A focused AI strategy workshop for founders and executive teams, prepared around the business agenda and followed by a concise decision record, priorities and next-step roadmap.
THE DIRECT ANSWER
It should produce a shared executive position, prioritised opportunities, explicit trade-offs, material questions, named owners and a practical next step rather than an unranked list of ideas.
The agenda is built from the decisions leadership needs to make, supported by a short review of current initiatives, business priorities, constraints and available evidence. Participants receive clear questions rather than a generic introduction to AI. Relevant use cases and tensions are surfaced before workshop time is used.
The session aligns leaders on the outcomes AI may support, the role it should play in the business and the principles that will govern investment and use. Existing activity is made visible and conflicting assumptions are tested. The conversation stays grounded in the organisation rather than becoming a tour of tools or trends.
Candidate opportunities are compared using value, feasibility, information and process readiness, consequence, adoption effort and ownership. The group identifies the strongest first moves, questions requiring further evidence and activity that should be paused. Trade-offs and dissent are recorded instead of being smoothed away.
The follow-up captures the executive position, priority opportunities, material risks, immediate decisions, owners and recommended next step. Depending on the need, this may be sufficient on its own or become the starting brief for an AI readiness review, business case or defined transformation project.
HOW THE SIDEKICK WORKS
Connect the ambition, evidence, operating reality and competing views before committing to the answer.
Create an executive-ready view of the options, commercial implications, risks and evidence still required.
Shape the brief, partners, governance and business change so the work lands beyond the technical build.
FROM “WE SHOULD” TO “WE DID”
THREE WAYS TO WORK
A focused working call for one AI, technology or strategic question. Leave with the decision, the next move and a short written note.
90 minutes · £90Book a Sidekick Session02 / COMMISSION ONE OUTCOMEA defined review, business case, roadmap, digital build or transformation mandate with clear scope, ownership and handover.
Bounded scope · clear outputExplore a Sidekick Project03 / ADD SENIOR CAPACITYEmbedded strategy, transformation or Chief of Staff support when the work needs continued judgement and follow-through.
Fractional · outcome-ledExplore a Sidekick PartnerKEEP MOVING
Questions, answered
Usually the smallest useful group of executive sponsors and leaders from the functions affected by the likely opportunities, such as operations, technology, data, risk, finance and people.
It produces a concise executive position, prioritised opportunities, key questions and risks, named owners and a recommended next step.
No. The workshop is designed around business decisions. Technical and specialist questions are identified clearly and assigned to the right experts.
It can establish direction and decisions. A complete investment roadmap may need further evidence, stakeholder input or specialist assessment depending on scope and consequence.
The next useful move
Share the decision, idea or priority that needs to move. We will identify the lightest useful next step.
Discuss the live priority