Choosing the Right Software Partner, Part 3: Evaluating Experience

Experience is the best teacher. When evaluating custom software development partners, it’s important to know if your potential partner has a track record of success with companies like yours and projects of similar complexity.


This is the third post in a four-part series aimed at helping you select the best software development partner. The series covers each of the characteristics you should look for in potential partners:

  1. Longevity
  2. Great people
  3. Experience
  4. Engagement management process


In this post, I’ll focus on experience.

Below, I’ve outlined the questions I would ask when evaluating a firm’s experience, and I’ve included my perspective on answers I’d like to hear. The goal is to help you evaluate potential partners at a foundational level and focus on what’s really important at this stage.

Evaluating Experience

I want my partner to have relevant organizational experience with projects and companies like mine.

I would share as much as possible as I could about the vision for my product or project, the complexity of my company, and the expectations I would have from partners. Then I’d ask the three questions below to help me evaluate my potential partner’s fit based on their experience.

1. Can you provide three examples of how you navigated the contracting and engagement process with a company of my size?

I want to hear stories of my potential partner helping companies like mine find success. If my company is large, I’m interested in how my potential partner has worked through contracts in the past. Are they able to accommodate my company’s payment terms and insurance requirements?

If I’m a small company, does my potential partner have a master services agreement and statement work terms? I like to see these standard materials in place so I don’t need to invest in creating my own.

If I have a lot of stakeholders, how will my partner help drive alignment? If I’m a product manager with a high degree of autonomy, how will my partner act as my trusted guide?

2. Do you have experience in the technical domains I plan to use?

I favor working with seasoned technology generalists over specialists because generalists understand higher-level patterns and know how to apply the best technology for a specific problem. Specialists tend to apply their specialty to any general problem.

That said, I want my potential partner to have experience with some technologies in the domain I plan to use. For example, if I’m building a mobile application, I’d like my potential partner to have mobile development experience.

Maybe I want to use a cross-platform mobile technology that my partner hasn’t used before. I don’t think this is a big deal; a good generalist service provider should be able and willing to work with my preferred technology stack. It’s more of a risk to hire experienced web developers with no mobile development experience to build a native mobile app or vice versa.

3. Please provide three examples of how you have created products or worked on projects of similar complexity to mine.

Many people naively believe that their problem is uniquely complex due to industry or knowledge domain. But while it’s true that every industry has its own jargon and knowledge domain, the underlying problems that technology solves are common to many industries.

I believe it’s a good idea to hire a generalist development partner with experience in many industries. They may help me see solutions from other industries that I wouldn’t be aware of otherwise.

It’s not important that my potential partner has solved a problem just like mine in my own industry. What I really want to know is if my potential partner has worked on a project of comparable complexity.

For example, if I want to create a cloud-backed mobile application with a consumer and administrative web interface in the health and wellness industry, I’d be excited to see that my potential partner had built a similar solution suite in the financial industry. I’d rather see the experience with technical complexity than experience in the health and wellness industry.

Choosing the Right Software Development Partner

This is the third post in a series on choosing a software partner. In the next post, we will be taking a look at how to evaluate a company’s engagement management process.

  1. Longevity
  2. Great people
  3. Experience
  4. Engagement management process

Questions? Disagreements? Please leave a comment below.