Checklist for Understanding Project Context

This checklist is a summary of the initial business analysis in Understanding Project Context. This is an excellent tool to on-board new team members and consultants like myself.

One way I can be useful to clients is by helping them to define a problem and explore the solution space for the right one. The right solution is one that will give my client the edge over competitors and provide users what they really need, even when often it is not what they are asking for. The business analysis conducted in the first phase of a project “Understanding Project Context” is critical to clients making the best decisions to move their products in the right direction. This work is done at the beginning of the project before a solution is explored and a course of action is set.

For a PDF and print version use this link: Checklist for Understanding Project Context

For more detail in each area, visit previous posts where I discuss each one.

so now what?

What is the problem?

Clarify the problem
Determine what clients/users have the problem
Write down where in the business this problem occurs
Identify the event or time periods when the problem occurs
Describe why the problem happens
List the business outcomes desired for solving the problem
Identify how the business outcomes will be measured

so who are you

Who are the players?

Identify the people on the project team
Identify the executive leadership responsible […]

Understanding Project Context: What are the Tools of Engagement?

At the beginning of each project it can be exciting to dive right in and learn about the client. However, there are a few basic logistical items to address with regard to which tools facilitate our work together.


I have a system to share with each client. Some clients choose to let me access their systems internally and others don’t for security reasons.

  • What tools are we going to use to work together, share documents, and communicate?
  • Can I use my email or do you prefer to provide me with your company email?
  • What desktop sharing do you use? Do you have an external service or use something internal like MS Lync?
  • Where are we going to store and share files? How do we display the current state of the work being performed?
  • Are the teams used to working in a distributed manner? What are your standards and policies?

My preference is to join the team and use tools they already have on their desktops so they do not need to acclimate to something new.

We need 3 basic tools for communication and collaboration:

  1. textual communication (e.g. email, Google Chat, HipChat)
  2. file storage and sharing (e.g. Google Docs, Dropbox, Outlook 365)
  3. desktop conferencing and sharing (e.g. Google Hangouts, Webex, GotoMeeting)

Copyright 2015 Frictionless Design LLC

Understanding Project Context: What is your product management process?

Each organization I have worked with over the years has a different process for product management. Many of the front line (or basic) activities may be the same but who employees report to, what they are responsible for, and how they take direction, is different in each organization.

product management

  • What organization does Product Management report to? Product? Marketing? Engineering?
  • Are product managers responsible for the whole offering from beginning through delivery and usage? Are they responsible for an entire product or just one module?
  • Do your product managers see design as their responsibility?
  • How does product management work with the business owners, marketing, engineering, sales, customers, service, and release?

Understanding more about the product management process will help me understand where the organization sees design fitting in and what impact the design process will have on them.

Copyright 2015 Frictionless Design LLC

Understanding Project Context: What is the software development process?

Before we start the project in earnest, we need to examine the client’s product development process. In many projects, I work closely with the development/technical teams.

development process

Understanding how the development process functions is key to working effectively in the organization and influencing the direction of the implemented solution.

  • What process does development follow?
  • Is the process documented?
  • What is the team manager responsible for?
  • How are the teams built?
  • How are the teams measured?
  • How do they see their role in the organization?
  • How much do the technical people understand about the business and users of the target clients?
  • How much control do they have over the design process?

Getting buy-in from the development team requires an understanding of how they work. Many organizations may appear to have similar processes on the front lines, but in practice can vary significantly. With this information in hand, we begin to formulate how the new project will be embedded into the existing process or if some processes may need to change.

Copyright 2015 Frictionless Design LLC

Understanding Project Context: How is the product sold?

In the software engineering world, the technical folks rarely interact with the sales folks. Teams focus on features and delivery dates so the only message engineering may get from sales is to deliver fast and early so they can close more deals.

sales cycle

Gaining a better understanding how the product is sold will frame how the organization expects the product to be presented.

  • Who are the buyers, influencers, veto holders, end users, and superusers?
  • What is the sales cycle? How long does it take to sell and how long does it take to install?
  • Is this sold online, through 3rd party vendors, handshakes in a bar, or through long relationship-building?
  • What do sales people think of the products they sell?

The more engineering and product management know about the sales process, the more influence they have on positive first impressions in the sales demo and subsequent sales encounters.

Copyright 2015 Frictionless Design LLC

Understanding Project Context: Who are your clients & users?

When I begin a project and start digging in, I need to understand what you know about your clients and users.  A verbal walk-through and a pointer to representative case studies will help kick off the learning process.


Any description, profile, or conversations with clients and users will help frame what is known.

  • Tell me about your clients.
  • What part of their organization uses the products?
  • Who in the organization is targeted by the current products?
  • Who has the problem we are looking to fix?

Clearly understanding your clients and users is essential to solving the problem. Starting from what is known will help us identify what kind of research is required. Let’s start painting the picture of who your clients and users are.

Copyright 2015 Frictionless Design LLC

Understanding Project Context: Who is your competition?

When starting a project it is so easy to jump straight to ideas and potential solutions. Too often it is an afterthought to discuss the competition.


Understanding what the competition is and where they are succeeding helps frame the space and the expectations set for the project.

  • Which companies do you regularly encounter today when selling your current products?
  • Will this change when we have a solution for this new problem?
  • What are the current offerings in this space?
  • What do customers think of them?
  • What aspect of the offerings do customers like or not like?

In the design process, we will expand the definition of competition beyond just companies selling similar products to yours, but to other unrelated products that your users may know and like.

Copyright 2015 Frictionless Design LLC

Understanding Project Context: What are your current products?

Let’s take an initial look at your products and users. Walk me through end to end like a user interacting with your products. What are the various ways an end user might interact with the company to get their work done?


Let’s follow that trail and orient me to your current solutions.

  • Here we can go into more depth about the business, users and technology
  • Introduce me to typical pathways through the products and services
  • Give me some ideas of the challenges as we mimic the users

Walking me through the user’s workflows is an informal way to see how you see the users approaching your products and services. This information will help us better understand, at a high level, what the customer’s experience is like.

Copyright 2015 Frictionless Design LLC

Understanding Project Context: What are the current technologies used?

Given the different products you have as well as the skills in house, describe the technologies you have.

what's your click?

Understanding current technologies provides me with a frame of reference for what you are comfortable with and how the organization sees the world.

  • What technology do you use?
  • What are the skill sets of the employees you have?
  • Why was the technology picked?
  • What does the architecture look like?
  • What does the technology road map look like?

Technology decisions and biases add constraints to the design solutions available. Sometimes the past technology choices get in the way of understanding the options within the new technologies chosen. Understanding these constraints allows me to adjust the solution or challenge the assumptions being made.

Copyright 2015 Frictionless Design LLC

Understanding Project Context: What business are you in?

Even when I have a lot of experience working within a domain, it is crucial to get the business perspective from you, the client. Beyond your marketing materials and your website to what you really do.

your business

Understanding the direction and focus of your business will help frame the solutions we explore.

  • What business are you in? Tell me about your products, the market, your competitors.
  • Where does the problem we are trying to address fit into the overall business?
  • What is the focus of the work we will be doing as it relates to the business?

After this conversation, I have you turn me to more resources to read. The better I understand your business, the more directed we will be when exploring the solution space. The questions won’t end here. Sometimes the questions will be hard to answer and will bump up against long held assumptions. A clear understanding of the business you’re in, and how this project fits into your overall goals in the marketplace, will contribute to making the right design choices for your business.

Copyright 2015 Frictionless Design LLC