also creating enough structure that it’s not too chaotic. Its benefits seem so developers can make judgment calls and implementation choices
obvious and plentiful that any other approach seems ludicrous, with those independently, with less concern for how something gets done as long as it
clinging to the old ways simply because they fear change and losing control. happens and works.

But handing over the reins isn’t always that easy. It requires a level of
When done right, Agile inevitably trust and delegation that may feel foreign or uncomfortable for some

results in software getting shipped stakeholders. The lack of visibility and documentation may also be unsettling
for those used to exactitudes and command-and-control management
faster and more frequently. styles. Plus, some may not ever warm up to placing that much power in the
hands of technical staff.
When done right, Agile inevitably results in software getting shipped
faster and more frequently than before. The condensed feedback loop,
frequent and plentiful iterations, and efficiently handled changes enable
the team to keep putting themselves in the customer’s shoes and optimizing
the experience.

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Clearing up some commonly-held Agile falsehoods FALSE
Agile doesn’t scale.
Agile shares much in common with other major change management
TRUE
initiatives. Lots of socialization, education, and meetings can help, and it may
Agile scales just fine with proper high-level oversight.
take multiple go-rounds to build enough critical mass to win everyone over.

Agile is undoubtedly more manageable in smaller organizations with


One way to get some hesitant parties more onboard with Agile is to confront
less legacy, fewer stakeholders to manage, and a narrower focus, but its
its more suspect attributes and reputation head-on. CIOs, in particular, may
merits aren’t limited to startups and MVPs. Large enterprise organizations
need some extra convincing about why Agile’s benefits are worth it, as the
use Agile, including the likes of Microsoft, Procter & Gamble, and Apple.
fluidity and unpredictability of Agile doesn’t at face value mesh well with
However, being successful in larger companies and projects typically
senior leaders accustomed to lots of processes, documentation, and control.
requires a more standardized process and documentation to ensure
complete alignment and consistency.

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FALSE FALSE
Agile doesn’t care about quality. Agile means you don’t need to spend time on planning.

TRUE TRUE
Software built using Agile is tested more frequently than in Sprint planning sessions happen regularly, and there are daily
waterfall settings. check-ins to check status.

The focus is on adding incremental value through more minor, more Less time and energy get spent planning in an Agile environment than
frequent releases. In practice, this means doling out new features and a waterfall one, and Agile doesn’t mean anything goes. The process
functionality in smaller pieces versus one giant finished product. Still, each still needs agreed-upon long-range goals and objectives, prioritization
incremental addition or change must work before getting exposed to end- exercises, and planning sprints out in advance. The scope is more limited,
users and typically goes through a round of QA before each release. and the process can be more efficient, but planning is still a thing in Agile.

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FALSE FALSE
Agile is all or nothing. You don’t need product managers when you use Agile.

TRUE TRUE
Organizations can use whichever aspects of Agile they’d like. You really need product managers when you use Agile.

Individual teams, business units, or product groups can transition to Product managers play an essential role in an Agile organization. They
Agile without forcing the entire organization to do the same. How one must help define and communicate the vision and strategy, orchestrate
team works shouldn’t dramatically impact the approach others take. prioritization, and represent businesses and customers’ needs. Without
However, there may be an increased need for communication and strategic product management, the Agile teams wouldn’t know what they’re trying
alignment, mainly when one team’s work depends on the other’s, and there to accomplish, why it matters, or when it needs to get done.
may be scheduling impacts.

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FALSE FALSE
Agile only works when Scrum teams are colocated and sit in There’s no real strategy in Agile.
the same room.
TRUE
TRUE Agile only works because there’s a solid strategy understood
Agile works for distributed/remote teams. by the whole team.

While Agile does require more frequent communication with colleagues, Because Agile organizations can much better pivot, course correct, or
standups and other rituals can work just fine virtually, although the time otherwise react to changing circumstances, some mistakenly view Agile
of day may vary with team members spread across multiple time zones. A as 100% reactive. Agile is more reliant on strategy than waterfall. When
distributed team will, however, lean even more heavily on their tools and a team uses waterfall, no one asks “why” once you get past the MRD/
asynchronous communication platforms. PRD phases of the project; the strategic part is over, and now it’s just
execution. For Agile to work well, there must be a comprehensive strategy,
established goals, and—ideally—measurable objectives. It has a great
strategy that enables the Agile team to build, deploy, and iterate so quickly
because they understand the point of everything.

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FALSE FALSE
You don’t need project or program managers when you There’s no documentation in Agile.
use Agile.
TRUE
TRUE There’s not as much documentation in Agile.
Project and program managers don’t need to manage as
Note that “not as much” doesn’t mean “zero.” Development teams need
many details.
to document what they’re building so others can help maintain it. Testers
Although Agile teams won’t need project plans with as much detail and need scripts to run through when verifying that the software works as
specificity, coordination and scheduling don’t go out the window. Unless intended. End-users need help with documents, tutorials, and FAQs, as
the organization is so small, it only has one Scrum team for everything; does customer support. These things aren’t optional, but lengthy, detailed
there’s still essential for project and program management. Doling out product specs create a lighter-weight, more dynamic process.
assignments, building out release plans, and coordinating with the rest
of the organization are responsibilities that don’t disappear when you
go Agile.

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What is Scrum?

The word itself (“scrum”) comes from rugby, describing a sequence of play
where the entire team comes together and works interdependently on
securing possession of the ball. Coordination and joint effort are the only
options during a rugby scrum as teammates interlock their bodies and push

Agile in practice ahead toward their goals.

Product development using scrum doesn’t require close physical contact


While the Agile Manifesto represents an ideal approach to or a shower afterward, but the metaphor holds up. Scrum enables quicker
product development, executing things on a repeatable, software delivery by spreading out the responsibilities across the team and
ongoing basis generally requires a little bit more letting contributors work independently.
scaffolding and structure. Practitioners have several more
robust frameworks and processes available to them, such This decentralized resourcing model varies from the typical, top-down,
as Scrum, eXtreme Programming, and Kanban, discussed approach seen in many project plans in a waterfall setting. By huddling in a
further below. “scrum” daily, everyone still knows their place, working together precisely to
move things in the same direction and achieve a shared goal.

Scrum’s primary purpose is efficiency. Any wasted effort means that less
value gets delivered during each sprint, so if the team can get it right the first
time, they provide value faster, freeing up resources to take on the next thing
in the queue.

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And when looking back at any project that ran late or had disappointing path or waiting around for answers. When speed and efficiency are the
outcomes, poor communication is almost always one of the culprits. goals, these brief, regular pauses in activity pay significant dividends.
However, if everyone has frequently been providing fully transparent
updates, the team can mitigate problems if not altogether avoid them.
Scrum Masters are the ringleaders
Scrum Masters are the ringleaders in this framework, facilitating
in this framework, facilitating
communication ranks at the top of their to-do list. It begins by ensuring
the implementation team understands the sprint goals and overarching communication ranks at the top of
strategy, which empowers them to build toward the desired objective and
not just follow instructions in a vacuum. However, like product managers, no
their to-do list.
one reports to scrum masters, and they must gain authority through trust
and overall accountability. Because sprints are relatively short, only so much work can happen during
each one. The goals for each sprint need to be manageable and doable in
The communication continues with daily check-ins, so everyone knows short order, and there’s rapid confirmation that the desired functionality
how things are coming. There’s an open forum to share, ask for clarification, and approach to delivering it are working. “Chunking up” larger projects into
or triage and troubleshoot when things go awry. The frequency of these smaller pieces for each sprint enables major initiatives to proceed without
sessions keeps people from spending too long heading down the wrong cutting off the flow of additional value, making it to customers regularly.

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eXtreme Programming

eXtreme Programming (XP), another Agile framework, isn’t wildly different Practices intended to pump out software quickly like automated testing, pair
from Scrum, but it is an even more intense and dynamic version of the Agile programming, simple design specs, continuous integrations still work every
methodology in practice. XP takes the flexibility and rapid-release tenets of time. However, XP code is known to be a little rougher around the edges,
Scrum and slams on the accelerator. given the pace. To work well, XP usually requires smaller, colocated teams
that stay in near-constant communication to keep pace.
XP iterations are usually closer to a week in length versus the two-to-four-
week sprints seen in Scrum. Everything is worked on based on priority, with
no wiggle room to skip something at the top of the list for something easier
further down the line, which does occur within Scrum.

XP is also more flexible during an iteration. While sprints are “locked” once
they get underway, XP is more welcoming to changes or wholesale swaps
if requirements change or priorities shift. This customer-friendliness is one
of its key selling points, especially when customers aren’t exactly sure what
they want.

The process also differentiates Scrum from XP. Scrum has no set rules for
the actual engineering practices and procedures used during a sprint.
However, in XP, those elements are defined and adhered to because that’s
the only way the team can keep up with the rapid cadence and still deliver
meaningful value throughout every iteration. EXTREME PROGRAMMING

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Kanban

Kanban evolved from Japanese manufacturers’ “just-in-time” method for Moreover, many organization and planning tools use the Kanban model—
managing inventory and is a highly visual approach to managing product such as Trello, Asana, and Monday—but Kanban boards often feature in
development. It centers on the Kanban board, which indicates where in the more specialized tools. For example, ProductPlan includes a Kanban board
process each item stands—done, still in progress, or waiting in the queue. option for organizing and presenting which stage various initiatives reside.

Each card on the board represents a single work item, such as a user story.
The card’s location on the board indicates where in the process it stands.
Cards progress through the different stages, providing excellent visibility
into where everything stands.

Managing this flow of cards is key to Kanban, including limiting how many
cards can be in each stage of the Kanban flow. By restricting how many
items are being actively worked on and waiting on standby, those items
get finished faster, and the team can narrow its focus, which improves the
throughput and efficiency of the whole operation.

Kanban is exceedingly transparent because everything is on that Kanban


board. Anyone can see where a particular item stands, and bottlenecks
can be spotted and addressed quickly. Kanban also helps the product
development team avoid any downtime since when an engineer finishes
one card, they can grab the next one at the top of the queue.

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Scaled Agile Framework

For larger enterprises implementing Agile, the Scaled Agile Framework SAFe adds layers of oversight and standardization to ensure these teams
(SAFe) is one way to manage the complexity and scope of the operation can communicate and work together so that each piece of the puzzle fits
while still enjoying the benefits of Agile. Although some in the broader Agile together. Much like railroad tracks produced simultaneously by multiple
community disparage SAFe due to its top-down management culture and teams must be the same width and meet up at the correct location, Agile
upfront processes, it does remove some of the risks inherently associated for enterprise requires an extra layer of coherence and oversight, which
with implementing Agile in a larger setting. SAFe offers.

Because a single Scrum team cannot always handle big projects, they need
to be subdivided and spread across multiple teams. Additionally, in larger
organizations, those teams may be located in different parts of the company
and report to various managers, requiring coordination and collaboration
across teams.

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Agile roles and responsibilities For example

PetTree is a software company that allows pet owners to create family trees
for their four-legged loved ones. Their goal is “making family connections
Figuring out who does what remains a fundamental requirement for any
for pets.” Pet owners input information about their pets, and then PetTree’s
working arrangement, and Agile is no different. And while Agile does
big data/AI engine creates a living family tree for their pets. The data can
prize autonomy, that doesn’t mean everyone runs on the field and claims
identify siblings, grandparents, cousins, and other connections based on
whichever position they feel like playing today.
the combined knowledge they’ve accumulated through registries and

Agile organizations are structured and staffed for optimal efficiency. The user-provided data. They generate revenue through a subscription model

objective is to do more, do it faster, and then do something else. That to create and maintain the pet family tree and by using their information to

requires clearly defined ownership and boundaries, so there’s less time provide highly targeted marketing for select brands.

spent sorting out conflicts and more opportunities to build and ship value
to customers.

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Organizational structure At PetTree, product development has three Agile teams:

An Agile organization’s org chart won’t look dramatically different. Likewise, Mapping Team
the overall management structure doesn’t change, nor will departments
The Mapping Team handles the “big data” work of automated pet family
such as sales or marketing. The primary differences will be on the product
tree build-outs and augmenting the breed traits and histories database by
development side of the house.
integrating multiple data feeds.

It’s here that some less familiar job titles may be found (such as scrum
Community Team
masters and product owners). Another variation may be that the
development group has split up into scrum teams consisting of a handful The Community Team works on the parts of the product that help long-

of developers and assigned or shared scrum masters and product owners. lost pets connect with their relatives and builds breed-based communities

Those smaller development teams will still roll up under a CTO or VP of where users can share photos and discuss pet-related topics and events.

Engineering or similar role, with the primary differences occurring down at


Commerce Team
the execution level.
The Commerce Team builds out revenue-generating features and
Groups that interact closely with product development may align handles all user account and settings functionality. This team also
themselves similarly, such as assigning someone from quality assurance manages the website and mobile apps while supporting the marketing
or user experience to work with one or more scrum teams on a semi- team’s growth activities.
permanent basis.

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The various roles within an Agile ecosystem map against
these exact six words:

WHO
Which teams (and, later down the line, which individual members of those
teams) are doing the work.

WHAT
What to build to achieve the stated goal.

Who does what? WHERE


Admittedly a bit of a stretch, but very relevant for large organizations with

A good news story answers who, what, where, when, why, and how. multiple sites in different locations, especially when different geographies

But these “Five Ws and an H” extend beyond what you read in have varying areas of expertise and labor costs.

your news feed or watch on CNN. Product development must also


WHEN
answer these questions.
This relates to both major milestones and deadlines and more specific
schedules and resource allocation.

WHY
Defining the goals and objectives for the work to be done and the rationale
behind that.

HOW
This covers both the execution plan and the details of the particular
implementation.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 26


The table below indicates which role is at the helm for each area, although
others may have some input beyond this breakdown of responsibilities.

Who What Where When Why How

PROGRAM MANAGER

PROJECT MANAGER

SCRUM MASTER

TECH LEAD

PRODUCT MANAGER

PRODUCT OWNER

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 27


PROGRAM MANAGER TECH LEAD
Program management involves identifying and coordinating the Tech leads are the player-coaches of the development team. While most still
interdependencies among projects, products, and other critical strategic get their hands dirty and write code, they also decide who should do what
initiatives across an organization. Program managers identify all of these within their team based on their competencies, available bandwidth, and
interdependencies across various departments, working with the relevant preferences. In addition, they estimate the level of effort and map out how
stakeholders in each of these departments, and coordinating their efforts to various technical components mesh and integrate to achieve the overall
make sure everything that needs to get done to support the “program”—in goal of a project, release, or sprint.
this case, the launch of a product—is on track.
PRODUCT MANAGER
PROJECT MANAGER The two primary responsibilities of product managers are to set the long-
The project manager is responsible for breaking down strategic plans into term vision and strategy for the company’s products and then communicate
actionable, task-oriented initiatives. This process involves coordination, this strategy to all relevant participants and stakeholders. Product managers
delegation, and leadership, as the project manager must navigate must build consensus, break down (or at least work across) organizational
interdependencies, team dynamics, and one-off challenges, all while silos, and win over stakeholders to get their job done. Product managers
meeting a deadline with limited resources. typically own the product roadmap and are intimately involved in
prioritization.
SCRUM MASTER
A scrum master is a facilitator for an agile team working under the scrum
methodology. The scrum master serves as a point person responsible for
understanding the big development picture of each sprint. In addition, they
are responsible for delegating tasks appropriately and ensuring the team
is working on the right tasks at the right time. They also want to ensure the
team is fully deployed and not idle.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 28


PRODUCT OWNER
Primarily a bridge between the strategic and the tactical, this role varies Here’s what the Agile staffing looks like at PetTree:
depending on the organization. Product owners liaise between the product
The program manager oversees all three teams from a PMO perspective.
manager’s vision and the development team charged with executing that
They have two project managers, one for the commerce team and another
vision. Their role is to ensure that there is always a user advocate involved in
for the mapping and community teams.
development meetings. Accessible to the development team if they need
help or have questions, product owners attend daily Scrum meetings and The director of product oversees product management, but there is a
prioritize the backlog, ensuring the developers are working efficiently and technical product manager dedicated to the mapping team. Each team has
on the right items. a product owner that also reports to the director of product.

Each team has a dedicated scrum master and tech lead. The community
team has three other engineers, the commerce team has five other

An important caveat is that while the roles above can and often exist in an engineers and a user experience specialist. In comparison, the mapping

Agile organization, not every successful team has all of them. For example, team has eight other engineers and a dedicated architect. The team

smaller companies may not have a program management office or may members report to their respective tech leads.

do without a product owner, or sometimes the roles are combined. Not all
teams have the luxury of both a product owner and a product manager, so
one person may be tasked with strategic product management work while
also attending standups and working directly with developers.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 29


What’s the story with “self-organizing teams”?

To the uninitiated, this tenet of the Agile methodology may sound like a free- This independence and sense of ownership imbue the team with creativity,
for-all environment where everyone works with the people they like and on flexibility, and freedom while creating urgency and obligation. No one
whichever projects capture their fancy. There are some elements of truth in wants to let the team down, and their aggregate effort keys individual
that preconception, but it is slightly more nuanced. performance. That shared ownership and openness to collaboration
benefits the entire product development process, because the team invests
Self-organizing teams are not rogue outfits doing whatever they please. in meeting goals and overall success.
They take the initiative to select items to work on from the queue since
they’re empowered to do so and work collaboratively within the team
to maximize output without a higher-up handing down specific It’s important to remember that
marching orders.
teams must grow into their self-
The key to self-organizing teams is increased autonomy for all team organized self.
members. In its perfect state, a self-organizing team has a balance of
technical talent that, in aggregate, can handle any project that lands on its It’s important to remember that teams must grow into their self-organized
plate. The project goals are known and understood by the entire team, and self. When team members or the entire organization are still new to scrum,
they, as a team, break things down into smaller tasks and take them on as scrum masters still break down and assign tasks in coordination with the
they see fit. tech lead. But over time, they can take on more and more self-management
and independence.
That means no one is telling an individual team member what specific task
they should work on or how many they should accomplish in a given period. And, while self-organizing teams accomplish great things working amongst
Instead, the collective peer pressure to perform well and meet expectations themselves, that doesn’t mean it’s a total free-for-all. Agile does rely on
for each sprint serves as the motivation not to slack off and take on a smaller meetings, ceremonies, and a little bit of documentation to keep things on
workload than their colleagues. track and aligned across teams.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 30


Events

Regular events and rituals are core to doing Agile work because clear,
honest, and frequent communication is the only way to quickly move
without making mistakes or missing crucial pieces of the puzzle.
Stakeholders and contributors all benefit from these opportunities for
sharing updates, asking and answering questions, and taking time to get
aligned on priorities, responsibilities, and timelines, enabling them to focus

Events and artifacts on work when they’re heads-down designing and coding.

Although Agile prides itself on shipping software versus


Sprints
process, some structure and documentation are required
to make it all happen. These are some of the crucial Instead of time-boxing a development effort around the full completion
elements of a functional Agile framework. of a software release, Agile instead frames work effort in sprints. Typically
measured in weeks versus months, most teams settle on a cadence of one
sprint every two to four weeks.

The objective is to get new and improved functionality into customers’ hands
as quickly as possible, thus the short duration. This high-frequency pace
also enables the organization to measure and observe the performance of
previous releases and factor those learnings into upcoming sprints to iterate
on the product continually.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 31


Sprint planning sessions Daily standups/scrums

These meetings determine what will be in the scope of a given sprint. Each Daily standup is a quick session where each team member shares what
sprint gets a goal before setting the sprint backlog. The sprint backlog they accomplished yesterday, what they’ll try to accomplish today, and what
contains the individual items the team agreed to work on during this sprint. is blocking work from progressing. Standups are a critical element of the
agile development framework, as they promote frequent and high-touch
Sprint planning sessions allow the team to assess its capacity for the team communication.
upcoming sprint, determine the level of effort for each item, and then assign
tasks to team members (or allow them to claim them for themselves in a
self-organized setting). Each item in the sprint backlog gets an agreed-upon Sprint reviews
definition done while addressing any open issues or questions.
Sprint reviews are working sessions held after each sprint, covering the
previous sprint’s deliverables and updating the product backlog accordingly.
The scrum master, product manager, product owner, and development
team usually attend these meetings. They tend to run for two or three
While these meetings may touch on how things went during the previous
hours to cover everything and prepare the team for the upcoming weeks of
sprint, it’s not intended to be a full post-mortem (that’s what the spring
development activity.
retrospectives are for). Instead, the primary goal is to understand what’s
complete and begin queuing up items for the next sprint.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 32


Sprint retrospectives

The team holds sessions after a sprint gets completed and the release of the
latest version of the product. These meetings force the entire team to take
Sprint retrospectives allow the team to iterate how it works with
a moment and reflect on how the previous sprint went, determining what
external stakeholders to achieve sprint goals with an open and
worked well and what was problematic.
honest exchange. The meeting should be considered a safe
space for bringing up contentious issues and contrarian views to
Product managers often lead these retrospectives as they have the most
be as productive and insightful as possible.
cross-functional role, but an impartial third party can also moderate for
maximum transparency and fairness. The key to ongoing success is to let
people vent and identify and address problem areas for smoother sailing
in the future.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 33


Artifacts

Agile prioritizes shipping software over documentation, but that doesn’t


PRODUCT BACKLOG
mean there aren’t any artifacts for reference and tracking. These tools and
documents help the team stay aligned while moving at a rapid pace.
Task-level: user stories
and defects
Product backlog

A product backlog lists and prioritizes the task-level details required to


execute the strategic plan outlined in the roadmap. In addition, the backlog
should communicate what’s next on the development team’s to-do list as Primarily for product and

they execute on the roadmap’s big-picture vision. Typical items in a product development teams

backlog include user stories, bug fixes, and other tasks.

This giant to-do list is a living collection of potential development items and
Conveys tactical steps
requires regular maintenance, often referred to as backlog refinement. By
in execution of plan
periodically reviewing the backlog, the product owner can determine what’s
left in the queue and adjust prioritization based on new developments, such
as customer requests, competitor activity, or revised strategic goals.

Not everything in the product backlog will necessarily ever get built, 1 or 2 sprints
but it’s good to have a deep backlog full of every potential item under
consideration. Only those likely to be worked on soon require enough detail
that a developer can run with it independently.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 34


Sprint goals User stories

Set jointly by the product owner and the development team before a sprint A user story is a small, self-contained unit of development work designed
begins, these goals lay out clear objectives for each sprint. They should to accomplish a specific goal within a product. A user story is usually written
be narrow in focus, specific, measurable, and tie back to the larger product from the user’s perspective and follows the format: “As [a user persona], I
goals and themes the organization has prioritized. want [to perform this action] so that [I can accomplish this goal].”

While sprint goals may seem redundant if the team has already defined a The smallest unit of work within the Agile framework, each sprint usually
sprint backlog, they serve two essential purposes. First, they often provide addresses multiple user stories. They allow meaningful progress in every
the underlying context for why particular backlog items have been selected sprint and give the developers the proper context and motivation to solve a
for a given sprint and tie them together. The second is that if and when specific problem or use case.
things change during the sprint, the goals can continue to be the North Star
for that period..

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 35


Epics Themes

An epic represents a series of user stories that share a broader strategic Themes are the most significant “bucket” within Agile, aggregating
objective. When several epics share a common goal, they are together multiple user stories and epics to accomplish a broad-yet-defined business
under a still-broader business objective, called a theme. goal. Themes rise above the day-to-day (and even the week-to-week)
iterations and improvements on the product and comprise major new
This “interim” container of user stories helps break the theme down into
additions or modifications.
more manageable chunks. The audience for epics isn’t so much the product
development team itself as the other stakeholders who don’t need to deal Product roadmaps in an Agile environment are also typically based around
with the level of detail of individual user stories. themes. Epics and user stories are too granular for this level of planning and
shift the focus to specific dates and deliverables versus the high-level goals.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 36


Personas

Personas are profiles of a product’s typical customers. They help the product For example, in a two-sided marketplace, you have buyers and sellers who
management team understand different users’ traits, behaviors, goals, each have different goals and tasks they want to complete. With personas in
responsibilities, and needs. place, user stories can indicate which persona goes to each use case.

They serve multiple practical purposes for product organizations. First, The supporting information arms the Agile teams with enough data and
personas provide specificity and a connection with the end-user versus understanding of the objectives to work relatively independently on
a poorly defined, generic “customer.” Because there are often multiple value-adding tasks. But to know which epics, user stories, and themes
personas to contend with during the customer journey—since often those come first, Agile teams also rely on roadmaps and project plans to structure
making the purchase decisions about a product aren’t the folks using it—and their execution.
because there are sometimes totally different kinds of users.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 37


Roadmaps and project plans in
an Agile world
Roadmaps and project plans lay out the future, explaining what’s going to
happen, who’s going to do it, and when. Agile is worried about the next few
weeks. Yet, they all can—and should—coexist.

The key is understanding everything’s purpose and “why” concerning the


other artifacts and processes the company uses. Then, when structured
appropriately and clearly explained to stakeholders, they should all
compliment each other nicely.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 38


Roadmaps

Product roadmaps are a visual encapsulation of strategic priorities. Roadmaps are also essential for securing stakeholder alignment, letting the
Roadmaps tell a story about the product goals and the steps to higher-ups approve the product direction, and giving sales, marketing,
achieve them. and other teams enough of a preview of what’s to come so they can plan
accordingly. Roadmaps that include a message for each target audience
To be valuable and accurate, roadmaps in an Agile setting must stay high help them feel like participants in the process, and their concerns are valued.
level, which is why the best roadmaps use themes as their foundation. These Even if they don’t get every item on their wish list, acknowledging what’s in
describe the key initiatives the company has prioritized based on aligning and out and why goes a long way.
with the product’s strategic goals.

The roadmap itself isn’t dictating the contents of a given sprint, nor should
For product managers, roadmaps play an essential role in
it include anything as detailed as an individual user story (unless someone
an Agile setting. Since there’s less day-to-day oversight and
drills down into the details). Instead, agile roadmaps are directional and
precise specifications for individual elements of the product, the
inspirational, connecting the dots between all the minor tactical and
roadmap serves as the primary tool for conveying the purpose
incremental improvements and additions the team makes every couple
and context for each item product development builds. Ignoring
of weeks.
this opportunity to shape the overarching mindset with a

They are the big picture, the broad vision, and remain light on the details. roadmap emphasizing the goals and desired outcomes can lead

Using a theme-based, visual roadmap also influences what the audience to confusion and missed opportunities.

remembers and processes since humans remember visuals far better than
what we hear.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 39


Project plans

Agile project plans will look a little different than their waterfall peers. This ambiguity flies in the face of a primary goal of most project plans, which
Traditionally, project plans map out every step to deliver each item. is to choreograph everything down to the tiniest detail, so it all merges in
Resource assignment, level-of-effort estimates, and deadlines for key harmony with a fully-formed deliverable. Instead, the first sprint or two
milestones inform the process. Project managers then weave everything might have a ton of detail while things get blurrier and blurrier farther ahead.
together so that at the end of that months-long slog, the finished product As the team completes the sprints, the project plan gets fleshed out for the
includes all the bells and whistles promised upfront. next ones.

The other significant difference is that while usually a project plan gets
As the team completes the sprints, relatively locked down with variations requiring change requests and the

the project plan gets fleshed out for like, that’s not the case in Agile. The project plan will change based on how
sprints unfold, the strategy evolves, and what the product team learns from
the next ones. prior releases and experiments.

That level of specificity and detail clearly won’t work in an Agile setting, With a product roadmap setting the agenda while offering a shared vision

but it doesn’t mean project plans shouldn’t get scrapped. While a plan for for the product’s direction along with a project plan that explains how

the entire project may be far too challenging to construct in detail at the the team will get there, Agile teams have the background and context to

outset, it can still encapsulate a longer horizon than the next sprint. The main connect the dots between their projects and actions and the overall purpose

difference between waterfall and Agile in this context is that project plans of their work. With stakeholder alignment around these two essential tools,

become more and more vague the further into the future they go. Agile practices can quickly turn that strategic vision into a reality.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 40


Agile and strategic planning
The final fallacy that often stymies Agile implementation at some Strategic plans need to stay strategic. Things get messy when that strategy
organizations is the belief that strategic planning and Agile can’t coexist also tries to dictate the details of the implementation, be it specific delivery
and that one will always drive product development’s direction. Naysayers dates, UX choices, or technological tactics.
believe that the developer autonomy and rapid iterations based on learnings
shift the emphasis toward knee-jerk reactions and quick wins instead of
longer-term, larger objectives, which couldn’t be further than the truth. Agile works best when the business tells the product
development team what’s important and what the goals for the
Product-led growth and prioritizing work based on maximum impact doesn’t
project are. They then need to get out of the way and let the
derail product strategy, it supercharges it. Agile needs strategic alignment,
team build how they see fit.
so people build the right things, and so the strategy benefits from rapid
execution and accelerated learnings and feedback, which streamline the
opportunities for optimization.
It’s not always easy to take that step back. It takes trust and confidence
Agile practitioners desperately want thoughtful, comprehensive strategies that the requirements have been communicated and understood and that
in place. They recognize that a solid strategy is essential to creating products the team is diligent and capable of turning that into working software that
that customers want. The caveat is that engineers want a strategy versus a does the jobs it’s supposed to do. It can be scary, take a while, and there are
prescribed specific implementation, where conflict can sometimes arise. almost always some growing pains.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 41


Maintaining alignment with communication

Ongoing, open, honest communication makes Agile work. In its absence, People will have questions, and they need those questions answered quickly
opportunities arise for disconnects, false assumptions, and wasted work that to keep up the pace. In that same vein, since formal documentation often
detracts from the product strategy’s ongoing pursuit. takes a backseat in Agile, the conversations on asynchronous chat platforms
and the comments left in tools are essential tidbits of information that must
They keep up the pace and maintain the autonomy that Agile demands be shared and referenced to make it all work.
without excellent rapport and frequent interactions. It’s not so much about
the volume of information exchanged—Agile prizes succinctness above Teams should set expectations and standards for communicating critical
almost all else—but rather the frequency and transparency of it all. information. Assuming others are in the know when things are moving so
quickly is dangerous, and consistent use of tools and stakeholders that must
Silos and secrets don’t mesh with the recurrent and open conversations stay informed lets people do things on autopilot instead of having to pick and
that Agile organizations require. Unlike in waterfall, everyone needs to fully choose who to tell what every time.
comprehend the “why” behind every item in the queue to then apply their
judgment as to whether they’re meeting the desired need. Vagaries lead Most importantly, the extended team must all embrace open communication
to wasted work, and there’s nothing less appealing to Agile practitioners and not take questions personally. Peoples’ need for information must trump
than that. anyone’s feelings or desire to keep things to themselves.

To make it all work, Agile calls for both verbal and electronic interactions
from everyone involved. Some will happen during in-person or virtual
meetings—such as daily standups—but just as crucial is how the team uses
asynchronous communication tools such as Slack and Microsoft Teams and
tools in the product stack such as Jira and ProductPlan.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 42


Reality is a continuum and your mileage may vary

Agile doesn’t look the same everywhere, despite all the books, gurus, blog
posts, and consultants offering guidance and prescriptions for success. Agile
is in many ways an ongoing aspiration, and there are always opportunities to
work toward the ideal. But being 100% Agile won’t necessarily generate more
revenue or reduce the number of bugs compared to another company that is
more selective in which aspects of Agile they choose to adopt.

Like any new tool, technique, or process, it should always be adapted to fit
the current situation and the desired goal, with tweaks and changes along the
way. Sometimes the boss wants what they want, or a key customer makes an
ultimatum, which trumps prioritization and scheduling.

While this might irritate Agile absolutists to no end, companies are in


business to ship products, not to embody an ideal. But with a flexible
mindset, Agile can be a powerful, transformative method for getting the most
out of the available resources and expediting a product’s path to success.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 43


What we’ve learned

As we conclude, there are a few critical takeaways from this book as readers
go off and implement, adjust, or avoid Agile in their workplace:

AGILE AND STRATEGY CAN COEXIST DO WHAT WORKS FOR YOU


Agile without a solid strategy is a recipe for chaos and confusion. Product No Agile Inspectors are policing how any organization decides to implement
development teams desperately want to understand the context, goals, or borrow from Agile (although you can certainly pay a consultant to do that).
desirable outcomes, and measurable objectives the business has set for At the end of the day, every methodology, framework, and philosophy is only
the product. helpful if it helps the business get where it wants to go.

AGILE NEEDS STRATEGIC ALIGNMENT COMMUNICATION CREATES TRUST


If stakeholders aren’t on the same page about what they want and can Transparency and honesty combined with a track record of successful
expect from the product, all those rapid iterations will produce work that delivery increase everyone’s comfort level. From building consensus around
doesn’t meet important goals and may frustrate misinformed stakeholders. prioritization, roadmaps, and project plans to tell it straight during daily
standups, the more people know, the fewer questions and doubts they’ll have.
TRUST BEGETS BUY-IN FOR AGILE
Stakeholders’ comfort level with Agile’s lighter documentation and
increased autonomy grows when there’s confidence the team is building the
right things for the right reasons.

STRATEGIC PROJECT ALIGNMENT IN AN AGILE WORLD 44


About ProductPlan
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and more time shipping products.

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