Five Questions Founders Should Ask Their Technical Team Every Week

Why Weekly Check-Ins Matter

For founders, especially in high-growth or scaling startups, technical teams are the engine room of the business. But even the best teams can drift off course, get blocked, or miss critical risks if regular, meaningful conversations don’t happen. The right weekly questions can reveal hidden bottlenecks, align everyone on outcomes, and build a culture of trust and learning—without micromanaging.

Below are five questions that, when asked consistently, help founders stay connected to what matters most in their engineering teams.

1. What’s the most important thing we accomplished this week?

Why ask this?
It’s easy for teams to get lost in the weeds—shipping features, fixing bugs, or responding to customer fires. By focusing on the most important accomplishment, you help the team zoom out and connect their work to business value.

Follow-up prompts:

• Did this align with our priorities or roadmap?

• What impact did this have on our customers or business goals?

2. What’s blocking you or slowing you down?

Why ask this?
Blockers come in many forms—technical debt, unclear requirements, dependencies, or even team dynamics. When you create space to discuss obstacles, you show your team you’re invested in removing friction and enabling progress.

Follow-up prompts:

• Is this something I can help with, or do we need to escalate?

• Are there recurring blockers that we should address at the process level?

3. What’s one risk we’re not talking about enough?

Why ask this?
Unspoken risks—technical, organizational, or market-related—are often the ones that hurt the most. Asking about risks normalizes open dialogue and proactive problem-solving.

Follow-up prompts:

• What’s the worst-case scenario if this risk isn’t addressed?

• What’s a small step we could take this week to mitigate it?

4. What did we learn this week—about our product, process, or users?

Why ask this?
Continuous learning is the hallmark of resilient, high-performing teams. This question encourages sharing insights from experiments, user feedback, or even failures.

Follow-up prompts:

• How can we apply this learning next week?

• Should we share this insight with other teams or stakeholders?

5. What’s one thing we could do differently next week to move faster or smarter?

Why ask this?
Small, ongoing improvements add up to big gains over time. This question invites the team to propose process tweaks, tool changes, or new ways of working that drive efficiency and quality.

Follow-up prompts:

• Is there a process or tool that’s holding us back?

• What’s a small experiment we could try next week?

What the Experts Say

These five questions are rooted in best practices recommended by top engineering and product leaders:

• Marty Cagan (Inspired):
  “The key is to focus on what your team actually delivered for customers—not just what they worked on.”

• Camille Fournier (The Manager’s Path):
  “Ask your team what’s getting in their way, and listen for patterns. Bottlenecks rarely solve themselves.”

• Charity Majors (Honeycomb):
  “It’s not the risks you know about that hurt you—it’s the ones nobody’s talking about.” (Honeycomb Blog)

• Will Larson (Staff Engineer):
  “The most effective teams are learning organizations, always seeking to improve how they build and deliver.”

• Google re:Work Guides:
  “High-performing teams reflect regularly on what’s working, what’s not, and how they can improve.”

These questions also echo the weekly or biweekly rituals seen at companies like Stripe, Atlassian, and Shopify, where surfacing blockers and sharing learnings are built into engineering culture.

Closing Thoughts

Making these five questions a habit will help you spot issues early, drive alignment, and empower your technical team to create real business impact. Most importantly: don’t just ask—act on what you hear. When your team sees follow-through, you build credibility, trust, and momentum.

Ready to level up your technical leadership?
If you want a printable version of these questions or help customizing your team’s check-in process, let’s connect!