T2. Ask First toolkit
Toolkit
Great leaders ask before they tell. They use curiosity to unlock insight, build trust, and strengthen relationships. Drawing on Edgar Schein’s idea of Humble Inquiry and Michael Bungay Stanier’s reminder to “stay curious a little longer,” this toolkit helps leaders prepare for a specific conversation where listening and questioning will make the most significant difference. Questioning well transforms leadership interactions from directives into discoveries.
| Identify the Conversation |
| Choose an upcoming meeting, coaching discussion, or corridor conversation where you want to understand before advising. Clarify the purpose of the exchange and what you hope to learn. |
| Clarify the Purpose |
| Before offering advice, pause and ask what outcome the other person wants to achieve. Understanding their goal ensures your support is relevant and valued. |
| Seek to Understand |
| Ask open, non-judgmental questions such as “What’s working well?” or “What’s getting in the way?” to fully explore the issue. Listen actively and reflect back what you hear. |
| Dig Deeper |
| Use follow-up questions or the Five Whys technique to uncover root causes rather than reacting to surface symptoms. Stay curious and avoid jumping to solutions. |
| Encourage Reflection |
| Help others find their own answers. Ask, “What options do you see?” or “What would you try next time?” to promote ownership and independent thinking. |
| Reflection Prompts |
| How did my questioning affect the quality of the conversation? Did my curiosity help uncover something new? When did I speak too soon instead of listening? What habits could help me make questioning my default mode? |
| Leadership Question Bank |
| To Build UnderstandingWhat’s working well right now?What challenges are you noticing?How are staff or students responding?What do you think sits behind that pattern?What would success look like for you in this area? To Deepen ReflectionWhat have you learned from this so far?If you could start again, what might you do differently?What do you think is the biggest barrier to progress?What assumptions might we need to test?Where might we be over-complicating things? To Encourage OwnershipWhat do you think the next step should be?What support do you need from me to make that happen?How will you know if this has made a difference?What’s one small change you could try this week?Who else could you involve to strengthen this? To Build RelationshipsWhat are you most proud of this term?What’s been the most energising part of your role recently?Where do you feel most confident right now?What’s something you’d like to develop further this year?How can I best support you to do your best work? To Challenge and StretchWhat’s stopping us from being exceptional here?What would this look like if it were ten times better?If resources weren’t an issue, what would you do?What’s the boldest move we could make in this situation?What would happen if we did nothing? |
T2. Ask First: example toolkit
Role: Deputy Headteacher
| Identify the Conversation |
| I have a coaching meeting with a Head of Department whose team’s marking consistency is drifting. I will begin with questions to understand causes before offering advice. |
| Clarify the Purpose |
| The goal is to embed feedback sustainably without excess workload. I will first ask what outcome the HOD wants, so my support aligns with their priorities. |
| Seek to Understand |
| I will ask open questions such as what is working, where the challenges are, and how students are responding. I will listen, paraphrase, and capture themes. |
| Dig Deeper |
| I will use follow-ups and the Five Whys to surface root causes, such as unclear expectations or uneven modelling, and avoid superficial fixes. |
| Encourage Reflection |
| I will ask what they could try next and what support they need to build ownership and confidence. Follow-up will be framed as a partnership. |
| Planned Follow-Up and Learning Loop |
| After three weeks, I will return to the same questions about what worked and what to adapt, reinforcing reflective habits. |
| Intended Impact |
| The HOD will feel confident diagnosing challenges and leading solutions. Marking consistency will improve through ownership and reflection, and curiosity will become a cultural norm. |