You are evaluating IT providers. Maybe your current one is not keeping up with your growth. Maybe you are starting fresh after managing IT internally for too long. Maybe you just got a renewal quote that made you reconsider the relationship.
Before you sign with anyone, ask three questions. The answers will tell you more about the provider than any sales presentation ever could.
Question 1: "If I wanted to leave you in a year, how hard would that be?"
This question makes IT providers uncomfortable, which is exactly why you should ask it.
A provider whose architecture locks you in, whose documentation is thin, and whose configurations are proprietary will struggle to answer this honestly. They may not have designed for portability because it is not in their interest.
A provider who designs with vendor independence in mind will have a clear answer. Your data is backed up in a portable format. Your identity layer is independent of your collaboration tools. Your configurations are documented. Leaving would be a project, not a crisis.
The provider who makes it easy to leave is the provider who earns your business every year instead of trapping it. That is the provider you want.
Question 2: "What will this cost me in two years?"
Not the promotional rate. Not the first-year contract price. The real, steady-state cost of running your technology two years from now, including the license increases that are coming, the additional services you will likely need as you grow, and the price trends in the industry.
Microsoft 365 license prices doubled. VMware renewals went up 10x. These are not one-time events. They are a pattern. Any IT provider who quotes you today's price without acknowledging tomorrow's reality is either uninformed or hoping you do not notice until the invoice arrives.
CTP walks through total cost of ownership with every prospective client. We show you what you will spend today, what the trajectory looks like over the next two to three years, and what options you have if a vendor's pricing becomes unreasonable. That conversation happens before the engagement starts, not when the renewal shock hits.
Question 3: "When I call with a problem, will I talk to someone who already knows my environment?"
This is the question that separates a partner from a vendor.
A vendor gives you a ticket number and a queue position. A technician who has never seen your environment picks up the ticket, reads whatever notes exist, and starts from scratch. You spend the first ten minutes explaining your setup. Again.
A partner gives you a named person who already has context. They know your team. They know your systems. They know your priorities. When you call, the conversation starts with the problem, not with the backstory.
CTP assigns a dedicated point of contact to every client. Not a call center. Not a rotating roster. A person who knows your world and picks up the phone. After 25 years in business, we believe this is the only model that actually works.
What the answers tell you
If a provider cannot answer these three questions clearly, directly, and without hedging, that tells you something. It tells you their architecture is designed around their convenience, not yours. It tells you their pricing model depends on you not paying attention. It tells you their support model treats you as a ticket, not a relationship.
What good answers sound like
A good answer to the portability question: "Your data is backed up nightly through Veeam in a portable format. Your identity runs on Okta, which is independent of our collaboration platform. All configurations are documented. If you left, we would provide a transition plan and cooperate fully. We expect to earn your business each year."
A good answer to the cost question: "Here is your current monthly cost, broken down by service. Here is what Microsoft is likely to charge in two years based on their pricing trajectory. Here is what your licensing costs as you add employees. And here are the alternatives we have built into your architecture so you have options if any vendor becomes too expensive."
A good answer to the relationship question: "Your primary contact is [name]. They have been working with your account since onboarding. When you call our main number, you will be connected to them directly or to their backup, who is also briefed on your environment."
What bad answers sound like
"We would work with you on a transition." (Translation: we have not thought about portability.)
"Our pricing is competitive." (Translation: we are not going to tell you what things will cost next year.)
"Our team of certified technicians provides excellent support." (Translation: you will get whoever is available.)
One more question worth asking
If you are in a regulated industry, banking, financial services, or forensic science, add a fourth question: "Show me one piece of compliance documentation you have prepared for another client in my industry."
A provider who understands your regulatory environment will have this ready. A provider who does not will offer to learn about your requirements after the contract is signed. That difference matters on examination day.
Red flags during the evaluation
Beyond the three questions, watch for these warning signs during the sales process.
The proposal is entirely about products and licenses, with no discussion of your business, your workflows, or your specific risks. Any IT provider who leads with a product list before understanding your situation is selling what they have, not what you need.
The pricing is suspiciously low. IT services have real costs: skilled people, security tools, monitoring infrastructure, documentation time. A provider offering rates significantly below the market is cutting corners somewhere, and you will discover where during your first security incident or examination.
They cannot name a client in your industry. If you are a bank, ask for a banking reference. If you are a family office, ask for a private company reference. Domain expertise matters. A provider who has never worked with an examiner cannot prepare you for one.
They resist putting service level commitments in the contract. Response times, escalation procedures, documentation standards: if the provider will not commit to them in writing, they are not commitments.
They talk about themselves more than they ask about you. The first meeting should be mostly questions about your business, your technology, your challenges, and your goals. A provider who spends the first meeting presenting slides about their certifications and awards is telling you what they think is important, and it is not you.
Trust your instincts. The provider who asks good questions, listens carefully, and gives you an honest assessment of what you need, even when that assessment is "less than we could sell you," is the provider who will serve you well long-term.
Then verify those answers in the contract.