How Do You Answer That? Managing Tough Questions

Understand ‘the why’ behind the question.

– Dr. KK Owen

Every season in schools offers the opportunity to answer new and different questions. It’s highly probable that people won’t like, don’t agree with or will actively oppose the answers given. In this roundtable, Leader Coach Dr. KK Owen shared a recording from a recent Destination High Performance conference where she was joined by Dr. Janet Pilcher to tackle tough questions with effective responses.

In the roundtable, KK shared tough questions she’s been hearing recently from leaders in education. Additionally, our attendees had the opportunity to ask how to respond to their tough questions. Leader Coach Dr. Kathy Oropallo joined KK to help answer those questions and share helpful resources, including:

To view the recording, enter the recording passcode when prompted.
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Roundtable Resources


Tough Questions Worksheet | 9P

Unit your voices. Your stakeholders have a lot of questions about the ins and outs of your organization. Be ready to answer tough questions by preparing your leadership team with unified answers.

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Leader Connection Questions | 9P

The highest performing leaders are able to make the best decisions when they have solid and trusting relationships with others. To build trusting relationships, leaders regularly converse with employees about their work and transparently take action, showing employees they are valued. When combined with effective follow-up by leaders, this practice of checking in with employees also increases engagement and leads to improved outcomes across the organization.

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Leader reviews the data that makes the biggest impact on decision-making for improvement.

Effectively Using Data to Make Tough Decisions | Roundtable

In this roundtable, Dr. Pat Greco was joined by SDMF Superintendent Cory Golla, Director of Teaching and Learning Casey Blochowiak, and Leader Coach Robin Largue for a roundtable discussion to learn from in-the-field experts have built an “army of improvers” in the district, where staff is learning how to increase student engagement, improve parent confidence, keep their people safe and sustain learning outcomes in 45-day cycles of improvement.

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Did that Question Catch you Off Guard?

Tough questions arise from staff and employees, external stakeholders such as customers, families and the media – who all want to be informed. In addition, the number of tough questions we receive typically increases as we announce changes or decisions to relevant parties. Although we can’t eliminate tough questions altogether, we can communicate effectively and prepare to answer the questions that remain.


Toolkits are developed by our experts to guide leaders with a framework for complex solutions. View and download our interactive toolkits on communicating using the Execution Triangle, results rollout, execution and improvement, crisis communication and more.

Future Roundtable Sessions

Each week, our coaches lead a discussion with a community of leaders who are facing similar challenges. These 60-minute sessions are free and allow opportunities to learn from expert leadership coaches and have candid conversations with other leaders about barriers, share successful practices and re-center on what works.

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