Two Questions for More Effective Work Sprints

Most of us have work and projects that will take us weeks and months to complete.

Important work should do that.

If it was quick or easy, it would’ve been done already. That’s what makes it work, and that’s what makes it important, that it takes time and effort.

In the Cave, we often ask “what are you working on today?” The invitation to Cavedwellers is to update their Zoom name and share that with a breakout group. But I actually think it’s not the best question. When we answer things like “that big presentation” or “my novel”, “taxes” or “updating my website” it can feel like we’re Sisyphus– fated to push a boulder up a hill forever before it rolls back down, never able to complete the task.

There’s a fear most of us have in approaching big projects and work– a fear of finishing. Because then we either have to share it with the world (eek!) or decide what we’ll work on next (ahhhh!).

But if we changed our question to:

“What are you here to accomplish today?”

we might help Cavedwellers get more specific. “The opening slides” or “Chapter 6 dialogue” or “collecting receipts” or “writing my bio.” And when we get more specific, we know what comes next and the process of working is smoother. Not only that, but we’re more able to determine whether we’ve finished it or not.

Ultimately, being specific can make facing our fear of finishing a little less scary. So. What are you here to accomplish?

. . .

At the end of every Cave, we ask our community to share a win. It helps finalize the experience of the Cave on a high note as well as allows them to see progress.
Most Cave Guides will also invite the question

“How did that sprint go?”

Not just about wins and accomplishments. That moment is a chance to reflect on our focus, on where we got distracted, on what distracted us and most importantly, how we could do better next time. Improving our relationship to work starts with approaching our work intentionally, includes the ability to evaluate how we work, and then to continually improve that.

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Caveday is a company aimed at improving your relationship to work. We write regular posts on Medium and send out monthly newsletters with productivity tips, life hacks, and recommendations. Sign up for the mailing list here.

Jake Kahana is a cofounder of Caveday. Sign up for his personal emails, called “The Email Refrigerator” here.