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Steady counsel for uncertain ground.
2026-07-24

When Does a Business Actually Need a Strategy Consultant?

The question of when to bring in outside help is one that most founders and directors approach with some ambiguity. Consultants are expensive, the process takes time, and there is a reasonable concern that the recommendations will state the obvious. Those concerns are not unfounded. But there are specific conditions under which an independent perspective adds something that internal teams genuinely cannot replicate, and it is worth being precise about what those conditions are.

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— Harry Caldwell
2026-07-24

Independent Consultant or Internal Strategy Team: How to Choose

Businesses that have reached a certain size often face a choice: build an internal strategy capability or continue to rely on outside advice when strategic questions arise. The answer is not the same for every organisation, and the factors that determine it are worth thinking through carefully rather than defaulting to whichever option feels more familiar.

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— Harry Caldwell
2026-07-08

How to Run a Leadership Away-Day That Actually Produces Decisions

The leadership away-day is a fixture of organisational life, and its reputation is mixed for good reason. The format has a tendency to produce the appearance of strategic thinking without the substance of it. Teams spend a day discussing things they already broadly agree on, generate a long list of actions, and return to the office to find that the operational rhythm has absorbed the day's output within a fortnight. The problem is rarely the people in the room. It is the design of the day itself.

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— Harry Caldwell
2026-05-16

Organisational Design After Rapid Growth: A Practical Guide

There is a size at which most businesses outgrow their informal structures. It varies. Some organisations manage well at forty people with minimal formal design, others start to feel the friction at fifteen. But the transition is predictable enough that it is worth understanding in advance, rather than diagnosing after the fact when the symptoms have already become expensive.

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— Harry Caldwell
2026-03-30

What to Expect from a Strategic Review Engagement

A strategic review is one of the more substantial commitments a business can make to outside advice. Six weeks, a significant fee, and a process that requires real engagement from the leadership team. Before committing to that, it is reasonable to want a clear account of what the process actually involves and what it is likely to produce. This article is an attempt to provide that.

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— Harry Caldwell
2026-03-15

Succession Planning in a Founder-Led Business: Where to Begin

Most founders know they should have a succession plan. Fewer have one. The gap between knowing and doing is rarely about a lack of information. There is no shortage of frameworks and checklists available. It is about the fact that succession planning requires a set of conversations that are genuinely difficult to have, and that most businesses have no structured process for having them.

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— Harry Caldwell
2026-02-18

What a Leadership Advisory Retainer Actually Gives You

The leadership advisory retainer is the service that is hardest to explain to someone who has not used one. It does not produce a report. It does not have a defined end date. It is, in essence, a standing arrangement to have a trusted outside perspective available when you need it. For some founders and CEOs, that is exactly what they are looking for. For others, a project-based engagement is a better fit. The distinction is worth understanding before committing to either.

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— Harry Caldwell
2026-01-22

Why Change Management Programmes So Often Fall Short

Change management has a poor reputation in many organisations, and the reputation is not entirely undeserved. A significant proportion of structured change programmes produce less than they promised, and the reasons tend to be consistent enough that they are worth examining before embarking on one. Understanding what typically goes wrong is a more useful starting point than a framework for what should go right.

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— Harry Caldwell

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