Do you remember playing Monopoly as a kid? Once you chose the perfect game piece (my favorite was the race car, with the Scottie dog a close second) and got your seed funding, it was “go time!” 

It seemed so simple to earn money and succeed as long as you didn't end up in jail. Step by step, you acquired property and built a real-estate empire. Sure, there was some advanced strategy involved to build hotels instead of houses, but you kept moving around the board. You probably made some adjustments to your gameplay based on the other players. The stakes didn’t seem overwhelmingly high (it was play money, after all). And you regularly passed “Go” and collected your $200 paycheck with no taxes or fees involved.

Running a business used to be similar. It wasn’t as easy as moving around a gameboard, but it wasn’t rocket science either. You created and produced a solid product, priced it right, offered good customer service, made sales, and watched your bottom line grow. Sure, there were regulations, competitors, and tax for professional services to deal with, but that was all manageable. Unfortunately for many businesses, the times they are a-changin'.

Customers — all; Businesses — 0

We’ve entered the “Age of the Customer.” Some people feel we’ve been here for a long time (isn’t the customer always right?), but there’s been a definite shift in expectations over the past few years. It’s no longer enough to be the first to market, offer the fastest free delivery, or answer the phone in under 2 minutes. Organizations now need to be hyper-responsive, offer personalized services, and always be available, at a minimum. You know, be everything to everyone. All the time. 

And competition is growing. Companies used to have a handful of competitors in brick-and-mortar locations, but now it’s easy to launch a product with crowd-funding, a basic website, and drop shipping from the supplier. Thanks to technological advancements, the availability of remote and “gig” workers, and the ability to reach a large audience via social media, small companies are better able to compete and win against the enterprises that used to dominate.

What’s an enterprise to do to remain competitive and keep the lights on?

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Enter Agile methodology. To effectively contend with today’s evolving challenges and safely navigate roadblocks to growth, businesses need to be able to execute in real-time and operate at the highest levels at scale. Agile is one of the methodologies that have been developed to help companies adapt to quickly changing environments.

What is Agile?

Agile was created to help development teams work faster and respond more effectively to change. By focusing on short development cycles and incremental progress, products can be brought to market faster, and feedback from the market can be implemented faster too. This means businesses are in a better position to minimize risks and adapt to changing environments. 

Agile puts weight on the outcome, not the processes or tools it takes to get there. It’s built on change, collaboration, and feedback. By embracing these principles, teams and organizations of all kinds can be more nimble and better prepared to contend with constantly changing environments.

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This is in contrast to the step-by-step “waterfall” method of development, where each step in the process builds on the previous one. In waterfall, work begins once the plan is determined with no opportunity for feedback or revisions along the way. The end result can be outdated or may not meet the initial need. Agile is often considered a more modern approach, in keeping with the fast pace of business today.

“Enterprise agility is about the distinct qualities that allow organizations to respond rapidly to changes in internal and external environments without losing momentum or vision.” — McKinsey & Company

Roadblocks to success

It often seems like there are nothing but roadblocks in front of businesses:

  • A production delay due to a late shipment from your supplier
  • New regulations that must be vetted with legal and product management to ensure you can comply in a timely manner 
  • Funding constraints 
  • A burgeoning crisis that must be handled quickly and appropriately 

You may also need to deal with (or make changes to avoid): 

  • Information and data silos that exist between departments, technology tools, and management levels
  • Fragmented systems that don’t communicate, such as accounting and time management systems or budgeting and resource management systems
  • Fear of failure — let’s be real, everyone struggles with this and it can hold back entire companies if not addressed
  • Lack of focus on organizational goals or a lack of clear goals
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Those roadblocks are in addition to the multitude of expectations discussed above that are table stakes in the “Age of the Customer.” And let’s be honest — Agile is not an easy, “1-2-3-and-we’re-done!” kind of implementation. It’s an organization-changing, true culture shift and ongoing process that requires buy-in and participation from all levels to be successful. Are you ready to scream and cry yet?

There’s good news: You are not alone! Many enterprise companies are struggling to keep pace with customer demands, shift to Agile, and continue being successful. So bite back that scream, determine which of these roadblocks your organization is facing, and let’s talk about some tips to help with an Agile transition.

Play Monopoly, win in the real world

That may be a slight exaggeration, but your Monopoly-playing skills can help your organization be successful in its Agile journey. How, you ask? Well, the experience you gained running a real-estate empire, for one. Just kidding. But in all seriousness, much of what you learned playing the game transfers to the real world. Skills such as communication, collaboration, taking risks, and keeping your eye on the prize are useful life skills in general but particularly in the business world. When you’re implementing a transition to Agile, focusing on these 4 areas will help you and your organization succeed.

1. Communicate! Openly, often, and with everyone.

Remember teaming up with someone (possibly on the sly) to build your monopolies? You agreed that your brother wouldn’t go after Baltic Avenue so you could clinch your first monopoly, and you would let him have Reading Railroad. That required ongoing negotiation and communication. You set the plan, checked in, adjusted things as the game played out, and made it happen. Shifting to Agile is similar. It’s a process of constant communication, adjustment, and forward progress.

One of the many benefits of regular communication is that you should experience fewer issues with information silos. An information silo results when there’s a lack of transparent communication from and to all levels and teams or no communication at all. That’s not to say you should blast a message about your lunch plans to everyone in the company, but make sure that others you work with know what’s going on with your team. It could help their team do a better job and help another team they work with and cascade through the organization. 

On that note: Listen to all opinions, including those opposed to the Agile change (or any change). It’s not fun to listen to dissent, but it is valuable. You may learn something new and improve your process as a result. Or at least lessen some resistance.

2. Collaborate, collaborate, collaborate. And then collaborate some more.

The foundation of Agile combines collaboration and communication, so these are the first and most important tools to use in your transformation to an Agile organization. Teams are likely already collaborating amongst themselves but make sure you’re working with other teams too. Marketing should be collaborating with engineering and customer success. Business development should be collaborating with sales and strategic programs and so on. Perhaps rename the game Collaboration instead of Monopoly!

A critical step to make collaboration and communication easier is to ensure your tools and technology are up to the challenge. That doesn’t mean you need to have the latest and greatest laptops, peripherals, and software, but it does mean you should evaluate how your systems work together.

Organizations often have multiple systems in different departments with little integration, and that makes collaboration and information sharing a challenge. You want to encourage collaboration and communication, so consider a collaborative work management tool. These tools bring together teams, projects, assignments, deadline tracking, and more into one system that becomes your single source of truth. That means everyone is on the same page, and communication and collaboration are seamless.

3. Don’t be afraid to take a chance.

Ah, fear. Remember when you mortgaged two properties to buy a larger one and create your first monopoly? It was scary to take that risk but it paid off — the success of that acquisition lead to more until your empire dominated, and you won the game! Moving to Agile is a big change and brings some risks because it impacts your entire organization. But not every impact is negative, and you wouldn’t be making the change if you didn’t think it would have benefits, right? 

“The biggest risk is not taking any risk. In a world that is changing really quickly, the only strategy that is guaranteed to fail is not taking risks.” — Mark Zuckerberg

Part of preparing for the impacts of organizational change is to create a culture where it’s “safe” for both individuals and teams to take risks. Oftentimes, people don’t take risks at work because they fear the consequences. No one wants to get fired because they did something wrong! But what if what they did wasn’t “wrong?” What if it was acceptable to make a mistake and learn from your “failure?” 

Think about how many products, services, and tools we use every day that wouldn’t exist if someone had been afraid of the consequences of taking a risk. Remember that every “failure” is a learning opportunity and can help move you, your team, and your organization toward your ultimate goal. And consider the risks you face if you don’t take a chance and make changes. That could be far more damaging to the organization and its longevity.

4. Continue to focus on your goals, including delivering the best for your customers in every interaction every day.

When you played Monopoly, you had one goal — to win! And while that probably isn’t the best goal for daily life (you want to collaborate, right?), be sure to continue focusing on your goals. Think about the organizational mission and vision and how it applies to your work. That’s easier to do when you use a collaborative work management tool, and you can see how tasks and projects are interconnected. It’s much easier to be successful when the whole organization is aligned and in agreement with vision, goals, and actions to achieve those goals. 

Monopoly had one path to victory with some potential diversions and roadblocks, but you knew your goal and how to get there. Success in today’s world is anything but clear. There seems to be no shortage of paths you can take with branches leading to different outcomes, and success is not linear. Organizations must be willing and able to shift directions as needed.

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Ready to begin your enterprise Agile transformation? Wrike’s collaborative work management tool was built to empower organizations to do their best work by increasing visibility, improving communication, streamlining processes, integrating workflows, and promoting solid collaboration. It’s a great tool for organizations undergoing an Agile transformation because it’s customizable and configurable to deliver the right information when it’s needed.

Check out our new eBook, Embracing the Agile Movement: Strategies to Keep Pace in the Post-Digital Era, to learn specific ways your organization can use Agile principles to stay adaptable in today’s challenging environment.