Between Quicksand and Concrete

What Software Leaders Can Learn From Military History

Apr 30, 2024

"The further backward you can look, the further forward you are likely to see." - Winston Churchill, 1915

The Main Idea

Software plans – the roadmaps, forecasts, and schedules that are ruminated upon and closely watched by many – need to be flexible to adapt to shifting conditions. But they often become rigid due to universal human tendencies – our inherent biases. History is rife with examples in every domain of human experience. Nowhere are the stakes higher than in the realm of military campaigns. Software leaders can learn from examples of successful and failed military plans to improve their chances for spotting biases in their own planning and execution cycles.

A learning feedback loop is necessary in planning and execution iteration. Leaders must evaluate conditions, risks, constraints, and alternatives when seeking to hit strategic goals. Biases can slow or diminish the quality of this feedback loop. How teams and stakeholders collaborate as they navigate planning and execution shapes team culture – for better or worse. Leaders should combat the risks of biases through communication of strategic intent, fostering a culture of delegation and initiative, transparent feedback mechanisms, welcoming diversity of thought and contrarian debate, and close engagement between teams and stakeholders.

Unfired Clay, Not Concrete

A plan is a forecast of a potential future reality rendered as a fluid agreement between the business and product development teams. It exists in a dynamic continuum between quicksand and concrete. At these polar extremes, teams can either drown under too much change or be unable to flex when change is needed. The level of fluidity, decision ownership, and shared commitment for the plan at any given point in time is often weakly aligned across teams, leaders, and stakeholders, introducing the opportunity for biases to creep in.

A plan shouldn't be cast in concrete. Like unfired clay, it should remain malleable: firm enough for the team to stand on but flexible enough to yield to future learning. But the inertia of initial expectations can anchor teams and leaders. Biases can inhibit adaptation of the plan, opportunities for debate, or information from being transparently shared. While leaders navigate this continuum of plan flexibility, they must also strike a balance between focus on the vision – strategic foresight – and the “more, faster, better” pressures of execution. Despite the best of intentions, they can get stuck in decision making traps. Software product teams must resist and overcome the headwinds that can gum up their ability to develop a healthy culture and effectively execute.

What can we learn about biases in planning from past military failures and successes?

The Kaiser’s Plan: a Concrete Conundrum

In August of 1914, at the outset of World War I, before marching on Belgium, the German emperor Kaiser Wilhelm II expected his Imperial German Army to waltz through Belgium and conquer France in six weeks. His expectation was a result of a meticulously researched war plan created by Field Marshal Alfred von Schlieffen (the Schlieffen Plan) and his successor. Why did the plan ultimately fail?

At the turn of the 20th century, the German military, deeply influenced by Prussian tradition, emphasized discipline, hierarchy, and a strong command structure. This resulted in a plan of attack on two fronts that was magnificently detailed yet rigid. For example, it specified the precise number of train axles that must pass over each bridge in each train carrying troops and materiel, on a timetable. There was little room for feedback changing the expectations of the top brass. And while the concept of decentralized decision making and flexibility was expected of lower-level officers, the plan’s timetable constrained the amount of adaptation possible. WWI lasted 224 weeks and resulted in total defeat of the Germans and the Kaiser’s forced abdication from power.

Imagine a software team OKR meeting presenting a project timeline slip of over 3600%! Their quick sprint somehow turned into a four-year slog. Where did the plan go wrong for the Kaiser?

Underestimation of the commitment and capabilities of adversaries

Here’s how the German emperor misread each of his adversaries’ abilities and intentions:

Britain: The Kaiser was certain that Britain wouldn’t enter the conflict. But at least three high-ranking people with clarity on Britain’s likely response to Germany provided feedback, including the Kaiser’s highest ranking military advisor, his diplomatic ambassador to England, and in a direct conversation with the British Secretary of State for War. The message to the Kaiser was clear: Britain would not stand by if Belgium's neutrality were violated or France were attacked.

“If only someone had told me beforehand that England would take up arms against us!” - Kaiser Wilhelm II, anchored to his original worldview, after Britain declared war on Germany on August 4, 1914

Belgium: The Kaiser’s plan assumed Belgian troops would stand aside and let German troops pass through their neutral territory. By definition a neutral country must see any incursion as unfriendly, otherwise the neutral country voids its neutrality by effectively giving assistance to a belligerent. Belgium, completely outgunned and outnumbered, was obligated to resist. The Germans ignored this, even though it was international law*.

Russia: Germany overestimated their own speed of deployment and underestimated the speed of the Russian deployment. Russian troops moved faster than expected (2 weeks vs expectation of 6 weeks), forcing the Germans to have to divert ~250,000 troops from the Western Front to the Eastern Front.

France: Despite the universally-known French military adoption of the strategic doctrine of “the Cult of the Offensive,” the German leadership did not expect repeated and strong French counterattacks on the Western Front*. This information was readily available for decades prior to the beginning of the conflict. For example, the counteroffensive of the First Battle of the Marne in September 1914 stopped the Germans from making it to Paris and put an end to the prospect of the Schlieffen timeline*.

Overconfidence leading to lack of debate and learning

The plan was more than military doctrine for the Germans. It was a fixed orthodoxy that rendered the plan inflexible. Several ranking military leaders had reservations with the plan, but the status quo outweighed their expert opinion. Once things got rolling, even the Kaiser himself was unable to alter the drumbeat that paced the deployment and maneuver of troops.

Of course, the Kaiser wasn’t the sole decision maker. Reporting directly to him was General von Moltke, successor to von Schlieffen and the Chief of Staff and primary interpreter of his predecessor’s plan. Moltke demonstrated an inability to grasp the strategic basis of the Schlieffen plan when he made the grave strategic error of weakening the strength of the German right wing in Northern France. By reducing the strength of the right wing, which was intended to sweep through Belgium and northern France to encircle Paris, Moltke diminished the key idea of the Schlieffen Plan, wreaked havoc on the timetables of advancement, and unwittingly put Paris out of reach of the Germans. This changed the offensive strategy to a war of attrition as trench warfare emerged from the resulting stalemate. He was relieved of his command a month after his fateful decision.

The common thread: a weak understanding of “the why and the how” behind a plan might be overlooked when an overconfident leader lacks the resources to learn and engage in deep reflection and debate with their staff.

Impossible to adequately delegate resulting in failure in taking the initiative

There were too many interdependencies to allow for flexibility. Ironically the German doctrine of command, Auftragstaktik, or mission command, had been infused in Prussian military culture for over 100 years prior to WWI. This represented a command and control philosophy that emphasized the importance of understanding the strategic intent and granting substantial autonomy to subordinate leaders to achieve that intent. But pressed up against the logistical constraints of moving over a million men and their materiel, the ripple effects of any slight plan adaptation would have taken too much time to calculate. The pressure of local commanders to adhere to the schedule created risk aversion to change, rendering unrealistic the practical application of Auftragstaktik – the ability to take the initiative.

What did things look like on the other side?

Churchill’s Strategic Foresight

In the years prior to and throughout WWI, Britain’s competitive advantage was its navy, led by First Lord of the Admiralty Winston Churchill. As the skies gradually darkened leading to the conflict, Churchill was obsessed with deeply understanding the growth and capabilities of Kaiser Wilhelm II’s naval forces and the technologies being developed. Rather than underestimating German potential, he made assumptions that their production pace and capabilities were advancing faster than they actually were. He overestimated his adversary. Overcoming budgetary constraints and members of Parliament backing pacifism and neutrality, Churchill was successful in estimating the amount of time they had to engage in a pre-war naval arms race and ensure Britain’s ability to project power would outmatch Germany’s.

Churchill, who thrived on productive conflict, benefited from leading within a culture that had a political tradition of contrarian multiparty discourse. This aligned with his creative and generative personality, allowing him to flex with shifting situations and avoided the narrow-minded trap of single leader authoritarianism.

While the Kaiser was overconfident, inflexible, and underestimated his adversaries, Churchill:

… had a personality and history based on the merits of contrarian argument. His education and experience was cast in a crucible of debate. Ideas were destroyed or hardened based on their relative merits. What some leaders found exhausting, Churchill found all forms of conflict energizing.
… based his information on a diversity of sources when making plans. He was a voracious reader, he shared and spread ideas broadly as a prolific writer and speaker, and pulled in subject matter experts when evaluating problem areas, such as seeking military innovation.
… overestimated his adversaries’ potential, resulting in a numerical superiority of ships, a naval blockade of Germany, a convoy system protecting merchant shipping, and technological adaptations to counter the emerging U-boat threat
… clearly articulated military strategy through various communications channels while quickly adapting to new information. Churchill was, borrowing a quote from Jeff Bezos, “stubborn on vision but flexible on details.”

Leaders’ Needs and Their Headwinds to Success

After articulating strategy, leaders need time to learn so they can incrementally reformulate their approach to push through the fog of execution uncertainty to attain the objective – before their competitors get there first.

The Time Constraint and the Anchoring Effect

In software development, setting timelines is a delicate balance between ambition and practicality. While leaders should instill a sense of urgency and direction, it’s crucial that the timelines in software plans are not just anchored in optimism or leadership's vision, but reflect the realistic scope of work required for a successful launch. Startups are racing to achieve product-market fit. This requires continual delivery, learning, and pivoting on the path. However, this push for speed often leads to setting deadlines with little to no margin for the unexpected.

The anchoring effect can cause people to lean too heavily on initial assumptions and estimates, with less regard to current information on hand, hindering learning and adaptation. When there is resistance to changing the schedule, debate and reevaluation is forced to center exclusively on functionality or quality. Leaders can be forgiven for this tendency, since time is the only resource we have which is not fungible. But excluding the negotiation of this scarce resource from the discussion due to anchoring artificially constrains options. Anchoring is a powerful effect. Even when people are aware they are anchoring and have updated information suggesting more realistic timelines, it is hard to overcome the original expectation for a schedule*.

Adaptation to Learning and Overconfidence Bias

Software leaders have to balance the need to turn the feature production crank quickly, releasing and learning fast, with delivering a product that creates value with customers, preferably in a novel way. Anchoring on the initial schedule or hypothesis of value creation, overconfidence that the plan is infallible, and underestimating the frictions and risks to get to product-market fit can lead to a lack of debate at the critical moment when product learning begins to emerge. Leaders have to be bold enough to deliver incomplete features and strike a delicate balance of rolling out the feature just enough to learn but not too much to burn through their potential customer base. The iterations that follow require them to constantly ask “did we miss the mark?” and “is this an improvement over the last version?”

What are the stakes of getting this wrong?

Software users are increasingly sophisticated while their attention spans and patience for perfection shrink. They have a sixth sense for what feels right and will unforgivingly bounce away at the earliest twinge of displeasure. Software must be simple, glitch-free, trustworthy, and blazingly fast. V1 software features are often shipped in an inchoate, moments-beyond-vaporware state of minimum viability. Your customers don’t care about your planning constraints. Despite best efforts, a single bug at the wrong moment could earn a product a one star rating in the App Store.

Combatting Anchoring Effect and Overconfidence Bias in Software Planning

Scenario planning: Develop multiple scenarios, including worst-case situations, to understand how various factors could affect timelines. What’s plan B? What happens if your assumptions don’t pan out? Consider a formal process of strategic risk management.
Encourage productive conflict: Create an environment of constructive dissent and diverse perspectives where team members feel comfortable voicing concerns and doubts. - Identify devil’s advocates whose purpose is to find flaws and be incisively contrarian. - Borrowing a concept from military war games and cybersecurity, identify a Red Team of capable engineering leads who work together to imagine an alternate version of the future where the plan’s premises lead to failure.
Support a learning culture: By pinning decision making on incremental learning and setting short learning cycles into the pacing of production, leaders and team members are expecting plans to evolve.
Emphasize flexibility: Establish a planning method that values adaptability and the ability to pivot based on changing circumstances. When flexibility is needed, tap into the scenario plans to help decide on an appropriate pivot.
Communicate strategic intent with decentralized decision-making: Articulate the vision and empower subordinate leaders to take the initiative and make decisions based on real-time conditions, rather than strictly adhering to a pre-set timeline.
Be a strategic omnivore: Read about political, military and business history. Talk to your peers about their past projects. Identify where biases anchored the timeline or underestimated the adversary.

A Final Word on Underestimating the Adversary

For military leaders the stakes are higher but the annals of history are brimming with stories where their inability to fully imagine the resourcefulness, tenacity, and commitment of the adversary have brought great powers to failure. More examples include:

The 1812 Russian Campaign under Napoleon Bonaparte. Underestimation of the duration, conditions, and logistics of battle and unexpected tenacity of the Russians resulted in a casualty rate of 83% of Napoleon’s troops (half a million men). This marked a significant turning point in the Napoleonic Wars. It weakened Napoleon's reputation of invincibility, emboldened his enemies, and was a catalyst for the coalition that would eventually defeat him.
The 1915 Battle of Gallipoli under Winston Churchill. Churchill underestimated the abilities of the forces of the Ottoman Empire. He had long anchored on the perception that the Ottoman military was “a spent force, decrepit and paralyzed, unable to conduct a modern war." The scale of casualties (over a quarter of a million Allied men) and loss of confidence resulting from this nearly ended his political career decades before his pivotal leadership as Prime Minister of England during WWII.
The 1961 Bay of Pigs invasion under President Kennedy’s leadership immediately strengthened Castro and pushed him closer to the Soviet Union. More importantly, it harmed Kennedy’s trust in his military leadership, which had a significant impact on the recruitment and influence of the circle of “whiz kids” advisors who played a major role in shaping the future US strategy in Vietnam and Southeast Asia.
The complete surprise of the 1968 North Vietnamese Tet Offensive was the beginning of the end for President Johnson’s presidency, the strategic influence of the whiz kids, and shattered the illusion of America’s strength in the conflict.

Wrapping Up

Leaders need resources: access to enough financial capital, talent, and time to learn the way through the fog of uncertainty to get to the goal. Their adversaries are the constraints and unknowns that must be overcome. Biases lead to leadership overconfidence with regard to the potential of their resources (time and talent) and underestimation of their adversaries.

“Evaluation of enemy strength is not an absolute, but a matter of piecing together scraps of reconnaissance and intelligence to form a picture, if possible a picture to fit preconceived theories or to suit the demands of a particular strategy. What a staff makes out of the available evidence depends upon the degree of optimism or pessimism prevailing among them, on what they want to believe or fear to believe, and sometimes upon the sensitivity or intuition of an individual.” - Barbara M. Tuchman, Pulitzer Prize winning American historian