STRATEGIC PARTNERSHIP
IT Strategy Workshop.
A paid one-day strategy intensive for leadership teams approaching a decision they want to get right.
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1 day
on-site or virtual, your call
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4–6 attendees
leadership team scope
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$3,500–$6,000
fixed, by attendee count and prep depth
Why this matters.
Most leadership teams can identify the technology decision they're facing. What they often can't do — under their own steam, with their own meeting cadence — is structure the conversation that decides it. The conversation gets sidetracked by the loudest voice, defaults to whichever vendor has the most recent meeting on the calendar, or stays in the abstract until budget cycle pressure forces a rushed call. A facilitated outside session does the structuring work the team's own meeting cadence wasn't built to do — and produces a written record the team can hand to a board, an auditor, a parent organization, or whoever's asking the question that triggered the conversation in the first place.
What we do.
Two hours of pre-workshop discovery — a structured intake call with the executive sponsor, a brief stakeholder survey across the leadership team, a review of any existing strategy documents or vendor materials. A facilitated four-to-six-hour workshop with the full leadership team, on-site if you're within driving distance of Bedford, Bloomington, or Indianapolis, otherwise virtual. The session works through three to four prioritized questions: what we're deciding, what we know, what we don't know, and what the next ninety days look like. A written summary deliverable inside five business days — strategic priorities, ninety-day actions, identified risks and dependencies, and a recommended next engagement (which may not be with us).
What you walk away with.
A strategic priorities document with named ninety-day actions, a risk and dependency map, and a recommendation for what comes next. The deliverable is yours — to act on with your existing team, hand to your MSP, share with a board, or use as the framing for a separate engagement with us or anyone else. The session itself produces a working artifact; the written summary is the formal record. There is no follow-up obligation, no preferred-vendor language baked into the recommendations, no soft commitment to a multi-engagement path. If the session surfaces an ongoing leadership need, the vCIO Retainer is the recurring shape; if the environment needs a baseline assessment before strategy work makes sense, the IT Health Check is the right first step.
What's in scope.
Two hours of pre-workshop discovery (executive sponsor intake call, leadership stakeholder survey, review of existing strategy materials). Facilitated workshop session (4–6 hours, 4–6 leadership attendees). Working artifacts produced live during the session (priorities matrix, risk map, decision log). Written summary deliverable (strategic priorities, 90-day actions, risks and dependencies, recommended next engagement) inside 5 business days. One round of revision on the written deliverable based on leadership feedback.
What's out of scope.
Implementation work — that's a separate engagement, scoped against the priorities. Ongoing advisory between sessions (would convert to a vCIO retainer if the right shape). Multi-day strategy retreats or off-site facilitation (different engagement, different scope). Travel costs for on-site sessions outside the Bedford / Bloomington / Indianapolis corridor (separate at-cost). Vendor demos or sales meetings folded into the session (doctrinally not how this works).
This is the right engagement when…
- A leadership team is facing a major technology decision (acquisition, modernization push, board ask, infrastructure replacement) and the internal cadence isn't structuring the conversation well enough.
- A board, an investor, a parent organization, or a major donor has asked for an IT strategy document, and "we'll get a working group together" hasn't produced one in two quarters.
- You've been working on a decision for months and the meeting that's supposed to land it keeps getting moved — usually a sign the question is bigger than the meeting cadence can hold.
- You want a paid outside facilitator with senior IT context, not a free strategy session from a vendor with an obvious sales motion behind it.
What you receive across the engagement.
- Strategic priorities document The primary deliverable, typically eight to twelve pages. Top three to five priorities with rationale, named 90-day actions for each, risks and dependencies, and a recommended next engagement (with us or anyone else).
- Risk and dependency map Separate one-pager. Sortable by severity and by which priority each risk maps to. Ready to drop into a board or audit conversation.
- Working artifacts from the session Priorities matrix, decision log, parking-lot list. The raw material the team produced during the workshop. Not polished; useful for the team's own follow-up work.
- One round of revision Leadership reviews the written summary; we incorporate one round of feedback before final delivery. Inside the engagement scope; no separate billing.
- Optional 60-minute walkthrough Live presentation of the deliverable to leadership, the board, or whoever needs to hear it from the facilitator's voice. Inside scope if scheduled within 30 days of delivery.
Here's the shape of a session the workshop is built to structure.
How we're different.
- Paid productized work, not free strategy lead-gen. No vendor sitting at the back of the room with a sales motion. No "complimentary follow-up assessment" tied to the deliverable. The priorities document is yours whether you continue working with us or not.
- Principal-led facilitation. Corey runs the session and authors the deliverable. No handoff to a delivery analyst; no pre-templated decks dropped on the leadership team. The person you spec the engagement with is the person facilitating.
- Written deliverable, not a meeting recap. Most strategy workshops end with a verbal handshake and a follow-up email. The written priorities document is the output that survives the meeting — handable to a board, auditor, or successor leadership team.
Want to talk through whether a Strategy Workshop fits your decision?
Indiana · U.S. remote