When a leader is not delegating effectively, the solution often follows a predictable method: teach her to prioritize and assign work, establish check-ins, and hold her accountable for staying out of the details. That approach can produce immediate change when the leader wants to satisfy a leader, but it may do little to change what she needs to sustain the behavior long-term. Under pressure, she becomes involved again because the reason she remained close to the work was never understood, leaving her with knowledge of how to delegate but little conviction that she should.
I recently worked with “Lindsay,” an executive whose workload had become unsustainable. She was approaching burnout, and her team was frustrated by its limited authority to make decisions and own assigned work. Lindsay saw the problem as one of capacity, but as we examined how she was spending her time, we found that she remained actively involved in more work than her role required. Understanding why became more useful than creating another plan to redistribute it.
Lindsay reported directly to a CEO who asked detailed questions about the work, including the assumptions behind decisions and how the team reached its conclusions. She interpreted those questions as an expectation that she should know the answers herself and provide them immediately. Remaining involved allowed her to anticipate what he might ask, respond with confidence, and protect her credibility. Her team experienced the behavior as a lack of trust, while Lindsay believed she was doing what was necessary to serve her boss well.
Lindsay’s belief was straightforward: “I need to understand the details of what my organization is doing so I can be prepared for the CEO.” On the surface, this sounded like a reasonable expectation for an executive, which helped explain why she had not questioned how much time she was spending on the work. We completed a Cost–Benefit Analysis of that belief, a technique I learned from Dr. David Burns and use in executive coaching.
The exercise begins by writing the belief at the top of a page and listing the advantages and disadvantages of holding it. After completing both columns, the two sides are weighted on a 100-point scale according to their relative importance, rather than the number of items listed. One compelling advantage may outweigh several disadvantages, and the purpose is to determine whether the belief is working well enough so that the person still wants to retain it.
For Lindsay, understanding the details helped her remain informed, identify problems, and feel prepared when meeting with the CEO. As we explored what being prepared meant to her, she described how frequently he asked detailed questions about decisions, assumptions, and the work behind them. She had interpreted those questions as an expectation that she should know all the answers and provide them immediately. The costs of this belief included longer hours, insufficient attention to strategic priorities, slower decisions, and a team that had become reluctant to take full ownership because Lindsay was likely to step back in.
The analysis gave Lindsay a clearer view of the tradeoff and exposed an assumption she had not recognized – the CEO had never told her he expected her to know the answers to all his questions. She had been avoiding an uncomfortable conversation with the CEO about which information he expected her to know, when he was comfortable with her consulting the team, and whether his questions reflected a performance expectation or simply his way of understanding the business. Continuing to guess had become more costly than having the conversation.
Lindsay’s experience is a useful reminder that behavior often persists for reasons that are not immediately visible. When a leader continues returning to the details despite the costs, a Cost–Benefit Analysis can clarify what the behavior is providing, whether the leader genuinely wants to change it, and which assumptions may need to be tested. I hope this gives you a useful way to approach delegation challenges in your own organization.
