What should I ask in a coworking software demo?

Demos are your chance to see a product being used, just as you need to use it.

I sat down with our sales team and put together a list of questions to ask in a coworking software demo. Together, we’ve covered scenarios that cross all size businesses, from single sites to enterprise, and came up with high-level and detailed questions that should give you a sure footing of who can do what.

Try them out to come out knowing which solution fits your needs best.

1. Can you create a [insert a booking example here] for me?

Bring your biggest booking headaches and ask the rep to show you how the platform handles booking conflicts. You need to know that bookings are rejected in-app for the right reasons and that your members get an exceptional experience.

Question ideas

• Can a member make recurring bookings or added to a waitlist?
• Show me how I’d make a booking using member credits that respects buffer times and peak-hour rules.
• Can I see room or desk availability across different locations?

2. How does the platform handle memberships, invoicing and payments?

Ultimately you’re after a full, easily manageable audit trail, even when memberships change mid-cycle.

Ask how the platform manages payments and invoicing and if you can connect the software to your preferred payment gateway/s – ideally without middleware that lifts failure points and cost.

Then again, you might need a custom setup if you’re expanding into new markets or have unusual billing needs.

Question ideas

• Show me how to refund a deposit and a typical audit trail example.
• What do automated recurring payments and reminders look like?
• Do you integrate natively with [Stripe, GoCardless etc] already?
• Can I download a payout report that lists each payment, the fees, and the invoice numbers?
• Can we use your API and webhooks to run our own checkout, then tell your system when an invoice is paid or refunded?

3. Show me how members login and what they can manage

Can your members change their plan, use their credits, add mail handling preferences, buy things, or pay an invoice? Can they also use the platform socially? Ask your lovely rep to show you the platform solely from the members’ view.

Question ideas

As a member, from my phone, can I:

• Buy something from the cafe?
• Open/lock up the office?
• Print something and pay for it?
• Message other members or RSVP to events?

Pro questions:

• I offer virtual offices. Do you have features that support bulk mail and package management?
• Can my members login to my website?
• I don’t have a website, can I use the platform as one?
• Can I white-label the platform and apply my own branding?

4. How can I use the platform to manage events?

Think about the types of events you hold and see how resources, comms, and guests and visitors lists are centralised.

Question ideas

• Show me how I manage attendee and visitor lists.
• Can I visualise different event layouts and include resources like screens or catering?
• Does the platform sync access to the event remotely?
• Can I add records of signed documents, or include a booking buffer for setting up and clearing?

5. What happens when a member cancels?

How much can be automatic once a member leaves? How can you ensure security at scale once people have left? Does the platform show data that helps me reduce members leaving?

Question ideas

• Is access to the space and amenities immediately revoked?
• Can I set things up so information is automatically sent to leavers?
• Does the software offer analytics that reveal my least engaged members?

6. Take me from a lead → tour → quote/e-sign → payment → onboarding—end-to-end.

Look for a platform that has a set of features and integrations that report from first touch to conversion. And, can you send and store all of your important documentation from the platform?

Question ideas

• Does the platform have a built-in CRM?
• What can I do with it?
• Does it have built-in features to help me predict churn or retain customers?

Pro questions

• Can I integrate with HubSpot or Salesforce?
• Is it easy to integrate with GA4?
• I don’t want to risk duplicating records, are any of these integrations two-way?

7. What kind of reports can operators use?

Your lovely rep can demo reporting dashboards that make your life much easier. You want to know which growth signals you can see natively.

Maybe you’re looking to report on multiple sites with member activity into the hundreds of thousands?

Question ideas

• Do reports drill into space and resource utilisation?
• Can I see ARPM/ARPU (Average Revenue Per Member/User), revenue by product, churn and cohort reporting and event impact
• Once I’ve set up the reports I want, can I schedule them for weekly, quarterly etc intervals?

Pro questions

• I’m a multi-site operator and need to report on a lot of data.
• Do you have an open API?
• Do other customers create custom reports or hook into BI or BigQuery?

8. Walk me through your security and resilience

For data handling and security, ask if the platform is ISO 27001 or SOC 2 compliant. You’ll likely be directed towards badges, but you can request to see the reports issued.

What about platform failure and how that might affect your business? Ask how often this has happened in the last two years and how backups are handled. You should be able to access tamper proof timelines of all users of the platform to keep your operations secure and compliant.

Question ideas

• Can you show me a user’s audit log?
• Do you support SSO and 2-step verification (2FA) for staff logins?
• Where is our data stored, and how long do you keep it? Can we export or delete it on request?

9. What does onboarding and support look like?

Great software can still flop without a solid rollout. You want a clear project plan, confident data migration, role-based training, and clear SLAs (Service Level Agreements) so your team isn’t firefighting on day one. SLAs spell out response & resolution times, availability targets, escalation paths, and service credits—so expectations are explicit, measurable, and enforceable.

Question ideas

• Can you share a project plan with milestones?
• What training is included for each role (admin, front-desk, finance, community)?
• Is there on-demand training once we’ve launched?
• What are your support channels and hours?
• How does your Product team handle feature requests?

10. What is included and what is an extra?

Surprise costs kill ROI. Nail down what’s in the base licence vs. paid add-ons and usage-based fees. Clarify which integrations are included, which are premium, and where third-party costs (payments, SMS, printing, access control) apply.

Question ideas

• Which features are included in the core plan (bookings, CRM, events, virtual office/mail, tickets/helpdesk, white-label app/portal)
• Are automations or notifications an extra cost?
• Do you charge to access your API?
• What are the payment gateway costs and are there per-transaction fees?
• Are there support tiers (response/resolution SLAs) and what’s included at my plan level?
• Is onboarding included? How many hours and what’s billable after that?
• Will I be locked in to a contract, and for how long?

11. Don’t forget about automations and integrations

You can automate so many things, like billing, invoicing, check-ins, occupancy tracking etc. It’s best to think of your operational goals and ask the rep if there’s a solution for it. We’ve covered some already, but there are so many more. Bring your operational problems to the demo and see how different platforms solve them.

Question ideas for automations

• Are failed payments are chased automatically? Do retries and reminders go out? Can I apply grace periods? Can I limit access/Wi-Fi/printing after non-payment?
• Can I automate updates to bookings and check-ins? How accurate are occupancy dashboards? Can I monitor energy use or control energy when spaces aren’t occupied?

Software can be tailored and integrated to suit different scenarios, but you need to know if a system can be tweaked to suit you. If you’re starting out, think about what kind of goals you have. Share a goal or two in the demo and ask the rep if there’s a solution that would help achieve it.

Question ideas for integrations

• Our goal is x [cut no-shows by 30%]. What can we tweak out-of-the-box to hit that suing rules, reminders, access settings? Can you show it live?
• Can we add our own fields and steps to forms/bookings/invoices without a developer, and use them in reports and automations? Can we hide different aspects by job role?
• We use [HubSpot, Xero, Kisi]. Do you have a built-in integration, or would we use Zapier, a webhook or an API? Can you show data flowing both ways in the demo?

Now go get your demos!

Great demos should feel like a day in your space. Bring your real workflows, ask the rep to do them live in 2–3 minutes each, and use the questions above as a checklist you can score.

Get pricing, SLAs, and integration details in writing, and ask for a sandbox or trial. If they can’t show it, assume it’s not ready. Choose the platform that removes work on day one and has a clear path to grow with you.