Every IT company sounds good in the first meeting. They’ll all say they’re responsive, they take security seriously, and they care about your business. So the meeting itself doesn’t tell you much. What tells you something is the questions you ask and how they answer them.
You don’t have to be technical to do this well. You need a handful of questions that cut through the pitch, and you need to know what a good answer sounds like versus a dodge. Below are the ones that reveal the most. (If you want the complete list to take into your meetings, we put 16 of them in a short guide. The link’s at the bottom.)
Are they honest with you?
Start here, because everything else rides on it.
“Why shouldn’t we hire you?” This one catches people off guard. We’ve been asked it exactly once, and it made us sit up. No company is the right fit for everyone, and a company that can tell you who they’re not good for is a company that’ll tell you the truth when something breaks. If the answer is “honestly, nothing” — that’s the dodge. You’re looking for a real answer, like “we’re probably not the cheapest” or “we’re not a fit if you want someone available at 2 a.m. every night.”
“What makes you different, and how does that actually help my business?” Everyone says “great customer service.” That’s not a difference, it’s the price of entry. Listen for something specific that changes your day, and watch whether they tie it back to your business or just recite their sales lines.
Do they run on a process, or wing it?
The companies that frustrate you aren’t usually the ones who don’t care. They’re the ones with no system, so things fall through the cracks.
“Walk me through onboarding: day one, week one, month one.” A good company has a defined process with a real timeline. A vague “we’ll get you set up soon” or “you’re second in line” tells you they make it up as they go. You don’t have to be first in line. You do need them to give you actual start and end dates.
“What reports will I get, and how often?” You should see what your IT company is doing, at least monthly: security status, backups, tickets, what’s coming up. This isn’t optional. If the answer is “we’ll tell you if there’s a problem,” you have no way to know whether anything’s getting done. (We go deeper on this in our post on the reports your provider should be giving you.)
“What do you actually do in a month when nothing breaks?” This is the real test. The companies you’ve outgrown wait for your call. A good one is patching, watching, and planning in the background, whether or not you hear from them. Ask them to describe a normal month. A vague answer is its own answer.
What happens when things go wrong, or change?
You’re not just hiring for the good days.
“If we get hit with ransomware, what’s the plan?” No IT company can promise it’ll never happen. What separates the good ones is a calm, specific answer: how they’d contain it, how they’d get you running again, how fast, and what your part is. “That won’t happen to you” is not a plan.
“How often do you raise prices, and when did you last?” Most contracts spell out how much they can raise prices. This question tells you whether they actually do it aggressively. You don’t want to go through this whole search again in two years because you got priced out.
“If it’s not working and we leave, what does that look like?” A company confident in its work won’t trap you in a long lock-in or make leaving painful. Ask about the notice period, what happens to your data, and whether they’ll hand off cleanly to whoever’s next. (There’s a document called a runbook that makes that handoff smooth. A good company will know exactly what that is.)
The one most people forget
“Who will I actually be working with, and are you local?” Plenty of companies sell you with a senior person and then hand you to a rotating helpdesk you never meet. Ask who your day-to-day contact is and whether you’ll get to know a real team. And ask whether they’re local. When something needs hands on it, you want people who can show up, not a dispatch from three states away. For a smaller business around Portland or Vancouver, that difference shows up all the time.
What to do with the answers
You don’t need a perfect score. You’re listening for two things: do they answer straight, and do the answers fit how you actually run your business? The right company leaves you feeling like someone competent has it handled and you’ll always know what’s going on.
Want the full set to bring into your meetings? Grab our 16-question checklist. It’s free, no email required, and it’s built to print and check off as you go. Or if you’d rather skip the homework, book a 15-minute call and we’ll answer every one of these for you, plainly.
This post is part of our guide to choosing a new IT provider in Portland and Vancouver. See also our managed IT services.
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16 questions to ask before you hire an IT provider
The exact questions to bring into your meetings, grouped by what they reveal, with what a good answer sounds like versus a dodge. Built to print and check off as you go.
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