Great Diversity & Inclusion Questions to Ask Leaders

The corporate landscape is continuously changing, and with it, the emphasis on diversity, equity, and inclusion (DEI) has never been more critical. This guide sets out to equip you with strategic questions to explore the depth of DEI initiatives within your organization. Engaging leaders goes beyond inquiries or evaluation; it’s a step towards fostering a more inclusive, equitable, and diverse workplace.

The role of data in understanding DEI in the workplace

Like all organizational initiatives, dynamic and holistic diversity, equity, and inclusion (DEI) strategies require an insightful foundation of meaningful data points across the employee lifecycle. The right DEI data framework dispels assumptions by illuminating crucial gaps, opportunities, correlations, and impacts over time.

The importance of DEI data

Moving beyond basic demographic tracking, strategic DEI data analytics provide an X-ray revealing invisible facets of organizational culture. Metrics encompassing hiring equity, promotion rates, compensation, attrition, and retention patterns across demographic groups all provide indispensable perspectives. Additionally, granular engagement scores and sentiment pulsed from belonging surveys and focus groups add the flesh, blood, and heartbeat sensing inclusion’s lived impact.

Data-driven decision-making in DEI: Armed with insights from holistic DEI data analysis, leadership is empowered to charter an organization’s course toward equitable inclusion. This requires applying an intersectional lens to identify where invisible biases and barriers may unconsciously persist.

Organizations can set clear inclusion goals and timeline-driven metrics that can then progress through updated strategies adapted based on regular data review. Consistently linking data to policy and practice enhancements accelerates sustainable DEI change through accountability. In this way, data sheds light on the path organizations must walk – and gives leaders reasons to take each next step.

For example, using workforce composition data in the analysis can highlight diversity gaps, especially in the leadership team or certain departments. Thus, it can result in the development of targeted recruitment and development programs. Employee surveys provide a qualitative viewpoint, which makes the data more informative and rich by adding personal experiences and perceptions to it, thus, DEI strategies are formed more comprehensively.

With a deeper analysis of DEI, we can see the questions focusing on leadership commitment, strategies, and outcomes as the key to success. As we proceed, we will concentrate on the questions that can lead to the evaluation of DEI initiatives and form the basis of constant improvement and active participation across all levels in the organization.

The key is connecting DEI analytics to other HR data streams and operational impact. Which diversity variables most strengthen the innovation pipeline? How does inclusion correlate with customer loyalty or brand reputation scores amongst multicultural consumer groups? Where do DEI-driven gains or gaps show up on the balance sheet? Building out the full empirical picture accelerates the optimal allocation of DEI investments already delivering returns.

Key DEI questions for leadership

With meaningful DEI data as its foundation, securing leadership commitment remains essential to building an equitable, inclusive ecosystem from the inside out. Authentic buy-in addressing diversity, equity, and inclusion as interconnected foundational priorities multiplies DEI programs’ effectiveness.

The journey toward an affirmatively inclusive, engaging, and diverse culture is continuous, ever-evolving, and multipart. Leadership plays an indispensable role in championing this transformation. Hence, it is vital to engage them around meaningful questions assessing DEI progress. Below are key questions to consider:

1.     How do you define diversity and inclusion in our organization? Understanding a leader’s definition of DEI provides insight into the organization’s priorities.  Without it, organizations risk talking past each other or operating with mismatched, outdated or superficial definitions. Understanding how each leader conceptualizes and prioritizes DEI reveals gaps and common ground for aligning focus.

2.     What measures are adopted to diversify recruitment and retention? This question exposes the organization’s practical steps to attract and retain a diverse workforce. It’s all about getting to the deeper strategies beyond just policies to the actual implementation and impact.

3.     How do we measure the success of our DEI initiatives? Measurement and benchmarks are crucial for the evaluation of any DEI program. This question gives an idea about their effectiveness and if they result in something concrete.

4.     What training and resources are available to promote DEI education? DEI education is an ongoing process. The organization’s importance on educating its workforce on these vital issues can be determined by asking about available training and resources.

5.     How can we address unconscious bias and create a culturally inclusive environment? This question looks at what is done to prevent unconscious bias and to create an environment where all employees are valued and included.

6.     Could you give an instance of the dei initiative that has been successful in our organization? DEI success stories are a great source of motivation based on real-world examples. They clearly explain what has worked and how it can be applied or enlarged to similar situations

7.     How do we incorporate employee feedback and engagement into our diversity, equity, and inclusion strategy? Employee feedback is critical in ensuring that any DEI strategy is meaningful and impactful. This question probes how the organization is attentive and responsive to this feedback and uses it in DEI planning and implementation.

8.     How are we engaging underrepresented groups in leadership roles? Diverse leadership not only encourages a more inclusive culture but also provides a wide range of voices in decision-making. The question about support systems for underrepresented groups in leadership positions helps to understand how the organization deals with diversity from the top.

9.     What DEI implementation challenges have we faced, and how have we overcome them? Each DEI journey has its stumbling blocks. A good understanding and addressing these challenges can be a lesson and insight for future initiatives.

10.  As we Look into the future, what Is our top priority for improving DEI? This question asks about the vision of DEI’s future in the organization. It shows the long-term view and the fields of focus that will constitute the next DEI initiatives.

Engaging leaders on these issues brings transparency and accountability and gets leaders more committed to promoting DEI. It is a step towards the goal that DEI is not just a buzzword but a core element of the identity and values of the organization.


Beyond being an act of accountability, asking the right DEI questions to leaders is a fundamental step toward the organization’s comprehension and improvement of its commitment to these critical concepts. These questions mirror the current DEI landscape of an organization, showing its strong points and opening up the doors for further development.

No road map guarantees overnight inclusion transformation. But raising curiosity, accountability and transparency through ongoing dialogue promises steady progress in the right direction. Tracking inclusion indicators over regular intervals – quarterly or bi-annually – provides milestones proving measured change over time.

Kate Stone
Kate Stone
Kate Stone leads marketing at Diversio with 10+ years of experience in marketing and visual communications – over 6 of which are in the technology industry. Kate is passionate about communicating inclusion’s impact on businesses, workplace culture, and individuals. Kate is a US citizen and enjoys advocating for the environment and endangered species, improving her strength and endurance, and practicing watercolor painting and mixed media arts.
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Head of EDI, Canadian Institute for Advanced Research

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