Standard check-in questions like "What did you do yesterday?" and "Any blockers?" barely scratch the surface of what teams need to discuss. They also generate predictable responses that rarely lead to meaningful insights or action.
With today’s guide, we want to empower you to craft custom questions that turn routine updates into more valuable conversations. You'll learn how to create questions that 1) surface hidden risks, 2) spark new insights, and 3) drive alignment without necessarily adding more meetings to your calendar.
The art of asking
The questions you ask determine the conversations you have. When you replace standard check-in prompts with more thoughtfully designed questions, you:
- Direct attention to what actually matters rather than what's easy to report
- Surface information that would otherwise remain hidden
- Create opportunities for team members to reflect more deeply on their work
- Build connections between individual efforts and broader team goals
💡 When you change your questions, you change our outcomes. Better questions will lead to earlier problem detection and more creative solutions.
How to craft effective custom questions for team check-ins
1. Start with your purpose
Different questions clearly serve different purposes, so before writing any question, clarify what you're trying to accomplish:
- Are you trying to uncover potential risks or you need better visibility into dependencies?
- Are you looking to capture new lessons across the team?
- Do you want to strengthen alignment with more strategic priorities?
Being clear about your purpose keeps questions focused and relevant.
2. Follow question design principles
Effective custom questions share several key characteristics:
- Open-ended but specific - They can't be answered with a simple yes/no but are focused enough to guide thinking
- Forward-looking - They prompt people to anticipate what's coming rather than just report what's done
- Insight-oriented - They ask for meaning and implications, not just facts and status
- Action-enabling - They lead naturally to decisions and next steps
3. Tailor your questions to your team context
The best questions reflect your team's specific situation:
- Work phase - Early, middle, or late in your delivery cycle
- Team maturity - New teams need different questions than established ones
- Current challenges - Focus questions on your most pressing issues
- Organizational priorities - Connect questions to what matters most right now
Question library: Use the right question at the right time
If you don’t want to start from scratch, we’ve prepared a collection of proven check-in questions organized by purpose. Use these as starting points and adapt them to your specific needs.
a) For surfacing hidden risks 🧑🚒
These questions help identify potential problems before they become crises:
✽ What assumptions are we making that, if wrong, would significantly change our approach?
✽ What's the weakest part of our current plan that we should be paying more attention to?
✽ What might prevent us from hitting our milestone, even if everything currently looks on track?
✽ What concerns about our approach have you not shared yet because they seemed too minor?
✽ If you had to place a bet on what will cause us trouble in the next two weeks, what would it be?
📖 When to use these questions: Early in projects, during planning phases, or when things seem to be going "too smoothly" (often a warning sign that risks aren't being surfaced).
b) For managing dependencies 🪢
These create visibility across team boundaries:
✽ What are we waiting for from other teams that might slow us down?
✽ Who might be waiting on something from us that we haven't prioritized yet?
✽ What upcoming changes in our work could impact other teams we work with?
✽ Which of our dependencies feels most at risk right now?
✽ What information do we need from other teams that we don't currently have?
📖 When to use these questions: When working on projects that involve multiple teams, during integration phases, or whenever coordination is crucial for success.
c) For capturing learning 📚
These add your individual insights into your team’s “knowledge base”:
✽ What have you learned recently that might change how we approach our work?
✽ What surprised you this week that others might find valuable to know?
✽ What's something you've noticed that doesn't quite make sense yet?
✽ If you could go back two weeks with what you know now, what would you do differently?
✽ What's a mistake you made that others could learn from?
📖 When to use these questions: After completing significant work, when experimenting with new approaches, or during retrospective-like moments.
d) For strengthening alignment 🏹
These questions connect daily work to bigger objectives:
✽ How does the work you're doing now connect to [your key quarterly objective]?
✽ What could we shift resources away from to better focus on our priorities?
✽ If we could only accomplish one thing this week to advance our strategy, what should it be?
✽ What are we spending time on that might not actually matter to our users/customers?
✽ What's one thing we could do differently that would make a bigger impact toward our goals?
📖 When to use these questions: During planning sessions, when priorities shift, or whenever the team seems to be losing sight of the bigger picture.
e) For improving team dynamics ☎️
Use these to strengthen how your team works together:
✽ What communication pattern on our team could we improve?
✽ Where do you need more clarity or direction from me or others?
✽ What decision have we been avoiding making that's slowing us down?
✽ How could we make it easier for team members to ask for help?
✽ What's one thing we could do to make our check-ins more valuable?
📖 When to use these questions: When onboarding new team members, after reorganizations, or whenever team dynamics feel strained.
Implementing custom questions
Now that you have a library of questions, here's how to implement them effectively:
Start small
Begin by introducing just one custom question alongside your standard check-in format. This creates space for the team to adjust to deeper reflection without overwhelming them.
For example, if you currently use a "yesterday/today/blockers" format, add: "What's one thing you learned yesterday that might help someone else today?" one day.
Create structured opportunities for questions
Designate specific moments for custom questions:
- Daily check-ins: Add one rotating question that changes [weekly / every X period of time]
- Weekly updates: Include 2-3 questions focused on risks and alignment
- Project milestones: Ask reflection questions at key completion points
- Quarterly reviews: Use the more strategic questions about direction and approach
Match question timing to work cycles
Different questions make sense at different points in your work cycle:
- Beginning of cycle: Questions about assumptions, approach, and dependencies
- Middle of cycle: Questions about emerging risks, necessary adjustments, and coordination needs
- End of cycle: Questions about learnings, outcomes, and implications for future work
For instance, designate Monday for alignment questions, Wednesday for dependency questions, and Friday for learning questions. It’s a simple rotation, but it keeps your communication fresh and relevant.
Set response expectations
Create clear norms around how team members should engage with responses:
- How quickly should people acknowledge or respond to others' insights?
- Who is expected to follow up on identified risks or dependencies?
- How should valuable learnings be captured for future reference?
💡 Create a simple "insights" document where particularly valuable responses are collected, creating an evolving knowledge base for the team.
Model thoughtful participation
As a leader, how you respond to questions sets the standard. Demonstrate:
- Vulnerability when discussing risks and uncertainties
- Connections between immediate work and broader objectives
- Appreciation for insights that challenge current thinking
- Follow-through when responses reveal needs for action
Work on your questions
Don't let your custom questions become stale routines:
- Review question effectiveness bi-weekly/monthly
- Retire questions that consistently generate superficial responses
- Introduce new questions based on current challenges
- Ask team members to suggest questions they find valuable
💡 Create a "question of the sprint" approach, introducing a new strategic question based on the team's current focus area.
Using custom questions in different check-in formats
Custom questions can enhance any check-in format, let’s see:
For asynchronous written updates (our favourite!)
- Keep status brief (bullet points for what's done/what's next)
- Add 1-2 custom questions that change weekly
- Highlight particularly valuable responses to show what "good" looks like
Example template:
✽ STATUS:
- Completed:
- Working on:
- Blockers:
✽ THIS WEEK'S QUESTION:
What assumptions are we making about the user experience that we haven't validated yet?
For synchronous team meetings
- Send status updates ahead of time
- Use meeting time to discuss responses to 1-2 key questions
- Capture actions that emerge from the discussion
A meeting agenda might look like:
✽ AGENDA:
1. Quick status highlights (5 min)
2. Discussion: "What dependencies between our workstreams might we be overlooking?" (15 min)
3. Actions and decisions (10 min)
For one-on-one check-ins
- Focus on development and support rather than status
- Use questions that prompt reflection on growth and needs
- Rotate between different focus areas week to week
Sample questions rotation:
✽ Week 1: "Where do you need more clarity or support from me?
✽ Week 2: "What part of your work has been most energizing lately?
✽ Week 3: "What skill would you like to develop further in the next few months?
How to assess and improve on your questions
So how do you know if your custom questions are working? You might notice:
- Problems surface before they become crises
- Dependencies are managed more smoothly
- Insights from one team member benefit others
- Work more consistently focuses on what matters most
- Team members contribute thoughtful responses
The ultimate measure of any team check-in is whether your questions lead to better decisions, fewer surprises, and more effective collaboration.
However, even well-designed questions can fall flat. Here's how to address these situations:
a) When questions yield superficial responses
If your questions consistently generate shallow answers:
- Make them more specific and contextual
- Provide examples of thoughtful responses
- Ask follow-up questions that probe deeper
- Acknowledge and appreciate depth when you see it
b) When questions feel like interrogation
If team members seem defensive about your questions:
- Clarify that the purpose is support, not evaluation
- Start by answering the questions yourself, modeling vulnerability
- Focus questions on the work rather than the individual
- Use "we" language: "What might we be missing?" vs. "What are you missing?"
c) When questions generate anxiety
If questions create stress rather than insight:
- Build psychological safety by responding positively to surfaced concerns
- Balance risk-focused questions with questions about progress and learning
- Make it explicit that raising issues is valued, not punished (and follow through)
- Follow up with support rather than judgment
From questions to conversations
In the end, custom questions are about creating different kinds of conversations.
When you ask your team questions that prompt more 1) reflection, 2) connection, or 3) foresight, you turn regular check-ins from the mechanical updates they usually are into more meaningful exchanges that drive action and alignment.
As we like to say, the most successful teams aren't those with the most meetings or the most detailed status reports. They're the ones who've learned to ask questions that matter and create space for the conversations that count.
So what question will you ask today?
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