20 Questions to Ask a DMS Consultant Before You Hire Them

Hiring a DMS consultant is itself a selection process. The questions below help you evaluate whether a consultant genuinely understands document management — or just sells software. Our full guide to finding and hiring a DMS consultant covers the broader process.

About Their Experience

1. How many DMS implementations have you delivered in the last three years? — Look for a specific number (5–20 is typical for an active independent specialist). Vague answers suggest limited recent experience.
2. What sectors do you specialise in? — A consultant who has done 20 implementations in legal or healthcare has sector-specific knowledge that a generalist doesn't. Match sector experience to your industry.
3. Can you give me three client references from similar-sized organisations? — Anyone serious can provide references. Reluctance is a red flag.
4. What was the most difficult DMS implementation you've handled and what went wrong? — This tests honesty and experience. The answer reveals how they handle problems.
5. Have you ever recommended a client not proceed with a DMS project? — A good consultant sometimes advises against purchase. If the answer is "never," they may be primarily interested in billing days.

About Their Independence

6. Do you have commercial relationships with any DMS vendors? — Referral fees, reseller agreements, or white-label arrangements create conflicts of interest. They must be disclosed.
7. Do you earn commission or referral fees from vendor recommendations? — Same question, more direct. Get the answer in writing.
8. What DMS platforms have you recommended most in the last year? — A consultant who always recommends the same platform is probably a reseller in disguise.
9. What platforms do you recommend against, and why? — A genuinely independent consultant has opinions about what doesn't work. No opinions = no real experience.

About Their Methodology

10. What does your requirements discovery process look like? — They should describe interviews, document audits, process mapping, and a written output. A consultant who skips requirements and goes straight to demo is doing it wrong.
11. How do you handle a situation where the client's stated requirements conflict with what they actually need? — Experience shows that what clients ask for and what they need are often different. A good consultant manages this.
12. How many vendors do you typically shortlist and what's your evaluation framework? — 3–5 vendors is typical. A single vendor "recommendation" without a competitive process is suspicious.
13. How do you handle data migration? Who does the actual migration work? — Often sub-contracted or done by the vendor. The consultant should be able to specify who does it and how it's overseen.
14. What does a typical implementation timeline look like for a project of our size? — They should give you a realistic range. Optimistic timelines that don't materialise are a common source of client frustration.

About the Commercial Relationship

15. How do you charge — day rate or fixed price? — Either is acceptable, but understand which and why. Day rate on an ill-defined scope can escalate; fixed price requires them to scope accurately.
16. What's your estimate of days required for this project and how did you arrive at it? — They should be able to break down their estimate by phase.
17. What's not included in your fee? — Travel, expenses, software licences, vendor implementation fees, training materials. Understand what you'll pay separately.
18. What happens if the project scope changes? — Change control process should be clearly defined before you start.
19. What are the payment terms and milestone structure? — Paying everything upfront is not advisable. A milestone-based payment structure (discovery, selection, implementation, go-live) protects you if the project is terminated early.
20. Do you have professional indemnity insurance? — Any professional consultant should carry PI insurance. It's a basic indicator of seriousness. Ask for the certificate.

What the Answers Tell You

A strong candidate: gives specific answers with numbers and examples, discloses vendor relationships proactively, has a clear methodology they can walk you through, provides references without hesitation, and is honest about project risks and what can go wrong.

Walk away if: they can't provide references, they push a single vendor without a selection process, they're vague about conflicts of interest, or they give you an optimistic timeline with no contingency.