Independence
Which technology decisions are reversible
Most vendor choices can be undone in a weekend. Two or three cannot, and firms usually cannot tell them apart in advance.
Published
The distinction that matters
Not price, not features. Whether the system holds data you will need later, and whether other systems depend on it.
A tool that does one job and exports cleanly is reversible. A tool that becomes the record for something is not.
The ones that are hard to undo
Your custodian, because every process touches it. Your performance reporting, because the history lives there and rebuilding it is frequently impossible. Your CRM, because it accumulates the record of every client interaction.
Everything else is usually a weekend and some annoyance.
The question to ask every vendor
What happens to my data when I leave. The nine questions spell it out; this is the first of them.
Ask before signing. The answer given during a sales process and the answer given during a cancellation are different answers, and only the first one is available to you now.
Ask how you get out before you decide how to get in. The exit terms tell you more about the vendor than the demonstration does.
Integration claims deserve specifics
The second of the nine questions. Ask what specifically syncs, in which direction, and how often.
The failure mode
Not choosing the wrong system. It is choosing several systems that each solve a problem and together create the seams where data disagrees.
Every seam is a reconciliation someone has to perform forever, and that person is usually the founder.
The practical rule
Be slow on the three hard-to-reverse decisions and fast on everything else. Firms usually do the opposite, agonizing over small tools and choosing a reporting system in an afternoon.