Billions have been invested in industrial digital transformation. The majority has underdelivered.
David Baskett’s diagnosis of why is : “Not because the technology was wrong. Not because the use cases weren’t valid. Not because the people involved weren’t capable. Because nobody in the room could translate.”[1]
This is the problem most organisations have misdiagnosed, and it is about to become more consequential.
As AI tools move from experimentation to deployment across sectors, the translation gap is widening. The technology exists, but the capability to stand between what the tools can do and what the organisation actually requires - to make that connection reliably and well - is in short supply in most organisations, and is not being developed with any deliberateness.
The Translation Gap
More often than not, strategy failures are not failures of thinking. Rather, they happen because of poor translation: between the strategy's intent and the operational teams who have to deliver it; between what the board decided and what the delivery team hears; between what a process is supposed to do and what it actually does on the ground.
When we identify why strategies fail, the usual explanations appear: lack of alignment, poor communication, unclear ownership. These are all true, but they describe symptoms. The underlying issue is an absence of a function that translates - that moves intent through the organisation and makes sure it arrives intact.[2]
That function is embodied in generalism. Most organisations have not structured for it, do not develop it deliberately, and do not fully notice when it is missing.
Specialist vs. Generalist
The distinction between generalists and specialists is functional rather than hierarchical.
Specialists have deep expertise in a defined domain. They solve hard problems at scale within their field. Their value lies in mastery; in being the person the organisation reaches out to when a problem in their area lands on the table.
Generalists have breadth across multiple domains. Amongst other things, they make sense of how things relate to each other. They translate between strategic intent and operational reality, between what one function needs and how another is currently running. Their value lies in holding the connective tissue that keeps an organisation functional across its parts.
Most organisations have optimised for specialist depth. Hiring, promotion, career development, and structure all reward people who go deeper into a domain. The result is organisations with real excellence in specialist areas and significant gaps in the connective tissue that ties those areas together.
What Generalists Do
To translate between what an engineering team is saying and what a CFO needs to understand, a generalist needs: enough technical fluency to represent the issue accurately; enough financial fluency to frame it in terms of commercial risk; and enough organisational awareness to read the decision correctly. That combination is not common and is not the product of any single domain career path.
Beyond individual translation moments, generalists provide the connective tissue work: recognising when a decision in one function creates consequences in another; holding organisational memory across cycles and leadership changes; making trade-off calls when competing priorities need someone who can hold multiple perspectives simultaneously; noticing when silos are operating in ways that create organisational risk.
In my operations review work - mapping processes and assessing organisational health - the critical gaps I observe are often in translation: between what a process is designed to do and what teams understand it to do; between the view from leadership and the reality on the ground. The connective tissue is where things break.
Invisible Work
Specialist output is tangible. Code ships. Reports are delivered. Campaigns run. The contribution is attributable.
Generalist output is not tangible in the same way. It is the misalignment that did not happen. The strategic decision that was properly understood by the teams who had to execute it. The meeting that did not fail because someone held context across both sides of the conversation. These do not appear in a project deliverable or a performance review.
Career structures reinforce this invisibility. Progression means going deeper - developing more specialised expertise, becoming the recognised authority in a domain. Moving broadly reads, to most organisations, as unfocused ambition.
The result is that generalist capability is mostly developed 'accidentally' by individuals who are curious enough to move across functions, and organisations with strong translation capability are often unclear about how they acquired it. Or what they stand to lose when those individuals leave.
AI Raises the Stakes
Much of the AI narrative around synthetic capability suggests that intelligent systems will eventually bridge this translation gap - that if machines can synthesise across domains, the need for people who do that will decrease.
I don't think this will be the case. Deploying AI tools well is itself a translation problem. Someone has to stand between what the technology can do and what the business actually needs. They have to decide where AI applies across the organisation and where it does not. They have to recognise when a problem that appears to be a good candidate for AI is actually a problem that requires judgment and context rather than pattern recognition at scale. They have to hold the view across domains that specialists, by definition, cannot hold.
Specialists will operate the tools in their domain. Generalists will have to determine where those tools go – and where they should not. Organisations without developed generalist capability are likely to deploy AI haphazardly, applying it to the wrong problems, or miss strategic opportunities because no one holds the view across both what the technology offers and what the organisation genuinely requires.
The transformation investments already underdelivering are underdelivering for this reason. Adding more technology will not fix it.
Leading for Translation
Recognising the gap is the first step. Addressing it requires deliberate choices in hiring, development, and team structure.[3]
On hiring: Look for breadth alongside depth. Value people who have moved across domains and can show how they connected ideas between them. For generalist roles, a career that has crossed multiple functions is a qualification rather than evidence of a lack of focus.
On career paths: Build routes that reward connective and translation capability as well as specialist depth. When a person's value lies in how they hold the organisation together across domains, their career development should reflect that. Do not ask them to compete on specialist terms they were never optimising for. This is an active conversation in communities like Generalist World\[4\], where practitioners explore how to recognise, develop, and deliberately protect generalist capability.
On team composition: Most teams tip too heavily toward specialist depth. Mixing specialist and generalist capabilities changes how the team functions. The exact ratio depends on the work – but for most organisations right now, the answer is to have more generalist capability, not less.
On development: Cross-functional exposure creates generalists. It does not happen automatically. It requires deliberate rotation, visibility across functions, and the active protection of the people who translate. Translators are easy to take for granted and they are more easily lost than most organisations realise.
On knowledge structures: Organisational memory only adds value when it lives in documentation and systems, not only in someone's head. Investing in knowledge transfer is not an administrative task – it is how translation capability survives the changes in personnel that every organisation eventually faces.
The Retention Dilemma
Developing generalist capability is expensive and takes time. The better you develop a translator, the more attractive they become to other organisations – often larger, better-resourced ones that can reward what they offer more generously.
For SMEs with lean teams and constrained margins, losing a developed translator is a strategic vulnerability. There is no clean answer. There are only trade-offs, and the question of whether you manage them deliberately.
A forthcoming companion piece, 'Beyond Translation Heroics', will address the structural question of building resilience that does not depend on any single translator. That is the next problem. But it starts here: naming the capability accurately, valuing it, and developing it deliberately rather than depending on it to emerge.
Getting the Balance Right
Specialists give you depth and excellence within domains. Generalists give you coherence across them. The organisations navigating complexity, deploying technology effectively, and executing strategy reliably are the ones with both – in the right balance.
Most organisations have the balance wrong. Correcting the balance starts with recognising what generalists do, and treating that capability as essential rather than convenient.
References
- David Baskett, “Industry Has a Translation Problem”, Medium, March 2026.
- Ady Coles, “Mind the gap: Why strategy gets lost in execution”, Mantage Ltd, January 2026.
- Ady Coles, “Mind the gap: How to translate strategy into execution”, Mantage Ltd, January 2026.
- https://generalist.world
Ady Coles works with leadership teams to help strategy survive contact with reality. His focus is on strategy management and agile strategy delivery - designing the translation between intent and execution so that direction remains coherent as organisations move, grow, and adapt. He works as a fractional and advisory partner where clarity, judgement, and sustained alignment matter more than plans on paper.
He is also a community guide at Generalist World.