No More Digital Handcuffs: How to Grill Your Agency the Right Way
The real-world questions every client should ask their digital partner before anything goes live.
The email that nearly wiped a website
“Hey guys, can you update these DNS records for us?”
Harmless, right? Except the records pointed to Squarespace, while the client’s revenue-driving store sat on WordPress - thirty-plus paid plugins, years of SEO, the lot. One mis-paste and poof: goodbye products, goodbye data.
The long-time Marketing Manager had recently walked out the door – unsure of login hand-over and the subscription ledger.
Plugins were still chugging away on a company credit card.
The client’s new goal was crystal clear: “We want more control over the whole thing.”
Totally fair. But a platform jump to Squarespace (great for brochure sites) didn’t line up with their inventory system, and would have torched every WordPress integration they already paid for. So, WordPress stays (for now) while we sort the next move.
Why you need a “pre-nup” with your agency
A client should never feel welded to a platform or an agency. With that in mind, here are some of the key questions you absolutely get to ask - preferably in the very first discovery call.
Q1. “Do I own the website after launch?”
Sounds obvious, yet we still see agencies host a site on their own servers and charge a king’s ransom to “hand it over”. Your site is your intellectual property; code, content, images, the lot. Hosting through an agency is fine; being held hostage isn’t.
→ Ask: “What’s the exit process if we ever leave?”
Q2. “Who’s on the hook if the site is hacked, crashes or needs a backup restore?”
If the agency controls hosting, backups and security patches are their responsibility. Yes, even when a rogue plugin update trashes the homepage at 2am.
→ Look for: automatic off-site backups, a tested restore plan and no extra “rescue” fees.
Q3. “Do we need a retainer, or can we stay ad-hoc?”
Retainers make sense for SEO or paid-ad campaigns. They make no sense for a brochure site that you update once a quarter.
→ Push for: flexible hour packs or pay-as-you-go support.
Q4. “Which platform fits us today and in three years?”
| Scenario | Good fit now | Good fit later |
|---|---|---|
| Simple marketing site | Squarespace, Webflow, WordPress | If e-commerce looms, consider Shopify before year three |
| e-commerce | Shopify, WooCommerce, headless build | Scale with plug-ins/apps or custom middleware |
Don’t accept a rebuild every time your business evolves. Your agency should map the three-year view before they start wireframes.
Q5. “What’s the plugin or app game plan?”
Plugins are like phone apps: handy until you forget which ones you’re paying for. Every add-on carries a potential cost, a security risk and a maintenance load.
→ Agree on: a quarterly audit, a vetting process for new installs and a rollback plan for bad updates.
Q6. “How painless is content editing for non-tech staff?”
Not all platforms are built equally, and others are harder to self-manage without creating a visual mess. In 2025 this is a 110% valid requirement from a business owner. Your agency should be providing the least friction option of updating your site. Modern CMS tools (Webflow & Shopify) should let you add blogs, team members and testimonials without breaking the layout.
→ Ask for: a five-minute live demo—no devs, just you and a browser.
Q7. “Where are domains and email hosted—and who holds the master logins?”
Domains sitting in a personal GoDaddy account = disaster waiting to happen. Put everything in a shared corporate vault (1Password, LastPass) and document renewals.
→ Pro tip: align all renewals to the same month where possible; finance will love you.
Q8. “What’s the graceful exit plan?”
Leadership changes, strategies pivot – stuff happens. Your contract should spell out exactly how code, databases, assets and licences are handed over if you part ways. No surprises, no unreasonable “transfer fees”.
→ Insist on: a written de-coupling checklist up front.
Quick reality check on plugins
Need an Insta gallery? Plugin. Store-finder map? Plugin. Google reviews widget? Plugin.
Downsides?
Cost creep – $12 here, $29 there, commonly charged monthly in USD.
Security holes – poorly maintained plugins are hacker bait.
Fragility – one update can white-screen your checkout on a Friday night.
Audit every quarter and bin anything that is gathering cyber dust.
Your one-page control plan
Password vault shared with role-based access.
Billing calendar to keep on top of recurring subscriptions and renewals.
Daily off-site backups with a tested restore.
Exit clause baked into every agreement.
Good vs. Great
Control isn’t a toggle; it’s a mindset you build by asking blunt questions up front. These are only a few of the key questions you should be asking of your digital agency. A great agency will provide a full list and run you through on their discovery phase of the project before you've even spent a cent.
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