In this episode of The Learning Pro Live, I sat down with fellow learning designer Emma Pawson to discuss one of the most critical moments in any project: the client kickoff meeting.

Whether you call it a discovery session, a briefing, or a kickoff, this meeting sets the tone for the entire engagement. Get it right, and you build trust, clarify scope, and set yourself up for success. Get it wrong, and you are staring down the barrel of scope creep, misaligned expectations, and endless revisions.

Here are the key takeaways from our chat on the questions you simply cannot afford to skip.

Start with the “Why” and the “Now”

Before diving into content, we need to understand the context. I always start by asking about the business’s current state. What are your current challenges? Why are you doing this project now?

Understanding the business drivers helps you strategically position your solution. Are they reacting to a new government policy (like COVID-19 regulations), or are they proactively trying to fix a cultural issue? Knowing the “why” allows you to “future-proof” the content, ensuring it remains relevant and valuable long after the launch date.

The “One Stakeholder” Rule

This might sound controversial, but it is a lifesaver for freelancers: I insist on having one single point of contact for feedback and sign-off.

We have all been there—”Bob says this, but Anne says that,” and suddenly you are caught in the middle of internal politics. By establishing one primary stakeholder who consolidates all feedback, you avoid conflicting instructions and project paralysis. Emma added a crucial point: ensure this person actually has sign-off authority. There is nothing worse than getting approval from a middle manager only for the CEO to swoop in at the 11th hour and change everything.

Validate the Content Readiness

A classic trap is assuming the client has the content ready. Emma shared a brilliant question to ask: “What state of readiness would you consider your documentation to be in?”

Clients often think a few bullet points in a PowerPoint constitute “ready.” Asking this upfront lets you know whether you need to factor in extra time for a content workshop or subject-matter expert (SME) interviews. If the content isn’t ready, I won’t start the project. It is a recipe for disaster.

Digging into the Tech Stack

Never assume the technology. I always ask: Where will the learner access this? On a desktop? A tablet? A mobile phone? Does it need to be SCORM compliant? Do you have an LMS?

Emma shared a horror story of discovering a client’s desktops didn’t have audio capabilities after planning a video-heavy course. Asking these technical questions early prevents embarrassing (and expensive) pivots later on. If they want a mobile-first experience, don’t build a complex Storyline module that won’t scale down.

How Will You Measure Success?

Finally, the question that stumps almost everyone: “How will you measure the success of this program?”

Most clients will say, “Completion rates.” But completion is not success; it is just compliance. I push clients to think about business metrics. Do you want to reduce safety incidents by 50%? Do you want to increase retention rates? By helping them define tangible goals, you not only prove your value as a strategic partner but also give them the data they need to secure budget for future projects.

Watch the full interview above to hear us break down our complete question list, discuss how we handle tricky stakeholders, and explain why we treat storyboards like architectural blueprints.