Advisory
Advisory Retainer
The interpretation layer between your portfolio data and your executive table.
The problem
What looks normal from the inside often isn’t.
Every organization has a version of this: a team that’s been off track for two sprints, three sprints, a quarter, and nobody flags it, because inside the org it doesn’t look like drift. It looks like Tuesday. That’s not a data problem. Your platform is live. The dashboards work. The problem is that the people closest to the work are the least equipped to see when the work has quietly stopped serving the strategy.
This is where the Advisory Retainer sits: a monthly, outside set of eyes that knows your organization well enough to move fast, but sits far enough outside it to see what’s stopped looking unusual to the people inside it.
What's actually at risk
Run the numbers on a single mid-sized team. At a blended fully loaded US rate of $125 an hour, an eight-person team costs roughly $520,000 a quarter, over $2 million a year. Organizations waste an average of roughly 9 to 11 cents of every dollar invested due to poor project performance, year over year.[1] Do that math against your own number.
Pendo, the product analytics platform companies use to track real feature usage inside their own software, found that public cloud software companies collectively sank up to $29.5 billion in R&D spend into features that went unadopted or underused, based on usage data across 615 subscriptions.[2]
None of that requires a catastrophic failure to matter. It just requires nobody watching the drift between what leadership committed to and what the team is actually doing, quarter after quarter, until it compounds.
A note on where these numbers come from, because it matters: you’ll often see a claim that 64 percent of software features are rarely or never used, usually attributed to the Standish Group’s CHAOS database of over 500,000 projects. Tracked back to its source, that number actually came from a 2002 conference presentation covering just four internal applications, not the large database it gets credited to. It’s been repeated for over twenty years regardless. That’s exactly the kind of thing an outside advisory eye should catch, including in its own materials. The number above is the one that survived that scrutiny.
Additional data points, for scoping conversations with blended or offshore teams
Strategy execution research places well-formulated strategy failure at 60 to 90 percent, with poor execution costing companies close to 40 percent of a strategy’s potential value.[3] If part of your team is offshore, industry data shows 15 to 26 percent of project hours typically lost to rework and defect correction, rising to 30 to 50 percent when quality management is weak, driven mostly by requirement misunderstanding.[4] Cross-cultural research offers one explanation for why that misunderstanding runs higher, and surfaces later, on blended teams: India scores 77 on Hofstede’s power distance index versus 40 for the US, meaning deference to authority and reluctance to escalate disagreement are culturally normal there, not a communication failure.[5] The practical effect: a status call can end with US leadership believing the plan was confirmed, when what actually happened was a culturally appropriate response that wasn’t agreement at all.
The mechanism
Why you can't see it from the inside
There’s a well-documented reason insiders miss this, and it isn’t a lack of competence. Sociologist Diane Vaughan’s research on organizational culture, developed from her study of NASA’s decision-making before the Challenger disaster, describes a pattern called the normalization of deviance: when a practice repeats without an immediate, visible consequence, it stops registering as a deviation and becomes the accepted norm inside the organization, even when it would look obviously wrong to someone standing outside it.[6] The project management literature has since applied the same pattern directly to project environments: it’s usually only in hindsight that people inside an organization recognize their seemingly normal behavior was, in fact, off track.[7]
That’s the mechanism the Advisory Retainer exists to interrupt. Not by asking endless discovery questions, an outside advisor who has to relearn your business every engagement is expensive in a different way. But by staying close enough, monthly, ongoing, to translate what’s actually happening on the ground into the language your leadership table needs, while staying far enough outside the day to day that what’s become invisible to your team is still visible to me.
This is the same principle that makes executive coaching work on individuals: a trained outsider sees patterns a person can’t see in themselves, not because the person lacks insight, but because you cannot observe your own blind spot from inside it. The Advisory Retainer applies that same discipline at the organizational level.
What I deliver
Monthly portfolio translation
A single, leadership-ready portfolio view the CTO can take into every leadership meeting with confidence.
Strategic interpretation
Not dashboard configuration. Connecting execution data to the investment commitments leadership made.
Leadership-ready reporting
Language leadership actually speaks: investment, outcomes, strategic alignment, not burn rate and velocity.
Drift detection before it compounds
Watching for the normalization patterns that make misalignment look like normal operation from inside the team, and naming it before it becomes a missed quarter.
Who this is for
Post-implementation organizations where the platform is live but leadership still cannot answer the investment question with confidence. The data problem is solved. The interpretation problem, and the blind-spot problem, are not.
How this starts
I move fastest with organizations I’ve already worked with, through a Portfolio Diagnostic, Vendor Selection, an Implementation engagement, or Executive Coaching. That’s the home game: I’m not learning your business from scratch, I’m applying a lens I already have on an organization I already understand. Month one is a working month. Drift detection and portfolio translation start immediately.
If you’re starting cold, the same lens still applies, it’s just being pointed at your organization for the first time. That takes real orientation before the first leadership-ready translation lands, and I won’t pretend otherwise. What compresses that ramp is that the diagnostic thinking itself, the instruments, the questions, the way I look for drift, already exists. I’m not building a new methodology for your organization. I’m applying a proven one to new terrain.
Either way, the retainer is fractional: the hours scope to what the engagement actually needs, typically somewhere between 10 and 40+ hours a month, set in the first conversation rather than sold as a fixed package.
Coming from prior work together, or starting cold? Let’s figure out which path fits in the first conversation.
The business case
A fixed monthly retainer for fractional advisory time, scoped in the first conversation. You get ongoing senior-level interpretation, and an outside perspective structurally capable of seeing what your own team cannot, without adding headcount or committing to a full-time hire.
When leadership can finally see, and the organization still won’t move, that’s the other half of the practice: Executive Coaching.
Leadership asks the same question every quarter. Can you answer it?
References
[1] PMI, Pulse of the Profession® 2021, primary report. Wasted investment due to poor project performance was 9.4%, down from 11.4% the prior year. pmi.org
[2] Pendo, The 2019 Feature Adoption Report, primary report, based on feature usage analysis across 615 Pendo subscriptions. pendo.io
[3] Harvard Business Review-sourced strategy execution research, as summarized in: gwork.io, “The Strategy Execution Gap.” gwork.io (secondary source; underlying HBR article: Sull, Homkes, and Sull, “Why Strategy Execution Unravels,” 2015)
[4] Offshore rework and defect-correction industry data, as summarized in: SmartDev. smartdev.com (secondary/industry source)
[5] Hofstede cultural dimensions data for India and the United States: arXiv working paper, “E-banking and E-commerce in India and USA.” arxiv.org
[6] Diane Vaughan, The Challenger Launch Decision: Risky Technology, Culture, and Deviance at NASA (University of Chicago Press, 1996). Primary source.
[7] Direct academic application to project management, peer-reviewed: study of interviews with 21 project managers, International Journal of Project Management, via ScienceDirect. sciencedirect.com