Putin and the planning fallacy

Tower of the Oldehove, Leeuwarden, NL, built about 1530. Failed planning
 is of all times and we never  learn. During the construction of this tower so
much went wrong that it never has been finished.

Now, almost a week after the start of the Russian invasion of Ukraine, it is already clear that the war doesn’t develop as Putin and his military staff had foreseen. They didn’t achieve the targets they had set, like a quick fall of the Ukrainian capital Kyiv, beating the Ukrainian army and installing a puppet government. The invasion stagnates and the political resistance outside Ukraine is growing that fast that it is doubtful whether Russia (Putin) will achieve its targets anyway, even if Kyiv will be taken. Russia (Putin) has miscalculated what it could attain, and even if it will realize its plans as yet, it will have taken more time against much higher costs than foreseen. In other words, Russia (Putin) has become “victim” of the planning fallacy.
The planning fallacy (PF for short) has first been described by Daniel Kahneman and Amos Tversky (1979, see also their 1982). They also coined the term. Here I follow Kahneman’s Thinking, Fast and Slow and some internet articles. The planning fallacy is usually defined “as an erroneous prediction of future task duration, despite the knowledge of how many hours were used to accomplish similar tasks in the past.” (source) However, as discussions about the PF make clear, it’s not only the planned time for a project that is underestimated but usually also the costs. There are several reasons why planners often trap into the PF fall, such as:
- Planners tend to overestimate their skills and capabilities, leading to an underestimation of the time and costs needed for the project concerned. So, they are often too optimistic.
- Disregard of historical cases, like how you executed your plans in the past, and how others executed comparable plans.
- Ignoring possible risks and uncertainties.
- Pressure to present too optimistic plans, for example because you must execute them within a certain time or against certain costs; or because someone else might get the order.
In short, so Kahneman, we depend too much on the inside view: Planners focus too much on their own specific circumstances and search for evidence in their own experiences, when making plans. Information from the outside that doesn’t directly relate to the project concerned is usually ignored. A project is too often seen as a unique individual case with its own dynamics.
However, there is more, and maybe this is the essence of the planning fallacy: We fail to allow for what former US secretary of defence Donald Rumsfeld called the “unknown unknowns”. There are factors that we know to exist but cannot fill in or make concrete: the unknowns. However, there are also factors, the unknown unknowns, that we don’t know to exist and that only appear during the project execution. Planners seldom try to allow for them in some way.
The planning fallacy is not unescapable, though. We can do something about it or at least we can mitigate it, namely by taking the outside view. It involves that you must look for objective ways to judge your plans, especially:
- Look for reference cases and objective criteria to judge whether your plan is realistic. No plan is unique, and there are past cases (the so-called reference class of cases) you can learn from and that help improve your planning.
- Make several scenarios, both optimistic and pessimistic, how your project may develop. Usually a pessimistic scenario is more realistic than an optimistic scenario.
- Divide your project into parts and calculate the time and costs to execute them. Then add the time and costs necessary for the parts, and probably the sum will be higher (and more realistic) than the time and costs estimated for the project as a whole.
- Use reliable objective estimation techniques for your project and ask the opinion of outsiders.
If you take the outside view, certainly the effects of the planning fallacy will be mitigated if not avoided.
And how about Russia (Putin)? It’s clear that Russia (Putin) was overoptimistic about his military and political plans and trapped into the planning fallacy fall by leaning too much on the inside view, disregarding facts known to outsiders and ignoring warnings from third parties who felt themselves threatened by the invasion of Ukraine. Here are some planning mistakes that Russia (Putin) made, to my mind:
- Ignoring that often the defender is stronger than the attacker, as the military theorist Carl von Clausewitz wrote already 200 years ago.
- Ignoring that invading and occupying a country is not enough to win a war, so Clausewitz, but that you win only by breaking the will to resist. In 2014, when Russia (Putin) annexed Crimea, the Ukrainian will and power to resist was weak. However, since then and because of the annexation both have very much increased. Moreover, not only the will to resist of the Ukrainian people and the strength of its army have grown a lot since 2014, but this has been ignored or belittled by Russia (Putin).
- Russia (Putin) didn’t take seriously the warnings by third parties like the EU and the USA that they would feel themselves threatened by an invasion of Ukraine and that they would take serious countermeasures and would support Ukraine.
Briefly, although many see Putin as a very rationally calculating person who knows what he does, his calculations were based on the inside view. Putin disregarded the outside view and that’s why he trapped into the planning fallacy fall. 

Source
Daniel Kahneman, Thinking, Fast and Slow. London: Penguin Books, 2012; pp. 245-252.