IT Strategy Workshop

Get clear on what’s important for technology to enable business goals and translate that into objectives, key results, and a high-level roadmap to guide IT efforts over the coming year

Driver

If your technology team has experienced substantial change in the past year, you’ve sensed a disconnect between IT and business stakeholders, or maybe it feels like “what got us here won’t get us there” in the coming years, an IT strategy workshop may help get aligned around the best path forward.

Outcome

Getting clear on a vision, with a good sense for the strengths of and constraints facing the team, will allow the IT leader to set clear objectives and each team lead to create goals that clearly tie back to the overarching objectives. Having a transparent roadmap for how the team is aiming to accomplish shared goals supports making productive tradeoffs and clear decision-making, as everyone can see what is targeted for priorities.

In our experience, strategy workshops also build rapport that contributes to working more effectively together, in addition to the benefits from clarifying the vision and path ahead.

Approach

The FlexPoint team has a lot of experience scrubbing into the workshop facilitation role and in crafting IT strategies that move the needle. We’ll work with you to customize the below agenda, gather preliminary information, facilitate the workshop sessions, and lead the effort to create the technology strategy and roadmap after the workshop.

We recommend conducting the IT strategy workshop over two or three half-day sessions with the technology leadership team, preferably within the span of a week or two. (FlexPoint recommends including key business stakeholders in the preparatory survey and/or much of day one, and then in early reviews of outputs, to make sure that IT isn’t solving challenges in a vacuum. We’ll work with you to craft the best approach for your organization!)

Starter agenda, to be tailored to your specific needs:

  • Prep: we’ll have each participant fill in a survey around three topics, and we’ll compile/share themes during each relevant session

    • Look back: note lessons learned from successes and challenges over the past year

    • Look ahead: predict opportunities and potential challenges over the next several years

    • Ideate: bring proposed initiatives for the coming year

  • Day 1

    • Retrospective: discuss collective lessons learned from the past year

    • Scan the horizon: prioritize opportunities to pursue and potential challenges to mitigate

    • Prioritize: set goals for the next one, two, and five years

    • Set a north star (pt. 1): draft a new/updated vision and the year’s priorities

  • Day 2

    • Set a north star (pt. 2): define the vision and priorities for the upcoming year

    • Envision success: “what will have gone right to reach our north star?”

    • Set the structure: define objectives and potential milestones for the upcoming year

    • Tee up next steps: define an owner for each objective

  • Day 3 (optional)

    • If your leadership team’s time-in-role is relatively low or your vision and priorities are expected to change meaningfully, Prioritize and Set a north star may take longer than the allotted time within two half-days

    • In that case, Set the structure and Tee up next steps can be shifted to Day 3

  • Follow-up

    • Refine strategy: we’ll make the north star vision and priorities compelling and easy to understand

    • Create roadmap: we’ll work with you and each of your team leads to define, size, and sequence initiatives into a technology roadmap

    • Make a plan: each team lead will define key success criteria, additional stakeholders, and budget to meet their objectives

    • Publish strategy and roadmap: we’ll equip you to share the technology strategy and roadmap widely with internal stakeholders, starting with key business stakeholders and then cascading out to technology and business teams

Why half-day workshops?

We’ve found that full-day sessions have a greater tendency for participants to lose focus or to schedule “just a quick call” in the middle of the most important session.

Half-day workshops allow us to focus on the shared task at hand, and then return to other work or refresh for more productive work the next day.

Interested in learning more?