Feb13
Succession planning is difficult for most business owners because it asks them to confront three things at the same time: who they are, how their business is built, and whether the organization can function without them. Most leadership challenges live in one of those lanes. Succession planning lives in all three — simultaneously.
One reason succession efforts stall is that owners underestimate the identity shift involved. As succession advisor Abby Donnelly often points out, many business owners plan the transaction without preparing themselves for the personal transition. Research consistently shows that owners who exit without clarity around purpose, priorities, and what comes next are far more likely to experience regret — even when the exit itself is financially successful. This isn’t a failure of planning effort; it’s a failure of planning scope. You can’t separate the future of the business from the future of the person who built it.
At the same time, succession planning exposes structural weaknesses that successful companies can afford to ignore — until they can’t. Chuck Cooper, who works extensively in business transition and governance, emphasizes that succession risk rarely shows up in struggling organizations. It shows up in growing, profitable ones. As complexity increases, financial clarity, legal agreements, decision authority, and advisor alignment often fail to evolve at the same pace. Those gaps remain invisible while the owner is present, but under stress — illness, opportunity, or unplanned exit — they surface quickly and force decisions no one wanted to make.
And then there’s the systems issue which my company addresses: leadership depth. Succession planning is often framed as a CEO replacement exercise, but that framing misses the real risk. The issue isn’t whether one role can be filled; it’s whether the organization has a pipeline of capable leaders ready to step into critical roles without disruption. In lean organizations especially, the loss of a single leader can stall decisions, unsettle customers, and erode trust internally.
Succession planning is not an event or a date on the calendar — it’s an organizational system that must be actively built and maintained.
And that’s exactly why avoiding it is far riskier than doing the work.
Keywords: Entrepreneurship, Leadership
Succession Planning is Hard because it’s Identity, Structure, and Systems All at Once
The Corix Partners Friday Reading List - February 13, 2026
The Questioning Leader: Rethinking How We Learn, Listen, and Lead
The Straight Story of Leadership: Purpose, Patience, and Presence
Coherence Is Not Culture — It Precedes It
