Skip-levels

Skip-levels are one of the most effective ways to truly understand the health of an organisation, yet they are often treated as an afterthought or run as a one-off exercise. At scale, when you are several layers removed from the delivery teams, these conversations become a vital mechanism for maintaining cultural alignment, validating the effectiveness of your leadership layers, and ensuring the organisation’s operating model is working as intended.

They are not about bypassing managers or creating parallel reporting lines. Their value lies in creating a safe space for honest dialogue, building trust across all levels, and enabling the early detection of issues before they escalate. Done well, they become a key leadership tool for reinforcing clarity, culture, and strategic alignment.

Over the years, I have found the most effective skip-levels follow a consistent set of principles. First, they are intentional. I prepare by understanding the individual’s role, their team’s recent focus, and any relevant organisational context. This helps me tailor the conversation without turning it into a status update. Second, I set the tone from the outset. People need to know this is not a performance review. I make it clear the purpose is to listen, learn, and understand what’s working and what’s not, both within their team and across the organisation.

The best conversations are driven by them, not by me. I use open questions to draw out insight. What’s helping you do your best work right now? Where do you feel we’re slowing you down? If you could change one thing about how we operate, what would it be? How is your manager enabling you? These are not random prompts, they are designed to surface cultural signals, process gaps, and leadership effectiveness in a way that metrics alone cannot.

It is equally important to observe as much as you listen. Pauses before answers, repeated themes across different skip-levels, and the choice of language often tell you as much as the direct responses. Look for patterns over time, not just isolated comments, and use those patterns to validate assumptions or challenge your current view of the organisation.

The follow-up is where trust is either built or broken. If something important is raised, I like to ensure it is addressed by the right leader and that the person who surfaced it sees movement. This does not mean agreeing with every suggestion, but it does mean closing the loop so people know their input was heard and valued. Without this, skip-levels quickly lose credibility.

There are also common pitfalls to avoid. Over-relying on them as your only insight into the organisation will distort your view. They are one data point among many. Treating them as a forum to fix issues in real time can undermine managers and reduce psychological safety. Cancelling them repeatedly because you are “too busy” sends a message that they are optional, which in turn reduces the openness and quality of future conversations.

The real value of skip-levels emerges when they are embedded as a habit, not an event. When people know they will have a regular, unfiltered channel to senior leadership, they prepare thoughtfully and speak more openly. Over time, the conversations evolve from surfacing problems to sharing ideas, opportunities, and perspectives you would never have reached through formal channels.

Leadership at scale is about maintaining proximity to the truth while empowering your managers to lead effectively. Skip-levels are one of the few tools that let you do both. When run well, they not only reveal what is happening, but they shape the culture into one where insight flows freely, alignment is maintained, and everyone understands they have a voice in the organisation’s success.