The Daily Requirement

During Operation Haven in 1991 – the humanitarian operation in northern Iraq that followed the Gulf War – the uncertainty around enemy disposition and intent was not occasional. It was constant. You did not produce a plan and then refer back to it. You rebuilt the picture almost every day because the situation kept moving, and the intelligence was never complete.

The discipline that held throughout was enemy appreciation. Before any plan could be finalised, you were required to present the most dangerous course of action available to the enemy – not the most likely, not the most convenient, not the one that made the plan look straightforward. The one that, if it materialised, would put the plan under maximum stress. The one that required you to answer the hardest version of the question before you committed to anything.

This is not pessimism. It is not risk aversion. It is the recognition that a plan which can only beat a cooperative enemy is not a plan. It is a wish. The military calls the weaker alternative – planning against the version of the opposition that suits you – a failure of intelligence preparation. Most organisations do not have a name for it. They just call it strategy.

The Strawman and Its Cost

There is a term from philosophy and rhetoric that is worth introducing here. A strawman argument is when you misrepresent someone’s position – or someone’s capability – in order to make it easier to dismiss. You replace the real thing with a simplified, weaker version, argue against that version, and move on. The name comes from the idea of fighting a straw dummy rather than a real opponent. You win, but you have not actually fought.

The opposite is called a steelman. You take the argument, the competitor, the objection, or the risk, and you present it in its strongest possible form before you respond. Not the version that is convenient. The version that is hardest to answer. Then you answer it.

In business, strawmanning is not usually deliberate. It is what happens by default when there is no discipline to do the opposite.

When we were building the cloud and managed services business, we assessed Microsoft through the lens of its reputation. Large, corporate, slow to move. That was the version of the competition we were tracking. What we did not adequately account for was their capability to recognise a strategic imperative and decide to move differently.

They hit the ground running with BPOS (Business Productivity Online Suite), and then the shift to Office 365 gave them acceleration none of us had fully planned for. Wrapping the everyday productivity tools people already used into a scalable, subscription-based offering was a different kind of move than the market had seen from them before. We were caught by the speed, not the idea. There was a silver lining – the normalisation of consuming application services via subscription validated the market we were already in. But we had been arguing with the slow-moving incumbent. The version that moved quickly was already in motion before we adjusted our picture.

The cost is not always a defeat. Sometimes it is a surprise, and sometimes surprise is manageable. But you are still operating on a plan that was tested against the wrong opponent.

This failure mode shows up in three specific places. The first is how leaders handle criticism. When an investor, a customer, or an advisor pushes back on something, the instinct is to find the version of the concern that can be dismissed quickly. They do not understand the business model. They are being conservative. They are comparing us to the wrong thing. Each of these might be partially true. But they share a structure: they replace the actual criticism with something easier to dispose of, and the real signal goes unaddressed.

The second is competitive analysis. Most assessments describe the competition at its weakest – the features it lacks, the customers it has lost, the markets it has ceded. This feels like intelligence. It is actually motivated reasoning. You will be surprised by the competitor whose strengths you chose to ignore.

The third is internal dissent. A leadership team that consistently engages with the weakest version of concerns raised by its own people teaches those people to stop raising them. What follows is not harmony. It is a team that has learned to be quiet about the things that matter.

Where Building the Stronger Case Pays

The return on steelmanning is highest where the cost of being wrong is greatest, and the feedback loop is slowest.

When we needed bridging finance ahead of a Series A raise, we had a large deal on the hook that we were confident we could win if we moved early on the infrastructure. Taking that risk required a funding partner to come with us. We did not go into that conversation with the pitch. We went in having already answered the three questions we knew they would need to satisfy: why we needed it, how and when we would recoup it, and how it would materially benefit them as well as us. The strongest version of their concern was answered before it was raised. The deal followed.

Fundraising preparation is one of the highest-value applications. Due diligence – the process investors use to examine a business in detail before committing capital – is, in structure, the investor steelmanning the case against you. Founders who have only rehearsed the pitch are rehearsing against a compliant audience. Founders who have genuinely constructed the strongest version of the investor’s concern before the investor walks in arrive differently. The hard questions do not land as surprises. They land as questions that have already been given serious effort.

The exit decision is another example. The mutual decision to exit the business was informed by an honest assessment of the competitive landscape – specifically, that we were not going to be able to compete with organisations that had longer trousers and deeper pockets. The structural advantages they held were real, and they were not closing. Steelmanning the case for staying independent made the exit decision clean rather than reluctant. You do not make that call well if you have been arguing with the convenient version of the competition.

The Risk of Getting It Wrong

Steelmanning applied without judgment is its own failure mode.

Early-stage businesses need to move on incomplete information. The discipline required to protect a major strategic decision can cripple the momentum that early execution requires. If every decision – including low-stakes operational calls – requires first constructing and engaging with the strongest possible objection, the organisation slows down. Speed is not always the point, but it matters early, and a founder who steelmans everything is not being rigorous. They are using rigour as a mechanism for avoidance.

I have met a number of founders who arrived at exactly this position after conducting a deep analysis of their market and competitors. What they produced was not a better-informed decision to act. It was paralysis. The analysis surfaced a fear that was already present. The steelman made the risk sufficiently visible that moving forward required confronting it honestly, and some founders could not do so. The analysis became the cover for avoidance rather than its cause.

There is also a version where founders steelman the case for inaction, or the case for the incumbent, so thoroughly that they talk themselves out of something that was genuinely good. Incumbents look strong on paper. Their advantages are real and well-documented. Their vulnerabilities are often invisible until someone has tried to build against them. The founder who builds the most capable version of the incumbent before they even start, and cannot find the answer, is not being intellectually honest. They are doing the incumbent’s work for them.

The Skill Is Knowing Which Mode You Are In

The most effective leaders do not steelman everything. They move quickly on low-stakes decisions and apply rigour deliberately to the ones where the cost of being wrong is not recoverable.

The practical question is simple to state and genuinely difficult to apply honestly: if the strongest version of the case against this is right, what is the cost? Where the cost is recoverable, move. Where it is not – a strategic pivot, a major hire, a fundraise, a product assumption that has never been tested – take the time to build the most capable version of the objection and answer it before committing.

The difficulty is not identifying high-stakes decisions. Leaders usually know when something matters. The difficulty is being willing to slow down when everything feels urgent and the room is waiting for a call.

The military enemy appreciation process requires someone whose explicit job is to make the enemy as capable as the evidence allows. Not to be realistic. Not to assess probability. To present the most dangerous version of the opposition so the plan survives contact with it.

Most organisations have never put someone in that role. Most leaders have never asked someone in their own team to do the equivalent: to build the strongest possible case against the current plan and present it seriously before the decision is made.

When did you last do that? Not a devil’s advocate exercise – someone playing a role in a meeting. A genuine attempt to construct the most capable version of the opposition to your current position.

If the answer is that you have not, the question worth sitting with is whether that is confidence or avoidance.

I suspect most honest answers to that question are more uncomfortable than they first appear. I would be interested to know where this breaks down for you – where you think the stronger version of the opposition does not apply, or where applying it would cost more than it is worth.