Why Asking Pesky Questions Matters

They can make or break an organization’s culture.


Introducing EO-isms

I operate under a set of guiding principles that structure how I work. Most EO-isms have evolved from front line experiences and impressive mess-ups.

We kick off this series with one of my very favorite principles: Identify and ask pesky questions. What are the benefits? Read on …  

Overview

This article explores the transformative power of pesky questions in the workplace, showing how they catalyze critical thinking, foster open dialogue, drive meaningful change, and ensure you are prepared. By embracing the discomfort they bring, organizations can unlock insights and opportunities, proving that impactful breakthroughs often stem from the courage to ask the questions that no one else will. (Can I get an amen?)

Definition

Pesky question: a question that is typically discovered through critical thinking that needs to be asked, even if it is difficult or unwelcomed. Pesky questions can influence small or large details.

  • Examples:

    • A reorder of all business cards is about to go to print: Has anyone checked that all of the phone numbers and emails are functioning? Are the names spelled correctly?

    • The communications plan is finished and all materials written: Has this been routed for review by all of the appropriate people?

    • A media interview is scheduled: What are the questions we aren’t expecting, and how should we approach the answers?

    • The annual strategic plan process is under way: Can we add measurement goals to ensure we are making progress? Who will take on the added work? What are our priorities?

    • Before launching a new marketing campaign: Have we fully considered the potential backlash or misinterpretation of our message across different cultures, demographics, and social media platforms?

    • When introducing a new policy: How have we ensured that this policy does not inadvertently alienate any of our stakeholders or employees? What steps have been taken to communicate this policy transparently and address any concerns proactively?

    • In review of a crisis communication plan: How often is this plan updated and practiced to ensure readiness?

    • When evaluating the effectiveness of internal communications: No one fills out the survey, why?

Why do pesky questions matter?

Pesky questions matter because they are essential tools for critical thinking, innovation, and accuracy. Far from being mere provocations, they challenge assumptions, uncover hidden problems, and stimulate deeper understanding, driving organizations and individuals to reevaluate practices, plans, policies, and strategies. By asking such questions, we push boundaries, foster transparency, and encourage a culture of continuous improvement and learning. Ultimately, pesky questions are catalysts for change, leading to more resilient, adaptable, and forward-thinking entities capable of navigating complexities and achieving sustained success.

To set the stage for a work force and organizational culture that not only accepts pesky questions but demands them, let’s look at the roles of the professional and the organization:

Individual:

Developing or strengthening a pesky question approach involves cultivating a mindset that values curiosity, care and concern, critical thinking, and the courage to challenge assumptions. Here are key points to guide individuals in this process:

  • Embrace Curiosity: Cultivate a genuine curiosity about the possible consequences of your planning and decisions. Think through questions about everything, even if they seem basic or obvious. What are the questions no on is asking but should be?

  • Foster Critical Thinking: Enhance your ability to analyze and evaluate information critically. This involves not taking things at face value and looking for underlying assumptions or potential biases in arguments.

  • Research Thoroughly: Before asking questions, do your homework. Well-informed questions are more likely to be impactful and lead to meaningful insights.

  • Listen Actively: Good questions often arise from attentive listening. Pay close attention to what is being said, and equally important, to what is not being said.

  • Connect the Dots: By honing your ability to ask pesky questions, you enhance your skill in linking disparate pieces of information, leading to a deeper understanding of complex situations. This skill not only aids in identifying underlying issues but also in crafting innovative solutions that address the root causes, not just the symptoms.

  • Practice Empathy: Understanding different perspectives enhances your ability to formulate questions that probe deeply into the subject matter. Try to see the world standing in other people’s shoes.

  • Be Persistent: Don’t be discouraged by evasive answers. Sometimes, the most revealing responses come from asking the same question in different ways or from persistently digging deeper.

  • Encourage Open Dialogue: Foster an environment where others feel comfortable asking pesky questions too. This can lead to a more comprehensive understanding and innovative solutions.

  • Stay Informed: Keep abreast of developments in your field of interest. A well-informed questioner is more likely to ask questions that are relevant and insightful.

By integrating these practices into your daily work life, you can develop a pesky question approach that not only enhances your strategic communication efforts but also contributes to a deeper understanding and more effective problem-solving in any context.

 

Organizational:

Assessing the willingness of an organization's culture to foster and welcome pesky questions is crucial for nurturing an environment of open dialogue and innovation. Here are key points to guide this assessment:

  • Observe Leadership Behavior: Leaders set the tone for organizational culture. Observe whether leaders ask challenging questions themselves and how they react when faced with difficult inquiries. Do they welcome such questions, or do they discourage them?

  • Review Communication Channels: Examine the formal and informal communication channels within the organization. Are there platforms or forums that encourage the sharing of ideas and questions, regardless of hierarchy?

  • Evaluate Response to Past Failures: Look at how the organization has dealt with failures or mistakes in the past. An environment that learns from failure rather than punishing it is more likely to welcome pesky questions.

  • Assess Feedback Mechanisms: Determine whether there are effective feedback mechanisms in place that allow employees to voice concerns and ask tough questions without fear of retribution.

  • Consider Employee Engagement: High levels of engagement are often indicative of an open culture. Engaged employees are typically more comfortable voicing their thoughts and questions.

  • Analyze Training and Development Programs: Do training programs emphasize critical thinking, problem-solving, and open communication? Organizations that invest in developing these skills are likely to value pesky questions.

  • Look for Diversity in Thought: Organizations that value diversity and inclusion are often more open to different perspectives and challenging questions. Assess whether diverse viewpoints are encouraged or if there's a tendency towards groupthink.

  • Check for Transparency: An organization that operates with transparency is more likely to encourage scrutiny and questions from its members.

  • Survey Employee Sentiment: Conduct anonymous surveys to gauge employees' perceptions of the organizational culture. Include questions about their comfort level in asking challenging questions and whether they feel their inquiries are welcomed and valued.

  • Monitor Outcomes of Pesky Questions: Finally, observe what happens when pesky questions are asked. Are they addressed and acted upon, or are they ignored and dismissed? Is there follow-up? This can be a strong indicator of the organization's openness to such inquiries.

 

By carefully evaluating these aspects, an organization can assess its current culture's receptiveness to pesky questions and identify areas for improvement to foster a more open, innovative, and questioning environment.

Conclusion

The essence of successful strategic communications lies in the willingness to engage deeply with the process, to question, to challenge, and to innovate. By embracing a philosophy that values the power of inquiry and the courage to ask the pesky questions, we ensure not only the integrity of our communications efforts but also their effectiveness and impact.

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