The 'Why' Trap: How Our Go-To Question May Be Holding Us Back at Work

Imagine you’re on a call with a long-standing client. As you’re discussing future projects, they unexpectedly say, “We’ve decided to explore options with other vendors.” Caught off guard, you immediately respond, “Why? What have we done wrong?” The conversation quickly turns into a detailed critique of your company’s recent performance, leaving you scrambling to defend your team and feeling like you’ve damaged the relationship further.

This scenario illustrates a common workplace trap — the “Why” question. We’re drawn to “Why” questions like moths to a flame, a habit ingrained since childhood as we used them to make sense of the world around us. In our professional lives, “Why” seems like the key to unlocking understanding — promising to reveal root causes, uncover hidden motivations, and provide the insight we need to solve complex problems. Asking “Why” feels proactive and analytical, demonstrating our critical thinking skills and commitment to improvement.

However, as explored by Alan H. Palmer in his Harvard Business Review article, “Stop Asking ‘Why’ and Start Asking ‘How’”, this instinctive approach can often be counterproductive. While our instinct to ask “Why” stems from a genuine desire to understand and solve problems, it often backfires, leading to unintended consequences that can hinder our professional growth and relationships.

The very qualities that make “Why” questions appealing can also make them problematic. When we ask “Why,” we often inadvertently put others on the defensive. It can feel like an accusation, prompting people to justify their actions or decisions rather than engage in constructive dialogue. Moreover, “Why” tends to focus on past problems instead of future solutions, keeping us stuck in a cycle of explanation rather than moving us forward.

This backward-looking nature of “Why” can also reinforce negative biases, as it encourages people to dwell on what went wrong rather than what could be improved. Perhaps most insidiously, the seeming simplicity of “Why” can limit creative thinking. By framing the conversation around existing explanations or justifications, we may miss opportunities for innovative solutions or alternative perspectives.

In essence, while “Why” promises insight, it often delivers roadblocks, making it a potential trap in our professional communications. Understanding this paradox is crucial for improving our workplace interactions and problem-solving approaches.

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A Few Scenarios

01 Client Interaction Scenario:

A client emails to cancel a long-standing monthly service contract.

Account Manager: “Why are you cancelling our services? What went wrong?”

This approach may lead the client to list all their grievances, potentially damaging the relationship further and making it harder to salvage the contract.

Effective Alternatives: a. “I understand you’re considering canceling our services. How can we adapt our offering to better meet your current needs?”

b. “What aspects of our service have been most valuable to you, and where do you see opportunities for us to enhance our support?”

c. “If we could design an ideal service package for your business, what would that look like?”

These questions open a constructive dialogue about improvement and demonstrate a willingness to be flexible, potentially saving the contract.

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02 Leadership Scenario:

An employee consistently misses project deadlines.

Manager: “Why are you always late with your deliverables?”

This question puts the employee on the defensive and may lead to excuses rather than solutions.

Effective Alternatives: a. “I’ve noticed some challenges with meeting deadlines. What resources or support could help you complete your tasks more efficiently?”

b. “How can we restructure your workload or our processes to better align with your working style?”

c. “What part of your current projects do you find most engaging, and how can we build on that to improve overall productivity?”

This approach shows support and focuses on finding solutions rather than assigning blame.

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03 Team Collaboration Scenario:

A cross-functional project is falling behind schedule.

Project Lead: “Why is this project so far behind?”

This question may lead to finger-pointing and team members blaming each other for delays.

Effective Alternatives: a. “What are the main obstacles we’re facing, and how can we work together to overcome them?”

b. “Which aspects of our collaboration have been most effective so far, and how can we apply those strengths to the areas where we’re struggling?”

c. “If we were to restart this project today, what would you suggest we do differently to ensure smoother progress?”

These questions encourage team problem-solving and foster a collaborative atmosphere.

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04 Performance Review Scenario:

An employee receives lower-than-expected ratings in their annual review.

Employee: “Why did I get such low scores? I thought I was doing well.”

This question invites the manager to list all the employee’s shortcomings, potentially damaging morale and motivation.

Effective Alternatives: a. “What specific actions can I take to improve my performance and exceed expectations in the coming year?”

b. “Which of my current responsibilities do you think I excel at, and how can we build on those strengths?”

c. “Can you share examples of top performers in similar roles? I’d like to understand what specific behaviours or outcomes I should aim for.”

These questions show a growth mindset and a proactive approach to improvement.

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05 Remote Work Productivity Scenario:

Situation: You’re a team leader in a company that recently transitioned to remote work. You notice that one of your top performers, Jasmine, has been less productive lately. Her output has decreased, and she seems less engaged in team meetings.

Ineffective “Why” Approach: “Jasmine, why has your productivity dropped since we started working remotely?”

This question might make Sarah defensive and could lead to excuses rather than solutions.

Effective Alternatives: a. “Sarah, I’ve noticed some changes in your work patterns recently. What aspects of our remote setup are working well for you, and where are you finding challenges?”

b. “How can we adjust our team processes to better support your workflow in this remote environment?”

c. “What tools or resources would help you maintain the high performance you’ve always shown in the office?”

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06 Customer Churn in SaaS Business Scenario:

Situation: You’re the Head of Customer Success at a SaaS company. You’ve noticed a significant increase in customer churn over the past quarter, particularly among long-term clients.

Ineffective “Why” Approach: “Why are we losing so many long-term customers?”

This question might lead to finger-pointing among departments or focusing solely on negative aspects of the product or service.

Effective Alternatives: a. “What patterns or commonalities are we seeing among the customers who have stayed with us the longest?”

b. “How can we enhance our onboarding and ongoing support processes to better align with the needs of our long-term clients?”

c. “What additional value or features could we offer to make our platform indispensable to our client base?”

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07 Missed Sales Target Scenario:

Situation: You’re the Sales Director, and your team has missed its quarterly target for the first time in two years. The CFO is concerned and wants to understand the situation.

Ineffective “Why” Approach: “Why did your team fail to hit the target this quarter?”

This question could create a defensive atmosphere and might not yield constructive insights.

Effective Alternatives: a. “What were the key differences between this quarter and our previous successful quarters in terms of market conditions, client behaviour, or our sales approach?”

b. “How can we adjust our sales strategy to better address the current market challenges we’re facing?”

c. “What additional support or resources would enable the team to overcome the obstacles we encountered this quarter?”

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08 Employee Retention in Startup Scenario:

Situation: You’re the CEO of a fast-growing startup. Despite competitive salaries and benefits, you’ve noticed an increase in employee turnover, particularly among mid-level managers.

Ineffective “Why” Approach: “Why are so many of our managers leaving?”

This question might lead to generalizations or surface-level explanations that don’t address the root causes.

Effective Alternatives: a. “What aspects of our company culture and work environment are most valued by our long-term employees?”

b. “How can we create more growth and development opportunities for our mid-level managers?”

c. “In what ways can we improve our communication and feedback processes to better address concerns before they lead to departures?”

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09 Project Pivot in Agile Development Scenario:

Situation: You’re the Product Owner of an Agile development team. Midway through a major project, user testing reveals that a key feature isn’t resonating with users as expected.

Ineffective “Why” Approach: “Why isn’t this feature working for our users?”

This question might lead to defensive justifications of the original design rather than constructive problem-solving.

Effective Alternatives: a. “What user needs or pain points are we not addressing with the current design of this feature?”

b. “How can we iterate on this feature to better align with user expectations and behaviours?”

c. “What alternative approaches or solutions could we explore to achieve the core objective of this feature?”

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Conclusion

As we’ve explored through various workplace scenarios — from client interactions and leadership challenges to team collaborations — the instinctive “why” question often proves to be a double-edged sword. While “why” questions can sometimes be useful for root cause analysis in certain contexts, they often create more problems than they solve in workplace interactions. It frequently leads us down a path of defensiveness, backwards-looking explanations, and missed opportunities for constructive dialogue.

Those alternative questions in the above scenarios share common strengths:

• They avoid triggering defensive responses, maintaining a positive and open dialogue.
• They shift focus from past problems to future solutions, promoting a proactive mindset.
• They encourage collaboration and shared problem-solving rather than justification or blame.
• They often uncover more comprehensive information, leading to better insights and decisions.
• They preserve and strengthen professional relationships by avoiding accusatory tones.

By consciously moving away from “why” questions in our professional interactions, we open doors to more productive conversations, innovative solutions, and stronger workplace relationships. This shift in approach can lead to improved team dynamics, more effective leadership, enhanced client relationships, and ultimately, better business outcomes.

As we navigate the complexities of modern workplaces, let’s challenge ourselves to pause before asking “why.” Instead, let’s frame our inquiries in ways that invite collaboration, encourage forward-thinking, and unlock the full potential of our collective knowledge and creativity. By doing so, we can transform potential confrontations into opportunities for growth, innovation, and mutual success.

Remember, the goal isn’t to completely eliminate “why” from our vocabulary, but to use it judiciously and mindfully. When we do ask “why,” let it be in contexts where it truly serves our purpose — such as in-depth analysis or academic inquiry — rather than in sensitive interpersonal or professional situations where alternative questions can yield far better results.

In essence, by expanding our questioning toolkit beyond “why,” we equip ourselves to navigate workplace challenges more effectively, foster more positive professional relationships, and drive meaningful progress in our careers and organizations.