When it comes to technology projects—whether it’s e-commerce, websites, web applications, mobile apps, backend systems, integrations, or other initiatives—one of the first questions I often ask my clients is:

“What would a home run look like for you?”

I learned this powerful question from Jonathan Stark as a way to uncover the real outcomes my clients (& I) are striving for. It helps clarify your goals, align your team, and ensure everyone knows what success truly looks like.

But there’s another angle to this exercise. In Episode #7 of BizTech Superhero, Mat Winegarden introduced the concept of a Premortem for Tech Adoption.

Mat explained (paraphrased):

"When you're thinking about creating, buying, or implementing new technology, consider running a premortem. Ask yourself: 'Why did it fail?' This surfaces assumptions about the tool, clarifies misalignments, identifies adoption risks, and brings you back to the core problem you're trying to solve. It’s a way to define success by understanding failure."

I love this approach!

So, as you think about your next project—whether it’s technology, operations, staffing, or anything else—ask yourself two critical questions:

1. What would a home run look like if this went awesome?
2. What would a premortem reveal if it totally failed?

By thinking through both scenarios, you'll solidify your goals, roles, risks, and opportunities, which will give you a better foundation for success.

Your tech pal,

—Joshua

P.S. Ready to hit a home run with your next business or tech project? Let me know if I can help.

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Did you know you can book a one-off advisory meeting on-demand? If you're facing a challenging business or technology issue, I'd be happy to offer actionable advice to move you forward. Learn more & book here.

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Disclaimer: I use AI to help write emails like these. I review & edit all AI-assisted work I publish.