10 Questions to Help Choose a Software Development Company


A software development partner can offer key strategic advantages over in-house development (learn more here). But choosing the wrong partner is a real risk: Nobody embarks on a software development project with the goal of failing.

Unfortunately, failure is a real possibility if you don’t find the right development partner. The key is getting the right information to help you make the choice that’s genuinely right for your project. So how do you do that?

Simple. You need to ask the right questions, and make sure you get good answers. After all, even if you’ve heard amazing things about a company, you need to ensure they’re a fit for YOU.

You’ll of course ask questions about things like rates, billing practices, contracts, and whether they can meet your timeline. Those questions are important, but they shouldn’t be your only criteria. (We wish we could tell you otherwise, but making decisions on price alone is a surefire path to failure.) So what other questions really matter? What should you ask — and listen for — to gauge whether they’re going to deliver the goods that will help you succeed?

To help you get the information you need to make the choice that’s right for your business, Distillery put together a checklist of the ten most crucial questions to ask a potential software development partner. Following the checklist are explanations of the “why” behind each question. We’ve also included guidance on what to listen for and what else you may want to ask.

Software Development Partner Interview Checklist

1) Tell me about your company, as well as the specific team I’ll be working with.

2) Tell me about your experience completing projects similar to mine.

3) How will you ensure that you understand my project’s requirements?

4) What is your software design and development process and why?

5) How and when will you communicate with me?

6) What involvement will be expected from me throughout the process?

7) What happens after my product has been delivered?

8) How does your process reduce my risk and increase my chances of success?

9) Can you provide references?

10) Why is your company right for my project?

Provide-Information-About-Your-Company_ How-To-Choose-a-Software-Developer

1) Tell Me About Your Company, as Well as the Specific Team I’ll Be Working With.

Why It Matters

Most companies will have a readymade pitch. The content and style of it will tell you a lot about how they see themselves, how they see their customers, and what their company stands for.

Here, you’re hoping to get a sense of whether their company and team will be a fit with yours.

What to Listen for

Make sure they indicate years in business, as working with a brand-new company may not be the best choice. Find out how many developers they have (will bandwidth be an issue?) and their average years of experience.

You want to ensure they have specific developers, UX/UI designers, and/or product/project managers in mind who are available and well-suited to your project.

What Else to Ask

You might inquire if they have certifications (e.g., Microsoft, Oracle) or have won any awards. You could ask what kind of clients they generally work with. If they haven’t specifically addressed who’ll be on your team, ask again.

You want to make certain they’re prepared to staff your project and have put thought into how they’ll do it.

Talk-About-Project-Experience_ How-To-Choose-a-Software-Development-Company

2) Tell Me About Your Experience Completing Projects Similar to Mine.

Why It Matters

They should have a successful track record on projects at least somewhat similar to what you’re proposing. After all, you wouldn’t hire a house painter who’s never before painted a house.

What to Listen for

Focus on their experience with similar product features, technical stacks, and industries, as well as experience working with similar organizations (i.e., similar in size, style, or focus).

What Else to Ask

Ask follow-up questions to probe further, including what specifically they did to make each project successful.


3) How Will You Ensure That You Understand My Project’s Requirements?

Why It Matters

Too often, there’s a gap between what you have in mind and what the design and development team builds.

Understanding your requirements means achieving a clear and comprehensive understanding of your business issues, timeline, budget, and market objectives. It’s imperative that they validate that understanding with you, and that you understand why they’re proposing their solution to your specific business problems and goals. This exchange helps ensure that requirements are accurate and complete from the perspective of both the business and its users.

What to Listen for

Listen for words like wireframes, prototypes, proof of concepts, and minimum viable products (MVPs). These are tools development companies use to communicate their understanding, and give you the opportunity to expand and correct that understanding.

Bonus points if their explanation specifically references your project and business issues.

What Else to Ask

If you weren’t satisfied with their answer, ask the question again in a different way: “How will you ensure you didn’t miss any requirements?”


4) What Is Your Software Design and Development Process and Why?

Why It Matters

A good development partner will use a reliable, repeatable process that supports organization, consistency, and quality control. It should be a thoughtful process based on practical experience, lessons learned, and industry leading practices.

You also want to make sure their process includes delivering an evidence-based point of view and value-added ideas. You won’t benefit from “yes men” who do whatever you ask, regardless of whether it’s genuinely good for your project.

What to Listen for

They should talk about things like Agile processes, iterations, UX/UI research, QA/testing, logging, and starting with an MVP. These practices help ensure project success while expediting progress and reducing risk.

Again, bonus points if they talk about your project specifically. It shows they’ve put genuine thought into how they’ll work with you.

What Else to Ask

If they didn’t get specific, don’t let them off the hook. Have them walk you through what your project will look like from your perspective, or describe the process used on a similar project.


5) How and When Will You Communicate with Me?

Why It Matters

Your goal here is to ensure open communication and transparency throughout the design and development process. If they don’t have set communication protocols, you can’t count on timely issue identification and resolution. You also can’t count on achieving the product you hope for.

What to Listen for

They should address the who, when, and how of project communication, including the format and timing of updates; any tools to be used (e.g., Slack, Jira), as well as your integration into those tools; and who your primary points of contact (POCs) will be. They should specify which specific issues or questions will spur communication.

Bonus points if they ask about YOUR preferences.

What Else to Ask

Once they’ve identified your primary POCs, ask whether they can ensure that your team will have some degree of continuity. For example, can they ensure that you’ll have the same project manager or lead developer for the duration of the project?


6) What Involvement Will Be Expected from Me Throughout the Process?

Why It Matters

To get the right requirements — reflecting a complete understanding of your business and user needs — they’ll need a significant initial time investment and ongoing involvement. To ensure project success, your involvement should be much more than participating in updates and reviews. (That’s why communication is a separate question in our checklist.)

What to Listen for

They should expect you to be involved, period, and give clear expectations of what that involvement will look like. This is one moment when “don’t worry; we’ve got this” is the wrong answer.

What Else to Ask

Again, make sure their explanation is specific to your situation. It’s not helpful for you to know how it “generally” works. Ask how it will work with you.


7) What Happens After My Product Has Been Delivered?

Why It Matters

All software products will require post-launch support. There’s no getting around it.

What to Listen for

Ensure they’re capable of providing ongoing support, helping you with problems, improvements needed, or new features if desired. Make sure they address who owns the intellectual property (IP) (e.g., the source code and related documentation) post-delivery — and that the answer is YOU. If they insist on retaining ownership and charging you ongoing licensing fees, are they really thinking about your best interests?

What Else to Ask

Ask about any warranties or other service guarantees they’re willing to discuss.


8) How Does Your Process Reduce My Risk and Increase My Chances of Success?

Why It Matters

You want to make sure they’ll bring a whole-business perspective to the project. If they can’t readily answer this question, you may want to rethink working with them.

What to Listen for

A good partner will give you a thoughtful answer that echoes key tenets of their development process. For example, they may mention user research, iterations, starting with an MVP, communication protocols, cost and quality control, scope management, or other items.

What Else to Ask

If they don’t bring up the items mentioned in “what to listen for,” ask them about them. Make sure they’ve addressed your specific concerns (e.g., market viability, cost or schedule overruns, team continuity, IP security/insurance).


9) Can You Provide References?

Why It Matters


What to Listen for

The only answer acceptable is “yes.” A “no” is a giant red flag.

What Else to Ask

Make sure you’ll be permitted to interview the references they give.


10) Why Is Your Company Right for My Project?

Why It Matters:

With this question, you’re feeling out how well they understand your business, product, goals, and priorities. You don’t want to work with a partner that views you as a generic client. You also don’t want to work with one that hasn’t listened closely to everything you’ve said.

What to Listen for

Are they talking specifically about your needs, or are they just spewing generalities about why they’re so great? They should be able to tie their value propositions directly to things that you’ve said are important to you.

What Else to Ask

If you’re feeling crafty, consider flipping the question on its head, asking “Why is your company NOT right for my project?” Virtually no company will have a ready-made answer for this one.

If they give you an honest, thoughtful, and relevant response, that’s a great sign. If they give you a disingenuous cop-out, that tells you something, too.

The Single Most Important Question

Ultimately, there are a lot of software development companies out there. As you ask the right questions and listen for the right answers, it’s imperative to never lose sight of the single most important question you need to answer for yourself: Are they the right software development company for YOU?

While there are legions of impressive, well-qualified companies out there, what matters most is whether they fit your unique needs. You need to choose a development partner that will not only get the job done, but that understands your business and keeps your best interests at the forefront of every decision. That’s how you’ll give yourself the best possible chance at success.

Want to find out if Distillery might be a good fit for your development project? Let us know!