Most business leaders believe technology projects fail because they chose the wrong software.
After more than twenty-five years working with businesses of every size, I've found that's almost never true.
Technology projects usually fail long before anyone signs a contract.
They fail because organizations begin with the wrong question.
The wrong questions
The conversation often starts with:
"Which CRM should we buy?"
"Should we move to Microsoft 365?"
"Can AI automate this?"
"Should we replace our ERP?"
Those aren't bad questions — but they're not the first questions.
The better question
The better question is: "What business problem are we actually trying to solve?"
I've watched companies spend hundreds of thousands of dollars implementing software that worked exactly as designed. The project was technically successful. The business outcome wasn't.
Not because the software failed. Because leadership never aligned around the business objective.
Technology supports strategy — it isn't the strategy
Technology should never become the strategy. It should support the strategy.
When executives slow down and define success before evaluating solutions, the entire conversation changes. The vendor becomes easier to choose. The roadmap becomes clearer. The investment becomes easier to defend.
And most importantly, technology becomes a tool that moves the business forward instead of another system employees have to learn.
Where good decisions begin
One of the most valuable things an outside advisor can do isn't recommend technology.
It's helping leadership ask better questions before technology enters the conversation.
That's where good decisions begin.
If you would like a second, independent voice in the room before the next technology decision gets made, that is exactly what HaveSight does.
— Allan Sivils, founder, HaveSight