Real Talk on Tech Buys & 6 Questions to Ask Every Time

When selecting a new technology or technology vendor it is easy to get caught in the trap of only looking at what is “new and different.”

However, when approaching an enterprise technology purchase or vendor partnership there are many considerations that come into play. A technology buy is a long-term investment, and making the wrong decision can be very costly. Here, we will explore some key considerations and pitfalls of choosing new tech vendors.

Level Setting 

First, let’s come clean about about three things that will affect your ability to begin a new relationship with a supplier:

Buyers in industries that are late to embrace emerging technology—such as the legal industry—are often unprepared to ask the right questions.  There's no shame in this. If you are the lone technologist in your law department, then you need to be mindful of the fact that the folks who have entrusted you with making the right decision may need some hand-holding. And if you are a lawyer with limited technology experience, it's best to accept that you don’t know what you don’t know. You will have the wherewithal to obtain the information you need to make sound decisions, but the first step is to accept the challenges and constraints you face. The next step is to accept that you will need to invest time and effort into research. The alternative is to spend costly time and money moving in the wrong direction.

Once you’ve acknowledged what you don’t know, understand your company’s IT—and fess up to any limitations.  Frame your discussion in terms of what is technologically feasible within your enterprise. Business folks get caught up in the promise of new and different technology regardless of reality. The fact is, many of the snazzy tools you see on the market are either inappropriate for your enterprise or impossible given your current architecture. 

For many law departments embarking on broad change initiatives, large-scale tech buys may be premature; without the right legal and business processes in place, it may not be feasible to get to a meaningful articulation of requirements for the projects, let alone recoup a reasonable return on the technology investment. 

Even for forward-thinking, nimble legal teams, keep in mind that your team functions in a larger environment, with stakeholders spread across the organization. Flashy features are of no value if users won't engage with the technology to adapt their habits and workflows accordingly.

Think about how much you actually need the technology. What value will this purchase and implementation bring? Is it worth it? Is it feasible at this time given your financial and talent resources? Do you have the organizational capital to influence the necessary users across the relevant processes? Again, be honest with yourself. That is not to say you shouldn’t push the boundaries of your tech. You should. But be aware of the investment. And understand “turn-key solutions” rarely exist, no matter what the pitchman says. 

Finally, be mindful of your clout—or lack thereof.  When negotiating, remember that you're engaging in a business deal. Coming from a relationship-based business like legal services, you might be surprised if a vendor doesn't seem to think your business is all that important. It is not uncommon for premium vendors to turn down clients when the deal isn’t lucrative enough. Be aware of this fact and don’t be shocked or offended if they respectfully decline to work with you. It happens to all of us.  

6 Questions to Ask Potential Vendors, Every Time

Now that you’ve considered your specific context, you’re ready to start talking to suppliers.

First and foremost, remember that a technology buy is a business relationship.

These 6 questions will help you assess the vendor’s suitability for your purposes, both for your immediate needs and for your long term relationship.

1) Ask the vendor for a product roadmap.  A solid product roadmap is evidence of the vendor’s commitment to the product. Further, if you ask a vendor about a feature that is not currently offered, ask when it will be added. Lack of an answer might indicate lack of commitment to product development.

2) Ask the vendor about emerging technology.  If you are aware of trending technology that touches on what the vendor is offering, be sure to bring it up. Simply asking what the vendor thinks of new technology will tell you a lot. Follow up by asking how it affects the offering from a competitive standpoint or if it will be integrated in some way. 

This line of questioning is really designed to help you understand the vendor’s maturity in the field. Be unequivocal without being harsh. No one will be able to answer every question, but the dialogue should give you a sense of the vendor's openness and candor, not to mention a sense of perspective.  

3) Ask the vendor to list primary competitors.  Smart vendors will use the question as an opportunity to differentiate the offering, a sign you are dealing with a mature vendor. However, some will refuse to offer the list or, worse, say they don’t have any competitors. This might be a good time to end the conversation.

Why? First, you are making a reasonable request when asking about competitors. The answer can be advantageous to both you and the vendor. If the vendor is not confident enough about their offering to discuss other suppliers, you don’t want to do business with them. 

Second, this may be a sign that they do not know their own business—which in emerging technology fields happens with some frequency. 

To illustrate, one comment from vendors always hits me as a red flag: “We are the only vendor doing this.” If the comment is made in response to an RFP that goes triple. Chances are, I have three other vendors waiting in the hall to pitch the same tech. 

In sum, be wary of vendors who will not discuss the broader market, regardless of their reason.

4) Ask for examples of successful past integration.  This seems obvious but if you need the vendor to perform an integration with SharePoint, ask them for solid examples of when and how they have executed this integration in the past. If this is a particularly costly implementation you may even want references. 

Different technologies, even some by the same developer, often don’t play well with each other—when interoperability goes awry it can be one of the most frustrating and costly problems you will encounter. 

To avoid that, you should know two things: the base technologies and integration approach the vendor is using (web services, API’s, etc.), and the vendor’s method and format for sending and receiving data (JSON, SAML, etc.).

5) Discuss scalability early regardless of your growth trajectory.  You may not need 500 concurrent users today but you never know what your business will look like tomorrow. When discussing scalability early in your process, you need to keep three questions in mind: first, whether they have the ability to easily extend your service to account for growth; second, how the scalable solution may impact your internal systems or development resources; third, how scale effects cost.

To put this in perspective, consider online storage services such as Dropbox, Amazon Cloud Drive, and Google Drive. For each, when you reach your storage limit you receive a notification. You then have the option of increasing your storage limit by purchasing more space or cleaning some of the rubbish out of your drive to free up space. If you choose to increase storage—or “scale-up”—the process is seamless. That is, you pay a relatively nominal monthly fee and you are permitted to store more data with no behavior change or update needed on your end—reasonable, simple, cost effective.

The scaling process with those online storage services is the gold standard you want to pursue with your technology vendor—a practical approach to scale-up, limited interaction by IT and reasonable cost. 

6) Ask the vendor about support.  Support comes in many varieties: buy-up, hourly, packaged, etc. Understanding what support you are buying into is simple. Understanding how you will be supported is different. 

Here, you need to ask your vendor about the turnaround time when dealing with support issues and bugs. You also want to know when the support team is available and how you report issues. Mature vendors will have solid answers to questions about support. And while there is no single correct answer, you will know the wrong answer when you hear it. 

To help your own process, ask yourself: What am I comfortable with regarding turnaround time? How essential is the technology to my business? How much risk am I willing to accept? 

If the vendor’s process does not jive with your answers, walk away.

Final Words

Above all, remember that vendor engagements work best when your vendor is your partner.

Much like in a legal partnership, you need someone you can trust and work closely with but also someone with whom you can keep a cordial professional distance.

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