Project Misalignment Starts With How You Plan

Your project is “on track,” but users and the business are not better off? Most likely, you are getting exactly what you planned for: outputs, not impact.

Over the years, I have seen many failed projects. Almost none of them failed because people were lazy or sabotaging the work. Teams were fully committed and working hard, just not on what actually mattered. Plans focused them on deliverables, not on change in reality. Progress looked convincing internally, while users and business outcomes stayed the same.

In engineering work, the goal is the primary invariant. Deliverables, requirements, and plans have no independent value. They matter only as means to achieve a real change that satisfies a real need. When deliverables become the object of planning, they also become the object of evaluation. If real impact is profit, then deliverables, and the effort spent on them, are costs. The team ends up optimising and celebrating how well it spends the sponsor’s money instead of the value it creates.

One Practical Shift

A practical shift is simple: plan outcomes, not outputs.Every planning session should end with clear answers to three questions:

• Why, without this, users will not consider you the best product or service
  

• What you really lose if you do not do this at all
  

• And the key question, the first two are just a warm-up, why this is the most important thing to do today

If there are no honest answers, planning protects neither the goal nor the people involved. It only protects the plan itself.

AI-Assisted Sanity Check

Fortunately, we are not alone in this. GenAI can be a useful assistant, and, when used this way, an even more effective one, not as a generator of ideas, but as a strict and disciplined critic, if you ask it to be one.

Below is the prompt I share with my teams to run a first sanity check on their plans. It helps them test whether a plan is truly oriented toward goals and impact, rather than outputs and activities.

Role

Act as a ruthless but rational reviewer of product and project plans.

Your goal is not to be polite or encouraging. Your goal is to protect users, business outcomes, and limited resources.

Context

Here is our plan for the next milestone:

[paste your milestone plan here]

Your task

Critically review this plan and explicitly try to uncover the following failure modes:

1. Substitution of impact with deliverables
     – Where outputs are mistaken for outcomes
     – Where activity is presented instead of real change  

2. Cost optimisation instead of value creation
     – Where success is framed as “more delivered for less cost”
     – Where spending, effort, or scope is confused with progress  

3. Hidden, weak, or wrong assumptions
     – Assumptions that are implicit rather than explicit
     – Assumptions that are unvalidated or unrealistic
     – Assumptions that, if wrong, would seriously damage outcomes  

Instructions  

Be direct and concrete. Avoid generic advice.  
Point out where the plan sounds convincing but is logically weak.  Highlight where the plan depends on hope rather than evidence.  
Identify what would most likely be discovered too late.

Output format  
– Key risks and inconsistencies  
– Assumptions that must be made explicit  
– Missing or weak evidence  
– What you would challenge or stop before approving this milestone  

Do not propose solutions unless a problem cannot be explained without one.

A Minute on a Soapbox

A goal that is present in every movement of a project, in every action, and in every decision , a goal used as the single primary measure of whether something is reasonable and justified, is the foundation of a delivery approach that defends.

It defends the interests of users, stakeholders, and sponsors. It also defends the professional dignity of the team, even when it would be easier and more comfortable to simply spend the budget and keep moving.

A goal can never be a formal checkbox. If there is time for only one thing in the entire project, it must be a clearly understood and explicitly stated goal.

Even an average performer, when they understand the goal, has a chance to get there. Even a genius, moving without a goal, will only waste effort, time, and resources.

This is the type of thinking I bring as a CTOx: keeping work aligned with the goal, making assumptions visible, and stopping expensive mistakes early, before they become “successful execution of the wrong plan.”

If you need a calm, external check for a high-stakes initiative, I’m always open to a conversation.