Upfront planning vs. Agility: Why preparation enables flexibility

For years, the software development world has debated the merits of big upfront planning in traditional waterfall projects versus the minimal upfront planning associated with Agile methodologies.

A common misconception has emerged, where it is believed that upfront planning is outdated and should be abandoned in favor of complete flexibility.

However, my experience as both a strategic consultant and an American football coach has shown me that adaptability is not the absence of planning - it’s the result of great preparation.

The football analogy: Planning to adapt

In American football, we don’t just step onto the field and play. We plan the season, structure training sessions, and design game strategies. We anticipate what could happen and prepare for a wide range of scenarios:

• What if my quarterback gets injured?
• What if our running game is ineffective?
• How will the opponent adjust to our playing style?

Coaches spend hours scouting opponents, analyzing past games, and developing strategies. It’s not about controlling every move—it’s about being ready for whatever the game throws at you. The best teams are the ones that have prepared for multiple possibilities, allowing them to pivot seamlessly when circumstances change. This is exactly how Agile should function.

Let me demonstrate this:

It takes hours and even days to master certain plays in American football. Every player on the field needs to be aware of what is expected and needs to execute the play close to perfection if you are looking for positive yards.

Assume you have a strong-armed quarterback on the team and your main attack is the deep passing game, as demonstrated in the picture below:

Now let’s also assume, your quarterback gets hurt, is sick or on vacation (circumstances you typically have to deal with, when coaching an amateur team).

Chances are, you will rarely have a second quarterback with the same capabilities on the team. So, you need a different plan.

It simply means that the playing style needs to be changed wildly from a deep passing attack to a run-first offense out of Wildcat formation.

The issue is – you don’t draw that up on gameday. You need to be prepared for this scenario to be able to adapt on-the-fly.

The Agile planning onion: Structure enables flexibility

In Agile, planning isn’t discarded – it’s layered. The Agile planning onion, a model often referenced in Agile literature, outlines different levels of planning. Here’s how I relate this model to the American Football context:

Vision

The high-level goal aka “Why we play” (e.g., win a championship, develop talent, build a community impact). This might be something like “Our goal isn’t just to win games—it’s to dominate the field with disciplined, adaptable football and help each player grow into a leader.”

Roadmap

The season plan (e.g., major milestones, training cycles, key games). For a typical football team, it might be off-season in Q1/Q2 with the goal of athletics and conditioning, pre-season in Q3 with the training of techniques and plays, and in-season with game-day preparations and adoptions.

Release Planning

This might be the game-to-game preparation. E.g. for a match-up against a run-heavy opponent, the defensive squad installs specific packages with more linebackers and practices “run fits” intensively for that game.

Iteration Planning

Weekly practice plans, focusing on specific improvements. This might look like:

• Monday: Film study and light walk-through
• Tuesday: Full pads, offense install
• Wednesday: Red zone and 3rd down packages
• Thursday: Special teams and 2-minute drill
• Friday: Walkthrough and mental rehearsal

Daily Planning

Adjusting based on immediate observations and new data, e.g. weather shifts, injuries or availability of players. This might be switching from Field Goal Kicking to Punting on the Thursday practice if the kicker is not present.

This layered approach mirrors how football coaches plan, yet adjust when conditions shift – whether in practice, in a game, or throughout the season. The same should apply to Agile initiatives: establish a structured plan with room for flexibility, rather than attempting to operate in a vacuum. It’s about avoiding “Agile cherry picking.” For me, the main message here is (which is almost never the case): “Come up with a plan and be ready to adapt if the plan does not meet reality.”

The myth of No Upfront Planning

Many Agile teams mistakenly interpret agility as an excuse for avoiding planning altogether. This mindset often leads to reactive decision-making instead of strategic thinking, lack of alignment between stakeholders and teams, reinventing the wheel rather than learning from past experiences and inefficiencies due to unclear goals and priorities.

Agility does not mean abandoning structure; it means preparing effectively so that when the unexpected happens, teams can react swiftly and successfully.

The importance of market research: Scouting the opponent

Just as football teams scout their opponents, businesses must continuously conduct market research. Understanding the competition, industry trends, and customer behaviors allows companies to anticipate shifts and adjust proactively. Skipping this step under the guise of being ‘Agile’ is a recipe for failure.

Learning points: Strategic planning enables agility

• Plan with intent: Set meaningful goals upfront. Whether it’s winning a championship or launching a successful product, clarity of purpose is critical.
• Think through scenarios: Anticipate challenges, both known and unknown. This prepares teams to pivot quickly when necessary.
• Structure your approach: Use an Agile planning framework to ensure balance between structure and flexibility.
• Scout the competition: Market research isn’t a luxury – it’s a necessity for making informed decisions.
• Maximize efficiency: Just as football teams optimize practice time to get the most reps, Agile teams should optimize development processes to maximize value delivery.

Let’s explore these steps on a practical example from the industry:

A mid-sized fintech company planned to launch a mobile banking app aimed at millennials. The goal: acquire 100,000 users in the first 6 months and provide seamless experience with zero major outages. They defined key features upfront: account overview, transfers, savings goals, and card locking.

The team used pre-mortem analysis to consider possible disruptions like regulatory changes, security vulnerabilities, iOS/Android OS updates, and potential user feedback triggering redesign.

They mapped these into a risk register with mitigation strategies (e.g., flexible UI architecture, regular compliance check-ins).

They used Scrum with two-week sprints, and a quarterly planning cadence for broader alignment. Quarterly OKRs were set but reviewed every 4 weeks to respond to changes.

Competitor research showed that existing apps lacked customizable savings goals and had poor UX around peer-to-peer payments. The team prioritized these as differentiators and developed lightweight prototypes for early user testing.

Midway through development, Apple released an iOS update that broke parts of their biometric authentication. Also, early beta users reported that savings goal tracking was confusing.

The team adapted by reallocating one sprint to fix iOS compatibility, fast-tracking a redesign of the savings goal UI using design spikes and rapid testing, and pulling in a security expert from another team for a short-term pairing to harden biometrics.

Despite these changes, they still launched on time – by reducing scope on non-critical features (e.g., dark mode) and increasing test automation to free up developer capacity. Touchdown!

Conclusion: Be prepared to be Agile

Upfront planning isn’t the enemy of agility – it’s the foundation that makes agility possible. In both football and business, the best teams aren’t the ones who ignore planning; they are the ones who plan effectively, prepare contingencies, and execute with adaptability. When the play breaks down, your prep is what scores the touchdown.

So, the next time someone argues that Agile means ‘no planning,’ do remind them: adaptability without preparation is just chaos. True agility is about being ready for a wide range of circumstances – and that starts with preparing the right things upfront.