Reevaluating the Role of One-on-Ones in Sales Leadership
In today’s sales landscape, there is a growing belief that the traditional one-on-one meeting is no longer effective. Many frontline sales managers either cancel them due to time constraints or run them so inefficiently that their sales representatives fail to see the value.
However, research and experience suggest that the issue is not with the one-on-one concept but rather with how it is executed. In an episode of Coach2Scale, Andy White, Vice President of Sales at Trivy, shared his perspective on why one-on-ones remain essential and how sales leaders can refine their approach to drive better outcomes.
The Decline of the One-on-One: Symptoms of a Larger Problem
One-on-one meetings are intended to foster alignment, accountability, and performance improvement. However, many organizations are experiencing a breakdown in this critical sales management practice. A Gartner study revealed that nearly 90 percent of sellers feel disconnected from their organization, with half of them passively searching for other job opportunities.
Much of this disengagement stems from a lack of meaningful interaction between sales managers and their teams. Many one-on-one meetings, when they do occur, are reduced to routine deal reviews, missing the opportunity for skill development and professional growth. Others are canceled entirely due to competing priorities, reinforcing a culture where coaching is seen as optional rather than essential.
White’s experience in sales leadership has shown that ineffective one-on-ones contribute to an erosion of trust, decreased accountability, and ultimately, lower performance. When managers fail to dedicate time to structured, meaningful coaching conversations, sales representatives may feel unsupported, leading to higher attrition and lower productivity.
Rebuilding Effective One-on-Ones: A Structured Approach
To counteract this decline, White suggests a three-part framework that sales leaders can adopt to improve the structure and effectiveness of their one-on-one meetings. This approach ensures that conversations move beyond transactional deal discussions and focus on long-term performance and engagement.
1. Personal Check-In: Building Trust and Connection
The first portion of the meeting should focus on relationship-building. A sales representative’s success is often influenced by more than just their sales targets—it is also impacted by their personal motivation, confidence, and overall engagement. Managers should take time to ask about personal challenges, career aspirations, and any external factors affecting their performance.
By fostering a deeper connection, managers create an environment where sales representatives feel comfortable sharing honest feedback and discussing areas where they need support. This foundation of trust makes it easier to have difficult but necessary conversations about performance improvement later.
2. Professional Development: Moving Beyond Deal Reviews
The core of an effective one-on-one meeting should be dedicated to coaching and skill development. Too often, these meetings are dominated by discussions about specific deals rather than addressing the underlying behaviors and competencies that drive long-term success.
Managers should use this time to focus on key areas of growth, asking questions such as:
- What skill are you currently working to improve?
- What challenges are preventing you from achieving your goals?
- How can I support you in overcoming these obstacles?
Managers can ensure that each conversation contributes to the representative’s ongoing development by shifting the focus from deal status updates to meaningful skill-building.
3. Future Planning: Career Growth and Alignment
The final segment of the meeting should address long-term goals and career aspirations. Employees are more likely to remain engaged and committed when they see a clear path for growth within the organization.
Rather than relying on generic questions like “Where do you see yourself in five years?”, managers should encourage reflective thinking by asking:
- What aspects of sales do you enjoy the most?
- Where do you see opportunities to expand your skill set?
- What would success look like for you in the next year?
Aligning professional development with individual career aspirations motivates sales representatives and ensures that organizational goals are met with a highly engaged team.
The Role of Accountability in Sales Coaching
One of sales management’s most significant challenges is holding managers and representatives accountable for progress. According to White, many managers struggle to have difficult conversations about performance, leading to inconsistent coaching and minimal improvement.
To address this, managers should establish clear action items at the end of each one-on-one and follow up on them in subsequent meetings. Documenting key takeaways and expectations helps ensure that coaching conversations translate into tangible results.
Additionally, White recommends a practice that may initially feel counterintuitive: inviting feedback from sales representatives about the manager’s leadership effectiveness. Asking, “What is one thing I could do better as your manager?” creates a two-way accountability structure that fosters transparency and continuous improvement.
Reframing One-on-Ones as a Competitive Advantage
Organizations that fail to prioritize effective coaching risk high turnover, poor sales performance, and disengaged teams. In contrast, those who commit to structured, meaningful one-on-ones see greater alignment, higher quota attainment, and a stronger sales culture.
Sales leaders who rethink their approach to one-on-ones—focusing on trust-building, skill development, and accountability—will improve individual performance and create a more resilient and successful team.
The one-on-one meeting is not dead. It simply needs to evolve.
How CoachEm Can Help
For organizations looking to implement a more structured and effective coaching process, platforms like CoachEm provide AI-driven insights that help sales managers conduct more impactful one-on-one meetings. By analyzing CRM and call data, CoachEm offers tailored coaching recommendations to ensure every meeting focuses on the skills and behaviors that drive revenue growth.
To learn more about how CoachEm AI can enhance sales coaching, talk to a human!
