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How Do I Select the Best Custom Software Development Firm?

Custom software takes a significant investment of both time and financial resources. We understand finding a software development firm that’s a good fit for your business and likely to become a long-term partner is important. So, we’ve put together 10 questions to ask a software development firm you’re considering working with.

If you find other criteria useful in your search, please share them in the comment section below.

10 Questions to Help You Select the Best Custom Software Development Firm

1. Do they want to get to know your business?

Your business is unique. No one has the same value proposition, business processes, culture, and customer interaction as you.  You want your software to compliment your business while helping it to grow and scale.

Software can only do what you program it to do. It doesn’t make assumptions or read minds. So when dealing with a custom software firm, you really need someone who takes the time to understand your business so they can translate your needs into a software design and specification that developers can implement.

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When evaluating a software firm, pay attention to the questions they ask. Are they taking their time to learn more about you and what you want, or are they rushing to hand you a proposal and a quote?

2. Does your software firm offer new ideas?

Your software firm should do more than taking your specific ideas and translating them into software. They should ask you thought provoking questions and offer new ideas so that together you create an even better software product.

  • “Have you thought about this…”
  • “What if we tried it this way…”
  • “What would happen if your users did it this way instead?”

3. Does your software firm advise you on what works well and what doesn’t?

One of the benefits of working with a software development firm is their experience over the years with multiple projects. They will have tried things and came away with a few battle scars, which is to your benefit.

Your software firm should be confident enough to advise you on what works well and what doesn’t. They should have an opinion because you are hiring them as an expert, not an order taker.

Ideally, in your conversations with potential software development firms, you will hear them say, “Here is what we find works great in this situation…” or “We suggest doing it this way because of x, y, and z” or “We don’t think that is the best approach for you and here is why. Can you help us understand what it is that you like about this approach?”

Look for a firm that isn’t afraid to disagree and is willing to back up their opinion with reasons that are in line with your goals.

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4. Does your software firm educate you?

Technology constantly changes and it’s a challenge to stay relevant.  Don’t worry if you don’t understand the minutiae, but have your technology partner educate you. Ask questions such as

“Why does this matter to me?”

“How does my company or my software benefit if we do it this way?”

“Why is this technology, framework, component, library, approach, etc. the best choice?”

A true software development partner will take the time to explain what they are doing in a way that you can understand.

5. Does your software firm match technology to your needs?

Some software development firms specialize in how they deliver a software project. They may use a particular coding language, framework or software solution for all of their clients, like Microsoft Sharepoint or WordPress.

If the tools they use are a good match for your needs, then great.  But not all technologies are a good fit for all projects.

When you start out, consider talking to a few firms who use a wide variety of technologies in their solutions. They will be able to talk openly about your opinions, and what they feel is the best approach for your project. If it makes sense to specialize in a toolkit or platform, then you can feel good about doing your due diligence before going down that path.

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6. Does your software firm have a reliable process?

Building software is the execution of several hundred tiny steps. You want to partner with a software development firm that has a well-defined, repeatable process and a track record of success.

You can think of a software process like a detailed checklist of common tasks that all projects need, along with known steps of who does what, how they do it, and how they hand their work off to the next person.

In effect, a software development process is like a factory for building software that can be adjusted to fit your particular project needs.

Feel empowered to ask your potential software company about their process and why it works for them.

7. Does your software firm communicate well?

Building software is all about communication. At first, the communication is about sharing your ideas with your team, clarifying and refining those ideas, and eventually creating a final software design.

Then the communication is about scoping and budgets for the first release, building your software, asking and answering detailed questions about priorities and how things work until the project is complete.

You want to feel good about the quality and quantity of communication with your chosen software firm.  Software is mostly intangible so what gets built is a direct reflection of what gets communicated, and how it gets communicated.

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8. Is your software firm local, with an office you can visit?

While it may be common to outsource software development off-shore or to a team you have never seen, there is something to be said for developing face-to-face relationships with your team.

Building software can be a bumpy process at times, so taking the time to invest in a relationship helps both sides smooth out bumps down the road, knowing there is a real person on the other side.

9. Does your software firm offer long-term support?

Once a software project is delivered, it will need additional support. It may be infrequent or frequent, depending on your need for it to modified based on user feedback or changes to your business.

You want a software partner who will support you for the long-haul.

If your software partner doesn’t offer support, you will need full access to the source code and look for a software company that will support you and your business going forward.

It is wise not to assume that once a project is done, it is forever done.

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10. Does your software firm have case studies?

This one is not as important as the other questions, but ensuring there are other companies that have worked with the software firm before and are willing to share their experiences could be beneficial to you.

While you’ll hope to hear customer success stories, it’s important the firm is honest if they’ve had any major delays in projects or, simply any failures that they can share. Don’t be afraid to ask, as every company has had them. What you’ll be interested to hear is how they present those answers and explain what they did to ensure the project was still completed with the client’s approval.


Building a custom software solution is an exciting process. The possibilities are endless and you get to be in the driver’s seat. But you need a custom software firm who can deliver on your ideas.

When you select a custom software development firm, you want to get it right the first time.

After 20 years of helping individuals and companies see their software ideas become a reality, we still get excited about creating great custom software and getting to know each of our clients on a personal level. If you’re ready to get started on your custom software project, let us know. We’d love to help.


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