Top 10 Questions you must ask your software vendor

Do you have any questions for your software vendor? You should. The standard stuff like what is the size of the vendor’s team, what are their skills, how long have they been around are usually available easily at the vendor’s website, their brochure or they are more than will to just give you that information. What is more difficult to know yet vitally important for you are the answers to the not so easy questions.

Here’s our list of top 10 questions that must be asked before any software development relationship is set up with a new vendor. There are obviously a lot more, but we feel that these 10 must be asked no matter what and the answers to these should be discussed internally with your team to see if you see a good fit, to see if you agree or accept those answers or not.

1. What are the company's values and goals?

You might think this isn’t all that important for you as a customer, or it’s just some marketing blurb that you can by pass - but you’d be wrong. A software development project isn’t like many other projects around, it’s not like a simple product you buy and then you can pretty much live on your own. A software development project means a sustained relationship for a period of time (usually pretty long - remember it’s just not the development time, but all the maintenance, updates, upgrades and fixes of a software’s typical lifetime) . So what your vendor’s values are, how they see the business, what their goals are - all these matter because you’ll need to agree with them, be comfortable with them and at the very least accept them. For example if the vendor feels that their real goal is to become a giant in 5 years, then you need to think if that fits with your goal of working with a stable and small team.

A picture from 17 years ago at our old office where we had those beautiful mosaic patterns you don’t see anymore.

Sometimes alignment of values are a very good sign that things will work out in the longer term. I remember a long time back I was showing a prospective customer our old office space that had these beautiful, intricate mosaics and I mentioned that we love these patterns and we take extra care not to destroy them somehow. She just absolutely loved it and said her company was a 3rd generation owner company that valued traditions - and we knew we had a good alignment. And indeed over time that has proven to be so true, having worked with them for a long time and launching several of their flagship products.

2. What happens when you fail to deliver something?

This is the hard question that all software vendor will try their best to avoid. But you absolutely have to ask. Things do go wrong in software (actually all the time, some studies have shown that 78% of software projects fail, a recent post of ours tries to find a way software project plans can be done to avoid failure). So asking how the vendor will manage that risk is essential. If the answer to that sounds vague or if they say the impossible - “we don’t fail” then think hard if this is a good fit, dig in deeper to see how reliable that partner is. Every software project should have a disaster recovery plan - simple. If a vendor doesn’t have one or isn’t planning one then there is something wrong with that vendor.

What you should be looking for is a realistic yet confident approach towards delivery failures. There should be a risk management plan - a risk containment and mitigation approach. They should be ready to act when a failure happens, and draw on the experience and knowledge from past projects and from the team to minimize the impact to the project.

3. What happens if a team member leaves suddenly?

Software is very much a team effort where every team member is essential. Over time a team member becomes an expert of the project and its requirements. Developers grow the essential familiarity with the codebase, the features, the decisions and the compromises that make a software project work smoothly and efficiently. So when a team member leaves it puts a huge dampening effect on the overall project and the vendor must have a good plan to first manage the team so that doesn’t happen and then manage things when it does happen.

More on this theme on question 8 below and there is a reason to separate them out and ask them a bit spaced apart. You want to revisit this topic to see if the answers fit well.

4. Can you provide case studies of customers who have been successful with your software?

5. Can I speak with a client who is using your product now to get feedback on their experience?

6. How many projects like mine has your company completed in the past year?

This is pretty standard stuff - but sometimes these case studies are not shared publicly. Maybe an NDA prevents the sharing or there are some other reason why they don’t want to put these in their marketing material. So it’s essential to ask and then review these case studies. These are projects that has worked out so you should get a feel of your own project fitting in those - see if you can imagine your project being one of the case studies in the future. Ask questions that are not answered or issues that are not clear in the case studies.

7. What's the best way to reach you during and outside normal business hours?

8. Who will be my point of contact throughout the project?

Standard questions but you’d be surprised how many customers don’t ask this. You should have a clear picture about what to expect when the project is running in terms of communications. All projects will have at least one point in its history where you are desperately looking for a quick answer to a question. It could be during an important demo that you are giving to your prospective customer, it could a bug you spotted that needs a fix right away. You need to know about the contact points and be absolutely sure before any vendor is accepted.

9. How do I know that I can trust you with my data?

Data security if everything in software and it’s important you ask this question right at the beginning. There must be a very clear procedure for data security at the vendor’s site. They must have a plan and a process that ensures that the plan works.

10. How long have your employees been with your company, and how many years of experience do they have in this industry ?

This is a revisit on the team stability question of question no 3. Vitally important question and a revisit is needed to see if the answer to this fits with the answer to the other.

Good luck with your vendor hunting!