I see a lot of nodding and smiling in meetings between geeks and non-geeks. The geeks say something extremely technical using industry terminology, and the non-geeks say something very vague about how they want their web site or software to work or look, and both parties smile and say “that sounds great.”

This serves no one.

When you are hiring a technology vendor, you need to ask lots of questions, both about what they’re going to build for you and what they understand about your needs. You cannot be shy about this — you will be paying them for the solution they create for you, and you have both the right and the responsibility to be the most informed consumer possible.

Question 1: “Why are you choosing this solution instead of another?”

I am always so glad when my clients ask me why I am choosing WordPress over Joomla or vice versa. The same question can easily apply to almost any technology decision — why is your hardware vendor recommending a Dell laptop over an Asus laptop? Why is your social media consultant recommending Hootsuite over Buffer? Once you hear the answer, you may totally agree with the decision-making process your vendor used, or you may be able to add some insight she hadn’t yet considered. This description can get very technical and include a lot of jargon — be sure to ask for clarifications, explanations, and even some information to read later, when you can concentrate on the details.

Question 2: “What will be the limitations of this choice going forward?”

This question is HUGE for growing companies. If you expect to have different needs in two years or five years, you need to know what doors will be closed to you by the technology you choose. This doesn’t necessarily mean that you simply won’t be able to do whatever it is you’re planning, but it might mean that engaging the technology you’ll need later could be expensive or disruptive to your business or your customers. If your vendor knows what’s coming for you in the coming years, she may adjust her recommendations to suggest something more scalable.

Question 3: “Have you ever used this technology before?”

Most of the time, the answer to this question will be yes, since vendors are unlikely to recommend something with which they have no experience. However, sometimes there are pieces of the overall project that are uncharted territory for your vendor, and you do need to know what the game plan will be if your vendor stumbles.

Question 4: “What happens if I don’t like it?”

Assuming you have a nice, clear contract, you should know exactly what you’re getting from your vendor. However, even in the best, most detailed contracts, some details cannot be described — details like the exact color of red you land on for your logo, or the way the keys of your new laptop will feel under your fingers, or even your level of comfort with the demands of being on social media. It is totally reasonable for you to know what is involved in changing direction mid-project or even after the project is done. You’re not asking for your vendor to the work over again for free; you’re finding out which changes are the most expensive, which ones have a cascade effect on the rest of the project, and what you need to do if you feel the need to change course.

Question 5: “What could delay this project?”

Ideally, that fantastic contract you’ll sign will give you an idea of the timeline, but the fewer surprises you encounter, the better. It’s important to know whether the timeline depends on other things besides your cutting the check at the right time. There are many things outside the control of you and your vendor that could affect the timeline, including shipping of hardware or response times of third-party contractors. Find out what provisions your vendor is making to avoid as many of those as possible, and ask whether you should adjust your own expectations for launching that web site or ending contracts with other vendors to allow for unpredictable delays.

Question 6: “Can you provide a reference for a project like this one?”

This is different from just asking for generic references. This is asking to talk to one of your vendor’s previous clients who has been through a similar project to yours. Getting a reference from a client who has been through a much simpler project than yours doesn’t give you enough information, and getting a reference from a client who worked with your vendor for months longer than you’ll works together doesn’t allow you to see how it will be to work together for a short time. Asking for comparable references is smart.

Question 7: “How long will this last me before I need to change something?”

This question varies with the type of technology you’re buying, but it could be reworded in several ways:

  • When will I need to replace this laptop?
  • When will this software need to be upgraded?
  • How often do I need to change my social media strategy?

You need to assume your technology purchases are far from one-time purchases. You have a budget to plan, so be sure you know what you’ll need to put aside each quarter/year/decade.

Question 8: “What is the best way to reach you?”

This one sometimes surprises people, but I ask it of my clients and am regularly surprised. Some of them are best reached by phone, some by text, some by email, and one actually prefers Facebook chat. You never know, and you’ll spend a lot of time frustrated by unanswered voicemails if you don’t take the time to find out that email is the medium of choice.

Question 9: “When is the best time to reach you?”

The world is changed from the 9 to 5 office hours of the twentieth century. Don’t assume your vendors keep to the same schedule you do. Some people prefer to get one email per day with all of the day’s requests and questions, while some will answer twenty emails a day. Some people prefer to have a fifteen minute check-in phone call at the end of their work day. Get this worked out before the project begins, and you’ll feel far fewer frustrations along the way.

Question 10: “What happens when this project ends?”

The project is over when your vendor has delivered everything in the contract to you. After that, she is under no obligation to answer your questions, upgrade your software, give you advice, or make recommendations for next steps. (If she wants your repeat business, she’ll do some of that anyway, but she isn’t obligated.) Given that, what happens next? What’s the exit plan, the maintenance offer, the hourly rate for service outside the contract? Find out what your options are before you even sign the contract, or you might find yourself with a completed project, a hundred questions, and a vendor who is onto her next project with no time for you at all.

If you have more questions than these, that’s even smarter. It is better to ask the questions than to wonder whether you really understand what you’re buying — and a vendor who has translated her knowledge into coherent descriptions for the non-geek is one who really understands it well herself.

What are your questions? Send me an email, or reach out on Facebook or Twitter.