What is the one thing we must get right to make this website/application worth undertaking?
Unless you are working with an organization that has already developed a detailed project plan, this question should generate a lot of different answers. Especially if you talk to different departments with different vested interests. Knowing where the specific tensions exist will inform specific activities you can do to define priorities and explore feasibility during the kickoff meeting.
How does your organization define success? What is the role of the website/application in achieving that success?
Nothing happens without a larger context. In tough economic times it can be an uphill battle just to secure the budget for a project, and it can be easy to lose sight of why the project was needed in the first place. Knowing the difference between project goals and organizational goals will help you define priorities and scope. If a specific functionality isn’t critical to organizational success, it’s a “nice-to-have” and a good candidate to leave out of your kickoff meeting discussion, and possibly the project altogether.
What aspects of the internal culture or external environment could put this redesign/application at risk to fail?
There’s something that everyone thinks is going to derail this project: They just haven’t told you what it is yet. The sooner you know, the better. Have they tried this before, only to fail? If so, why? During the kickoff meeting, you must establish how this project is going to be different than other previous, possibly unsuccessful, attempts. Knowing insider history and the team’s unique understanding of the market in which this website will thrive are the building blocks of differentiation.
(Follow up question) Assuming we mitigate that risk, what would exceed your wildest dreams?
The flip side of the previous question is that everyone has a fantasy version of the project in their heads. You never know what great ideas might be lurking in those fantasies; ideas that haven’t been shared yet because they were considered too unrealistic or outrageous might be the most exciting ideas.
During project-based work, every freelancer, agency, or internal department has “the kickoff meeting.” In theory, this meeting should have all the energy, excitement, and potential of the opening salvo of the Superbowl. Project team members should be inspired coming out of that meeting, full of ideas, and a desire to begin exploring solutons. Agencies and freelancers should begin to see their clients as friends and collaborators with unique insights that can only come from frank, open discussion of the design challenge at hand. But this rarely happens.
Every meeting is an opportunity. Why waste your first one?
In reality, kickoff meetings range from somewhat boring to straight-up awkward, and can be an expensive reiteration of project details we already know, assembling the most expensive, busiest people and generating little measurable project benefit. We have to start the project somewhere, but something is often missing in the kickoff meeting; something that is an obvious part of the football analogy—analysis and strategy. Before that kicker sends the ball across the field, coaches spend a lot of time reviewing tapes, applicable statistics, and more—what we in the web business call “research.”