Selecting the wrong software negotiation advisor is expensive twice: once in advisory fees, once in the savings you failed to achieve. The market includes genuine specialists with deep vendor expertise alongside generalists, former vendor employees with questionable independence, and firms with undisclosed conflicts. This 25-question checklist, drawn from our CIO & CFO Software Buying Guide, will help you separate them.
We recommend running this process with at least two firms simultaneously — competition between advisors during selection often reveals pricing and methodology that wouldn't otherwise emerge. For guidance on what advisors charge and how to compare fee structures, see our companion pricing guide. For ROI benchmarks by vendor, see our ROI guide.
Section 1: Track Record & Expertise (Questions 1–8)
Question 1
Critical
How many engagements have you completed with this specific vendor in the last 24 months?
Why it matters: Vendor specialisation is the strongest predictor of outcomes. A firm with 5 Oracle engagements cannot benchmark Oracle pricing as precisely as a firm with 200. Ask for a specific number, not a general claim. Anything fewer than 20 engagements per vendor per year should prompt further questioning about data quality.
Question 2
Critical
Can you provide 3 verifiable reference clients with deals comparable to ours in size and vendor?
Why it matters: References must be comparable — same vendor, similar deal size (within 50%), similar sector where relevant. Generic references from different vendors or deal sizes are insufficient. Ask the references: "What savings were achieved? Was the lead advisor the same person who will lead our engagement?"
Question 3
Important
What is your average savings percentage on [specific vendor] deals at our deal size?
Why it matters: Demand a specific number with a methodology explanation — not a range pulled from best-case scenarios. Ask how savings are calculated (from initial proposal vs current spend) and what the distribution looks like (average, median, 25th percentile). Any firm unwilling to provide this data has something to hide.
Question 4
Important
What was your lowest-performing engagement in the last year, and why?
Why it matters: Good advisors know their outliers and can explain them honestly. Evasiveness about underperformance is a red flag. Look for structural explanations (short lead time, internal stakeholder interference, vendor lock-in) rather than blame-shifting. The answer tells you more about the firm's honesty than their best-case stories do.
Question 5
Important
How long has your lead advisor worked specifically on [vendor] negotiations?
Why it matters: Years of general consulting experience is not the same as years of vendor-specific negotiation experience. Former vendor employees may have deep product knowledge but limited negotiation or benchmarking expertise. Ask specifically for negotiation experience — how many deals have they personally led?
Question 6
Good-to-Know
Do you have relationships with the vendor's senior commercial leadership, and have you ever escalated a deal to executive level?
Why it matters: For complex, high-value deals, account manager-level negotiation has a ceiling. Advisors with executive escalation relationships can unlock commercial concessions that aren't available at account level. Ask for specific examples — which vendor, what outcome, who the contact was (they don't need to name individuals).
Question 7
Important
What are the limits of your expertise? Which vendor negotiations would you not take on?
Why it matters: Honest advisors know their boundaries. A firm that claims expertise across every major vendor almost certainly has shallow expertise in most of them. A specialist that tells you "we don't do SAP" for an Oracle engagement is being appropriately honest — and this is a positive signal about their integrity in areas they do claim expertise.
Question 8
Important
Is your firm Gartner-recognised or peer-reviewed in any independent analyst coverage?
Why it matters: Independent analyst recognition — whether Gartner, Forrester, or other credible sources — provides third-party validation of a firm's market position and capabilities. It doesn't guarantee outcome quality, but it does indicate market credibility and client scale sufficient for independent evaluation. See our
rankings methodology for how we assess firms independently.
Section 2: Conflicts of Interest (Questions 9–13)
Warning
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Conflicts of interest are the most underappreciated risk in advisory selection. An advisor that receives referral income from vendors, earns implementation revenue from deals they advise on, or employs former vendor staff with active vendor relationships may have structural incentives that conflict with your interest in maximum savings.
Question 9
Critical
Does your firm receive any compensation, referral fees, or commissions from software vendors?
Why it matters: Any vendor compensation — however structured — is a fundamental conflict of interest. This includes "partner" status, reseller arrangements, referral programmes, or joint marketing agreements. Pure-play advisory firms receive no vendor income. If the answer is anything other than "no," ask specifically how this is disclosed and managed.
Question 10
Critical
Does your firm have an implementation or systems integration practice that works with the same vendors?
Why it matters: A firm that earns implementation revenue from Oracle, SAP, or Salesforce implementations has an incentive to ensure you buy more software — not less. Big 4 firms and large SIs face this conflict acutely. Ask for explicit separation policies and how conflicts are managed in practice when both advisory and implementation work are in scope.
Question 11
Critical
Do any of your advisors have a cooling-off restriction from working for or with the vendor we're negotiating against?
Why it matters: Former vendor employees may maintain active professional relationships with their ex-colleagues — relationships that can compromise negotiation leverage or leak sensitive information. Ask specifically about employment history with the relevant vendor and whether any cooling-off periods apply or have recently expired.
Question 12
Important
Are you simultaneously advising any other clients in active negotiations with this vendor?
Why it matters: Advisors running multiple simultaneous negotiations with the same vendor may inadvertently share pricing intelligence across clients, or may be constrained in their leverage tactics to protect other relationships. Ask about current active engagements with the same vendor and how conflicts between clients are managed.
Question 13
Important
Do you have any relationship with our incumbent software vendor's channel partners or resellers?
Why it matters: Channel partner relationships — even indirect ones — can compromise advisory independence. An advisor who is also a Microsoft Licensing Solutions Provider (LSP) is in a structurally conflicted position when advising on Microsoft deals. Ask about all licensing, reselling, or channel relationships across the firm's entire practice.
Section 3: Methodology & Data (Questions 14–18)
Question 14
Critical
What is your benchmarking database — how many comparable deals, what time period, and how is it maintained?
Why it matters: A negotiation firm's data is its primary competitive asset. Ask for specifics: how many Oracle ELA deals at £10M+ ACV in the last 18 months? How is pricing normalised for currency, region, and product mix? Vague answers about "access to market data" are red flags — the best firms have proprietary transaction databases, not general market reports.
Question 15
Important
Can you show us an example benchmarking report (anonymised) for a comparable deal?
Why it matters: Requesting a sample output tests the firm's transparency and the quality of their analysis. A high-quality benchmark report shows unit pricing by product, discount depth by tier, market comparators, and an explicit methodology statement. A generic market overview with no transaction data is worth very little in a negotiation room.
Question 16
Important
How do you develop competitive alternatives and BATNA for our negotiation?
Why it matters: Benchmarking data alone has limited leverage if the vendor knows you have no credible alternative. Strong advisors help develop genuine competitive pressure — migration assessments, alternative vendor demos, alternative technology roadmaps. Ask what they would do specifically for your situation, not what they do in general.
Question 17
Good-to-Know
What contract terms beyond unit pricing do you typically improve, and what's the typical value?
Why it matters: Top advisors generate significant value from non-price contract improvements: price escalation caps, audit rights restrictions, termination-for-convenience rights, data portability, and liability provisions. A firm focused entirely on unit price reduction is leaving value on the table. Ask for specific examples of contract term wins and their commercial value over the contract term.
Question 18
Good-to-Know
How do you handle situations where the vendor refuses to move? What's your escalation strategy?
Why it matters: Vendors routinely use "final offer" tactics. An advisor with a credible escalation playbook — executive escalation, competitive alternative introduction, deal delay — will generate better outcomes than one who accepts the vendor's position. Ask for a specific example of a deal where initial vendor resistance was overcome and how.
Section 4: Team & Access (Questions 19–22)
Question 19
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Critical
Who specifically will lead our engagement — can we meet them before signing?
Why it matters: The "bait and switch" — where senior partners pitch the deal and junior analysts deliver the work — is endemic in consulting. Always meet the actual lead advisor before signing. Ask about their specific experience, current workload, and whether they'll attend all negotiation calls personally.
Question 20
Important
How many active engagements does the lead advisor currently have?
Why it matters: An advisor managing 8 simultaneous deals cannot give your engagement the attention it deserves. Top boutique advisors typically manage 3–5 simultaneous deals at most. High utilisation rates — common at Big 4 and large firms — directly compromise the quality of work on any individual engagement.
Question 21
Important
What is your availability model — will you be reachable during critical negotiation periods?
Why it matters: Enterprise software negotiations often reach critical junctures on short notice — the vendor's quarter-end, an unexpected escalation, a last-minute commercial ask. An advisor who operates standard office hours on a 48-hour response SLA will be less effective than one available for rapid response during critical periods. Get the response commitment in writing.
Question 22
Good-to-Know
How do you work with our legal team, procurement team, and business stakeholders?
Why it matters: A good advisor integrates with your team rather than working in isolation. Ask about their preferred governance model, how they handle conflicting internal priorities, and what they need from your side to be effective. An advisor who can't explain how they work with legal and procurement is likely to create friction rather than resolve it. See our
negotiation team structure guide for the optimal internal setup.
Section 5: Fee Structure (Questions 23–25)
Question 23
Critical
If using gain-share, what is the savings baseline definition, and is there a fee cap?
Why it matters: The baseline definition is the most consequential term in a gain-share agreement. Savings measured from the vendor's initial proposal will always be larger than savings from current spend — and the advisor's fee follows. Always insist on the more conservative baseline (current spend or previous contract value) and a hard fee cap at 2–3× the equivalent fixed-fee. See our
gain-share guide for full detail.
Question 24
Important
What happens if your engagement does not achieve measurable savings — is there a performance commitment?
Why it matters: Most established advisory firms will offer some form of performance commitment for well-scoped engagements — a minimum savings threshold, a partial fee refund if outcomes fall short, or a reduced retainer rate in underperforming quarters. A firm that refuses any performance commitment for a fixed-fee engagement may lack confidence in their own outcomes.
Question 25
Important
What is included and excluded from your fee, and what can trigger scope expansion charges?
Why it matters: Advisory engagements can expand in scope if the vendor introduces unexpected complexity, additional products, or audit issues. Understand exactly what triggers out-of-scope billing before signing. Ask for a complete list of work items included in the quoted fee and the day rate that applies to any out-of-scope work.
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Scoring the Responses
Use this simple scoring framework when comparing multiple firms:
- Critical questions (1, 2, 9, 10, 11, 14, 19, 23): Any unsatisfactory answer is a disqualifier. These cover the fundamentals — without them, no amount of strong responses elsewhere compensates.
- Important questions: Score each 1–3 (1 = weak/evasive, 2 = adequate, 3 = strong/specific). A total below 24 out of 36 should prompt serious concern.
- Good-to-know questions: These differentiate top-tier from adequate firms. Strong responses across all four indicate a firm that thinks about client outcomes comprehensively.
After reference checks, request a preliminary benchmark for your specific deal as a final test. Most top firms will provide this at no charge. The quality and specificity of the benchmark is the most reliable indicator of the firm's actual data quality and analytical depth.
For independent rankings of top-rated negotiation firms by vendor, see our overall rankings and vendor-specific pages for Oracle, SAP, Microsoft, and Salesforce. For the complete advisory selection framework, download our IT Negotiation Playbook.
Frequently Asked Questions
How long should I spend interviewing a licensing advisor before hiring?
Budget 90–120 minutes per firm — 60 minutes for initial questions, 30–60 minutes for a preliminary benchmarking discussion. Rush this process and you risk selecting a firm that sounds impressive in a pitch but lacks the data quality or vendor-specific expertise to deliver results.
What's the most common mistake buyers make when hiring a licensing advisor?
Selecting based on brand recognition rather than vendor-specific expertise. A globally recognised firm with a famous brand but limited Oracle deal history will consistently underperform a boutique specialist with 200 Oracle deals in their database. Vendor specialisation is the strongest single predictor of negotiation outcomes.
Should I tell the vendor I've hired an advisor?
This varies by situation and advisor preference. Some firms prefer to advise from behind the scenes while buyers lead discussions. Others prefer to negotiate directly. The advantage of disclosed advisory is that it signals serious intent and resets vendor expectations; the risk is that vendors sometimes apply additional pressure when they know an advisor is involved. Discuss with your advisor what approach is optimal for your specific vendor relationship.
How many advisory firms should I interview before selecting?
Two to three firms is the recommended minimum for deals above £5M ACV. Running a competitive process between advisors often improves the proposals you receive — both in fee structure and in the preliminary benchmarking detail firms provide to win the business.