Your Tools & Systems
What tools are you running your business on?
Let's start with the basics — what software and systems you're using day to day.
1 How would you describe the software tools your business runs on?
Modern cloud-based tools — we're pretty up to date
A mix — some modern tools, some old ones we haven't replaced
Mostly older or desktop-based software
I'm honestly not sure what we're running or why
2 How much of your business runs on spreadsheets?
Very little — we use proper tools for most things
Some spreadsheets but nothing critical
A lot — spreadsheets run key parts of the business
Almost everything lives in spreadsheets
3 Do your tools talk to each other, or does data have to be entered manually in multiple places?
They're well connected — data flows automatically
Partially connected — some manual steps still
Mostly manual — we enter the same data multiple times
Everything is disconnected — it's a real problem
Day-to-Day Operations
How smoothly do things run?
We're looking at how well your technology supports your team's daily work — and where it creates friction.
4 If a key employee left tomorrow, how confident are you that someone else could step into their role using your current systems?
Very confident — our processes are documented and not person-dependent
Somewhat confident — some things are documented
Not very confident — a lot lives in people's heads
Not at all — we'd be in serious trouble
5 How do you manage customer information and follow-ups?
We have a CRM — customer data is clean and organized
We have a CRM but it's messy or underused
Customer info is in spreadsheets or email
No real system — it's informal and inconsistent
6 How would you describe the amount of manual, repetitive work your team does?
Minimal — most repetitive work is automated
Some — we've automated the obvious stuff
Quite a bit — my team spends real time on manual tasks
A lot — manual work is a daily drain on productivity
Costs & Vendor Relationships
What are you paying for — and is it worth it?
Most businesses are overpaying for software they don't fully use. Let's see where you stand.
7 Do you have a clear picture of all the software subscriptions you're paying for each month?
Yes — we review them regularly and cut what we don't need
Mostly — I know the big ones but not all of them
Not really — subscriptions have piled up over time
No idea — I'd have to dig through the credit card statements
8 Are there tools your team pays for but doesn't actually use?
No — we audit this regularly
Probably a few small ones
Yes — a few tools are underused or duplicate others
Definitely — we're paying for things nobody uses
9 How do you manage contracts and vendor relationships?
We have a clear system — contracts are organized and reviewed
Tracked in a spreadsheet or shared folder
Informally — someone knows where things are but it's not organized
Not really managed — contracts are scattered or forgotten
Security & Your Data
How protected is your business?
A data breach or security incident can shut down a small business. Let's see where your exposure is.
10 Does your team use unique passwords and two-factor authentication for business accounts?
Yes — we use a password manager and MFA across the board
Partially — some accounts have MFA but not all
Rarely — people mostly use the same passwords
Not at all — we've never really addressed this
11 How are your business files and data backed up?
Automatically backed up to cloud — tested and reliable
Mostly in the cloud but no formal backup process
Local backups only or inconsistently done
No real backup — if a computer died we'd lose data
12 If your primary computer or server failed today, how quickly could you be back up and running?
Same day — everything is cloud-based and recoverable
A day or two — we'd recover but it would hurt
Several days — we'd lose work and it would be painful
Weeks or never — we'd potentially lose critical data
Growth & Future-Readiness
Can your tech keep up with where you're going?
Your current tech needs to support not just today's business but the one you're building toward.
13 If your business doubled in revenue over the next two years, would your current tech stack handle it?
Yes — our systems are built to scale
Mostly — with some upgrades we'd be fine
Probably not — we'd need a significant overhaul
Definitely not — our tech is already a growth bottleneck
14 How much visibility do you have into your business performance in real time?
Strong — I have dashboards and clear metrics
Some — I check reports but it takes effort to pull
Limited — I mostly find out how things are going after the fact
Very little — I'm mostly flying blind on performance data
15 Overall, how much does technology feel like an asset vs. a headache in your business?
Mostly an asset — tech makes us more efficient
Neutral — it works but I know we could do better
Mostly a headache — problems come up regularly
Definitely a headache — tech is a constant source of frustration
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