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5 Questions to Ask a Prospective Development Partner


If you’ve been following our series on custom software development for the non-technical founder, you should know what to look for in a dev shop and what to avoid. Now, it’s time to draw up a list of questions to ask your shortlist of prospective partners.

Interviewing several dev shops is a great way to learn more about their experience, understand their processes and get an idea of what your project could look like. Go deep when asking questions. The deeper you go, the more likely it will be that you find the ideal development partner.

With that in mind, we’ve outlined five probing questions we think every prospective client should ask a custom software development team.


‘How Do You Measure Your Predictability?’

Most prospective clients will ask a development shop about their previous projects, what the process looked like, what they delivered and, ultimately, the results. Far fewer will ask for hard data about the KPIs of previous projects. We think this is a mistake.

Customers should ask dev shops how they measure their success on projects and, specifically, how they measure their predictability. This is vital, says Kingsmen Software CEO and partner Bill Clerici, because if you aren’t predictable you can’t set accurate expectations.

“Predictability is hands-down the most important metric for software engineering teams and the broader organization,” says Raleigh Schickel, VP of engineering at Stoplight. A good software team will almost always deliver somewhere between 85 to 115 percent of what they estimate, he writes.

When teams are that predictable, you can rely on them to hit delivery dates every single time. It also helps other teams (e.g. sales, marketing) to plan and meet their goals.

Ideally, your development partner would be able to show how they measure everything related to their work, including:

  • The capacity at which their teams work.
  • How frequently they miss deadlines.
  • How many points they deliver.

If someone tells you it’s going to take six months to deliver your project, they should have data from previous software projects to validate this estimate.


‘What Do You Do First?’

Far too many development shops dive head-first into coding when taking on a new project. This often leads to serious problems in the future.

Rather than starting to code as quickly as possible, dev shops should spend a significant amount of time in the discovery phase.

Humberto Farias, chairman at Concepta, says discovery is “the single most underrated phase of software development.” Companies regularly rush the discovery process, he writes. But then they get “blindsided” during development with an issue they could have predicted and solved before coding started.

“The situation is all the more frustrating because—while it’s never possible to plan for everything—so much chaos could be avoided with a solid discovery,” he says. “It’s like a flexible roadmap for development.”

Even the most thoughtful non-technical founders rarely have a firm grasp of what they are asking a development shop to build, says Bill Clerici. Translating a vision into units of work is a skill that takes years to hone.

A thorough discovery process ensures everyone understands what the project entails and what it needs to achieve. Where timelines are stretched, it lets product owners prioritize features. And it even helps managers sell the project back to stakeholders.



‘Can I Speak to Former Clients?’

This is the best way to gain insight into the firm's performance, communication style and the overall experience they deliver. You can also learn about any challenges the team faced during the development process and how they overcame those challenges.

In particular, you should be looking for a proven method. “If the agency can’t talk about results or provide proof of having achieved results, be wary,” writes Jason Wilson, CEO of consulting firm Strategy, LLC. He’s talking about marketing agencies, but the advice applies here just the same.

“In addition, if you don’t understand what they are doing or why they are doing it, back away. The best agencies have proven methodologies and can talk through and show examples of results they have achieved for their clients.”

When asking for references, you should focus on clients with similar requests and goals, rather than just companies in the same industry as you, writes Brad Shorr, director of content strategy at marketing company Straight North.


‘Will You Become a Partner?’

When you’re a non-technical founder, the last thing you want is to work with a custom development firm that is going to do exactly what you ask, says Bill Clerici. You want a team of people who know when to push back against requests, take agency of the project and offer their technical expertise.

That’s why Cagan Yuksel, founder and creative director at GRAFX CO, says this is the most important question. Your dev shop must be interested in having “skin in the game” and take steps to become a true partner.

You shouldn’t find it too difficult to find teams willing to take on this role. Christian Beck, executive partner of growth strategy and design at Innovatemap, says more development shops are doing this better than ever before.

“But there are still a lot of dev firms that will build exactly what you want,” he writes. “You want developers to be your partners, and challenge you when they see a red flag. The quickest path to failure is finding a firm that does exactly what you ask.”

Consider the future, too. Developing custom software is not a one-time event. It requires ongoing maintenance, updates and improvements. That's why it's crucial to ask a prospective firm if they have the potential to become a long-term partner, too.

In a successful partnership, the team will provide ongoing support and improvements to your software as your business evolves, ensuring that it continues to drive value for the foreseeable future.



‘How Will We Collaborate and Communicate?’

Clear and consistent communication underpins every successful development. Without effective communication, misunderstandings can occur, deadlines can be missed and the project can suffer.

“Miscommunication can become a huge problem,” writes Solomon Thimothy, president at OneIMS. “To avoid possible concerns, ask your potential agency partner how they are going to manage communication and collaboration and what degree of your involvement they expect to have.”

That's why it's important to ask prospective dev shops about their communication style and communication processes. Find out who your main point of contact will be and how often you can expect to receive updates on the project's progress.

The ideal agency will establish a structured communication routine, EY Belgium’s Anne Moreau and Celine Rossavik write. “For example, a short weekly or bi-weekly call to measure the current situation and have the latest status in order to propose the best and most appropriate services/responses, a longer meeting every few weeks to see the progress made, etc.”

But don’t be afraid to ask to what extent the dev shop can accommodate your communication style and preferences. You’re the client, after all, and there’s no reason your development partner can’t put you first.


Consult Kingsmen Software on Your Custom Dev Project

Ready to ask us the hard questions?

Kingsmen Software provides end-to-end custom software development for non-technical founders. Our predictable, collaborative process ensures we build the most valuable application possible for your business.

Contact our team for an initial consultation to start asking us the questions above.


Images used under license from Shutterstock.com.


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