The time it really takes, or the definition of "done"
Even experience doesn't prevent us from underestimating the effort and the time required to reach an objective.

It all comes down to the definition of "done". Let me illustrate this with a simple example. If I state that "the objective is to implement a new format of project status", most people will assume that once we have a nice template of project status satisfying the needs, the job is done, whereas I expect the project status to be used by the teams, hence a series of tasks for validating, communicating, presenting, and controlling the use of the new project status format. We have a natural bias to focus on (1) analytical work and (2) work than mainly involves ourselves and not others. In other words, we tend to overlook tasks that require collaboration and communication, and more generally how much effort is needed to implement the change in order to reap the benefits.
When estimating how much time and effort are needed, I go through this simple list.
- Formulate the needs and identify stakeholders. Don't forget to check stakeholders' availability.
- Validate needs with client
- Break down into tasks
- Perform initial analytical tasks (by myself)
- Adjust deliverables by collaborating with relevant stakeholders
- Validate final version of deliverables with stakeholders
- Prepare communication material (ex: PPT, how-to)
- Publish relevant material
- Present and promote solution to users
- Coach users as needed (over specific period of time)
- Control results, adjust deliverables if necessary
- Report final results to client
It's like a mini-project, really.
Poor estimates will focus on tasks 3-to-6 and then assume that the work is done. In my experience, in any complex organization the effort for tasks 1-6 seldom exceed 50% of the total effort.
To summarize further the previous list of generic tasks, let's look at the 3 main activities:
- Initiate (tasks 1-3)
- Execute (tasks 4-6)
- Implement (tasks 7-12)
The main effort consists in implementing the solution, i.e. making sure "users" use the solution as intended, without any need for supervision. In this light, we understand that any "small" change, to a process for example, triggers several tasks that go far beyond changing the process in itself. There are actually two dimensions of complexity in any change: analytical and organizational. To me, the organizational dimension is by far the hardest to handle because it involves stakeholders whose reactions (and resistance) is difficult to anticipate.
Many organizations are plagued by half-baked initiatives, things that have been started but never properly completed. They incurred most of the costs, but little of the benefits. Unsurprisingly, it's usually the implementation part that is lacking. Folders of organizations are full of great analyses and recommendations that have not been deployed. Avoid this huge waste: determine what "done" means from day one.
One of the reasons I believe in Agile principles is that it emphasizes what "done" means: it's done when it delivers value to the users. It has been designed primarily for software development but it can be applied to any subject.
