Q&A: How Tax Advice Became a Deal Risk Discipline — Not a Cost-Saving Exercise
Before founding his own policy-focused organisation, Dan Neidle spent more than two decades at Clifford Chance, rising to become the firm’s senior London tax partner. During that time, he advised multinational corporates, financial sponsors and boards on some of the most complex tax questions embedded in major transactions.
Today, his perspective on tax advice reflects how dramatically the role of the tax lawyer has changed — particularly for dealmakers navigating acquisitions, exits and reputational exposure.
Finance Monthly spoke with Neidle about why tax advice is no longer about optimisation, how historic decisions now shape deal outcomes, and what sophisticated clients really want from their legal advisers.
FM: When dealmakers think about tax, many still assume it’s about minimising liabilities. Is that how clients approach it today?
Dan Neidle:
Not at the serious end of the market. Large corporates, institutional investors and private equity sponsors are not looking for clever tricks. They’re looking for certainty.
“Tax advice today is fundamentally about risk. Clients want to know what could go wrong, what might be challenged, and whether something done years ago could suddenly become a problem in the middle of a transaction.”
That’s a very different mindset from the past. The emphasis has shifted from optimisation to exposure management, particularly when deals are under scrutiny from regulators, investors and the public.
FM: How does that change play out in M&A and investment due diligence?
Neidle:
Tax advisers are increasingly focused on the past rather than the future. In acquisitions, the key question is often not how to structure the deal, but what the buyer is inheriting.
Historic tax positions — sometimes taken decades ago — can sit quietly until a sale, IPO or refinancing forces everything into the open. Some of those positions were taken in a very different legal and enforcement environment, and they don’t always stand up well today.
For buyers, that can affect valuation, warranties, indemnities, insurance, and occasionally whether the deal goes ahead at all.
FM: Is enforcement really tougher now, or is that perception overstated?
Neidle:
It’s very real. Tax authorities are better resourced, better coordinated internationally and much more confident about litigating.
“The era when large companies could rely on complexity or opacity to manage tax exposure has gone. If something is aggressive, it will eventually be challenged — and in most cases, the taxpayer will lose.”
Courts are also far less tolerant of artificial arrangements. That reality feeds directly into how boards and deal teams think about risk.
FM: How much does reputational risk now influence tax advice?
Neidle:
In many cases, more than the legal risk itself.
Clients don’t just ask whether something is lawful. They ask how it would look if it were public, how it would read in a prospectus, or how it might be interpreted by a regulator or parliamentary committee years later.
Tax behaviour has become a proxy for governance. Advisers have to factor that in, because a technically defensible position can still be commercially disastrous if it undermines trust.
FM: Do you still see aggressive tax planning among major corporates?
Neidle:
Very rarely — at least where serious capital is involved.
“The cost-benefit calculation no longer makes sense. You might save some tax, but you introduce uncertainty, delay transactions, and potentially invite scrutiny that far outweighs the upside.”
What clients increasingly want are boring, defensible positions. That may not sound exciting, but when you’re executing a complex deal or preparing for an exit, boring is exactly what you want.
FM: How does this affect founders or private equity sponsors preparing for exits?
Neidle:
Exits are where historic decisions really surface. When you prepare for a sale or IPO, everything is reviewed in detail — often far more closely than when those decisions were originally made.
Structures that were put in place early on, sometimes with limited documentation or poor advice, can suddenly become very visible. Even if they don’t derail a transaction, they can slow it down or reduce value.
Good advisers help clients identify and address those issues early, before buyers start asking uncomfortable questions.
FM: You’ve spoken publicly about the misuse of legal pressure. Does that have lessons for dealmakers?
Neidle:
Yes — particularly around strategy and judgement. There’s a tendency to assume that legal force automatically gives you control over a situation.
“Threatening litigation can be a spectacularly bad move, especially in matters that touch on public interest or governance. Instead of containing an issue, it can amplify it.”
Part of modern legal advice is telling clients when not to escalate. Just because something is legally possible doesn’t mean it’s strategically sensible.
FM: Does complexity in the tax system itself create deal friction?
Neidle:
Absolutely. Decades of anti-avoidance legislation have produced a very dense system that increases compliance costs without necessarily improving outcomes.
From a deal perspective, complexity slows transactions, increases advisory spend and creates uncertainty. Simplification would benefit business without materially reducing tax revenue — but it requires political will.
FM: How do you see the role of the tax lawyer evolving?
Neidle:
Technical expertise will always matter, but judgement matters more.
As automation and AI take over routine analysis, the value of advisers lies in assessing risk, anticipating scrutiny and guiding clients through grey areas with confidence. Tax lawyers are increasingly strategic advisers embedded in deal teams from the outset.
FM: If you were advising a board entering a major transaction today, what would you tell them to prioritise?
Neidle:
Defensibility and clarity. Understand your historic positions, document your reasoning and avoid anything that relies on optimism rather than evidence.
Deals are hard enough without carrying unnecessary tax uncertainty into the process.
What Dan Neidle does now
After leaving Clifford Chance in 2022, Neidle founded Tax Policy Associates, a non-profit organisation that works with a network of tax and legal professionals to investigate tax avoidance, enforcement failures and systemic weaknesses in the UK tax system.
Rather than advising individual transactions, his work now focuses on evidence-based analysis for policymakers, journalists and institutions — bringing transparency to areas of tax risk that often only surface once deals are already done.
For dealmakers and advisers alike, his career arc reflects a broader shift in the profession: from clever structuring behind closed doors to accountability, defensibility and long-term risk awareness.
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