Thoughtful questions to ask clients, stakeholders, and teammates for a successful start to your project.
Kick-off meetings are the sometimes the first opportunity you'll have as a designer to hear from your client, project stakeholders, and new teammates about team roles, client expectations, and business goals. These meetings provide a chance for you to ask questions that will define the project scope and goals, provide an understanding of business requirements and how you'll measure success, and help you gauge how to successfully work with teammates and stakeholders. Asking the right questions at this stage also lays the foundation for your design as it provides insight into the problem you'll be solving, who you're solving it for, and why it's important to do so now.
Here are some questions that will help start your project off on the right foot. However, not all of these questions may be answered in the kick-off meeting and they may not apply to all projects, so use your best judgement when creating your list of questions.
Project Purpose and Goals
Gaining a better sense of your client's (or stakeholder's) goals, motivation for the project, and expected deliverables will help you create a project plan and will provide the necessary background you need to design an impactful solution. Try these questions:

How would you describe the current product and what would be your ideal vision of what the product could be in the future?
What is the problem we're trying to solve with this project?
Who are we solving the problem for?
How is the problem currently being solved?
Why is it important to solve this problem now?
What are the most common problems users and customers face?
Which user tasks are critical for the success of the project?
What work has already been done for this project and what were the key insights?
What is the history of the product? How long has it been available?
Success Metrics, Constraints, and Deliverables
Asking questions related to project logistics and measurements of success will help you gain alignment between external and internal teams, give you a north star for making design decisions, and help identify project risks and opportunities. It will also define success criteria and allow you to confirm these with your stakeholders. Try these questions:

What are the target outcomes of this project?
How does the client and our team measure success?
What does success look like for this project?
What metrics do you currently track and how do you track them?
Do you have a project roadmap or requirements document?
What are the constraints for this project, including any related to scope, timeline, budget, technological and/or device constraints?
What do you think are the biggest risks for this project?
What do you think are the biggest opportunities?
Who are your biggest competitors and why?
The Team
Identifying your teammates, client(s), project stakeholders and their responsibilities for the project will give you an idea of the needs, expectations, and perspectives of key players. Use the kick-off meeting to learn who the decision-makers are and how teams best work together and communicate. This will help you understand how to collaborate, communicate, and provide documentation across teams so that progress is made, issues are resolved, and deliverables are presented in a way that resonates with the intended stakeholder, ensuring that your project is successful from the start. Try these questions:

Who will be involved with this project?
Who are the primary decision-makers for the client and our internal team(s)?
What are the preferred structures, processes, and tools for collaboration, communication, and handoff for both external stakeholders and internal teams?
What are the team expectations?
What is the team's availability?
Final Thoughts
As the kick-off meeting wraps up, I find it's really useful to ask a final open-ended question that gives others in the room a chance to make clarifications, ask questions, provide additional context, or discuss something that I might have missed. Try this question:
Is there anything else you’d like to discuss that wasn't covered?
As always, I hope this list helps and I wish you much success on your future projects!
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