I'm about to give you a list of questions that might talk you out of hiring me. I'm fine with that. If a question below makes you think twice about the person you're talking to, that's the question doing its job, and it's a much cheaper lesson to learn in a first conversation than six months into a contract.
Here's why this matters more than people expect. A CRM implementation isn't like buying a piece of software off the shelf. It's closer to hiring a builder. Get the wrong one and you don't just waste money, you end up with a system that half works, that your team avoids, and that costs more to unwind than it would have cost to build properly the first time. The questions below are the ones that actually separate someone who'll do that properly from someone who'll leave you with a demo dressed up as a CRM.
A good answer starts with questions about how you actually sell, before anyone opens HubSpot. A bad answer jumps straight to a screen share of the default pipeline stages. HubSpot ships with a generic template (Appointment Scheduled, Qualified, Presentation, Decision), and almost nobody's business actually runs on those stages. If the person you're talking to doesn't ask about your process first, they're going to configure a demo, not a system.
Plenty of agencies sell the senior person on the discovery call and hand the actual build to whoever's free that week. There's nothing wrong with a team doing the work, as long as you know who's accountable and who you can actually reach when something breaks. Ask directly. A straight answer here tells you a lot about how the rest of the relationship will go.
This is the one that matters most, and the one people forget to ask. Most CRM projects don't fail because the software was wrong, they fail because nobody revisited the setup once the initial enthusiasm wore off. Ask whether there's a 30, 60, or 90 day check-in built in, or whether the relationship ends the day the system goes live. If it's the latter, budget for the fact that you'll likely be back in the market for help within a year.
Not a generic case study PDF, an actual example close to your industry and size. A trades business and a professional services firm need genuinely different pipeline structures, and someone who's only ever set up HubSpot for SaaS companies is going to bring assumptions that don't fit you. This isn't about finding someone with a perfect match, it's about confirming they can explain, specifically, why their approach would look different for your business.
A vague number is a red flag. A good consultant can walk you through the actual components, seats, tiers, the specific Hubs your business needs, onboarding fees, and what's genuinely optional versus what's not, and tell you plainly what they don't yet know without your real numbers. If someone gives you a confident total in the first five minutes before asking about your team size or contact volume, that number isn't real yet.
Ask whether your system is documented and understandable without them, and whether your data is genuinely yours to export and take elsewhere. Some consultants build you a system. Others build you a dependency. The difference usually only becomes obvious the day you try to leave, so it's worth asking while you're still free to walk away from the conversation entirely.
Worth asking, but worth a caveat too. Certification is a real signal, it means someone's put in the study and stayed current. It's not a guarantee on its own, partner tiers can be earned through spend as much as skill. Treat it as one data point among the others here, not the whole decision.
Ask them, in plain terms, what your business actually loses by doing nothing for another six months. A good consultant can answer that specifically to you: leads sitting unclaimed, a follow-up gap costing you conversions, reporting that can't tell you what's actually working. A weak one falls back to generic urgency, "you're leaving money on the table," without ever saying what that money actually is or where it's going. Specificity is the tell.
I'd genuinely rather you ask me every question above before you book a call, not just because it's the right way to hire anyone, but because I'm confident in how I'd answer them. If you're weighing up who to bring in for your HubSpot setup, use this list on every option you're considering, mine included.
Book a Free CRM Chat and ask me anything on this list. No pitch, just straight answers.