Ask Your Dev Team how they report progress

If the only time you learn what your developer has been working on is when the invoice arrives, something is broken.

Weekly demos are non-negotiable

I’m not going to tell you to sit in daily standups. That’s your developer’s internal process, and it’s not a good use of your time. But a weekly video meeting where they show you working software is a must.

Not a slide deck. Not a status update email. Working software. Something you can see, click through, and react to.

Weekly demos keep the project honest. They surface misunderstandings early. And they give you a chance to course-correct before a small miscommunication becomes a two-week detour.

One important distinction: demos are not a replacement for updated dev or staging environments. You should have access to a running version of the software you can explore on your own time, not just during a scheduled meeting.

Proactive communication

A good developer surfaces problems before you have to ask. Blockers, risks, and budget concerns should come to you as soon as they’re identified, not at the end of a sprint or buried in a status report.

Ask your developer:

• “How will I know if we’re falling behind schedule?” The answer should involve early and direct communication, not silence until the deadline passes.
• “How do you handle blockers?” Sometimes they need a decision from you, sometimes they need to work around it. Either way, you should know.
• “Will I ever be surprised by a cost?” If the answer isn’t a confident “no,” dig deeper.

The rule is simple: no surprises. On anything.

Budget and billing transparency

Invoices should not be the first place you learn what something cost. Your developer should provide some regular cadence of updates on hours spent, budget remaining, and whether the current pace is sustainable.

You should have visibility into:

• Estimated work vs. actual cost, at the ticket, milestone, or phase level
• Current sprint progress and what’s in the backlog
• Hours or budget consumed relative to the overall engagement

This doesn’t require a specific tool. Jira, Linear, Notion, a spreadsheet — the tool doesn’t matter. What matters is that the information exists and you can see it.

What to ask

1. “What does a typical week of communication look like?” You’re looking for a rhythm: a weekly demo, regular async updates, and a clear escalation path.
2. “Where can I see what’s being worked on right now?” You should have access to whatever system tracks work in progress.
3. “How do you report on budget and hours?” Look for proactive reporting, not just invoices after the fact.
4. “What happens when something is going to cost more than expected?” The right answer is that they tell you before the overage, not after.

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Expect better. Build better.