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Hiring a Custom Software Development Partner? Here’s what to ask

Developing custom enterprise applications is serious work – we know. Most enterprises simply don’t have the resources or specific technology knowledge to develop solutions in-house.

Srđan Peter Jozić, Senior Business Development Manager

Software development

Software development

October 23, 2024

May 29, 2025

Developing custom enterprise applications is serious work – we know. Most enterprises simply don’t have the resources or specific technology knowledge to develop solutions in-house. And when the need arises, you need to turn to a custom software development partner.

But how do you know which one is right for you?

We’ll arm you with all the questions you should ask – as well as why you should ask them – and set you on course to find the right development partner for your project.

Two main answers you should know:

1. Why hire a custom enterprise software development company?

For all the enterprise solutions that exist, sometimes the one you need simply isn’t one you can grab off the shelf.

Maybe you need to modernize your legacy systems to improve security, add new features, and improve performance. Or you just want the right solution that perfectly solves your unique business need. In these cases, custom development is the only way to go.

For example, when Strabag approached us, it was because they knew that an off-the-shelf solution wasn’t right for their need – which was to pool data from hundreds of parallel ongoing projects worldwide and make it available in a single real-time dashboard. By the way, we developed that for them, cutting out entire days of lost productivity.

2. Is this something we can afford – or can’t afford not to do?

Off-the-shelf versus custom, whether it’s furniture, suits, shoes, or software – custom costs more.

Consider a ballpark budget. Start by considering how much not solving your challenge is costing you right now. Or how much customizing an off-the-shelf solution could cost. For this, factor in how much your challenge costs you regarding opportunity costs, lost time, lost business, productivity losses etc.

Once you know that a) you need a custom solution and b) you can afford it (or can’t afford not to have it), it’s time to start asking development firms these following questions:

“Have you developed solutions for our industry before?”

Industry experience matters when it comes to enterprise app development. Some development partners specialize in a particular industry or niche where they’ve left their mark.

Ask about any solutions that they’ve developed for your industry in the past. Any experience from the past will help them navigate your industry-specific project since they’ve charted those waters before.

“What is your main tech stack?”

This is an important qualifying question that can help you zero in on the most suitable software development firms.

Ask about the technologies they use to address compatibility with your project, but also to get an idea about their experience and expertise. This conversation will show how technically versed they are when it comes to advanced technology and how they apply it to your project.

“What methodology do you use?”

Scrum? Waterfall? Spiral? There are quite a few methodologies in use, and each has its pros and cons.

Waterfall is well suited to projects with clear structure and documentation.

questions to ask custom software development partner - methodology

Agile suits projects that require flexibility and collaboration with a product owner. In agile, the scrum master works closely with the client all throughout the development process, which helps adapt to changing needs.

Further, agile breaks the process down into smaller, more manageable pieces. This way, stakeholders and customers can provide detailed feedback at each step of development.

This flexibility accelerates development, helping products go live, quicker and with fewer risks.

Ask which methodologies your software development partner works with so that they can adapt to your way of doing things. Flexibility here is key, and a partner that values transparency will adapt to their client’s preferred method of methodology to keep them up to speed.

“Do you recommend staff augmentation or a dedicated team?”

Once you have a clear picture of your project requirements, it helps to get an idea of who is going to execute the project and how they’ll be involved throughout.

Ask whether they recommend staff augmentation or a dedicated team for your project.

dedicated team of relevant specialists from various fields, such as business analysts, project managers, UX/UI designers, QA, and developers, is assigned to work on your project exclusively from start to finish. The team can become part of your team, or remain a stand-alone development team.

This works best when you have a scalable, long-term project in mind and lack in-house general resources or necessary expertise.

Staff augmentation is the recommended model for situations requiring a specialized professional or a team of professionals to enhance your existing workforce and fill skill gaps.

Besides their expertise, cultural fit and lack of language barriers will be crucial, too. After all, your team is getting new teammates

The model type depends on your specific project requirement, duration, available in-house resources, and more.

“How will you start my project?”

Ask about the first step of the development cycle to gain an understanding of how they approach laying the foundations of your project.

Typically, the first steps of development will start with a discovery workshop involving key business stakeholders to go over the project in great detail.

This discovery process should give the development team a clear picture of your vision and business goals. The clearer this picture, the easier they can meet the project objectives.

“What project management tools do you use?”

If you want to stay in the loop throughout the process and receive critical updates, then ask about which project management tool the development company uses.

Most development partners are flexible and willing to work with project management tools you’re familiar with. Alternatively, if you don’t use any project management tools, they’ll suggest options that will help keep you up to date.

Using project management tools like JIRA, Notion, Clickup, etc., for example, ensures progress tracking and updates and helps everyone involved track time spent, which could be crucial depending on the pricing model (more on that later).

Asking this question gives you a good idea of how seriously the company takes its commitments.

“What quality assurance processes do you follow?”

Quality assurance processes thoroughly test applications to ensure they perform without flaw.

Ask about their QA process, test methodologies, and any third-party tools their QA team uses to identify – and squash – any bugs.

If a company doesn’t have a QA process, they shouldn’t have your business, either.

“What pricing models do you offer?”

There are two main pricing models in custom enterprise app development and one hybrid model. These are time and material-based, the hybrid capped time and material, and the fixed-price model.

  • The time & material-based model is the most common pricing model. It calculates the project cost by factoring in time spent and level of expertise used in delivering a project. This model is best suited to agile software development projects, which are characterized by evolving requirements and frequent changes based on user feedback.
  • The hybrid capped time and material model provides resources to the client for a predetermined price. In this model, development partners supply the engineers while the client manages the team and the outcome.
  • With the fixed-price model, a rate is determined at the very beginning of the project. The client provides a user-required specification (URS) that outlines the project requirements. Provisions are made for potential change requests to allow for any changes to the project scope. The fixed-price model is rarely used for custom enterprise-grade software development; however, given the tight budget restrictions, it is more often used for integrating off-the-shelf solutions.

“How much will this cost?”

Usually, this will be the first thing you want to know. And that’s perfectly reasonable since you need to be mindful of your budget.

However, the answer to this question relies on a multitude of factors, starting with the project itself and the requirements, whether you need a dedicated team or staff augmentation, etc.

More complex projects will require deeper discovery, and only then will a rate begin to take shape, whereas simpler projects will be easier to provide a ballpark estimate for earlier on.

“Where are you located?”

This question is important for a few reasons. Depending on where you’re based, your outsourcing may be subject to certain legal requirements and general standards. This also applies to the development team, so make sure you ask about where their developers are located.

Proximity plays an important role, as well. For example, when using an IT staff augmentation model for your specific project, it’s easy to work with a nearshore team. Or if you need daily updates for your project manager, then it helps to be in the same or an adjacent time zone.

questions to ask custom software development partner

In addition to removing (or minimizing) geographical barriers, understanding common languages, cultural, and business customs can help things go smoothly. Especially in terms of communication.

“Can you provide a portfolio?”

Ask your shortlisted application development agencies for a portfolio and any references. Then, compare these with your company, industry, project, etc. The more commonalities between what you’re looking for and what the developer can provide, the better.

Choose the right software development company.

Outsourcing your software development to the right partner is no easy task. But armed with this list of questions, you’ll have an easier time finding which one is right for you.

You can find the answers to some of these questions on a company’s website. Or you can simply reach out and contact them to find out if they’re the right software developer for you.

We’re ready to answer all these questions for you. Contact us!