Choosing the Right IT Partner: Lessons from Financial Planning
My wife Lynette and I recently met with a financial professional for future planning—because, let’s face it, you have to deal with the unpleasant stuff, too. The advisor carefully reviewed a list of questions, and we answered them as best we could. From that discussion, she proposed a direction, sketching out a few diagrams on the back of a sheet of paper to show how everything flowed and fit together. I nodded along as she laid out the path and plan. It all sounded totally reasonable, and I could follow along while she explained it step by step. But if I’m being honest, there’s no way I can say I fully understood what we just agreed to do.
Later that evening, when we got home, I could tell Lynette still had concerns. As we talked, she explained that the whole planning experience had felt unclear and unsatisfying. She wanted to make sure we were making the right decisions and asked me to walk her through it again.
I have to admit, I really don’t understand it well enough to explain it to you.
As a math teacher, she’s used to mastering a subject before acting on it. She isn’t someone who makes decisions lightly; she takes the time to fully understand things, whether it’s a new teaching method or a major financial decision. Sitting through a meeting, following along in the moment, and then later realizing she didn’t have a firm grasp on everything—only to find out I was a bit lost, too—was frustrating for her.
She looked at me, clearly trying to make sense of it all. Then asked me why did you agree to do it?
I told her, it is a lot like my business. People ask me for advice, I walk them through it, I draw diagrams, and I outline a plan that’s good for their company. They nod along and ask a few questions, and I know that later, when they get home, they probably have the same conversation with their spouses. I try to make things as straightforward as possible, but I also know that full understanding doesn’t always happen right away.
She considered that for a moment but still didn’t look satisfied. I could tell she thought I was going through the motions—checking a box rather than genuinely engaging with the process.
She shook her head. So that’s it? You just go along with it and hope it all works out?
I exhaled. No, it’s not blind trust. I explained that I’m a bit more accustomed to relying on other’s expertise than mastering things myself and maybe even a bit broken down from running a small business. Between regulations, taxes, insurance, marketing, state and local filings, and the 10 other obligations that come with my role, I’ve already made peace with the fact that I seldom have more than a vague understanding of what I’m buying or signing. I just do my best to make informed decisions and keep moving forward. That doesn’t mean I’m reckless—I still make the best decision I can with the information I have.
She listened carefully, and I could see she was still processing it.
After a moment, I said: So, why did I trust the financial planner’s advice? Because she was referred to us by someone we both know and trust. I know there are laws and rules that govern her industry. But at the end of the day, I’m not able to spend the time getting an accounting degree or going to law school just to verify every detail myself. At some point, I have to trust that she’s acting as our partner, working in our best interest, and just let go.
Lynette thought for a moment, then shook her head again. I get what you’re saying, but that’s a lot to take on faith.
I shrugged. Maybe. But that’s the reality when you’re in the deep end.
Choosing the Right MSP Is About More Than Just IT Support
This experience made me realize that hiring a financial planner isn’t all that different from choosing an IT provider. In both cases, you’re trusting an expert to guide you through complex decisions—ones that you may never fully understand but still have to commit to and support. The key isn’t just technical expertise; it’s finding someone whose approach and philosophy align with yours.
You can’t become an expert in every field, whether it’s finance or IT. At some point, you have to trust that the professionals you hire have your best interests in mind. That’s why shared values matter.
If your company relies on proactive planning, lifecycle management, and minimizing downtime, your IT partner should work the same way. If they don’t, you’ll constantly be at odds with how they operate.
At Keystone, we believe IT should be a strategic advantage—not just a necessary expense. We work best with businesses that want long-term partnerships, proactive management, and security-first strategies.
If that sounds like what you’re looking for, let’s have a conversation about whether we’re the right fit for your business.
