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The Questions That Matter: How to Uncover and Overcome Business Roadblocks

January 30, 2025

Every business reaches a point where growth slows, profitability dips, or the team feels stretched to its limits. While these challenges are common, they’re often symptoms of deeper underlying issues that require a strategic and collaborative approach to resolve. Jacqueline Cloudt, founder of Puzzlewise, believes that with the right mindset and tools, business owners can break through these barriers and unlock new possibilities for growth.

In a conversation with Natalie Evans, Partner and Head of Assurance and at GGFL, Jacqueline shared her expertise on navigating the complexities of business growth. Her insights offer practical guidance for entrepreneurs who are ready to tackle challenges head-on and create lasting change in their organizations.

CLICK HERE TO WATCH THE COMPLETE INTERVIEW.

DOWNLOAD NAVIGATING CHALLENGES: THE GUIDE TO ASKING THE RIGHT QUESTIONS

Recognizing the Signs of Stagnation

For many businesses, the first step toward growth is identifying what’s holding them back. Jacqueline has worked with countless entrepreneurs and sees recurring patterns that signal it’s time for change.

Businesses often hit a wall when profitability doesn’t align with growth, leaders feel overwhelmed by day-to-day demands, or teams experience burnout,” Jacqueline explains. Communication silos, misaligned priorities, and reactive decision-making can further compound these issues, creating a sense of stagnation that’s hard to shake.

However, these “red flags” are also opportunities. They provide a starting point for asking deeper questions about what’s really causing friction and how to address it. As Jacqueline points out, “It’s often not the problems we see, but the ones we avoid asking about, that hold the biggest opportunities for transformation.”

Shifting the Leadership Mindset

At the core of overcoming growth barriers is a shift in leadership mindset. Many business owners feel they must solve every problem themselves, but this approach can limit the potential of both the business and its team.

The hardest part for leaders is learning to let go of control,” Jacqueline says. “It’s not about doing it all; it’s about creating the conditions for others to succeed.” By delegating not just tasks but also responsibility, leaders empower their teams to take ownership and contribute to the business’s success.

Jacqueline recommends starting small. Assign manageable projects, set clear expectations, and provide regular feedback. This builds trust and allows leaders to focus on high-value activities, such as strategic planning and vision-setting. “When leaders stop being the bottleneck, the entire business can move forward more effectively,” she adds.

Asking the Right Questions

Jacqueline emphasizes the importance of curiosity and self-awareness in tackling business challenges. “You don’t know what you don’t know,” she says, “so start asking questions.” She suggests beginning with broad discovery questions to understand the context of the issue before digging deeper into root causes. [Click here to download Jacqueline’s GUIDE TO ASKING THE RIGHT QUESTIONS.]

A key part of this process is involving the team. Employees on the front lines often have valuable insights into operational inefficiencies or cultural challenges. “Your team is a powerful resource,” Jacqueline notes. “By listening to their perspectives, you can uncover issues you might have overlooked.

Bringing in an external advisor can also be transformative. An outsider’s perspective can challenge assumptions, ask new questions, and provide solutions that may not be obvious from within the organization.

Building Momentum

Once barriers have been identified, the next challenge is sustaining progress. Jacqueline advises businesses to take a structured approach, with clear priorities, timelines, and accountability measures. She also stresses the importance of celebrating small wins along the way.

It’s easy to get overwhelmed by the big picture,” she says. “But recognizing progress, no matter how small, builds confidence and keeps the team motivated.” This approach also helps create a positive cycle of improvement, where success breeds more success.

Creating a Culture of Growth

For businesses to thrive, leaders must foster a culture where growth is both a priority and a shared responsibility. This means encouraging open communication, being receptive to feedback, and staying adaptable.

It’s about embracing both the challenges and the opportunities,” Jacqueline explains. “Growth isn’t linear—it’s a process of trial and error. The key is to remain committed and keep moving forward, even when setbacks occur.”

At its heart, this approach is about creating a business that is resilient, agile, and capable of sustaining long-term success. As Jacqueline puts it, “It’s not just about solving today’s problems but building a foundation for future possibilities.”

A Path Forward

Breaking through growth barriers is no small feat, but it’s far from impossible. With a mindset focused on collaboration, curiosity, and persistence, business owners can turn challenges into opportunities and unlock their true potential.

Take a step back and reflect,” Jacqueline advises. “Start with small actions, involve your team, and don’t be afraid to ask for help. Growth is a journey, and every step forward counts.

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