25 Questions to Assess Your Company’s Digital Readiness

Which questions measure how ready your company is for digital transformation?

The best questions test daily work, not intentions: do you know your balance today, where are customer conversations kept, is there a recent backup? The list below has 25 questions across five areas: management, processes, customers, data, and technology together with the team. Score each answer, then start with the weakest area.

Part 1: Management and strategy (1 to 5)

1. Do you have a written digital goal for this year?: Such as replying to customers faster or getting stock under control. Without a goal, tools get bought without direction.
2. Is someone responsible for following up the digital transformation?: They need not be full-time, but their name should be known and they should have the authority to follow up.
3. Have you set aside a budget, however small, for tools and training?: Ad hoc spending at every crisis usually costs more than a planned budget.
4. Can management see business figures without waiting for a manual report?: If not, decisions are delayed or made on guesswork.
5. Have you tried a new digital tool and measured its effect in the past year?: Trying and measuring is the mark of an organisation that learns, not one that buys and forgets.

Part 2: Daily operations (6 to 10)

6. Are the sales and purchasing steps written down and known to everyone?: An undocumented process varies from one employee to another and is hard to digitise.
7. Is the same information entered more than once?: Such as writing an order on paper, then in Excel, then in a message. Every repeat wastes time and invites errors.
8. Do you know your actual stock without a manual count?: A recurring gap between the book and the shelf is a sign of a process that needs tightening.
9. Do approvals go through without waiting for an absent person’s signature?: Work stopping when the manager is away shows too much reliance on paper and physical presence.
10. Does essential work continue when the power or internet goes down?: In Syria this is a practical, everyday question, and the answer determines which tools suit you.

Part 3: Customers and communication (11 to 15)

11. Do you have a single customer list the team can access?: Not on the salesperson’s phone or in a private notebook, but in a shared, protected place.
12. Are WhatsApp chats with customers kept on a number the company owns?: If an employee leaves with their number, customer relationships and order history leave with them.
13. Do you know how many enquiries you received last week and how many became sales?: Without this number you can’t judge your advertising or your sales team’s performance.
14. Can customers easily find you on Google Maps with correct details?: A wrong address or an old phone number loses you customers who are actively looking for you.
15. Can a relative abroad easily order and pay for their family in Syria?: Many services are paid for by Syrians living abroad, and making that easy is a real competitive advantage.

How to score the results and use them

01
Answer with a small team
Bring together the manager, someone from sales and someone from accounts or the warehouse, and answer together so the picture doesn’t come from one angle.
02
Score each answer
Yes is worth two points, partly one point and no zero. Add up the points for each area separately.
03
Find the weakest area
The area with the lowest total is usually the place to start, even if the others look good.
04
Pick three negative answers that are easy to fix
Such as backups, a company WhatsApp number or a single customer list, and start on them this month.
05
Repeat the questions after a phase
Answer again after the first set of improvements and compare the scores to see what has really changed.

Parts 4 and 5: Data, technology and team (16 to 25)

Area	Question	Follow-up question
Accurate numbers	16. Do two people give the same figure when asked for this month’s sales?	17. Is every amount recorded with its currency, exchange rate and date?
Organised data	18. Does each type of data have one approved source?	19. Are duplicate and outdated records corrected regularly?
Using and protecting data	20. Do you know the profitability of each product or service?	21. Is there a recent backup of your important files outside the office?
Devices and accounts	22. Does each employee have their own account instead of a shared password?	23. Are your main work devices in good condition, with licensed and updated software?
Team	24. Do staff use the current tools confidently without going back to one person?	25. Is the team open to trying new ways of working when the benefit is explained?

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Frequently asked questions

Are these questions enough instead of a full assessment?

They are a good, quick start. A full assessment adds interviews, observation of real transactions and a review of systems, and helps when you are preparing for a bigger project.

What if most of our answers are “no”?

That is common in companies that run on paper and Excel, and it is no cause for alarm. Pick the questions that are easiest to fix and start there; improving the basics shows results quickly.

Do the questions suit non-profit organisations?

Most of them do, with small changes, such as replacing customers with beneficiaries, sales with projects and management reports with donor reports.

Should we answer the questions for each branch separately?

If you have more than one branch, yes. Branches often differ in discipline and infrastructure, and a single combined answer may hide a branch that needs special attention.

Can an outside party review our answers?

Yes. You can share them with an adviser you trust or with the ONE DIGITAL team, who can help you read the result and set priorities.

25 questions to assess your company’s digital readiness yourself