The Questions I Wish I’d Asked Every Client Sooner

Have you ever had one of those moments where a client casually mentions something and your stomach just sinks? They say something like, “oh, by the way, we’re opening another office next month,” and your first thought isn’t what it should be, which is congratulations! It’s more like: wait, why am I hearing this just now?

I want to share one of the biggest lessons I learned in this industry, one I wish I had figured out much earlier. If you’ve ever felt like you’re always the last one to hear about the really important things happening in your clients’ businesses, you’re not alone! I think every MSP I’ve talked to has experienced it.

The Meeting That Changed How I Ran Every Meeting After

We assume that if something important is happening, our clients will naturally tell us. But they usually don’t, and it’s not because they don’t value you. They’re simply busy running their business!

I remember a meeting with a client we’d had for probably 20 years. I expected a routine quarterly business review: tickets were getting answered, everything running smoothly. Exactly the kind of meeting you hope for.

But as we wrapped up, I asked something almost by accident: “so, what’s changing in your business this year?” The owner leaned back and said they hoped to open a new location in a few months. Another location? We’d just spent a whole quarterly review together and hadn’t touched on that at all!

They’ll need phones, workstations, Wi-Fi, security cameras, I thought. But none of it had come up, not because they were hiding anything. To them, opening a location wasn’t an IT project; it was the next step in growing their business, and they were there for an IT meeting.

Driving back to the office, I kept replaying that conversation. We’d done a great job managing their technology, but not a very good job understanding where their business was headed. That one moment changed how I approached every client meeting from then on.

Technology Never Starts the Story

Here’s what I learned: technology almost never creates the opportunity. Business change creates the opportunity. A company hires 20 employees; they need technology. They acquire another business, expand into a new office, or the owner starts planning to retire; they need technology. A new compliance requirement comes along; they need technology.

Technology isn’t the beginning of the story. It’s the result of it. But as MSPs, we often spend our meetings on backups, network health, computer issues, questions that don’t usually uncover what’s coming next.

Things changed for me once I stopped leading with technology and started leading with the business. Once I understood where their business was going, the technology recommendations became obvious. The best opportunities weren’t hidden; they were just sitting on the other side of asking better questions.

The Questions I Kept Coming Back To

A handful of questions became regulars in my client meetings, not because they were scripted, but because they consistently opened up conversations I never would have had otherwise.

The first: what’s changing in your business over the next 12 months? That one question alone uncovered office expansions, acquisitions, hiring plans, and growth opportunities I never would have known about.

Another: where are your employees getting frustrated? Clients almost never answered with a technical problem. They’d say things like our sales team can’t get information on the road, or everyone complains about how long a certain process takes. Suddenly we were talking productivity, and technology needs followed naturally.

I also liked asking what keeps you up at night? Sometimes it was cybersecurity, sometimes compliance, sometimes finding good employees. Every answer helped us understand their business better. Then: what are your growth plans, since growth always creates technology needs? And finally: is there anything on the horizon that could change how your business operates? That’s where ownership changes, retirement plans, or new regulations would surface.

None of those questions start with technology. They start with understanding your client and their business. That’s the point: clients don’t buy technology because they want more technology. They invest in it because something in their business is changing.

Your Challenge This Week

Don’t overhaul your whole meeting. Just add one question: what’s changing in your business over the next 12 months? Then stop and listen. You might learn more in that one conversation than you have in months!

Don’t forget to check out our Cloud Academy if you’re an MSP. It’s free, and there are plenty of done for you campaigns and webinars out there to help grow your business.

One thing I’ve learned working with a lot of MSPs is that the strongest client relationships aren’t built by the ones with the deepest technical knowledge. They’re built by the ones who understand their clients’ businesses best.

“Most people do not listen with the intent to understand. They listen with the intent to reply.” – Stephen Covey

Have a great week and weekend!