100 days plan for creating a Lean Portfolio

Context

You are in an organization where you are driving different initiatives and they are being approved in silos, without having a strategic view about where each one of these initiatives are going on.

Better understanding of the ROI of the investment is required, to keep the pace of construction is desired, understand there is not duplicated capabilities that are not justified, improve synergies and to understand there is alignment with overall business objectives is key.

Under a big amount of software development teams working in different directions that are creating great value, there is a moment where some governance is required and here the role of portfolio manager jumps into scene.

Purpose

Cover how to start-up a portfolio: governance, processes, tools and events that will enable a decision making process that contributes to the alignment of all these initiatives.

Where to start

The portfolio should not start from an empty space, there is a place in the organization that is the right place to start, gain some speed of execution and then extend into other areas of the organization.

Some people prefer to start from an empty space and avoid bias though some niches.

Both starting points have pros and constrains, so evaluate which one fits better for you.

Authority, context and governance

Let’s start with authority, this has to be defined, communicated and respected by the rest of the organization. This sounds simple and stupid, but I have lived situations where this was not done and the result was a complete lose of time, energy and motivation.

Gain a good view about the context, how?. Analyzing the climatic patterns that are affecting the organization, identifying the predominant doctrines that teams are living, and identifying the main bottlenecks they have in terms of capabilities.

Governance, there should be a set of simple definitions at different levels, and these should have to be adapted as the portfolio grows and evolves. Long story short:

• Strategic level: define vision, values, methods, objective and measures.
• Tactic level: define specific actions to start with. For instance: decision events, rules for certain documentation.
• Operational level: work on existing processes, put in place changes to them, increase the efficiency and adapt them to the new needs. You will discover that there are people already doing portfolio type of work and that is working well, take advantage of that and reduce the aversion to the new entity (the portfolio).
• Communicate, communicate, communicate.
• The methodology I would apply: Lean Portfolio Management combined with Lean Six Sigma and Wardley Maps.

It’s a 13 weeks work

The summary of activities for the 100 days is:

• Day 1 – Let us be Honest
• Day 2 to Day 20  – Map it!
• Day 21 to Day 50 – Analyze in deep & build the portfolio entity
• Day 51 to Day 80 – Work on a specific scope
• Day 81 to Day 100 – Evaluate and roll-out

Day 1 – Let us be Honest

• Define vision, values, methods, objective and measures.
• Define a calendar of meetings to discuss with the Sponsor of the initiatives and define the rules of communication with this person (escalation, delegation of authority, basic rules of engagement…).
• Describe the main pain points of the organization, areas where the communications are not good…
• Prepare a specific speech for each set of stakeholders about goals and benefits of your plan. The benefits of this speech have to be linked to the needs of the audience.
• Then communicate, communicate, communicate…

Day 2 to Day 20  – Map it!

• Understand the roadmap of the different teams, their direction, complexity and their boundaries.
• Discover how they are organized.
• Capture a snapshot of the projects under execution and forecasted initiatives.
• Define a list of stakeholders.
• Define OKRs.
• Draft strategic themes and portfolio vision.
• Learn about the level of participatory budgeting that exist.
• Start to draw a RACI chart with the main areas of work. Who is who and what they really do.
• Communicate, communicate, communicate…

Day 21 to Day 50 – Analyze in deep & build the portfolio entity

With all data and information gathered within the organization, it’s time to sit down with the sponsor, convene the strategic themes, define the portfolio vision, and define how to start the portfolio.

• Define a future date, a significant one, to derive the new requests into the portfolio. For instance, if today is June 20th , for the new requirements for January 1st they all should be received by the portfolio entity. The amount of time given should make sense for the existing backlogs and the business: there is space to adapt, and there is not interruption on the execution teams.
• In this way, these new requests can be reviewed, and completed with information from other relevant stakeholders. You should have already identified gaps in terms of quality of the documentation and communication, so there should be room for providing value there.
• The decision process and the criteria for assigning priorities to the initiatives should be defined. This should contain a set of qualitative metrics (for instance MoSCoW), quantitative parameters (for instance WSJF) and ground rules for the events where all this will be discussed.
• Work in deep the nature and different sizes of the requests. Create a classification.
• Define spending guardrails, practices and processes by value stream, by nature of the work and size of the request.
• Define rule to measure actual expenditure Vs. planned expenditure.
• Create an assessment form for evaluating the maturity of each value stream.
• The definition of a range of budget for the following period of time should be known, and how this budget is going to be invested too (the decision process). All this should be communicated and feedback should be gathered.
• The portfolio has to be immersed in the rest of the teams. Put an eye on the fact that portfolio management is another value for the rest of the teams and has to be part of them.
• In case you are not familiar to the predominant doctrines in the organization, evaluate them. The table suggested by Simon Wardley about doctrines is very useful (https://doctrine.wardleymaps.com/).
• Communicate, communicate, communicate…

Day 51 to Day 80 – Work on a specific scope

• Pick with the sponsor a specific scope (ART, a set of groups or whatever is more convenient).
• Work with them on concrete things: definition of requests, their quality, their roadmap, their backlog, the way they estimate, the way they set priorities.
• Focus on what-if scenario modeling, when doing it compare trade-offs and compromises.
• Rank the investment requests by business drivers, and by the quantitative rules you have defined.
• Learn from all that, adapt the processes and tools to fit into it. It will not be perfect, but make it work.
• Improve the participatory budget process in case is required.
• Be in the middle of the dynamics and understand how to increase the speed of execution. Avoid to be a stopper or slower of the development process.
• Related to the budget expenditure, promote flexibility, autonomy, and speed within the value stream, while maintaining cohesion across the portfolio.
• Look for the value that is created, the concrete benefits this has into the organization.
• Enable that the team adopts the new processes and the use of the proposed tools.
• Understand the link between the value stream goals and the organization goals.
• Communicate, communicate, communicate…

Day 81 to Day 100 – Evaluate and roll-out

• Evaluate the results obtained during this short period of time.
• Define a scale of level of implementation of the portfolio into the team, and set the scope you have worked on it.
• Discuss with the sponsor what worked well, bad, what should be improved, etc.
• Decide about the best way to perform the roll-out of these processes/tools into the rest of the teams.
• The preferred approach could be by business priority, by the maturity of the teams, and many other criteria. Pick the one that better fits into your organization.
• Refine the tools and processes and continue being engage with the scope you already are engaged in.
• Communicate, communicate, communicate…

Tools

All this should be supported by tools, so the portfolio and all different stakeholders can manage that huge amount of information in an organized way. But which ones?

Well, probably the organization already have something where different backlog activities and other agile knowledge is being tracked. So, with the exception that the lack of tool or the fact that tools are a relevant problem, that will be the place where the portfolio needs will be hosted in one way or other.

If the tool is Jira Align you are a lucky LPM 🙂

Basic events you should build

• Strategic Portfolio Review (Quarterly)
• Participatory Budgeting (Quarterly)
• Portfolio Sync (Monthly) (for months without Strategic Review)
• PI Planning (Quarterly) (one month after strategic portfolio review)

Challenges of real life

All this is a change and people will perceive it as a change, so you have to pay attention to the perception all this have in the existing environment.

There are other typical hurdles you will face as:

• Lack of definition of the epics that delay the process.
• The teams are not ready to execute on the underlying business problem. There are always gaps, and work on them are necessary.
• Not enough attention to enablers: so many times, we have to invest on horizontal aspects which ROI is not direct to the value stream but that is an enabler for future value creation.
• Lack of capacity: resources, the right skill/experience resources, tools…
• Lack of insight in the execution: the portfolio manager so many times lack of details and there is a gap of information between sides that needs to be bridged.

What happens after the 100 days?

Ideally, you can do all this in a quarter, but do not desperate if this timing is not enough. After this quarter you should have build something concrete with more or less impact but that is there and depending on the resources you have and the speed of the things in the organization, this should give you a better view about a realistic roll-out for the rest of the organization.

You are trying to deploy a new set of capabilities and value into a set of value streams that are not ideal, each one has their challenges, their problems and they are probably working and evolving on them, while they are delivering. Keep this in mind.

As usual, any feedback is welcomed!