Rekindling Connection: An Undercover Boss Approach

I’ve seen many business leaders grapple with the challenge of staying connected to their teams. It’s a common scenario: as the business expands, or during periods of rapid growth, the distance between the leadership and the front lines often increases. 

This detachment can lead to a lack of understanding of the day-to-day challenges faced by the team, ultimately impacting the overall health of the organisation. Despite often telling my clients to ‘get out of the weeds’, there are absolutely times when you need to get back amongst them, rekindling the connection with your teams. 

 one of my clients recently demonstrated a remarkable strategy to bridge this gap, taking inspiration from the TV show “Undercover Boss.”

This client, a founder experiencing the growing pains typical of a successful business, felt increasingly detached from her team. Recognising the issue, she decided to take proactive steps to reconnect with her employees. Instead of remaining in her executive bubble, she actively participated in various operational aspects of her business. She joined meetings, planning sessions, and even client calls, immersing herself in the “shop floor” activities.

The twist here was that her team was fully aware of her identity. The goal wasn’t to spy or surprise but to genuinely understand the evolving nature of their roles and the challenges they faced as the company grew. This hands-on approach provided her with invaluable insights and helped her to reconnect with her team on a deeper level. 

This experience offers several key takeaways for other business leaders:

  1. Be Present in the Trenches: Occasionally step out of your leadership role to experience the day-to-day operations of your business. This hands-on approach allows you to understand the challenges your team faces and offers a different perspective on your business operations. Note: being present does not mean steamrolling in with answers and opinions – if you trust your team this is an exercise in understanding, not control. 
  2. Open Channels of Communication: Encourage open dialogue. Being involved at the operational level can make you more approachable and foster a culture of transparency and trust.
  3. Adapt and Implement Feedback: Use the insights gained from these experiences to make informed decisions and adjustments. This can range from streamlining processes to implementing new tools or strategies that address the challenges faced by your team.
  4. Foster Empathy and Understanding: Experiencing the front-line work firsthand cultivates empathy. Understanding the intricacies of your team’s work can lead to more empathetic leadership decisions.
  5. Reinforce Team Morale: Your involvement at the ground level can be a powerful morale booster. It shows your team that their work is valued and that their voices are heard.
  6. Lead by Example: Embracing this approach can set a precedent for other leaders in your organisation, promoting a culture of active engagement and continuous learning.

By taking a step back from our executive roles and getting involved in the nitty-gritty of our businesses from time to time, there’s an opportunity for real learning and invaluable insights, build stronger relationships, and lead our organisations with a renewed sense of purpose and understanding.



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