A vendor-neutral guide to the ten questions that reveal whether a technology firm will still be worth having a year from now. Written by Canaan One — but useful no matter who you hire.
Choosing an IT partner is one of the highest-leverage decisions a business makes, and one of the hardest to reverse once systems, data, and habits are entangled. The questions below cut past the sales polish. Ask every candidate the same ten, write down the answers, and the right choice usually becomes obvious.
The people who win the contract are often not the people who do the job. Ask to meet the actual lead and confirm they stay through delivery.
“Fast” is meaningless without numbers. Insist on response targets by severity, stated in the contract, with monthly reporting against them.
A good partner keeps you exit-ready: your documentation, credentials, and code are yours, current, and handed over on request. Lock-in is a red flag.
Scope always shifts. What matters is whether changes are quoted and approved in writing before work proceeds — or billed as a surprise afterward.
Direct access to the project board and repository beats a monthly summary. Transparency during the work predicts honesty when something goes wrong.
Security should be a default, not an upsell: least-privilege access, encryption, MFA, tested backups. Ask how they secure their systems, too.
Tickets closed and features shipped are activity. A real partner defines success in your terms — hours saved, downtime avoided, revenue enabled.
The most valuable partner talks you out of spending money you don’t need to. Candor over comfort is worth more than agreeableness.
Documentation and team redundancy mean your systems don’t live in one contractor’s head. Ask what happens if that person is unavailable.
References, case studies, or a scoped paid assessment all reduce your risk. Be wary of anyone unwilling to prove capability before a big commitment.
The short version: hire the firm that answers these plainly, puts the answers in writing, and seems more interested in your outcome than your signature. That’s the standard we hold ourselves to — and the one we’d want you to hold anyone to.