Matthew Henderson

Clear thresholds let teams resolve routine issues close to the work and reserve executive attention for decisions that need it.

Henderson traces a slipping project’s escalation from the project manager to a director, delivery leader and executive team, then recommends setting rules for resource changes, extra effort, margin erosion and scope changes.

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Henderson recommends clarifying process ownership, how work enters the organization, which systems hold authoritative information and where automation can replace manual coordination.

Henderson describes a company growing from 30 to 100 people as teams create separate spreadsheets and software, leaving employees to link the systems.

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Faster activity is not enough: leaders should connect an investment to a measurable business result.

Before approving an AI initiative, Henderson says to identify the problem, current baseline, expected improvement, full delivery cost and a metric for deciding whether to continue. In a separate post, they warn that automating a broken process can simply reproduce its problems faster.

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They should weigh short-term savings against the delivery capacity and capabilities those cuts may weaken.

Henderson suggests comparing executives’ time spent on escalations and resource conflicts with time spent on strategy and talent development, while tracking indicators such as capacity, utilization, margins and forecast confidence. They also list cuts that can look good for 90 days but lead to slower delivery and lower quality later.

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They frame the process as assessable across several defined dimensions.

The Tipstyrs Candidate Experience Score covers communication, transparency, candidate effort, process efficiency, closure and follow-through, and candidate sentiment. Henderson’s point: a rejection can follow a good process, and an offer can follow a poor one.

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Start here to understand the business behind the name.

Henderson writes that after 30+ years leading projects, PMOs, professional-services organizations, transformations and operating teams, the same failure kept appearing at companies of every size: project delivery is harder than it should be.

• Priorities compete, resources stretch, reporting describes what already happened instead of what to do next, tools multiply and governance turns into bureaucracy.
• Problems surface too late.
• Waypost is presented as the answer, with PMO strategy and modernization, project rescue, transformation, work-management technology, change management and flexible access to experienced delivery leaders.
• Its Waypost Talent Network offers practitioners for fractional, interim, advisory and project-based work.

For brands planning a campaign

For a fractional PMO or delivery-transformation buyer, this frames the opening conversation around Waypost’s listed services—PMO modernization, rescue work and fractional delivery leadership—rather than a general consulting pitch.

This post is where Henderson explains it directly, so newcomers can see why a company tied to the name no longer operates.

Henderson announces that Kolme Group, which ran for almost nine years, has shut down operations.

• The post says it grew into a global professional services firm with more than 1,700 clients and a team across three continents, and was named to the Inc.
• 5000 along the way.
• They call the outcome hard, say the experience made them a better leader and state they are looking for a next role in senior professional services, PMO or operations leadership.
• They describe themselves as strongest with high-growth organizations that need someone to build the operating systems to scale.
• The post closes with an open offer to reconnect, including in the Fort Collins, Colorado area.

For brands planning a campaign

This pivotal career-change item signals active availability for senior delivery or operations work, shaping both the timing and form a fractional or interim engagement could take.

It shows what PMO work means in practice.

Henderson describes a recurring professional-services pattern: a project slips, the project manager escalates to a director, the director to the delivery leader, the delivery leader to the executive team, and leadership ends up debating staffing, scope, margin and recovery.

• Occasional escalation is necessary, they argue, but constant escalation signals that the delivery organization lacks built-in decision authority.
• A mature PMO should set thresholds: when a project manager can adjust resources, when delivery can approve added effort, when margin erosion must escalate, when a scope change triggers commercial talks and when executives genuinely need to be involved.
• Without those rules, everything becomes a judgment call, and judgment calls tend to move upward.
• The line to remember: a good PMO is not an escalation factory but a business operating system that pushes better decisions closer to where the work happens.

For brands planning a campaign

Use the threshold questions as the first diagnostic in a delivery-transformation engagement: undefined decision rights send work up to executives, where the resulting escalation can be measured.

Henderson writes that rapid growth can make a company look successful and dysfunctional at once.

• New customers and revenue lead to team growth, but processes that worked for 30 people stop working for 100.
• Teams create their own spreadsheets, departments buy their own software, and people become the integration layer between systems.
• The company ends up running on messages, files, tribal knowledge and a few heroic employees.
• The instinct is to add people or technology, but they argue the better move is to revisit the operating model: who owns the process, how work enters the organization, how decisions are made, which systems are authoritative and where automation should replace manual coordination.
• Growth, in this view, needs more intentional structure, not more complexity.

For brands planning a campaign

A natural first conversation with a fast-growing client: where has growth outrun the operating model, and which parts of delivery are held together by individuals rather than systems?

Useful for readers seeking a concrete test rather than a framework.

Henderson suggests that an executive's calendar often reveals a company's operating health.

• Time spent on status meetings, escalations, customer issues, projects turning red, resource conflicts and revenue surprises can be compared with time spent on strategy, market opportunities, capability building, talent development and innovation.
• When almost everything is urgent, leadership becomes the company's exception-management system, which does not scale.
• The proposed fix is better leading indicators, so executives see conditions forming: capacity trending down, utilization climbing, pipeline weakening, margins compressing, milestones slipping and forecast confidence declining.
• Forecasting, they argue, is less about predicting the future perfectly than creating enough visibility to intervene while options remain.

For brands planning a campaign

A strong discovery question for a prospective client: what would you have needed to see earlier to act before the deadline was missed or the forecast changed?

A current, concrete demonstration of the argument that systems and metrics come before tooling.

Henderson flags the sentence "AI will make us more productive" as a dangerous premise in business cases because it rarely answers by how much or where the gain shows up in money.

• The post covers what organizations typically buy—licenses, copilots, pilots, consultants and infrastructure—and the question that comes months later: what was the actual benefit?
• It cites Foundry's 2026 State of the CIO research, reporting that only 19% of respondents said their AI initiatives had met or exceeded ROI goals and only 47% had formal success metrics.
• Before approving an AI initiative, they want five things: the business problem being solved, the baseline cost or performance today, the expected operational improvement, the total cost of delivery and the metric that decides whether to keep investing.
• A task dropping from four hours to one only counts if it reduces cost, raises capacity or revenue, improves margin, cuts risk or accelerates delivery.

For brands planning a campaign

Positions Henderson for buyers weighing AI investment in delivery and operations, with a concrete talking point on ROI discipline and success metrics before spend is approved.

Henderson describes decisions that look fantastic for a quarter: freezing hiring, delaying training, cutting implementation resources, reducing investment in systems, pushing utilization higher and deferring infrastructure work.

• Six months later, the effects show up: slower delivery, lower quality, burnout, customers noticing, growing technical debt and stalled growth.
• The post calls this one of the hardest executive tradeoffs: balancing today's profit and loss against tomorrow's operating capacity.
• Utilization can be pushed so high that the best people have no capacity to mentor, improve processes, support sales, build new services or handle the unexpected.
• The answer, in Henderson's framing, isn't short term versus long term, but an operating model that makes the tradeoff visible.
• Leaders can then ask what happens to next quarter's revenue, what capability is being reduced and what demand assumption is being made.

For brands planning a campaign

Useful framing for a fractional engagement aimed at protecting delivery capacity while meeting margin targets, and for identifying which apparent cost savings are really deferred capability.

Henderson describes building Tipstyrs and the question that drove it: what exactly are we rating?

• Not whether you got the job, whether you liked the recruiter or whether the interview questions were easy, but the quality of the hiring process itself.
• The post lays out six dimensions—communication, transparency, candidate effort, process efficiency, closure and follow-through, and candidate sentiment—that combine into a Tipstyrs Candidate Experience Score.
• The underlying principle is plain: a rejection can come from a great hiring process, and an offer can come from a terrible one.
• The post invites people to add their own recent hiring experience to the platform.

For brands planning a campaign

Broader than a PMO brief, but it shows a habit of turning a fuzzy experience into a structured, measurable score—useful to any client that values measurement design.

One post traces a slipping project as it moves from project manager to director to delivery leader to executive team, then lists thresholds a mature PMO should define: when a project manager can adjust resources, when delivery can approve extra effort, when margin erosion requires escalation, when scope change triggers commercial discussions, and when an executive genuinely needs to get involved. A good PMO, the post concludes, is not an escalation factory but an operating system that brings decisions closer to the work.

For brands planning a campaign

For a fractional PMO engagement, use this as a discovery frame: ask where decisions stop, which thresholds are missing, and how often routine issues reach executives. The talking point is governance that creates speed, not more reporting.

Examples: Source 1

The post lists costs that accumulate through licenses, copilots, pilots, consultants, and infrastructure, then cites Foundry’s 2026 State of the CIO research: only 19% of respondents said AI initiatives had met or exceeded ROI goals, and only 47% had formal success metrics.

• Henderson’s five approval questions cover the business problem, baseline cost or performance, expected operational improvement, total delivery cost, and the metric for deciding whether to keep investing.
• AI becomes transformative, they argue, when it reduces the number of decisions executives need to make, not merely the amount of information they receive.

For brands planning a campaign

For an AI or transformation conversation, lead with the baseline, total cost, and decision metric. Ask which approvals could be removed or handled at a lower level if AI performs reliably within agreed thresholds.

Examples: Source 1 · Source 2

If the underlying process is broken, AI helps execute a broken process; if data is poor, AI results are poor; if approvals are unclear, automation makes unclear decisions faster; and if five systems hold different versions of the truth, AI inherits all five. The post asks whether a workflow would exist in its current form at all, then recommends removing unnecessary steps, clarifying ownership, standardizing inputs, connecting systems, and defining decision rights before introducing AI to eliminate friction.

For brands planning a campaign

For delivery transformation, start with process ownership, data quality, and decision rights before tooling. Automation without operating-model repair can create a more sophisticated version of the same chaos.

Examples: Source 1

A $400K tool versus a $250K tool looks like $150K saved until contract termination penalties, additional modules, onboarding, and operational impact are included.

• The business case, they say, should compare current total cost of ownership with future total cost, transition cost, and operational impact, and ask which operating system produces the best financial outcome.
• Related posts describe software-stack chaos: three teams using different tools for the same problem, and applications no one wants to retire because ownership is unclear.
• Henderson recommends starting with an application inventory that records each application’s owner, purpose, primary users, and data created.

For brands planning a campaign

A consulting firm can propose an application and workflow inventory as an early paid diagnostic. Position it around ownership, data authority, and total cost rather than license-price comparisons.

Examples: Source 1 · Source 2 · Source 3

Six months later, delivery slows, quality drops, employees burn out, customers notice, technical debt grows, and growth stalls.

• The post asks what happens to next quarter’s revenue if a cut is made today, what capability is being reduced, and what assumption is being made about future demand.
• Henderson frames the answer as an operating model that makes the tradeoff visible—not a choice between short term and long term.

For brands planning a campaign

In a margin or utilization conversation with a professional-services leader, use this to separate expenses from investments in future capability. The engagement angle is visibility into capacity, delivery risk, and demand assumptions.

Examples: Source 1

Most organizations focus on project approval, while far fewer focus on termination.

• Stopping the wrong project can create more value than starting a new one because every project consumes budget, talent, leadership attention, and organizational capacity.
• If a project is no longer aligned to strategy, continuing it is avoidance.
• A related post says an executive’s calendar can diagnose operating health: too much time spent on status meetings, escalations, resource conflicts, and revenue surprises means leadership has become the company’s exception-management system.
• Henderson recommends better leading indicators, including capacity, utilization, pipeline, margins, milestones, and forecast confidence.

For brands planning a campaign

For a PMO or portfolio review, offer stop/continue criteria and executive reporting that surfaces problems before deadlines are missed. This is a practical entry point for governance work.

Examples: Source 1 · Source 2

Processes that worked for 30 people stop working for 100; teams create spreadsheets; departments buy their own software; people become the integration layer between systems.

• The company starts running on Slack, Excel, tribal knowledge, and a few heroic employees.
• Henderson recommends revisiting the operating model: who owns the process, how work enters the organization, how decisions are made, which systems are authoritative, and where automation should replace manual coordination.
• Growth requires more intentional structure, not simply more people or tools.

For brands planning a campaign

For high-growth organizations, frame a PMO or delivery transformation engagement around process ownership and work intake. Ask which systems are authoritative and where manual coordination is holding the model together.

Examples: Source 1

Instead of saying there is no cloud, AI, or cybersecurity talent, organizations can look for engineers who want to grow, analysts eager to learn, project managers ready for bigger challenges, and team members who have never been given the opportunity.

• Not every gap requires a new hire; some require a development plan.
• Another post says upskilling programs fail when treated like homework: learning should be scheduled, protected, measured, and rewarded as part of the operating model.
• A third says capability beats headcount and leaders should know where expertise should live, inside or with a trusted partner.

For brands planning a campaign

A consulting firm can frame engagements around capability transfer and development plans rather than staff augmentation alone. Talking points include protected learning time, internal talent pipelines, and where external expertise genuinely adds capability.

Examples: Source 1 · Source 2 · Source 3

The Tipstyrs Candidate Experience Score covers communication, transparency, candidate effort, process efficiency, closure and follow-through, and candidate sentiment.

• The principle is that a rejection can come from a great process and an offer from a terrible one.
• A separate post defines ghosting for the methodology as no offer, rejection, next step or meaningful status update within 21 days after at least one meaningful interview, while measuring communication and follow-through separately from process duration.
• A lighter post praises Procore Technologies for a streamlined Workday application workflow.

For brands planning a campaign

This is a separate venture from Henderson’s PMO and delivery consulting themes. It is relevant to employer-brand, recruiting, or candidate-experience conversations, but should be scoped separately from a fractional PMO engagement.

Examples: Source 1 · Source 2 · Source 3

The post lists PMO strategy and modernization, project rescue, transformation, work management technology, change management and flexible access to experienced delivery leadership. Waypost is also growing a Talent Network of project, program, PMO, change, transformation and work management professionals for fractional, interim, advisory and project-based engagements.

For brands planning a campaign

This directly overlaps with a fractional PMO and delivery transformation engagement. Clarify how Waypost delivery compares with the firm’s model, whether Henderson would work through a firm or their own network, and what capacity is available.

Examples: Source 1

They describe building a global professional services firm that grew to 1,700+ clients and a team spanning three continents, with a place on the Inc.

• 5000.
• They say the experience made them a better leader and that they are now looking for the next challenge in senior professional services, PMO or operations leadership, ideally with high-growth organizations that need someone to build operating systems to scale.

This is a personal career update, not a general teaching post, so it should be read as context for current availability rather than as a topic framework.

For brands planning a campaign

This is key context for availability and motivation. Before proposing an engagement, ask what current commitments exist, whether fractional or interim work is intended, and how Waypost and Tipstyrs fit alongside a firm engagement.

Examples: Source 1

Examples include the escalation pattern in delivery organizations, the five AI approval questions, the tool-consolidation cost formula, and the executive-calendar diagnostic. The posts are framework-driven rather than case-study-driven; they use repeated hashtags and a newsletter invitation, and they rarely name client outcomes or provide detailed examples.

Diagnostic-list format: provocative claim, bulleted symptoms, decision questions, operating-model conclusion.

For brands planning a campaign

A collaboration can reuse the diagnostic-list format for short-form content on PMO, governance or delivery risk. Ask for client-specific examples, implementation details and outcomes.

Examples: Source 1 · Source 2 · Source 3 · Source 4 · Source 5 · Source 6

The same post announces the Waypost Talent Network, a curated group of project, program, PMO, change, transformation, and work-management professionals available for fractional, interim, advisory, and project-based engagements, and points readers to the Waypost company page. This is the current business at the centre of their consulting work.

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One post sets out how Tipstyrs defines hiring "ghosting": a candidate has completed at least one meaningful interview and 21 days have passed without an offer, rejection, next step, or status update, with communication and follow-through measured separately from process duration.

• Another describes the six dimensions behind the Tipstyrs Candidate Experience Score (CXS): communication, transparency, candidate effort, process efficiency, closure and follow-through, and candidate sentiment.
• Both posts invite candidates to submit their hiring experiences at Tipstyrs.com.

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They describe building it into a global professional services firm that grew to more than 1,700 clients and a team spanning three continents, with a place on the Inc.

• 5000, and say founding and operating the company made them a better leader.
• The relationship is historical: the post records the closure and their search for a senior professional services, PMO, or operations role next.

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Horowitz examines cumulative execution risk across a strategic portfolio and signals that decision rights and priorities have become unclear.

Horowitz addresses boards and executive teams on enterprise-wide oversight and strategy execution. Henderson focuses on project delivery, PMO governance and professional-services economics, including practical thresholds for escalation and tool cost.

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Shcherbakova writes about permanent change, transformation fatigue and the limits of constant reinvention. Henderson warns that automation over broken processes and short-term cuts can damage future delivery capacity.

Shcherbakova focuses on the finance function and CFO agenda, including AI, ESG, shared services and data governance; Henderson focuses on project delivery, PMOs, professional services and tool rationalization.

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Ciampoli connects plant data, documentation and procedures to better decisions; Henderson makes the same case for project delivery and operating models.

Ciampoli writes about industrial manufacturing and ERP/operations-intelligence work, including ECIC and OPSIDIAN; Henderson writes about PMOs, professional services and delivery leadership, with more emphasis on executive decision rights and AI business cases.

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Horowitz writes about whether a board can see the enterprise's capacity to deliver its whole strategic agenda, not just each initiative's business case.

• In a September 2026 post, Horowitz notes that directors rank oversight of strategy execution as their top improvement area, and argues that AI investment, M&A integration, restructuring, operating-model change, and cost transformation often run at the same time — each defensible on its own, with the cumulative demand on the organization largely invisible until milestones slip or talent leaves.
• A May 2026 post makes the related point that executive teams are operating from adjustment rather than conviction, adding approvals and oversight that slow execution underneath.
• If the client's real problem is that governance reviews every priority independently and nobody owns cumulative delivery capacity, Horowitz's framing is closer to the sponsor's language than their project-level diagnostics.

The tradeoff is depth of delivery mechanics.

• Horowitz's posts stay at the portfolio and governance level: they name execution risk and ask how boards gain visibility into it, but do not supply escalation thresholds, resource decision rights, project rescue methods, or utilization and margin tradeoffs — the working content a fractional delivery lead is hired to bring.
• A firm would still need hands-on material from Henderson or a similar practitioner to run the engagement.
• Horowitz has two posts, dated May and September 2026; ask for an engagement model, client outcomes, and availability.

Examples: Source 1 · Source 2

Shcherbakova's May 2026 post describes finance operating in permanent change — AI, automation, ESG reporting, cloud systems, shared services, data governance — and argues that transformation fatigue is a business risk affecting trust, productivity, adoption, and value creation, not only a wellbeing issue.

• The June 2026 follow-up closes the point: the future finance function will be defined by change capacity, and stable processes, trusted data, strong routines, and leadership discipline matter more than constant reinvention.
• For a client whose finance organization has a long roadmap and a tired team, that framing produces a concrete first question — how much change can this function absorb this year — that Henderson's delivery-focused posts do not raise.

The tradeoff is scope.

• Shcherbakova's posts do not cover project delivery, PMO design, escalation authority, or professional-services economics, so they would not address a professional-services firm's delivery-transformation needs.
• The posts are outline-style: they name nine points in a series and state conclusions, without the working method, sequence, or measures a firm could use to run an audit.
• Only two posts, dated May 21 and June 6, 2026, are available; ask for case studies, rates, and availability.

Examples: Source 1 · Source 2

Ciampoli's October 2026 posts describe ECIC's work on operational improvement, ERP alignment, process optimization, and plant visibility, and OPSIDIAN, an operations-intelligence platform that connects plant data, documentation, and knowledge.

• One post asks the direct question — your plant changed, did your procedures change with it — and links documentation falling behind to operational risk, with the goal being visibility and consistency rather than better paperwork.
• That is a sharper alternative for an industrial client where the delivery problem shows up as inconsistent procedures and stale knowledge on the floor, and it comes with a named product to inspect.

The tradeoff is context.

• This is manufacturing-floor work, not a professional-services delivery organization, so the posts do not address the escalation thresholds, decision rights, utilisation economics, and PMO design such an organization needs.
• There are two posts from early October 2026, both written around a Manufacturing Day booth and a product launch.
• Before treating this as a like-for-like alternative, confirm the client's industry and ask for an engagement method, client outcomes, and evidence of how the platform performs in a live plant.

Examples: Source 1 · Source 2