VI #007: How to Choose a Great Contractor For Your Ambitious Software Development Project

Read time: 4.5 minutes

Earlier this week, I was chatting with a startup founder with an ambitious vision for their company who was seeking help deciding between an offshore developer with lower rates versus a more expensive onshore developer that was potentially more aligned with their needs and quality expectations. Given this is a relatively common challenge, I decided to collect and share some of my thoughts on this here.

Choosing a software development contractor can be challenging due to reasons such as lack of technical knowledge, lack of experience in the software development process and in leading high-performing teams, and fear of wasting money. In many situations, simply an acceptable contractor is needed to handle some relatively basic project requirements and get a job done. Much has been written about this online. More ambitious projects involving more complex requirements and advanced technologies can require more expertise and ability however, that often comes at an additional cost and can take more skill to select. However of course, higher cost does not always mean better value.

It is possible to choose a great contractor that provides a great partnership and business value for ambitious projects, when you know what to look for. Here are five considerations I’ve found helpful for identifying such contractors:

1. They exhibit thorough problem-solving, strong ownership, and bias for action

A competent software development contractors will be able to solve problems as they arise. They’ll be able to analyze a problem logically, provide creative solutions, research options, and prioritize approaches based on feasibility and effectiveness.

A great contractor, however, proactively identifies and manages issues and risks, works rapidly and collaboratively, thinks more in terms of broader context and systems, designs more innovative solutions perhaps by drawing upon seemingly unrelated domains, and persists in trying new approaches. They may respectfully challenge your asks a bit too, to help maximize the project budget and optimize outcomes.

To assess their skills, it can help to share the context of the business or customer problem, imagine that you’re both working together, and have the contractor walk through how they would solve it and work with you. Observations should be made of their thought process, and the following questions may be asked:

1. How does this problem compare with the most complex technical problem they’ve solved for a previous client?
2. How rigorous is their problem-solving process?
3. How do they handle unexpected issues or changes in scope?

A great contractor will have successfully completed projects similar or more complex than your current needs, will have a thoughtful and logical problem-solving methodology, and will proactively let you know about unexpected issues and provide sensible solutions to minimize disruption to project timelines and budget.

2. They understand how things work “under the hood” and leverage this appropriately to get things done

When it comes to technical expertise, a software development contractor must have a solid understanding of how to use relevant programming languages, debugging, troubleshooting, and software tools.

However, a contractor that stands out and that is likely to handle more complex needs will deeply have a deep understanding of how the internals of these tools, technologies, and techniques work “under the hood”. They will also be up-to-date on the latest technologies and industry trends, and take a proactive approach to optimizing their solutions.

To evaluate a contractor, ask about their software architecture design process, how they ensure efficient code, how they stay updated with new tech, and references and demos of their past work. Look for rigor, agility, passion for learning and building, and a track record of delivering projects to completion and satisfied clients. Also ask them about any side projects they may have - how people choose to spend their spare time can be a great indicator of their passions and expertise.

3. They communicate proactively, adaptively, and empathetically

Good communication skills are important for any contractor, but a great software development contractor will excel in this area by demonstrating empathy, adapting their communication style for different audiences, proactive communications, consistency, reliability, transparency, and cultural awareness.

Ask them how they would handle conflicts and disagreements, and how they would keep you informed about project status. Look for a well-defined and efficient process for providing regular updates and being responsive to inquiries.

4. They have obsessive attention to detail

Great software development contractors have an almost obsessive and proactive attention to detail that goes beyond identifying and fixing small errors in code or spelling. They call out and track problems and risks before they arise, identify and eliminate inefficiencies, and factor in potentially challenging yet important requirements such as security, privacy, and regulatory compliance.

While they contractor being assessed is walking through the problem-solving exercise, expect a well-defined process for testing and quality assurance, consideration of edge cases and exception scenarios, thoughtful user experience design, scalability planning, and prioritization of security, privacy, and regulatory compliance.

5. They drives tangible business outcomes

A great software development contractor should have business acumen in addition to technical expertise, including the ability to identify opportunities for innovation, understand the market, mitigate business-related risks, and create partnerships. While assessing the potential contractor, questions to consider asking include how their proposed solution helps provide differentiation and sustainable competitive advantage in the market, how it will ensure to deliver business value, how they like to stay informed about market trends, and how they would balance cost, timeframe, and resource constraints.

That’s all for today.

In summary

Anyone can choose a great contractor able to successfully take on ambitious projects, when they know what to look for. Five characteristics of great contractors for such projects include that they:

1. Exhibit thorough problem-solving, strong ownership, and bias for action
2. Understand how tech, tools, and techniques work “under the hood” and leverages them appropriately to get things done
3. Communicate proactively, adaptively, and empathetically
4. Have obsessive attention to detail; and
5. Drive tangible business outcomes

I hope this was useful. See you next Sunday.

Whenever you’re ready, there are 2 ways I can help you:

1. Work with me 1:1 to build your team, product, platform, or career in tech.
2. Book a free discovery call with me to explore if your business needs would be a good fit for my advisory services. If we’re not a good fit, rest assured I’ll kindly let you know.