It’s October, which means that leaves are turning beautiful colors, pumpkin-flavored everything is all around, and a lot of organizations are working through their annual budgeting processes. While many CIOs are focused on ‘big rocks’ and major initiatives for their budget, there’s also value in putting a few small, targeted investments in your 2024 budget to help your team deliver better and to set yourself up for long-term success.

Here are examples of five small investments for technology leaders to make in 2024:

  1. IT Strategy Workshop: rationalize your priorities into a comprehensive vision and roadmap

  2. IT Stakeholder “Voice of the Customer” Review: enhance your partnership with customers to accomplish business and technology goals while boosting satisfaction

  3. Change Control / Demand Management Optimization: address top priorities transparently, get requests right the first time, and better predict workloads

  4. Agile Delivery Health Check: realize the full Agile value proposition with minimal disruption to progress

  5. Program Health Check: identify course corrections that can energize and equip the team for long-term success

For each, below you’ll find information on when they each make sense to pursue, along with the what, who, why, and how of accomplishing them.

We’re rooting for you to make 2024 count – if the FlexPoint team can help you make sense of these or lend a hand in accomplishing them, let us know!


IT Strategy Workshop

If your technology team has experienced substantial change in the past year, has sensed a disconnect between IT and business stakeholders, or feels that “what got us here won’t get us there” in the coming years, an IT strategy workshop may be a great item to include in your 2024 plan and budget.

What

The IT strategy workshop is a multi-day workshop to discuss how the IT team has been working together, align on a vision to drive continued success, and create a roadmap to achieve the vision.

Who

This effort will include the technology leadership team and a workshop facilitator

Why

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.

How

Adjust the following agenda to fit your specific needs in two or three half-day workshops with the technology leadership team, preferably within the span of a week or two.

  • Prep: have each participant fill in a survey around three topics, and have the facilitator 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 [update timeframe for your planning horizon, here and below]

  • Day 1

    • Retrospective: discuss collective lessons learned from the past year

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

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

    • Set a north star (pt. 1): draft the year’s vision and 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 milestones and objectives 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 roadmap: facilitator will work with each team lead and IT leader 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 roadmap: IT leader will share the technology roadmap widely with internal stakeholders

(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 the group to focus on the shared task at hand, and then return to other work or refresh for more productive work the next day.)

How We Can Help

The FlexPoint team has a lot of experience scrubbing into the workshop facilitation role and in creating technology roadmaps. If you’d like our support, we’ll work with you to customize the agenda, gather preliminary information, facilitate the workshop sessions, and lead the effort to create the technology roadmap after the workshop.


IT Stakeholder “Voice of the Customer” Review

If your technology team is feeling friction with customers or is experiencing customers working to solve their technical challenges without IT, it’s a good time to step back and understand the voice of the customer.

What

The IT stakeholder voice of the customer review includes discussions and/or surveys with stakeholders and internal customers about their experience working with IT, compiled into an analysis of strengths, limiters, and opportunities, and used to inform recommendations to improve effectiveness and customer satisfaction levels going forward.

Who

This review will need the IT leader, along with a small cross-functional Voice of the Customer (VOC) team that leads and represents stakeholder groups.

Why

Technology teams don’t exist in a vacuum: typically, the IT team’s goals cascade from business objectives, and achieving those goals is most effective in partnership with business teams. So, healthy interactions with IT customers are more effective and, frankly more enjoyable, than a disjointed relationship. Hearing directly from IT customers about their engagement with the technology team is an important data point to shape the effective partnership.

How

  • Assemble a VOC team: identify a small cross-functional Voice of the Customer (VOC) team that leads and represents stakeholder groups; this group is the actor in below steps unless noted otherwise

  • Design and plan

    • Map out stakeholders: compile a comprehensive list of IT customers (likely by team or function)

    • Determine optimal information gathering techniques: determine the optimal mix of surveys (best in the case of dozens or hundreds of participants) and/or interviews; recruit unaligned interviewer(s) and scribe(s)

    • Identify participants: plan out stakeholders to request feedback from via survey and/or interview; make sure that all stakeholder groups are well represented, and expect less than 100% participation (so include more people than you may think!)

    • Create questionnaire: draft survey and/or interview questions, focused on the stakeholder’s experience with IT, any areas where their expectations and reality differ, and any recommendations they have for improvement; prioritize open-ended questions, with the potential for a few ranking/multiple-choice questions

  • Gather information

    • Request feedback via survey: send the survey to participants, preferably from the VOC team member that is closest to their functional area; share that responses are anonymous and give a target deadline (with some buffer for late responses and compilation)

    • Request feedback via interview: ask to schedule interviews with participants, with the request preferably coming from the VOC team member closest to their functional area; inform them that specific comments will be shared anonymously within VOC team and that themes will be shared more widely

    • Interview participants: unaligned interviewer(s) and scribe(s) facilitate interviews with humility and curiosity, focused on learning and understanding (not explaining or defending how things are today)

    • Compile findings: unaligned interviewer(s) and scribe(s) synthesize responses by question; identify key themes and findings; call out surprises or anomalies to investigate further

  • Conduct strength, limiter, and opportunity analysis

    • Review findings: within the VOC team, discuss summarized findings and surprises; plan out further feedback sessions as needed

    • Identify strengths: call out very specifically what is going well today

    • Name limiters: name perceived limiters (note that they may not fully reflect what is possible or what is happening, but perception is reality in customer service); represent clearly and non-judgmentally

    • Uncover opportunities: based on direct feedback and analysis, describe opportunities for the IT team to excel in partnership with its various stakeholder groups going forward

  • Compile recommendations

    • Summarize analysis: VOC team, interviewer(s), and scribe(s) compile strength, limiter, and opportunity analysis

    • Review analysis with IT leadership team: VOC team and IT leadership team discuss findings and analysis, noting surprises and perception differences

    • Create recommendations: list and prioritize recommendations, then refine in discussion(s) with the IT leadership team

    • Align on next steps: VOC team and IT leadership team select the recommendations to pursue and set a first set of goals

  • Share next steps

    • Review next steps with IT team: VOC team and IT leadership share summarized analysis, recommendations, and next steps with IT team

    • Review next steps with survey and/or interview participants: VOC team and IT leadership share summarized analysis, recommendations, and next steps with those requested to participate

    • Review next steps with internal stakeholders: VOC team and IT leadership share summarized analysis, recommendations, and next steps with impacted internal stakeholders

How We Can Help

If this sounds like a lot of details to get into and discussions to lead, the FlexPoint team can help. We’d be happy to facilitate the VOC team sessions, create questionnaires and emails, lead/document interviews, compile findings, and lead up the analysis and recommendations effort.


Change Control / Demand Management Optimization

If it’s difficult to predict when new project requests are coming in, IT team members don’t have clear priorities between their various tasks, or business requests aren’t given sufficient attention around sizing, sequencing, and planning, it’s time to take a careful look at IT change control and demand management.

What

A change control / demand management optimization effort includes an assessment of current state, requirements definition, designing and piloting new processes, defining implementation and change plans, then launching the optimized approach and driving adoption.

Who

This initiative will include technology leadership, business analysts, and a small group of business champions from across functional areas.

Why

An effective IT demand management process improves productivity of technology efforts through clear roles and expectations, minimizes project failure by setting clear expectations upfront and gathering needed inputs in a consistently thoughtful way, and improves the partnership between IT and business areas through a transparent consideration and prioritization process. (Adding a transparent technology roadmap to productive IT change control makes the whole cycle even sweeter!)

How

  • Assemble change control team, including:

    • Technology leaders, who will be integral to rolling out and maintaining the new process

    • Business analysts, who often have a unique vantage point on the interactions between business and technology teams

    • Business champions, a small group of cross-functional leaders who can represent their functional area’s demand management needs and support their functional areas through effective adoption of the new process

  • Assess current state

    • Understand the existing process and context around why it was designed in this way

    • Comprehend what is working well, in addition to pain points

    • Note where the current process isn’t being followed and seek to understand why

  • Define requirements and key use cases

    • List and prioritize what is needed from the change control / demand management process, technology, and people

    • Create key use cases to illustrate end-user needs

    • Design new processes

  • Draft refinements to the change control process

    • Identify critical roles throughout the process, and draft associated responsibilities

    • Map processes onto technology

    • Conceptually run key use cases through the new design and refine as needed

  • Pilot new system

    • Create a minimum scalable version of the optimized change control system

    • Run a small-scale test of the new system with the change control team, and iteratively incorporate refinements based on feedback

    • Run another small-scale test with individuals who often submit requests with the technology team, and incorporate their feedback

  • Create implementation and change plans

    • Draft the proposed set of activities, training, and communication to roll out the optimized system

    • Take care to address “what’s in it for me?” for various stakeholder groups in change management and communication plans

    • Identify measures to track through and after roll-out to understand levels of adoption and proficiency with the new processes

  • Launch the optimized approach, prioritizing early adoption

    • Roll out the optimized approach, potentially in a phased manner

    • Provide extra context and training where adoption doesn’t meet expectations

    • Spend extra time in early weeks to navigate the new processes with people if they’re not catching on

    • Methodically phase out the previous change control system

How We Can Help

An individual or small team from outside the organization can be really helpful in this type of effort, as it can be easy to defend the status quo (or at least reasons it came about) and hear only some of the feedback that various stakeholders are sharing. The FlexPoint team has come alongside clients and created scalable, intuitive change control processes that reflect input from throughout the organization. If this perspective, expertise, and support may be helpful to you, let us know.


Agile Delivery Health Check

Shifting to Agile mindsets and methods is a big change for any organization. So, if you’ve started adopting Agile delivery methodologies, it’s good to take a thoughtful step back every once in a while to check how things are going.

What

An Agile delivery health check includes reviewing delivery and collaboration from various perspectives, flagging opportunity areas and discussing options to address, and aligning around targeted next steps and metrics to gauge success.

Who

This health check will involve the IT leader and representatives of team members, internal customers, and potentially external customers.

Why

Excelling in Agile delivery enables customer-centric design, effective collaboration, iterative delivery of value, and continuous improvement – but the process of realizing the full Agile value proposition is certainly a journey. Taking time to assess progress thus far and identify practical opportunities for improvement can be a helpful step on your Agile path.

How

  • Assess delivery and collaboration practices, structures, and rhythms

    • Understand the specific Agile methodology, cadences, and roles chosen within the organization

    • Meet with delivery teams to understand how reality does and does not reflect intended practices and cadences

    • Talk with internal customers and potentially external customers to understand how delivery and collaboration does and does not meet expectations

    • Comprehend what is working well, in addition to pain points

    • In every conversation, seek to understand why processes aren’t being followed or expectations aren’t being met (there are often meaningful reasons and tradeoffs that may not be obvious at first glance)

  • Prioritize opportunity areas

    • Compile and prioritize opportunity areas

    • Discuss options to address opportunities with key stakeholders within delivery team

    • Take shortlisted opportunities for improvement to internal customers to get their feedback

    • Consider reviewing the opportunity list at a high level with external customers to gain perspective and increase buy-in

  • Align around success criteria

    • With a shared sense of high-priority improvement opportunities, define metrics to gauge success

    • Set clear objectives and key results for delivery team over the next few quarters

  • Define next steps

    • Determine what it will take to accomplish objectives, aligning as many actions with the Agile practices and cadences already defined (that is, most of next steps should fit into the continuous improvement framework that’s already set up, rather than prompting a bunch of new projects!)

    • Clarify owner and next steps for each improvement initiative, again, largely aligning with Agile roles

  • Assess progress regularly

    • Make sure success measures (and progress against them) are easily accessible

    • Include improvement initiatives in Agile cadences like planning and retrospectives 

How We Can Help

The FlexPoint team has implemented and worked within a wide variety of Agile structures, all with their own unique adoption challenges. We can lead this Agile delivery health check for you, providing an external perspective, expert facilitation, and Agile expertise to support your ongoing success.


Program Health Check

Transformation programs often span several years, include many divisions throughout the organization, and require new capabilities and mindsets to drive success. That’s a lot to ask of your teams. If you’re in the thick of a transformation program and are sensing a stall in progress, or simply that motivation and morale are low, a program health check can be a good investment in 2024.

What

A program health check is a systematic evaluation of project health — scope, budget, practices, teamwork, and more — to identify opportunities to improve the chances for success. This will likely include practices to continue that are working really well, team members who are critical to driving success, and some areas to consider a different approach.

Who

This health check will include at least the transformation program executive sponsor, everyday leader, and a neutral facilitator. In this case, the facilitator will meet with the two participants to understand program goals, progress, financial position, team feedback, and more.

A more thorough health check includes stakeholders throughout the effort, with representation throughout divisions, functional areas, and technical teams. If contractors are involved in the program, the facilitator will get targeted feedback from them as well.

Why

We often see team members, stakeholders, and end users experience transformation fatigue midway through multi-year transformation journeys. Early on in the project, everyone's excited about the promise of transformation, and late in the journey, people can see the light at the end of the tunnel, but it's the middle that can be really frustrating and where organizations and individuals are most likely to give up.

Acknowledging the fatigue, incorporating some course corrections, and reenergizing the team can help everyone persevere through the messy middle.

How

  • Scope and progress review

    • Review recent documentation to understand how the program goals, scope, and progress are represented to various stakeholder groups

    • Meet with participants and understand the clarity of what’s being delivered: how closely do people summarize the effort when they describe it in their own words? do they have simple, intuitive, accessible artifacts to point to around goals and solutions? do they understand the reason for this transformational change?

    • Understand how much of the intended scope has been completed (and, again, if there is consistency in how progress is measured across stakeholders)

    • Discern the quality of what’s been delivered, preferably through discussions with end-users

  • Stakeholder engagement and alignment review, considering the quality of engagement and level of alignment…

    • Within the delivery team

    • With functional stakeholders

    • With customers

    • With key vendors

  • Budget and/or timeline check

    • Review the budget and/or time allotted for the transformation program

    • Candidly discuss performance against the budget with the executive sponsor, everyday program leader, and project managers: how are we really doing? If we’re behind schedule or over budget, what are realistic options to address?

  • Practices and cadences

    • Understand the delivery methodology being used and the degree to which it’s being followed

    • Discuss delivery practices with technical and functional team members to discern what is working well and what isn’t

    • Review program governance and decision-making: are decisions being made clearly and swiftly? is everyone honoring decisions that have been made? if not, what seems to be at play?

  • Team dynamics, roles, and responsibilities

    • Look at project management, product management, and/or scrum master practices: are priorities and guidance flowing clearly to teams? are resource needs being escalated and resolved quickly? are goals being attained?

    • Assess change management: is the people side of change being attended to? are specific, well-trained individuals responsible for preparing end users for new and updated processes and solutions? do they have sufficient resources and influence?

    • Review team dynamics: are individuals and teams working productively with each other? when conflicts or tradeoffs arise, are they resolved amicably, clearly, and completely? are all types of voices being heard in planning and retrospective sessions?

How We Can Help

The FlexPoint team has led and worked in many transformation programs, some from the beginning and some where we started in the middle. We’re well versed in discerning how things are really going, even if the status report has green all the way down. We can provide an objective perspective, backed up by decades of experience in the space, to help you, your team, and any partners re-align the program for success.

Kim Ehrman

Kim Ehrman is a Director of Business Transformation with FlexPoint Consulting. She specializes in creating an ambitious vision and achievable plan for transformation and then working with clients to implement effectively, with an emphasis on customer experience, business readiness, and change management.

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