In this edition of "Ask the Board," we feature Darrin Murriner, CEO and Co-Founder of Cloverleaf, a comprehensive personal and team development technology that provides automated coaching via the tools employees use every day, such as email, calendar, Slack, and Microsoft Teams.
Automated coaching is the delivery of personalized, behavior-based development through technology to give people timely, relevant insights into their behavior, habits, effectiveness, and efficiency. Below, Murriner shares seven key benefits of automated coaching and why it’s transforming professional development in modern organizations.
Closes the leadership development gap
For decades, workplace coaching has been reserved for a select few, primarily senior leaders or high-potential employees. While traditional coaching still has value, its exclusivity creates a development gap that leaves most employees without the guidance they need to grow.
Without access to coaching, the following happens:
- Emerging leaders struggle, leading to costly promotion failures.
- Managers lack coaching skills, because they’ve never been coached themselves.
- Employees are left to "figure it out," missing key opportunities to build communication, resilience, and collaboration.
Automated coaching removes these barriers by delivering personalized, on-demand coaching at scale. Whether an employee is preparing for a difficult conversation, adjusting to a new role, or navigating team dynamics, they receive real-time insights tailored to their specific needs, ensuring coaching is no longer reserved for a select few.
Provides support exactly when employees need it
Most coaching happens in scheduled sessions, but what about the other 99% of the time when employees truly need guidance?
Traditional coaching is often disconnected from the moments that matter most. Employees don’t always need coaching in a scheduled session — they need it right before they lead a meeting, navigate workplace conflict, or give critical feedback.
Today’s workforce, especially younger generations, expects learning to be:
- Accessible — available instantly when needed.
- Relevant — tailored to their real-world challenges.
- On demand — not just something they have to wait for in training sessions.
Automated coaching shifts learning from a one-time event to continuous growth by delivering bite-sized, just-in-time insights inside the tools employees already use (Slack, Microsoft Teams, email, and calendar integrations). Instead of insights getting lost in a PDF or forgotten after a workshop, employees receive timely nudges so they apply what they’ve learned in real situations.
Traditional coaching is expensive and difficult to measure. Automated coaching delivers ROI at scale, without additional workload on human resources.Darrin Murriner, CEO and Co-Founder of Cloverleaf
Allows employees to stay engaged, reflective, and growth-oriented
Research consistently shows that self-reflection is critical for leadership growth, yet most employees don’t take the time to pause, reflect, and adjust their behaviors.
A study from the Journal of Occupational and Organizational Psychology found that daily coaching prompts encourage self-reflection, which leads to:
- Greater self-awareness. Employees recognize their own strengths, growth areas, and stress triggers.
- Increased motivation to learn. Employees actively seek opportunities for improvement.
- More effective decision-making. Teams work with greater intentionality and emotional intelligence.
Automated coaching fuels self-reflection by delivering coaching nudges that prompt employees to think about how they work, communicate, and improve, reinforcing key behaviors without adding extra meetings or coursework.
Improves company culture
Leadership isn’t solely about individual growth — it’s about teams growing together. Yet, most coaching programs focus on training leaders in isolation rather than fostering collective development.
This creates a disconnect where:
- Managers struggle to apply what they’ve learned with their teams.
- Employees lack shared tools or frameworks to improve collaboration and trust.
Automated coaching shifts development from an individual experience to a teamwide practice. Instead of waiting for structured training sessions, managers and employees receive real-time coaching that helps them:
- Understand each other’s communication and decision-making styles.
- Adapt feedback approaches to reduce misalignment and frustration.
- Turn workplace conflict into productive conversations.
- Build a shared language for collaboration.
By fostering collective development, automated coaching ensures that learning isn’t a one-time event, it’s an ongoing process that strengthens entire teams.
Supports employees at every career stage
Coaching isn’t a one-size-fits-all experience. The challenges that an entry-level employee faces are vastly different from those of a mid-career manager or executive leader. Yet, most leadership programs treat development as a static, one-time process.
Employees need coaching that evolves alongside their career, offering support at key moments:
- Onboarding: New hires need help integrating into the team culture and understanding the company’s expectations.
- Early career growth: Coaching provides skills development in communication, collaboration, and resilience.
- First-time leadership: New managers need guidance as they transition from individual contributor to leader.
- Mid-career development: Coaching can strengthen one’s leadership presence, decision-making, and their conflict resolution skills.
Automated coaching ensures that employees receive relevant, role-specific guidance at each career stage, so they’re never left to navigate alone.
Delivers measurable ROI without overhead costs
Traditional coaching is expensive and difficult to measure. Automated coaching delivers ROI at scale, without additional workload on human resources (HR).
One of the biggest challenges with leadership development is proving its impact. Traditional coaching relies on anecdotal feedback and lacks clear return on investment (ROI) tracking.
Automated Coaching changes that by:
- Providing data-driven insights on engagement and coaching interactions.
- Scaling without increasing HR costs — coaching for every employee, not a select few.
- Embedding coaching into workflows so it actually gets used, not forgotten.
Companies that implement automated coaching see higher engagement, stronger leadership pipelines, and a culture of continuous learning without the high costs of traditional coaching.
Scales a company’s coaching initiatives without overloading HR
HR and learning and development teams play a vital role in employee development, but they can’t personally coach every employee. Traditional coaching programs require significant time, budget, and administrative effort, which makes them difficult to scale.
Automated coaching solves this by:
- Removing manual effort from HR while still providing personalized coaching at scale.
- Ensuring that every employee gets access to development without increasing HR’s workload.
- Embedding coaching into existing workflows so it is used, not forgotten.
With automated coaching, organizations can expand leadership development without additional HR overhead in turn creating a more self-sustaining learning culture.
CO— aims to bring you inspiration from leading respected experts. However, before making any business decision, you should consult a professional who can advise you based on your individual situation.
