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25 Questions To Ask When Assessing IT Outsourcing Companies

Whether you’re outsourcing a contract for the first time, or your experience with software outsourcing hasn’t been as stellar as you’d hoped, knowing the right questions to ask as you assess IT outsourcing companies will ensure that your next venture will yield the results you want. Here’s a rundown of some good questions to ask a development outsourcing company when considering potential development partners.

25 Questions to Ask When Assessing IT Outsourcing Companies

Software development companies and digital agencies in particular often need to outsource development work when it’s time to scale up quickly. But as they say, there’s many a slip between cup and lip.

As a nearshore outsourcing firm, we’ve learned that the best clients ask the best questions at the outset. Here’s a list of those piercing questions we think contribute most to making sure a client’s expectations are met with flying colors.

Opening Questions to Determine Experience and Capacity

What kinds of companies do you typically do work for?  

Ask about the size of companies with whom they worked, and ask for examples of the kinds of projects they do.

Have you done any project similar to mine, regarding the Industry/Technology/Product Features? Obviously, experience counts. Take a look at their client list.

How do you try to deliver the product that will match both our expectations and the market’s expectations?

Some of the largest client-developer conflicts arise out of mistaken assumptions. See how they work on figuring out what you really need, before they start billing out work.

Tell me about your hiring process. Where do you find your candidates and what do you look for when hiring new developers?

There are many flavors of software development and you want to ensure the prospective firm has the necessary skills for your project. Because software developers are in such high demand there has been pressure to come up with short term solutions to meet the need. Some IT outsourcing companies have started their own boot camp programs to train people to become programmers through intensive, short training programs for advanced coding. If your potential company has an elaborate and well thought-out hiring process they’re most likely considering quality over volume when forming their team.

Questions About Work Flow, Management and Communication

What collaboration tools do you use during the project?

With the wide choice of online project management tools available on the market, hopefully you and they will have at least some crossover, or one of you should be willing to adopt the other’s platform. Here at Jobsity, we use Slack, Trello and Zoom to move our projects along between team partners.

Will we use an instant communication system and if so, which one?

IM is great for frequent, quick questions or sharing quick links; just make sure there’s one you agree on before getting started.

Will the developers assigned to my project work on any other project at the same time?

It is way more efficient when a developer is committed to one project only. At Jobsity, every assigned team is 100% dedicated to one client only.

Will the same people be assigned to my project for the length of the development effort?

The cost of ramping up new staff on a complex project can be significant. This is an important question where you are trying to determine if your prospective partner can deliver and retain staff experienced with your software during the development phase and provide support and enhancements over time. There are numerous follow up questions that you can ask here such as:

  • Will your staff work full time on my project?
  • Will I be told if you are changing the staff that works on my project?
  • Are the assigned staff employees of your firm or do they work as contractors?
  • What is the turnover rate at your firm? If it is consistently more than 10% on an annual basis it could signify retention issues and pose a risk to your project. At Jobsity, we are proud to have one of the lowest turnover rates- - > 3 years -- in our industry.

What do you expect from us and what should we expect from you during the cooperation?

Define everyone’s roles in the new-forming team. There’s no one way to set it up, but it is good to know what to expect from the beginning and what are the scope of responsibilities for each party. Most businesses looking to outsource their software development are used to seeing role definitions in the form of the Professional Services model, where management responsibility is also outsourced. Increasingly, businesses are finding that the Staff Augmentation model works better for them, because they directly manage the work of their dedicated  external team, which still gets paid through their contracting agency.

How do we communicate during a project to surface the progress, plans and problems? Establishing a regular schedule of check-ins will make sure you always know what’s going in the project. With a staff augmentation model, you will be the one who is managing the work of your developers, even though they are offsite.  Still, you will need to know asap if anything goes wrong, so make sure you set up an early warning system of some kind.

How do you ensure we know when things go wrong? (Follow-up question): tell me how you handled a project in the past that went wrong. First, nobody wants to deliver bad news. Make sure they have a mechanism in place. Second, nobody’s perfect, so there must be a case that went wrong – listen to what lessons they took from it.

[Free Guide] Building Distributed Teams through Staff Augmentation: Download the Guide

Technical Questions

How do you ensure software quality?

Do they use, for example, peer code review or automated tests?

Will I own the source code?

Here is where you’ll need to read the fine print on any proposed agreement, to make sure.

Do you work on technical documentation?

You will want a road map to the critical pieces of code and methodology they’ll be using to build your product, so asking for technical documentation is a good way to assure you have it in the end.

Could you share with me your best practices for writing the code?

Find out if, for example, they use a handbook, or an eslint company file or other means to assure consistency and correctness.

Credentialing and Business Questions

Why are you better than other software houses? What makes you special?

You want to find out what is in their “secret sauce” that gives them an edge -- does the firm have a special reputation for something, or offer unique perks to attract the top developers in their region?

How easy will it be to scale a team by 1/3/5 developers? How much time do you need?

If you plan to scale the team, communicate it to the software development company ASAP. Around 1-3 months should be enough to scale the team.

What is your pricing structure? What does it include?

Sometimes, contracts can include the services of a PM or QA or Senior/Architect Mentoring.

Could you provide any testimonials or references from past or current clients?

Check B2B Research & Reviews, have a Skype call with one of the customers, check Facebook Reviews or simply Google “reviews of [company name].”

Once you have all these answers, your decision process will be far more informed, and you’ll have a much better idea if all your expectations can be met. We are sharing these tips because we want to be asked these questions. Our goal is to set up long and fruitful relationships with our clients. So far, it’s been working as our average client retention rate is five years. Ask us if we can be of help to you on your next project.


Apr 02, 2018



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