Imagine that a company's leadership team just dropped a new request on its product teams — a list of features added to its flagship product. The bosses explain the strategy behind the request, and say they need it in several months for the next major release. Then their questions start: When can engineering confirm their ability to deliver? What resources will they need to make it happen? What impact will these plans have on other priorities?

This product team is Agile. They've embraced Agile's short, iterative cycles and the customer-obsessed mindset. Their collective blood pressure is spiking. The bosses' questions keep coming, requesting a detailed roadmap for the work ahead.

This. Is. Not. Agile.

It's extra maddening because leadership had encouraged product teams to transition to Agile in the first place. They even celebrate Agile in company speeches. But when it's time to work, here come the top-down requests and extremely un-Agile questions.

But, swing the perspective to leadership's side of the table, and they're also frustrated. Investors are making demands, supply chains must be considered, distribution and marketing plans must be made. Why can't their managers provide answers? And come to that, why are product teams always so negative about every request? They put off giving concrete answers, and yet there seems to be plenty of time for ping-pong and Nerf gun wars on their side of the office. Why is this so complicated?

So: Leadership never believes product teams are doing enough, and product teams always believe they're being asked to do too much. Who is right?

Both are, in their way. These conflicts are often not about the personalities involved — at least, not completely — but instead are an inevitable byproduct of Agile teams clashing with leadership that is still beholden to rigid demands from outside the organization.

Can't leadership be more Agile?

Probably, yes. But even if company leaders strive for more agility, they are straitjacketed in multiple ways by elements beyond their control.

Regulatory burdens or simple logistics might be thornier than you expect, especially for certain industries. As the Harvard Business Review put it: "Imagine the adverse consequences of encouraging wide variation, on-the-spot experimentation, and decentralized decision-making — all hallmarks of agile — in areas such as food or drug safety, antidiscrimination and harassment policies, accounting standards, and quality control."

Other factors might be holding them back:

• Fiduciary responsibilities to shareholders, investors or other governing boards
• Event-based launches that are tied to drop-dead dates on the calendar
• Releases that sync up with third-party efforts or materials, such as suppliers or distributors
• Complex budgetary and financial requirements to maximize value or even just stave off cash crunches
• Agreements with large customers and partners
• Beating competitors' similar offerings to market

Market windows are a key example. Timing a product launch or upgrade can be key to its success. And if your product is aimed at a specific group at a specific time — such as students returning to school in the fall or splashy corporate events — a whole constellation of dependencies need to be timed accordingly, often months in advance.

Agility doesn't work like that

Leadership teams have to keep a multitude of parties in mind, spreading out their attention over a wide array of factors. Agile teams, by contrast, are notable for the purity of their mandate. Focus is squarely on the customer. Iterate and adapt, iterate and adapt, over and over. Teams are empowered to make decisions and encouraged to work face-to-face. This bolsters team members' ability to make stronger contributions and creates an exciting environment for great new ideas. To do this, product teams are given tools, such as Jira, that support Agile thinking.

Ideally, the rest of the corporate world would convert to more Agile principles as well. The coronavirus pandemic showed that quicker moves are indeed possible — when the world shut down abruptly, plenty of creaky corporate bureaucracies had to pivot with lightning speed. It can happen. But it took a world-altering event to make it so. In the normal course of business, agilists are still outnumbered.

More than workplace drama

These clashes have real impacts on organizations' success. In cases such as the hypothetical issue at the top of this article, the awkward fit of Agile teams within a waterfall organization leads to:

• Pointless arguments about deadlines. It's futile to ask product teams to predict the future when circumstances are certainly going to change. For all the reasons discussed above, leadership wants to know when they can see results, and Agile teams cannot provide details further than a few iterations out. Tools like Jira are simply a way of recording expectations — and projects with a thousand tasks and requirements provide a ton of opportunities to screw up those expectations. What's more, leadership is likely to change its original requests as the project wears on, and unforeseen events are likely to throw off projections as well. Altogether, it leads to continuous arguments about timing that leads to higher stress and wasted efforts from product teams. It also creates frustration within leadership as they struggle to manage long-term plans.
• Unpredictable — and therefore inefficient — finances. In Jira, every ticket represents an employee's time. Leadership wants to know how long a project will take and how many personnel hours it will require so they can understand the financial resources they will need to tap. As with deadline conversations, financial planning is a slippery target. Being able to predict the timeline and expenses associated with a project, as well as the date at which the project will contribute to revenue, is important for keeping financials strong.
• Lack of clarity around value. Companies often have no idea how much value a product or project has really brought them. When finances are fuzzy and resourcing is hard to measure, no one can confidently claim which activities the organization should continue versus which ones need course-correction. The continuous back-and-forth on deadlines and resources make it harder to parse after the fact.

The primacy of planning vs. creating something great

These are thorny issues, and understanding their causes can help show a path forward. The first step is to defuse the emotion from that constant clash between leadership and product teams.

The bosses are detached from the creation process, and the product-focused teams are isolated from all the context surrounding leadership's decisions. The bosses are often tied to fixed demands from all kinds of external forces, while their employees are set up to be nimble. Work between those two oppositional forces can be inefficient at best and chaotic at worst. Understanding this dynamic can help make conflict feel less personal and allows everyone to bring a good-faith effort to the project.

Regardless of the quirks of your organization and its people, most Agile organizations have some variation on this problem. Regardless, you all still have to work together to accomplish your goals. Attempting to create a more objective decision-making process that acknowledges both sides' needs is a good place to start.