How to Leverage Estimation Meetings when Onboarding Remotely

Bringing new teammates up to speed can be a challenge, especially in the current world of remote collaboration. As a new team member, you’re not always sure what else you need to learn. As a seasoned team member, it’s hard to realize how much context you’ve gained along the way that needs to be shared.

If you’re bringing a new teammate on board, consider leveraging estimation meetings to find knowledge gaps and create learning opportunities.

Create a Safe Space

Estimation meetings can be pretty stressful for new team members. Since the whole team is there, it’s intimidating to speak up and ask questions. It’s also frustrating and a little embarrassing when you estimate a story way off from the consensus of the rest of the team. The truth is, those kinds of estimates are really valuable!

To leverage value from moments like that, make estimation a safe space. Make it clear that there’s no such thing as a perfectly written story, and encourage teammates to ask questions when work items are unclear or need more context.

Remind your team that estimation meetings are for evaluating stories, not people. Having an estimation that’s drastically different from the rest of the team is okay. It reflects the need for more context; it doesn’t reflect on your intelligence. Don’t sweat it when a wild estimate inevitably happens.

Be Honest with Your Estimates

While this applies to the whole team, it’s especially important for new team members. If you feel overwhelmed during an estimation meeting, it can be tempting to guess what number your teammates will show rather than thinking through an estimate on your own. This “cheating” is especially easy in a digital world, where you can see everybody’s cursor pointing at their choice. Make sure to turn that feature off.

If you estimate based on a teammate’s estimate, you’re missing out on a great learning opportunity. If your estimate is twice as large as somebody else’s, it might be because you’ve never touched that part of the app and would need ramp up time. It might be because you don’t understand the story. It might be that you have no idea how implementing the story would work. Those are all valid reasons, and they indicate that you’ll need more context before you can be successful with that story. If you’re honest with your estimate, you can start probing around the project to find out what you don’t know.

Take Notes

Since nobody wants to sit in estimation meetings that go on for hours, take notes when you notice a learning opportunity. A new team member should take notes about stories they don’t understand. And a team member in a mentor role should take notes about patterns of misunderstanding or places where their teammate needs more context. Jot down a reference to the work item, plus a few words to remind you why the estimate was so far off.

Take a break after the meeting to stretch and clear your brain. Then pair up and go over the notes to start filling in more knowledge gaps about the system.

One thing I find particularly helpful about this system is that it front-loads learning. New teammates can start acquiring knowledge before the work gets into their queue. They’ll have time to digest the information and come back with any questions before starting, so they’ll be better equipped to contribute.