Trigger events
Technology leadership becomes urgent at very specific moments
Nine of them, and every one has a window that closes. Each page below is what is actually going on underneath, what to do in what order, and the questions somebody is about to put to you.
You just announced an acquisition
Two companies, two systems, one deadline.
90days · before the temporary becomes the architecture
You've had a security incident
The breach you found is rarely the only way in.
30days · while the incident still has everyone's attention
Your MSP contract is up for renewal
You suspect you are overpaying. Proving it is the hard part.
120days · before the renewal date, not the notice date
Your IT lead just resigned
What lived in one person's head is about to leave the building.
2–4weeks · and the last week is worth nothing
A major system decision is looming
ERP, CRM, or a platform migration you will live with for a decade.
7+years · is how long you will live with this
Cyber insurance renewal is due
Answering wrong is worse than answering no.
60days · before the application is due
You've outgrown your IT provider
You may not need a different provider. You may need a different function.
90days · long enough to see the pattern, short enough to still have options
New compliance requirements landed
The requirement arrived from outside, with somebody else's deadline attached.
60days · and the first two weeks decide the size of the job
Investors are asking hard questions
The board wants a technology plan tied to the thesis, not a tools list.
6weeks · and everything is discoverable