Second Order Advisory

Value is created
in the second order.

Decisions are judged on immediate outcomes, on what can be easily measured. The work that matters happens before anyone starts on the answer: in how the problem gets framed, what gets measured, and what does not.

The Lens
I work on the question before anyone starts on the answer. The decision that creates or destroys value is almost always made before execution begins.
In how the problem gets framed, what gets measured, and what does not. That is where leverage is highest, and where most advisory work never reaches.
Not sold as time. Engaged at the moment the decision matters, before scopes are locked and before the internal narrative has hardened.
Who I Work With

Four markets. One lens.

The legal market is restructuring. Firms, departments, law companies, and investors are all navigating the same shift, but from different positions. The questions differ. The stakes are the same.

Law Firms

Practice positioning in a post-AI market

Managing Partners · Practice Group Leaders · COOs · CMBDOs

As AI compresses the routine and redefines what is science versus art, value is migrating from execution to judgment. Most firms are still priced and organized for where value used to sit.

Legal Departments

Operating model for a faster, cheaper world

General Counsel · Chief Operating Officers, Legal

Efficiency gains do not remove pressure, they relocate it. From volume handling to trust, judgment, and internal alignment. The operating model needs to catch up.

Law Companies

GTM anchored in real pain, not features

CEOs · Founders

Technology amplifies demand, but only if it is anchored in an existing, urgent problem. Most positioning is not. I help reframe solutions upstream, around what legal buyers actually feel.

Investors

Signal versus story in legal tech diligence

Legal technology and services focused funds

In a crowded market, narrative coherence is a leading indicator of product-market fit. Pre-investment diligence and portfolio acceleration: cutting through story to what is actually there.

How I Engage

Not sold as time.

Three engagement modes, each designed to meet the problem where it actually sits, not where it has been presented.

Diagnostic

The problem is not clear yet

“We know something is wrong, but cannot see it clearly.” A short, fixed-fee engagement to define the real problem, identify where value is being created or lost, and reframe the options before any scope is written.

2-4 weeks · Fixed fee · Output: clear framing, decision points, next moves
Advisory

The problem is clear. The response is not.

“We can see it, but do not know what to do.” A defined engagement with a specific outcome: designing the commercial or operating response, tied to value rather than inputs.

Defined scope · Fixed fee · Output: decision-ready plan tied to value
Ongoing

The decision needs to hold over time.

“We need judgment in the room as this plays out.” Embedded at key decision points, challenging, refining, and adapting as conditions change.

Fractional or retainer · Output: sustained judgment and course correction
In Practice

The reframe in action.

Two examples of how second-order thinking changes what gets built, and what it is worth.

Law Company

The problem was not awareness. It was switching.

Framing
More reach, more awareness equals more demand. Invest in SEO and outbound email campaigns.
Question
“Even if customers read the email, would that make them switch?” Buyers already knew the category. Switching was not about logic, it was political and psychological risk.
Shift
Stop trying to be found. Start trying to be experienced. Build trust outside the buying moment. Become the host of valuable conversations.
400+ GCs engaged through a global events series · Oversubscribed in under 18 months · Inbound demand with trust already established
Legal Department

The problem was not pricing. It was the deprecation of relationship.

Framing
Reduce outside counsel spend through procurement. Run RFPs, push down rates, apply commodity logic.
Question
Rate pressure shifts cost, it does not remove it. Adversarial buying reduces flexibility and drives defensive behavior. Procurement optimizes for price comparison, not value creation.
Shift
Reduce panel size. Concentrate work with fewer firms. Rebuild trusted relationships that allow cost to be actively managed.
Multi-million cost avoidance without blunt rate cuts · Stronger relationships, increased flexibility · More predictable spend · Better outcomes with fewer firms
Matthew Todd

The point of view comes from having lived it.

Not observational knowledge. The kind formed from operating across firms, in-house, and law companies at a senior level, with real P&Ls, real trade-offs, and real skin in the game.

I do not simply optimize work. I challenge whether it should exist in that form. I think in commercial models: positioning, pricing, packaging, delivery. And I stay out of implementation, so the advice is not conflicted by follow-on work.

Elevate Executive Leadership Team · 10 years · General Manager, ElevateFlex
JPMorgan Chase Executive Director, Legal Operations — built the global Legal Operations function
WilmerHale · Reed Smith MD Information & Research Services, CKO equivalent
CMS Practicing UK Solicitor · SRA Compliance Officer for Legal Practice
Value is created in the second order, not in what can be immediately measured, but in how the problem gets framed before anyone starts on the answer.
  • Operated across firms, in-house, and law companies at senior level: lived the incentives and P&Ls, not just observed them
  • Thinks in commercial models: positioning, pricing, packaging, delivery, not just workflow optimization
  • Works across analytical, operational, and narrative simultaneously
  • Anchored in where value is moving post-AI, not where it used to sit
  • Stays out of implementation, so the advice is not conflicted by the prospect of follow-on work

The first conversation is a pressure test.

Of the problem as it has been framed. Of the assumptions underneath it. And whether the question being asked is the right one. That is often where the most valuable work happens.

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