Hosting a Project Kickoff Workshop Remotely

computer and note pad sitting on desk


During the last decade, our team has hosted a significant number of kickoff meetings, or as we call them discovery workshops. Over the course of a few days, our client, their stakeholders, and our team work to understand what problems our client is currently facing with their technology solution, what issues their users face, and what it means to have a successful launch.

And while there is something about being in the same room as a group, getting to know your new client, and spending a few days diligently planning out the next several weeks or months, hosting a project kickoff meeting virtually can lead to just as much success.

If you are planning on kicking off a new client project in 2020 – or any time for that matter – and can’t be in the same room as your client, here are a few thoughts from our team on how to host a successful, online exploratory workshop.

Pre-Meeting Planning

First and foremost, we spend quality time planning out our workshop’s agenda. Attention spans are short for virtual meetings. Distractions come easily and the conversation or exercise can go sideways quickly.

We start by writing up everything we feel we need to understand or know for the first phase of work. This generally means we want to understand our client’s user base and how they interact with, or more importantly, don’t interact with the current product. What roadblocks are they facing and how might a new technology solution solve these problems?

Next, we write down the names and titles of everyone we want to hear from.

Typically, we want to hear from any stakeholders who might have opinions on the new website or web product but won’t be involved with the day-to-day implementation. It’s important to hear from these individuals as early as possible as they bring a different perspective to the project. Moreover, it’s best to avoid any late scope changes or rushed design updates due to a lack of planning.

Lastly, we take a simple poll of when to host this meeting. We want to make sure we are not backing up our meeting with any others and that our participants have ample time to get ready for the critical thinking that will take place. This means we try to avoid the early morning hours when people are just waking up and the evening hours when people are gassed and ready to wind down for the day.

With these notes in hand, we sit down and create a custom agenda with specific time boxes for each day to ensure we remain focused on the task at hand.

Focused, Concentrated Daily Agendas

Any virtual meeting that lasts over three hours is too long. Nope. Stop thinking of a reason to have a longer meeting. It’s too long. Period. End of story.

You run the risk of losing an individual’s attention or worse a sudden stop due to a work emergency. When these sudden stops occur, typically this means you do not get all of the information you needed from your client and you leave the meeting before you can all get on the same page – which defeats the entire purpose of having a kickoff meeting.

Before we host a virtual discovery workshop, we plan out the agenda down to the minute. It doesn’t always go according to plan and that’s OK. Tangents and rants can be good. They lead to new ideas or new ways of thinking about solutions. However, having a plan and set schedule allows your client to be prepared. If the participants know during the first conversation that they will have to introduce themselves and explain their role on the project, then they will come with a prepared statement.

Don’t put your clients on the spot. Let them absorb the agenda and come prepared to participate.

A sample agenda might look something like this:

Day 1

10:00 a.m.Team Introductions15 mins
10:15 a.m.Project Overview & Problem Statement30 mins
10:45 a.m.User Persona Development60 mins
11:45 a.m.Quick Break15 mins
12:00 p.m.Mood Boarding & Visual Strategy30 mins
12:30 p.m.Recap & End of Meeting5 mins

Day 2

10:00 a.m.Content Voice & Tone Discussion60 mins
11:00 a.m.Sitemap Development60 mins
12:00 p.m.Recap & End of Meeting15 mins

Notice how each exercise has a time limit that does not exceed 60 minutes. This keeps your team focused and allows them to stay in the moment without drifting or thinking about other work-related tasks.

This initial meeting is to get the ideas flowing and your client thinking about the ways you can improve their product or bring their product to life. You will most certainly have follow-up questions and meetings. But having a plan and sticking to that plan will get your project started off on the right foot.

Engaging Online Tools

Lastly, it’s important that you make these meetings as interactive as possible. Not having in-person meetings means you don’t get the chance to cover an entire wall in sticky notes, or sketch out ideas on a large whiteboard. But you can however use a few online tools that mimic these actions.

I want to pause and note that I’m not suggesting you use or purchase any of the products outlined below. These are just the tools my team has used to make our kickoff meetings more interactive.


Whimsical is an online tool that allows your team to create a wall of sticky notes, user flows, wireframes, and sitemaps. The real-time web application allows you to chat on your favorite conference line while also filling an entire viewport with Post-it Notes of website issues, features, or user habits.

We find this tool is great to get people “moving” around. It forces them to use the same brainpower that they would use if they were writing their ideas down on sticky notes. Short, concise ideas that can be categorized and organized for further discussion. Moreover, it allows your team to come back to the board at a later date and review the project’s initial brainstorming.


Another great, real-time web tool for team collaboration. I’ll be honest, it takes a bit more setup and you have to train your clients a bit on how to use it. But one nice thing about doing all of your discovery work in Figma is that you don’t have to leave this tool when you start to design. All of the brainstorming and thought collection is right there for you.

A plugin for Figma to test out during your next kickoff meeting is called Workshops. Similar to Whimsical you can create sticky notes quickly and time box your exercises.


Lastly, one of our personal favorites, Trello. It’s not just a project management tool. Trello can be used in many different ways. We find that the use of boards and lists are a great way to categorize cards during various exercises. Often times we will create a board just for “website issues.” Then we create a few lists. One for performance issues. Another for accessibility issues. Then one for user feedback and finally a catch-all. Then during our project overview and problem statement exercise, we ask the individuals on the call to take 5-10 minutes to create cards and place them under the list that best applies. This way we can create a list of ideas and issues to work through.

To wrap up, no virtual meeting will go as smoothly as an in-person meeting. There are aspects of the meeting you just can’t recreate or even control – wifi. However, doing plenty of pre-meeting planning, keeping your agenda concise and to the point, and trying to make it as interactive and engaging as possible will help get the project started off on the right foot.