The Two Questions That Drive Long-Term Success in Customer Relationships

Have you ever delivered exactly what was requested, only to find it wasn’t what the customer truly needed? Asking the right questions can make all the difference.

Great leaders and customer-facing professionals aren’t just good at solving problems—they excel at uncovering the right problems to solve. Whether you’re working with internal teams or external customers, it’s easy to focus on "what" questions, such as “What does the customer want?” However, true value comes from asking "why" and "how" questions, which lead to deeper understanding, strategic alignment, and creative solutions.

The Framework: How to Ask "Why" and "How" Effectively

This simple framework can be applied in any customer-facing role, whether you’re collaborating with external customers or managing internal projects.

1.?Start with Context ("What") Define the Request: Begin by clarifying the immediate ask or challenge. This ensures you understand the customer’s perspective and sets the stage for deeper exploration.

2. Dig Deeper ("Why") Uncover Motivations and Connect to Strategic Goals: "Why" questions go beyond identifying the root cause of a problem. They provide insight into motivations, challenge assumptions, and help align actions with long-term goals. This approach fosters a deeper understanding of challenges and sets the stage for effectively asking ‘how’ in the next step.

?3.?Guide the Solution ("How") Create Tailored Solutions: Now that you have a deeper understanding of the objective, use "how" questions to collaboratively explore various approaches and ensure alignment with strategic goals. This step allows you to communicate more effectively, involve the right stakeholders, and design solutions that address both short-term needs and long-term objectives. By fostering broad alignment and creating a shared sense of ownership, "how" questions enable you to move beyond reactive problem-solving and develop impactful, sustainable solutions.

Example from My Experience: Creating a Collaborative Roadmap for Long-Term Success

Let me share an example from my experience to show how this framework helped solve a customer’s challenge and set us up as a long-term partner.

A customer expressed concerns that our support wasn’t consultative enough, and they weren’t seeing the results they expected, leaving them frustrated and uncertain about the direction of their efforts.

• Start with Context ("What")

?Begin by understanding the customer’s expectations with questions like: “What specific results are you expecting?” and “What areas do you feel are not meeting expectations?”. We observed that the customer’s focus on short-term priorities was not yielding the desired results, which highlighted a disconnect between their operational efforts and long-term goals. This understanding set the stage for deeper discussions about strategic alignment.

• Dig Deeper ("Why")

To explore Short-term focus, I asked, “Why do you think these priorities haven’t delivered the results you hoped for?”. This question was aimed at helping the customer reflect on whether their focus on short-term goals was detracting from their ability to achieve long-term strategic outcomes. This revealed that their immediate priorities lacked connection to long-term objectives. After detailed discussion with customer, it was important to assess internal contributions as well, so I asked our team, “Why haven’t we proactively guided the customer to align operational goals with their strategic vision?”. This identified that we have a gap in collaboration and planning.

• Guide the Solution ("How")

I then asked myself, “How should we create a process that ensures both teams’ efforts are aligned with strategic goals while providing the transparency needed for success?” This led to the creation of a roadmap that included both short-term and long-term objectives. The roadmap involved contributions from all key stakeholders, including customer leadership, operational managers, and our internal teams. This collaborative effort ensured alignment, transparency, and shared accountability across both organizations.

Outcome: By uncovering the root causes behind the customer’s dissatisfaction and lack of strategic alignment, we created a roadmap that enabled tailored solutions for both short-term wins and long-term objectives. The roadmap involved contributions from all key stakeholders—customer leadership, operational managers, and our internal teams. This roadmap was not intended as a quick fix but as a strategic step in the right direction, ensuring that long-term objectives were not ignored. It brought the right people to the table and facilitated meaningful discussions, fostering alignment, transparency, and shared accountability. This process empowered the customer with a clear direction and strengthened our partnership as a consultative partner.

Expanding the Framework’s Impact Across Scenarios

Beyond the detailed example shared earlier, these quick scenarios demonstrate how 'why' and 'how' questions can unlock impactful solutions in different contexts.

Scenario 1: Rethinking Project Delays for Efficiency

Request: “We need to extend the project timeline.”

• Start with Context: “What specific reasons are driving the request for a timeline extension?”
• Ask Why (Customer): “Why do you think the delays are unavoidable? Are there inefficiencies or dependencies on your side that we can address?”
• Ask Why (Internal): “Why haven’t we identified and mitigated these risks earlier? Are there internal bottlenecks or misalignments?”
• Follow Up with How: “How can we revise our approach to gain efficiency or reduce costs during the delay, ensuring value for both teams?”

Outcome: By asking the right questions on both sides, we identified areas where tasks could overlap or run concurrently without compromising quality. We also streamlined resource allocation internally and provided the customer with strategies to improve staff availability for critical phases. This approach minimized the cost impact of the delay and demonstrated our commitment to efficiency and strategic thinking, fostering greater trust and collaboration with the customer.

?Scenario 2: Transforming a Request for More Reports into a Strategic Solution

?Request: “We need additional reports to improve operational insights.”

• Start with Context: “What specific data points do you feel are missing?”
• Ask Why: “Why do you need these additional reports? Are there inefficiencies or manual processes we can address?”
• Follow Up with How (Internal team): “How can we help our customer better leverage existing tools to address their needs?”

Outcome: This framework allowed us to uncover that the customer needed visibility into operational metrics for Executive Leadership. During discussions, we identified that the customer’s challenges weren’t due to a lack of reporting or data but an underutilization of existing BPM dashboards. Collaboratively, we worked on customizing these tools and training their teams. This approach empowered the customer to effectively use the BPM dashboards, reducing their dependency on custom reports and enabling them to gain operational insights more efficiently. The result was a streamlined process that addressed their immediate concerns while building confidence in the system’s capabilities.

While these scenarios demonstrate the transformative power of "why" and "how" questions, implementing this framework isn’t without its challenges.

Addressing Challenges

Here’s how to tackle these barriers more effectively and ensure impactful outcomes:

Lack of Confidence

• Challenge: Fear of seeming intrusive or confrontational.
• Solution: Reframe your questions as collaborative inquiries to foster trust.

For example: Instead of asking, “Why are you doing it this way?” reframe as, “Can you help me understand how this process was designed? I’d love to align our solution with your approach.”

Create an environment where customers feel comfortable sharing their challenges without defensiveness.

Insufficient Preparation

• Challenge: Struggling to ask meaningful questions without enough context.
• Solution: Come to the table prepared:

Research and Analysis: Review the customer’s background, current workflows, and pain points. Use pre-meeting notes or team briefings to anticipate potential needs.

Predefined Questions: Prepare open-ended "why" and "how" questions that encourage deeper discussions. For example: "Why do you feel this approach will address your pain point?", "how can we measure success for this initiative?"

Fear of Resistance

• Challenge: Concern that questions may cause defensiveness or resistance.
• Solution: Use empathetic and non-judgmental phrasing:

Acknowledge their perspective: “I see why this might feel like the best option. Can we explore why this is critical and how we can make it even better?”

Highlight collaboration: “We’re in this together, so understanding your challenges helps us deliver the best possible solution.”

Overlooking the Bigger Picture

• Challenge: Focusing too narrowly on immediate tasks, missing strategic opportunities.
• Solution: Tie every conversation back to strategic goals:

Use questions like: “How does this initiative align with your organizational priorities for the year?” or “What larger goals should this project help achieve?” Regularly revisit long-term objectives in discussions to ensure alignment.

Conclusion

Asking "why" and "how" questions transform customer interactions and demonstrates strategic thinking. While most of my examples come from roles involving customer engagement and strategic collaboration, it can be easily applied to other environments. The principles of uncovering root causes, enabling tailored solutions, and fostering long-term trust are universally valuable. Based on my experience I realized that this framework is a great way to approach problems thoughtfully, encourage meaningful conversations, and ensure alignment with broader goals. Whether you’re leading a team, managing a project, or collaborating across functions, these questions can provide clarity and guide better decision-making.

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