How to Evaluate a Technology Advisor: Questions to Ask Before You Sign

The title tells you almost nothing

"Technology advisor" is an unregulated title — anyone can use it, regardless of how they're actually compensated or how many vendors they genuinely represent. Evaluating one requires asking specific questions and judging the quality of the answers, not the confidence of the title on their website.

The questions that actually matter

1. "How exactly are you compensated, and does it change based on which vendor we choose?"

A good answer is specific and doesn't hedge — it names the mechanism (placement fee, commission, retainer) and states plainly whether the amount varies by vendor. A vague answer, or one that avoids the second half of the question, is the clearest warning sign in this entire list.

2. "How many vendors do you actually work with in this category, and can you name them?"

An advisor claiming neutrality should be able to name a genuine, comparable set of options — not just the one or two they mention most often. Reluctance to name specific vendors, or a list that's clearly padded with options they never actually recommend, both suggest less neutrality than claimed.

3. "What happens to your fee if we decide to do nothing?"

A genuinely zero-cost, transaction-based model has a clean answer: no transaction, no fee. If there's a consulting fee, retainer, or "assessment fee" hiding behind the "free" framing, this question surfaces it directly.

4. "Can I see an example of an engagement where you recommended against a purchase?"

An advisor who has never once recommended not buying anything is either compensated in a way that discourages that outcome, or hasn't been doing this long enough to have hit that case. Either answer is informative.

5. "Who actually does the assessment work, and what's their background?"

Distinguish between an advisory firm with genuine operating experience (former CIOs, CISOs, practitioners) doing the actual assessment work, versus a sales-oriented team with a thin technical layer. Ask for the specific credentials of the person who would work on the engagement, not just the firm's marketing bio.

6. "What does your engagement actually produce — a report, a recommendation, ongoing support?"

Confirm the concrete deliverable and timeline before starting, so expectations are set against something specific rather than a general promise of "guidance."

Red flags versus reasonable answers

Reasonable answers are specific, sometimes come with caveats, and don't oversell certainty. Red flags are vagueness on compensation, reluctance to name competing vendors, and pressure to sign quickly — a genuinely neutral advisor has no structural reason to rush a decision they aren't paid based on speed of.

Putting this into practice

MALA's answers to all six questions are on the About page and the compensation model post — worth reading before any first call, with any advisor, not just this one. Talk to an advisor to see how these answers hold up directly.