How a Pry and Resist spiral between CEOs and CXOs is toxic to company culture, collaboration, & growth

user Mark Teitell

A trace of “Pry and Resist” naturally exists in every leader-subordinate relationship. But for growth-stage CEOs (particularly Founders), it’s common to show such deep interest in the work of C-level functional leaders — and for these CXOs to balk at what they see as unproductive interference — that a vicious and damaging relationship cycle can begin. Left unchecked, it can become a toxic spiral of diminishing trust that corrodes collaboration, permeates organizational culture, and limits growth. At its worst, this leads to protracted, unproductive internal debates rather than focusing on customer needs and looking outward at the competitive landscape. It wastes energy that should be invested in collaboration and innovation. And it leaves the CEO, the involved CXO, and “witnesses” up and down the organization collectively wondering if the company has the right leadership team in place.

Pry and Resist is most common when the CEO has deep expertise in one business function but relatively little in others (either doing or managing the other functions). For example, think of a highly-funded tech company with a technically brilliant, first-principles thinker at the helm — someone who feels intense reward from diving into an unfamiliar discipline by starting from its most basic assumptions or truths, and (sometimes) coming up with innovative non-conventional approaches. When this CEO hires a CMO, or Head of People (for example), they encounter someone who draws on years of experience that the CXO expects to (and feels they’re getting paid to) bring to bear. In this situation, the Pry and Resist spiral has the potential to become an unresolvable “black and white” clash of logic and reasoning versus intuition and experience that undermines organizational goals.

How the Pry and Resist spiral can turn: 

  1. The CEO with all good intentions is interested in a level of detail and a level of participation that’s greater than the CXO would expect.
  2. The CXO perceives from that interaction there’s some disconnect or misalignment with the CEO about things they hold to be obvious and true about how to run this type of function. The CXO starts to either actively or passively avoid interacting with the CEO when they can (a dynamic made all the more possible by remote work).
  3. The CEO senses the avoidance and becomes mistrustful about the competency of the CXO and/or about their collaborative nature and ability to be a learning leader. 
  4. The CEO demands to get more into the details, or insists on more collaborative time together… and if they can’t get it, they sometimes start seeking out people who report to the CXO. 
  5. The CXO sees this happening and decides they have to pull further away and create more distance — for themself and, protectively, their people. This is partly out of defensiveness and partly based on the conviction that they know what to do, and in the end will be remembered for succeeding at it (or blamed if they let themselves get “wagged around” by the non-expert CEO). 
  6. And the spiral continues… 

The Pry and Resist spiral happens with non-technical CEOs, too. Imagine a CEO of a company seeking to “productize” what it does, who comes from a sales or marketing background. The CEO tells their Product/Engineering leaders: “Here are five things I want our product to do really quicklyx…” From the technical executives’ perspective, they are thinking about tech debt that needs to be resolved, the need for a stable roadmap, concern about fragmenting their product and engineering teams, and the need to develop bulletproof enterprise-class service for things they’ve already launched. But a non-technical CEO has never lived through the painful lessons of standing up technical offerings. So the same spiral can occur.

The remedies

We’ll explore the remedies in-depth in the next piece. But to give you a flavor of how to tackle Pry and Resist, here’s a preview:

  1. “Name it to Tame It.”. Becoming aware of the risk of this pattern, and speaking openly and with common language about how it happens and what it impacts, is a huge first step.
  2. Start with the question “What’s my contribution here?”. Each person’s role in Pry and Resist is a challenge for their own leadership development – their mental and emotional flexibility, ability to put aside ego, and recognition of the assumptions, biases and fixations they bring to the situation 
  3. Embrace the Paradoxes of a Complex World. In this case, this calls for recognizing that it’s not “Logic OR Experience”…it’s an “AND.” 


In 99% of industry and competitive situations, the consciousness and psychology of leadership is the single biggest determinant of a company fulfilling its maximum potential. And with the time pressures and money pressures that grow exponentially as privately-held companies raise more capital and create higher criteria for success, the Pry and Resist dynamic is one of the most important patterns that great leaders need to recognize and transcend. 

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