aka “How to understand what your key stakeholder wants to ship”

Your key stakeholder is person who’s ultimately accountable for what gets shipped.

Whom your key stakeholder is will vary. They could be a Product Owner, Product Manager, Team Lead, or even a senior executive. For your key stakeholder, the project is their “baby”. By the time you’re chatting with them, it’s likely that they’ve already done a fair bit of work convincing others across the organisation that their project is worth shipping.

Listen more, talk less.

Aim to be talking for about 20% of the session, with your key stakeholder talking for the other 80%. If you weren’t able to achieve this ratio, then it wasn’t a good session.

Why? At the start of a project, your key stakeholder may not have a clearly defined requirements for exactly what they want to ship. They’ve identified a strategic opportunity, and determined that their project will benefit your organisation, but how the exact end product looks and works, the exact database fields that need work, the API endpoints that must be built - all of that is still hazy.

As a designer, you need to get information from your stakeholder so you can help them figure out if and how Design should be involved. That’s why your stakeholder needs to do most of the talking.

Try to use the words “our” and “we” where possible.

Avoid “your” as much as possible. Ideally only use “your” when you’re talking about roadmaps, timelines, and deliverables.

Using “our” and “we” whenever possible primes your stakeholder to see you as being on the same “side”. It’s a small thing, but it can make collaboration a lot smoother down the track.

Set clear expectations for what you’ll cover during the session.

Send a short chat message or email to your key stakeholder to explain that you’d like to have a short session to help you get a high-level understanding of the project. This isn’t absolutely necessary, but it is considerate, and helps to build goodwill. Try to contact them at least a week in advance, so that it’s easier for them to manage their schedule.

Sample chat message

You’ve made an upcoming booking with Design for work on project name.

I’d like to set up a session with you next week for project name, just to get us on the same page with how we’d like to work together.

Do you have a preferred day/time in mind, or are you happy for me to book a free slot on your calendar?

Book in the session as soon as you’ve found a date and time that works for your stakeholder. Clearly state what you’re aiming to cover in the session. This helps in 2 ways. Firstly, it assures your stakeholder that you have a plan, and that the session will be a good use of their time. Secondly, it gives them an opportunity to think a little more about you’ll be asking about.

Sample booking email

Hi K. Stakeholder, Let’s have a chat about project name, so we know we’re on the same page, and are better able to coordinate resourcing and deliverables based on shared expectations. I hope to cover: …Why we are building project name …Challenges/issues we’re hoping to address. These could be customer problems we’re trying to solve, challenges we’re facing at Company name, or a mix of both. …What success looks like …High-level definition of our MVP …How you’d like Design to help …Roadmap & delivery timelines Cheers, You R. Name

Run the session with a clear structure.

This ensures that after the session, you and your stakeholder have a shared understanding of what they’d like to ship.

Structure: