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Endertech Team

The Customer Journey Series Pt 3 – Talking to a Software Development Company


So, what’s it like talking to a software company? There are many questions that you’d like to have answered, reassurance that you’re not going to embarrass yourself and that you’ll be prepared for the first meeting.

For this article, I asked Gabriel Richards, founder, and CEO of Endertech, to answer some questions and provide perspective from the software development side. Gabriel has over twenty years of experience talking with clients and building software. Therefore, I was thrilled to hear what he had to say!

This article looks at contacting, preparing, questioning, and understanding a custom software development company.

Contacting the Company

Initially, contacting a company is the easy part. Simply reach out, via phone or email, including your name, position, and relevant details. Remembering to include:

  • Software type (see the first article in the series)

  • The general geographic location of your company

  • Meeting purpose

    • Start a working relationship

    • Get a quote

    • Learn more about the company

These details allow the custom software company to determine if you are the right client for them (perhaps previous information mislead you on what type of software they develop).

Technical Background

It’s common to feel technically inadequate when first interacting with a software development company. Therefore, as previously mentioned, you should state your position when first making contact. This hints at your level of technical expertise. Companies are accustomed to working with people that have varying technical backgrounds.

For example, Gabriel says he is approached by small business owners, directors, managers, marketing, operations, and IT personnel.

Before the Meeting

Importance of Initial Meeting

You might think I’m spending too much time on the first meeting. However, many important questions are answered at the first meeting and, if things go well, the trajectory of a good relationship is set in place. Furthermore, both sides should reach an understanding of what the other wants and can deliver.

A bad first meeting occurs when parties are unprepared or hesitant to ask probing questions to better understand each other.


As a client, here are a few things to remember for the initial meeting:

  • Timeline

  • Budget

  • Validation

The client needs to provide some estimate on the timeline of the project. Additionally, they should know what their budget range is. The client does not need to share this information, but they should know their limits. Finally, the client should think about how they will validate their assumptions about the company.

Gabriel pointed to process and past experience being the most important things for a client to understand during the initial meeting, “[…] with custom software development, you really need a detailed plan to produce an accurate estimate. It’s like building a house, the architect’s work comes first, and then the builder. Arriving at a good plan, and executing that plan, requires a process: repeatable methods for achieving consistent results.”

Remember, you—the client—have already researched the software development company. Similarly, someone may have referred them to you for specific reasons. So what questions can you ask them to confirm your assumptions of their development processes, professionalism, and experience?

How do you confirm experience with a custom software development company when all of their projects are custom? Gabe answered this effectively, stating, “While it’s not critical that your development partner has built something exactly the same as what you want, it is important that they’ve built projects of similar complexity.” He recommends reviewing their portfolio of projects and identifying components where the complexity, or need, is similar.

Common Misconceptions

“As they say, necessity is the mother of invention. With unlimited funds, sure, you can have it exactly the way you imagine it, but maybe that’s not really what you need to get started and prove your concept. By working with your dev [development] partner inside of your constraints, together you can find creative solutions that get you where you need to be.”

– Gabriel Richard, CEO/Founder of Endertech

 On the software side, it’s well known that clients underestimate the time and cost of custom software development. Subsequently, they don’t want to disclose their initial thoughts on estimations because they may be embarrassed. However, as Gabe stated in the quote above, a smaller budget can inspire creative solutions.

Conversely, you can build a frame of reference if you collect a quote or two. But, how should you react if the topic of price or time is brought up and the timeline is too long? Or, the cost is way lower than other estimates you have received? Again, a good response is to get curious about the company’s process or experience.

Questions to Ask Software Development Companies

Suppose your estimation about price or time are off, especially if you have received quotes from other companies. In that case, it’s beneficial to get an understanding of the process and experience of the company.

Gabriel suggests asking about the companies’ processes for understanding requirements, suggesting appropriate solutions, producing accurate estimates, executing the project, launching and supporting the project. Again, you can probe the companies’ previous projects that they believe are similar to your project.

However, Gabriel didn’t stop at processes. He warned that clients should be concerned if a company gives an ambiguous answer on “[…] how they go about trimming scope when needed […]” Implying that a company failing to indicate their ability to adapt to constraints is a red flag.

Finally, Gabriel suggests asking who will be working on the project. Seemingly, this question is to see if the company currently has the resources and trusted personnel to take the project on. Or, conversely, will they try to acquire the resources after you have committed to the project?

Remember, a bad fit goes two ways. Typically, both sides of the agreement will feel the sting if they can’t talk clearly about their goals, expectations, and abilities.

Non-Disclosure Agreements

This article doesn’t offer legal advice because I am not a lawyer. Still, some may be concerned that discussing an idea with a potential custom software company may jeopardize the concept behind the project.

In my experience, clients have only asked me to sign a non-disclosure agreement (NDA) after agreeing to work together. Regardless, you should consult legal counsel if you’re concerned about intellectual property rights, copyrights, or patents.


In this article, we started by talking about reaching out to a software company and expectations about technical background. Then, we took a look at ways a client can prepare for the initial meeting with the software company and common misconceptions or underestimations.

Next, the article dipped into how you could better understand the software development company you’re meeting with. Especially if you’re trying to validate your assumptions or if something seems off. Finally, we laid out subjects to base questions on when talking to custom software companies.

An essential part of talking to a software company is that communication is consistent, keeping the lines of communication personable, respectful, and honest.