On-Site Strategy Day – align IT roadmap, spend and risk with your business agenda.
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Executive Add-On • On-Site • Strategy Workshop

On-Site Executive IT Strategy Day

One focused day on-site with your CEO, leadership team and key IT stakeholders to align IT roadmap, spend and risk with your real business plans – in plain English, without vendor pressure.

Explore an On-Site Strategy Day Back to Executive IT Strategy Club
Available primarily across Canada & USA. Travel is capped and discussed up front.
At a glance
  • ✔Pre-session planning call and agenda design
  • ✔Full-day facilitated strategy session on-site
  • ✔Written summary and 90-day action outline

Typical investment: From $5,250 USD plus capped travel
Priority access for Advisory & Counsel members.

What an On-Site Strategy Day achieves

Unified roadmap

Bring projects, wish lists, vendor proposals and “we really should fix that” items into one prioritized, time-phased roadmap.

Clear ownership and cadence

Clarify who owns which initiatives, how decisions will be made, and how progress will be monitored at the leadership level.

Board-ready narrative

Turn the day’s outcomes into a simple, repeatable message for boards, lenders and staff about where IT is headed and why.

Typical agenda for the On-Site Strategy Day

Morning – where we are today
  • ✔Business context and growth / efficiency goals
  • ✔Current IT environment: high-level view of systems, providers, and tools
  • ✔Key pain points, risks and “we lose sleep over this” scenarios
  • ✔Snapshot of current IT spend (if available)
Afternoon – where we’re going next
  • ✔Drafting an 18–36 month IT roadmap aligned to business plans
  • ✔Prioritizing initiatives by impact and effort
  • ✔Defining ownership, success measures and decision checkpoints
  • ✔Agreeing a 90-day action plan and communication approach

You’ll also receive a concise written summary of the day, including the agreed roadmap and 90-day actions, suitable for internal or board updates.

Discuss an On-Site Strategy Day

Good fit if...

  • ✔You have multiple IT initiatives competing for time and budget.
  • ✔Leadership is aligned on business goals, but not on IT priorities.
  • ✔You want a vendor-neutral facilitator, not a sales pitch.

Probably not a fit if...

  • You only want a 60-minute high-level overview with no working time.
  • Your leadership team cannot commit to a full-day working session.

Common questions

Can this be delivered virtually?

Yes, we can run a virtual or hybrid equivalent, but for complex environments or sensitive discussions, on-site often works better.

Do you provide a formal report?

You receive a structured summary with roadmap, priorities and 90-day actions. A more formal report can be scoped if required.

Can our MSP or CIO participate?

Yes. We typically include them for parts of the day to ensure realism and buy-in, while keeping the focus on business outcomes.

Give IT a seat at the strategy table – without the jargon.

An on-site day can move IT from “foggy cost center” to a clear, prioritized business enabler.

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