What are the most important questions to ask vendors during an interview?

It's always a good formula if you can find a vendor that is a 'have done' and a 'have done recently'. While it may be difficult to find a vendor that has worked for a direct competitor it would be nice to know how close they can come to providing specific examples that match your services/products. It's always best to ask these questions prior to providing the vendor with your target, so they don't emphasize what you need as a specialty when in reality it isn't. If the vendor does proclaim to specialize in your target area, then have some follow up questions prepared that focus on the latest software, solutions, methodologies, gov't regulation changes, etc that will reveal how deep the vendor's knowledge in the area actually is.

Timely communication is paramount to providing good service. Even more important is being confident and comfortable delivering 'bad' news or disappointing updates. Sometimes things don't go according to plan, and many projects have an 'oh ya', 'yes but', or the dreaded 'gotcha' moment. While all projects have a budget and a timeline, the vendor point of contact must be comfortable communicating these occurrences quickly to the customer, so management expectations can be properly calibrated. So a great question to ask a new vendor, "When was the last time something didn't go according to plan? How and when did you inform the customer and what was the result?"

Quality and performance are often measured differently by customer and vendor. It's a great move to put these expectations and measurements on the table up front, especially if there isn't an agreed to SLA. But performance and quality can go beyond SLA's, it can often get as granular as how frequent and in what form you contact the customer. So scheduling a monthly/weekly status call can be a great way to keep an agreed to monitoring system that will provide the customer with a regularly scheduled opportunity to voice their concerns. This can reduce unwanted calls/emails and allow the customer to provide a list of priority or watch issues and their desired resolution.

Contract negotiation is an art form, not a science. One strategy will not fit all clients. If your contracts are rigid and cannot be changed, that can cost you business or the support of a great vendor. So some flexibility is required in the art of contract negotiation. Often times negotiations can get mired in legal phrasing and verbiage, that can make even the most level headed vendor's head spin. Patience is a must, keep your eyes focused on the prize (winning a new customer or bringing in a new vendor). Sometimes your legal department / council can seem to be at odds with your goal. I highly recommend maintaining control during contract negotiations as opposed to handing it off. This requires careful review after each revision.

I treat my clients the way I like to be treated. That means to find ways to highlight their positive attributes and being a good professional. No one likes to be talked down to, at the same time telling someone what they want to hear isn't going to work either. Deliver what you say you will deliver, exceed expectations and discuss how you can improve the business relationship for each other's benefit.