Hiring outside go-to-market help is easy to get wrong, because the thing being sold is judgment, and judgment is hard to evaluate before you have bought it.
These are the questions that separate advisors who will change your revenue from ones who will hand you a well-formatted document.
On diagnosis
1. What would you measure in the first two weeks? You want four specific metrics covering demand, conversion, activation and expansion. An answer beginning with brand or messaging before measurement reveals a preference for opinion over evidence.
2. How would you decide which problem to fix first? The right answer involves sizing each leak in revenue terms and ranking by cost. "Whatever is most broken" gets you the visible problem rather than the expensive one.
3. What would make you tell me I do not need you? Anyone who cannot answer has either not thought about it or will not say it. Genuine answers exist: too few customers to see a pattern, or a motion already working that simply needs execution capacity.
On hospitality specifically
4. How does seasonality change a pipeline forecast? Someone who has sold in this category will immediately describe uneven close rates and the futility of pushing an in-season migration. Someone who has not will talk about pipeline hygiene.
5. Who actually decides in an independent versus a management company? These are different buying processes with different stakeholders and timelines. An advisor treating them as one segment will build one motion for two markets.
6. What is the real objection behind a stalled hotel tech deal? The good answer is operational risk, usually unstated. Feature gaps and price are what buyers say instead, and taking those at face value is how deals get mis-tagged for years.
On the work itself
7. What will exist at the end that does not exist now? Push for artefacts: a documented motion, instrumentation, playbooks. A strategy is not an artefact.
8. Who on my team owns this when you leave? If the answer is nobody, the improvement leaves with them and you will be having this conversation again in a year.
9. What do you not do? An advisor who does everything does nothing in particular. Be especially wary of anyone offering to sell on your behalf, because that produces revenue you cannot reproduce.
On evidence
10. Tell me about an engagement that did not work. Everyone has one. An advisor who cannot name a failure is either inexperienced or managing you, and both are disqualifying.
11. Can I speak to a client where you finished and left? References from ongoing relationships are weaker evidence, because the person is still being paid. You want someone who kept the system running afterwards.
12. What results can you commit to, and in what timeframe? The credible answer acknowledges that hospitality cycles and seasonality push revenue effects at least a quarter beyond the work, and commits to leading indicators inside the engagement instead.
What the answers tell you
The pattern matters more than any single response. Specific answers to specific questions, willingness to describe limits, and at least one honest account of something that went badly.
Vagueness on any of those three is the most reliable predictor of a disappointing engagement in this category. It is also the easiest thing to detect in a first conversation, if you ask questions that cannot be answered with enthusiasm.
Related reading
How do I evaluate a go-to-market advisor?
Does hospitality experience actually matter?
What should a GTM engagement produce?
Should I ask for guaranteed results?
What is a fair way to structure the engagement?
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