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By SteveOctober 23, 2024In Strategy

42 Questions Marketing Leaders Should Ask

Abstract – Asking the right questions is more important than ever for marketing leaders. This article presents 42 thought-provoking questions marketing leaders should ask across seven key areas: leadership, stakeholders, team, clients, market, data, and personal reflection. These questions challenge conventional thinking, encourage deeper insights, and drive strategic decision-making. By exploring these questions, marketing leaders can foster transparency, uncover hidden opportunities, and ensure their strategies are aligned with long-term business success.

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  19 Minutes Read

Questions Marketing Leaders Should Ask to Drive Strategy and Growth

In an age of data-driven decision-making, marketing leaders are expected to navigate constant change while driving growth and innovation. Yet, success often comes from asking the right questions—not just of your data, but of your team, stakeholders, clients, and even yourself. According to a recent study, 58% of companies say they base their business decisions on incomplete data, leading to missed opportunities and inefficiencies. This highlights the importance of asking deeper, more challenging questions that uncover hidden insights.

The questions marketing leaders should ask are not always obvious; they should provoke thought, inspire action, and challenge the status quo. Whether it’s aligning with C-suite priorities, understanding client needs, or keeping your team motivated, asking the right questions can be the key to sustained marketing success. In this article, we explore 42 critical questions marketing leaders should ask to help navigate complexity, drive impact, and future-proof their strategies.

Questions to Ask Your Leadership

The C-suite and board members are pivotal in shaping the organisation’s vision and strategy – so asking the right questions of them ensures that marketing efforts are aligned with the company’s long-term goals and values, creating cohesion at the highest levels of decision-making.

1. What are we not willing to sacrifice for growth?

Knowing what you won’t compromise defines the integrity of your strategy.

Why ask this?
This question forces leadership to establish clear non-negotiables, clarify where ethical, operational, or cultural lines are drawn and ensure growth doesn’t come at the cost of the company’s core values. By defining these limits, leadership can avoid decisions undermining the company’s long-term sustainability and reputation. It encourages a focus on growth that aligns with integrity, attracting stakeholders who respect those boundaries.

2. If we vanished tomorrow, would our market miss us—or simply replace us?

If your absence doesn’t leave a gap, your presence doesn’t add value.

Why ask this?
It challenges leadership to assess the company’s genuine impact and uniqueness in the market, which shifts the conversation from mere market presence to creating indispensable value. This question drives leadership to think beyond short-term performance and prioritise building deep, lasting customer relationships. The outcome is a sharper focus on innovation and distinctiveness, ensuring the business occupies a critical, irreplaceable role in the market.

3. Are we solving problems we think exist, or the ones our customers actually feel?

Focus on the customer’s reality, not your perception of it.

Why ask this?
Marketing leaders often operate under internal assumptions that can skew their company’s strategy or confuse strategy vs tactics. By utilising the questions marketing leaders should ask, they are forced to realign their efforts with their customer base’s actual pain points and priorities. These questions ensure that strategic decisions remain customer-centric and grounded in actual market needs. The result is more effective solutions, higher customer satisfaction, and increased brand loyalty.

4. How much of our success is driven by our strategy versus external forces?

A lucky break can disguise a weak plan. Try to distinguish between strategy and serendipity to build sustainable success.

Why ask this?
Leaders often attribute success to well-executed strategies without considering the role of external circumstances. This question promotes a clear understanding of how much is truly within their control and what might be attributed to market conditions, timing, or luck. By differentiating between internal performance and external forces, leadership can develop more robust, adaptable strategies. This self-awareness reduces overconfidence and prepares the business for market shifts, ensuring long-term stability.

5. What’s the one metric we’re afraid to measure but should?

The numbers we avoid often reveal the truths we fear.

Why ask this?
Many businesses shy away from measuring certain KPIs that may expose uncomfortable realities. This question encourages leadership to confront potential weaknesses head-on and embrace transparency, and by focusing on these neglected but critical metrics, the business can identify blind spots and address critical issues. 

6. Does our leadership inspire confidence, or compliance?

Leadership isn’t about power; it’s about influence. People follow passion, not titles.

Why ask this?
This question helps leaders reflect on their influence within the organisation and distinguishes between leadership that motivates and inspires versus leadership that relies on authority and compliance. If leaders inspire confidence, they foster a culture of innovation, ownership, and collaboration. The outcome is a more engaged and proactive team that drives the business forward rather than merely executing instructions. This leads to higher performance and morale across the organisation.

Questions to Ask Your Stakeholders

Stakeholders are invested in the success of your business, but their perspectives often go unexamined. By asking these critical questions, you can align their expectations with marketing initiatives, ensuring sustained support and minimising potential friction.

7. What outcome would make you pull your investment from us?

Every relationship has breaking points; the wise marketer knows what they are.

Why ask this?
Marketing leaders need to understand why stakeholders invest and what might drive them away. Knowing these red lines can help pre-emptively address issues that may undermine confidence. By understanding potential deal-breakers, marketing can align strategies that reinforce stakeholder confidence. This transparency leads to proactive measures safeguarding relationships and ensuring continued support despite market fluctuations.

8. How much risk do you think we should be taking, versus what we’re actually taking?

Marketing innovation requires calculated risk, but not at the expense of trust.

Why ask this?
Marketing leaders often push boundaries, but knowing how much risk stakeholders are comfortable with ensures that innovation doesn’t jeopardise investment. Unfortunately, misaligned risk can lead to tension or hesitation in support. This question fosters alignment between marketing’s ambition and stakeholders’ tolerance, and the result is a balanced approach, where innovative marketing initiatives proceed with full stakeholder backing, leading to more consistent funding and less internal resistance.

9. What’s the most unspoken expectation you have of us?

Unmet expectations lead to frustration, even when they’re never voiced. Marketing succeeds when it meets explicit and implicit needs.

Why ask this?
Stakeholders may have expectations they don’t articulate, assuming they are understood. This question helps uncover hidden pressures that could influence their satisfaction with marketing performance. Uncovering these unspoken expectations allows marketing leaders to realign efforts and priorities. 

10. What long-term challenges do you see that we’re not addressing today?

Marketing is about foresight, not just responding to present needs. Stakeholders often have a broader view of long-term risks.

Why ask this?
Stakeholders may see long-term risks or market shifts that internal teams overlook. This question ensures that marketing strategies are forward-looking and address emerging challenges before they become critical. This question sharpens a marketing leader’s ability to future-proof strategies. By proactively addressing potential challenges, marketing can build resilience and maintain stakeholder confidence, even in the face of long-term uncertainties.

11. Are we investing in relationships that are likely to still matter five years from now?

Short-term partnerships may boost immediate results but can hinder future growth.

Why ask this?
Marketing often focuses on immediate wins, but stakeholders are interested in sustainable growth. This question prompts marketing leaders to think long-term about the value of partnerships and client relationships. Focusing on lasting relationships ensures long-term business health, and the outcome is a marketing strategy that doesn’t just chase short-term results but builds a strong foundation for sustained success, earning stakeholder respect and trust.

12. What would you want to see us do, that no one else in our market is doing?

Stakeholders often have a unique perspective on where bold moves can be made.

Why ask this?
Stakeholders can offer fresh insights on how the company can stand out. By leveraging the questions marketing leaders should ask, they encourage stakeholders to highlight what’s missing in the market, allowing marketing leaders to tap into opportunities for differentiation and competitive advantage. These questions foster innovative thinking and may uncover unique opportunities competitors aren’t exploring. The result is a marketing strategy that positions the brand as a market leader, meeting stakeholder expectations for innovation and growth.

Questions to Ask Your Team

Your marketing team is on the frontlines of execution. Their insights and frustrations can offer invaluable feedback that drives strategy. Asking these questions fosters transparency and empowers your team, unlocking their full potential to innovate and deliver results.

13. What’s the one strategic decision we’ve made that you disagree with, but won’t say?

The most valuable insights often come from dissenting voices.

Why ask this?
Marketing leaders need candid feedback to refine their strategies. Team members may hesitate to voice disagreement, but uncovering it ensures that potential blind spots are addressed before they become issues. By encouraging honest feedback, this question fosters a culture of transparency and trust. The outcome is more robust, resilient strategies that benefit from the full spectrum of team input, not just the consensus.

14. How would you still achieve your goals if we had 20% fewer resources?

Innovation thrives on constraints. Limited resources breed creative solutions.

Why ask this?
Marketing teams often face budget cuts or operational constraints. Focusing on the questions marketing leaders should ask prepares teams to think creatively about resource allocation and strategic prioritisation, ensuring they can still deliver results in lean times. These questions drive efficiency and spark creative problem-solving. The result is a team that becomes more adaptable and resourceful, maintaining or exceeding performance expectations under challenging conditions.

15. How would you run this department differently if you were in charge?

Those on the ground often have the clearest view of what needs to change.

Why ask this?
Team members often have valuable insights into how processes or strategies could improve. By encouraging them to think like leaders, you foster innovation and identify areas for growth that may be overlooked at the leadership level. The team feels empowered and valued, leading to greater engagement and initiative. 

16. What is one customer problem that frustrates you because you can’t fix it?

Marketing success relies on addressing real customer issues, not just promoting solutions.

Why ask this?
Your marketing team often has direct insights into customer issues but may feel powerless to address them. Identifying these frustrations can reveal opportunities for strategic improvements that better serve the customer. By acting on these insights, marketing leaders can make their strategies more customer-centric. The outcome is a more effective marketing effort that addresses real needs, improving customer satisfaction and loyalty.

17. Where do you feel your voice isn’t being heard within our team?

Inclusivity breeds innovation, and unheard ideas are wasted opportunities for growth.

Why ask this?
Teams often feel there are hierarchies in whose opinions carry weight. This question encourages marketing leaders to ensure inclusivity and make space for all team members to contribute meaningfully. Fostering an environment where every voice is valued leads to a more collaborative, innovative, and motivated team. The net result is a culture of inclusivity that drives creativity and helps the team function at its highest potential.

18. If you were poached tomorrow, what’s the one reason you’d go?

Understanding why people leave is as important as why they stay.

Why ask this?
Retention is a key challenge for marketing teams, especially in competitive industries. By addressing this question head-on, marketing leaders can uncover underlying issues that might otherwise go unspoken until it’s too late. By addressing retention concerns proactively, marketing leaders can create a more engaging, supportive, and rewarding environment. 

Questions to Ask Your Clients

Clients are your company’s lifeblood. Understanding their real needs and concerns ensures that your marketing efforts meet and exceed expectations. These questions help deepen client relationships and ensure your services remain relevant and valued.

19. What’s the one thing you wish we’d stop doing?

Knowing what irritates your client is as important as knowing what delights them. True partnerships evolve through honesty, not avoidance.

Why ask this?
Clients may tolerate aspects of your service that frustrate them, but unvoiced concerns can harm the relationship over time. By focusing on the questions marketing leaders should ask, constructive criticism is invited, helping to improve the client experience. Addressing these frustrations allows marketing leaders to eliminate friction points and strengthen relationships; the result is a more satisfied client who feels heard and valued, ultimately increasing loyalty and retention.

20. What’s the last time our solution genuinely surprised or delighted you?

Surprises strengthen emotional bonds in professional relationships.

Why ask this?
Understanding what aspects of your service resonate with clients allows marketing leaders to repeat and scale these moments. This question helps identify where your brand excels beyond basic expectations. By focusing on what delights clients, marketing leaders can create experiences that foster deeper connections. This can lead to increased client satisfaction and advocacy, with clients more likely to recommend your services.

21. What problem are we solving for you that you didn’t realise we were solving?

Your clients may not fully understand the value you provide; hidden value often goes unnoticed until it’s highlighted.

Why ask this?
Sometimes, clients benefit from your services in ways they don’t immediately recognise. This question reveals the hidden value your marketing efforts provide and can help shape future communication strategies to highlight these benefits better. By uncovering hidden value, marketing leaders can refine their messaging and strengthen the perception of the brand’s relevance. The result is a more deeply appreciated service, increasing client satisfaction and loyalty.

22. If you had to explain why you work with us in one sentence, what would you say?

The simpler the reason, the stronger the value proposition.

Why ask this?
This question forces clients to distil their reasons for working with you into a simple, compelling statement. It’s a litmus test for understanding the essence of your value from the client’s perspective. The insight gained from this question can sharpen your marketing message, ensuring it aligns with the real reasons clients choose you. The by-product is more transparent communication and robust positioning in future client interactions and marketing campaigns.

23. What’s one question about our product or service you’ve never asked but should?

Clients may avoid critical questions that could expose gaps or opportunities. Encouraging curiosity deepens trust and transparency.

Why ask this?
Clients may have concerns or uncertainties they’ve never voiced, either because they assume the answer or feel uncomfortable asking. This question invites those deeper discussions, uncovering areas for improvement or innovation. By addressing unasked questions, marketing leaders can pre-emptively resolve issues and build a stronger foundation of trust. 

24. Who would you recommend us to, and why haven’t you yet?

Referrals are the ultimate endorsement, but hesitation tells a story. Understanding the barriers to recommendation reveals gaps in satisfaction.

Why ask this?
Referrals are a key indicator of client satisfaction, but hesitation to refer you can indicate underlying concerns or unmet expectations. This question helps marketing leaders understand why clients may not actively promote their services. Marketing leaders can strengthen the relationship and encourage future advocacy by identifying and addressing why clients aren’t referring you. The result is an increased likelihood of referrals, which can drive growth and reputation in the market.

Questions to Ask Your Market

The market dictates the landscape in which you operate. By asking the right questions, you can stay ahead of industry trends, identify new opportunities, and avoid the traps that competitors fall into. These insights ensure your marketing strategy remains forward-thinking.

25. What are the uncomfortable truths in our industry that no one is talking about?

Every market has its blind spots.

Why ask this?
This question prompts marketing leaders to explore industry-wide challenges that are often avoided or overlooked. This helps identify areas where the market is stagnant or resistant to change, offering opportunities for innovation. By addressing these uncomfortable truths, your marketing strategy can lead the conversation and drive industry change. The ‘big win’ is a competitive advantage, as your brand is seen as progressive and willing to tackle tough issues head-on.

26. Where are the gaps between what we say we offer and what the market truly values?

Marketing that speaks to real needs wins over marketing that shouts promises. The market’s values dictate your relevance, not your brand’s narrative.

Why ask this?
Marketing leaders must ensure that their messaging aligns with the market’s priorities. This question challenges you to look beyond your internal positioning and check if your message truly resonates with the market’s values. Closing this gap between messaging and market expectations strengthens credibility and trust. The outcome is more authentic marketing campaigns that deliver on promises, improving brand loyalty and reducing customer churn.

27. What is our market moving towards, that we’re actively moving away from?

Innovation must be market-driven, not just internally inspired.

Why ask this?
Markets evolve, often in directions that companies may not foresee or may even resist. This question helps marketing leaders identify where they might be misaligned with emerging trends and where course correction is needed to stay competitive. Recognising where you’re diverging from the market allows you to adapt your strategy before it’s too late. The result is greater agility and a brand that remains relevant in the face of changing market conditions.

28. What’s the most popular trend in our market that we should ignore?

Being selective about trends shows discernment, not risk aversion.

Why ask this?
Marketing leaders often feel pressured to follow the latest trends, but not all are valuable or sustainable. This question forces you to critically evaluate which trends align with your brand’s long-term strategy and which are distractions. By consciously choosing which trends to ignore, you focus your resources on a more meaningful, long-term approach. 

29. What are our competitors too scared to do, that we should embrace?

Innovation happens when you’re willing to take risks others avoid and bold moves often create the biggest market shifts.

Why ask this?
Competitors often avoid certain strategies or innovations out of fear of failure or risk. The questions marketing leaders should ask encourage exploration of areas where competitors hesitate, potentially uncovering untapped opportunities for differentiation. Embracing bold, uncharted territories can set your brand apart and establish leadership in new spaces. The result is a competitive advantage that positions you as a risk-taker and innovator, attracting attention and market share.

30. If our industry vanished tomorrow, what would our customers do instead?

Dependency on the status quo is a liability. Understanding alternatives reveals where your true value lies.

Why ask this?
This question challenges marketing leaders to think beyond the current industry framework and imagine a world where customers find alternatives. It forces a reassessment of how indispensable your offering truly is. By identifying what customers would turn to if your industry vanished, you can future-proof your brand by strengthening its unique value propositions. The outcome is a more resilient business model prepared for disruptive changes in the market.

Questions to Ask Your Data

Data is one of your most powerful assets, but it’s only as valuable as the questions you ask of it. These questions will help you uncover insights that drive smarter, more effective marketing decisions, ensuring you stay data-driven and develop analytics maturity rather than data-overwhelmed.

31. Which data point do we spend too much time on, and why?

Not all data is worth your attention. Focusing on the wrong metrics leads to misleading insights.

Why ask this?
Marketing leaders often fall into the trap of over-analysing data points that seem important but don’t contribute to meaningful action. This question encourages a reassessment of which metrics drive business decisions. By shifting focus from superficial data to actionable insights, marketing leaders can streamline decision-making and improve the effectiveness of their strategies. The outcome is a more data-driven approach that enhances performance outcomes rather than simply reporting numbers.

32. What’s the one question we aren’t asking our data, but should be?

The answers are often there, if you ask the right questions. Data reveals its true value through curiosity, not routine analysis.

Why ask this?
This question prompts marketing leaders to explore untapped insights beyond standard reports and metrics. It encourages critical thinking about what’s missing in the current data analysis process. By asking new questions of your data, you open the door to discovering previously overlooked opportunities or challenges. The result is richer insights that can inform more nuanced and effective marketing strategies.

33. How much of our data is historical versus predictive, and does that balance need to change?

Historical data tells you where you’ve been; predictive data tells you where to go. Focusing too much on the past can blind you to future opportunities.

Why ask this?
Marketing strategies rely heavily on historical data, but predictive insights are critical for future planning. The questions marketing leaders should ask encourage a shift from reactive to proactive decision-making, ensuring data drives growth and forward-thinking strategies. Balancing historical and predictive data helps marketing leaders prepare for future trends and shifts rather than simply analysing past performance. The result is a more agile, forward-looking marketing strategy that can better navigate changing market conditions.

34. Where does our data lie to us because of context or bias?

Data isn’t always objective; it’s shaped by how we collect and interpret it.

Why ask this?
Data is often influenced by how it’s collected, analysed, and presented, leading to potential biases. This question forces marketing leaders to evaluate whether their data might skew their understanding of performance or market conditions. Marketing leaders can make more accurate, reliable decisions by identifying and correcting for biases. 

35. What’s the most valuable insight that we consistently fail to act on?

Knowing isn’t enough—marketing leaders must use data to drive change. Consistent inaction on valuable data is a strategic failure.

Why ask this?
Marketing leaders may recognise valuable insights but fail to act due to operational inertia or conflicting priorities. This question prompts them to reflect on the gap between data-driven insights and their execution. Marketing leaders can unlock new growth opportunities or improve existing strategies by acting on previously neglected insights. The outcome is a more decisive, action-oriented approach to data that fuels tangible business results.

36. If we could only keep one dataset, which one would have the most long-term value?

Marketing leaders must prioritise data that drives sustainable growth.

Why ask this?
In a world overloaded with data, it’s crucial to identify which data points have enduring value. This question forces marketing leaders to prioritise the information that will continue to offer strategic insights over time. By identifying the most valuable dataset, marketing leaders can focus their efforts on long-term trends and patterns, ensuring that their strategies are based on enduring truths rather than fleeting metrics. This ensures a more resilient, long-term approach to data-driven decision-making.

Questions to Ask Yourself

Self-reflection is vital for personal and professional growth. These questions encourage you to step back, assess your leadership, and challenge the assumptions that may be limiting your effectiveness. Asking yourself these tough questions ensures you remain a dynamic, adaptive marketing leader.

37. Am I spending more time managing than I am learning?

Leadership without learning leads to stagnation. Continuous learning fuels innovation and relevance.

Why ask this?
Marketing leaders can become so focused on day-to-day management that they neglect personal and professional development. This question encourages reflection on whether enough time is devoted to learning new skills and insights to stay competitive. By prioritising learning, marketing leaders ensure they stay ahead of industry trends and maintain fresh perspectives. The outcome is enhanced decision-making, creativity, and long-term professional growth, which benefits the organisation.

38. Do I make decisions based on what’s right for the business, or what’s right for my career?

True leadership aligns personal ambition with business needs.

Why ask this?
This question forces a hard look at whether personal motivations influence strategic decisions. It helps marketing leaders stay aligned with the business’s best interests rather than prioritising short-term career gains. Marketing leaders foster trust, credibility, and more substantial alignment with company goals by focusing on the business’s long-term success. You will benefit from more sustainable decision-making and a reputation as a selfless, forward-thinking leader.

39. What am I holding onto that is no longer serving me—or the business?

Sometimes letting go is essential for growth. Marketing leaders must evolve or risk becoming obsolete.

Why ask this?
Some strategies, habits, or assumptions may no longer be relevant as industries and markets evolve. This question helps marketing leaders identify areas where they may be holding onto outdated practices that must be reconsidered or abandoned. By letting go of what no longer serves the business, marketing leaders create space for innovation and new approaches. The outcome is a more agile, adaptive leadership style that keeps pace with change.

40. What’s the last time I took a risk and it didn’t pay off? Why not?

Failure is a powerful teacher if you’re willing to learn from it. Marketing leaders must embrace calculated risks while learning from their mistakes.

Why ask this?
Marketing leaders who don’t reflect on failed risks miss valuable learning opportunities. This question encourages a candid assessment of past risks, helping leaders understand why certain initiatives didn’t succeed and what they can learn from them. By analysing past failures, marketing leaders can make more informed decisions in the future, refining their risk-taking strategies. The result is a more courageous yet calculated approach to innovation, driving smarter experimentation and growth.

41. How often am I more focused on being right, rather than being effective?

Ego can derail success. Effective leaders prioritise outcomes over personal validation.

Why ask this?
The questions marketing leaders should ask help determine whether ego interferes with making the business’s best decisions. These questions shift attention from proving a point to ensuring the best outcomes for the team and organisation. By prioritising effectiveness over personal validation, marketing leaders can foster a more collaborative and results-driven environment. The result is better team alignment, more robust performance, and a culture where ideas are judged on merit rather than authority.

42. If I weren’t in this role, would I admire how I’ve led?

Perspective reveals true leadership impact.

Why ask this?
This question prompts marketing leaders to step outside their positions and view their leadership objectively. It encourages reflection on how they’ve handled challenges, relationships, and responsibilities. By fostering self-awareness, this question drives improvements in leadership style and decision-making. The end goal is a more empathetic, authentic leader who earns the respect and admiration of their team, stakeholders, and peers.

Conclusion

The questions marketing leaders should ask are not just a tool for better decision-making but a pathway to deeper insights and lasting success. By consistently challenging assumptions, encouraging transparency, and embracing innovation, marketing leaders can align their strategies with both internal and external needs. These questions are designed to provoke thought, drive action, and ultimately ensure that marketing efforts are both practical and adaptable. Asking the right questions is the key to staying ahead and fostering long-term growth for your organisation.

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