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Foundational learnings and observations for driving transformations

Few months back I had the opportunity to speak at an Agile event organised by a Fortune 500 Company. The talk was quite well received as it had plenty of real-life learnings based on various customer engagements around driving great transformations.

The intent of this writeup is to share with you some of those learnings and especially some of the scaling activities which act as low hanging-fruits and deliver value quickly across different levels of the Organisation.

The content is setup around “Observations and Concerns” , which is coming from the customer’s CIO (or similar role) and “Comments & Activities” which are the comments and learnings coming from a Jira Align solutions architect.



Following is one of common struggles of any senior executive in a large organisation


To help increase transparency and visibility, we can work with relevant customer’s stakeholders (LACE) to take the Organisation on a Scaling Journey.


Starting with Team Agility, here are some of “Observations and Concerns” which are generally shared by the leadership and the relevant “Comments & Activities” which can address some of the team level practices and make them scale ready.



My observations: Teams are delivering stories, but the alignment to business value might be missing and also no clear way of managing dependencies and risks etc

We should then ask ourselves, are our teams ready to scale -

  • Are there any clearly defined overarching business objectives which teams feel they are contributing towards (and not just sprint goals)

  • Does our Kanban team just exist only on a Jira board or is it actually doing Kanban - few pointers being - WIP limits, monitored throughput, uniformity in sizing etc.

  • Do our Scrum teams have some sort of synchronicity in cadence?

  • Are our Jira Team boards pulling work from 3 or more projects? Thus creating a spaghetti of board-project mapping

  • Do the Jira epics have 30 + stories as children, because higher the number of child stories, higher the delivery risk for that epic. Even for epics pertaining to tech debt or regular maintenance we should be able to measure the effort spent on such activities and hence complete them within a quarter rather than dragging them forever.

  • Can you clearly demarcate the teams in your Jira instance using a proper custom field or is it that some teams are using labels, some components and some teams just projects and hence there being no way to clearly fetch issues the teams are working on and completed so far.

Some of the these activities are low-hanging fruits which might not require lot of change management but can surely make your teams scale ready. The teams should be also looked at as “Data hooks” for the levels above and if the data rolling-up is of good quality then we know that there will be better predictability and consistency at the levels above the team.

Now, moving onto the next level i.e. the “team of teams” (Program/ART etc), here the teams are planning together at a regular cadence (Big Room planning, PI planning etc) and collaborating towards delivering business objectives, while identifying risks, dependencies and being organized around value.


Following are the “Observations & concerns” that we see shared by the leadership for the program level and the “Comments & Activities” which can help provide better alignment to strategy and value.



So, even if we have a “team of teams” construct like an Program, Tribe or an ART, we need to ask ourselves some fundamental questions -

  • Are they organised around value?

  • Are the teams in good knowledge of how their work is enabling the flow of value

  • Do we have stability in the teams, wherein instead of creating and disbanding the teams we are actually bringing the work to the long lived teams which can be aligned to the products / solutions.

  • Where does our Feature backlog live, do the program stakeholders have ownership of this backlog or is there no clear feature backlog and teams are working haphazardly to deliver whatever is presented before them.

  • How are we identifying risks, dependencies and key business objectives and what are the relevant ceremonies involving the teams.

  • Do we have regular prioritisation and alignment sync-ups across the relevant stakeholders and the product team. This is key to make sure we are building the right stuff and also aligned with Portfolio leadership on delivering work that yields the highest business value.

  • Are we able to predict whether or not the programs have sufficient capacity to deliver work for the upcoming quarter based on historical trends and the current demand.

Addressing all of these points can seem daunting at first but if we start working towards them one at a time then surely we will see ourselves becoming better at alignment, prioritisation, predictability and demand management.

Let us now briefly talk about Portfolio Agility. Portfolio acts as a bridge between strategy and execution and by leveraging LPM principles we are focussing on the following key aspects

  • Value driven and outcome focussed portfolio investments over traditional projects with start and end date.

  • Using lean business case and value hypothesis to approve relevant investments.

  • Tracking value delivered to make that crucial decision to pivot or persevere.

  • Moving away from Annual funding to a more Lean quarterly budgets

  • Funding value streams over traditional projects.


Below are the “Observations & Concerns” which mostly Organisations have before embarking on a LPM journey. And the “Comments & Activities” which can help you jumpstart some key Portfolio practices.



So even if our current Portfolio practices are not Lean, we can start with some of the above mentioned activities rather than a big bang approach -

  • A mature portfolio kanban lifecycle can help streamline portfolio investments and provides much indeed transparency. Using relevant exit criteria for each process step of the lifecycle along with syncup sessions with the right stakeholders can jumpstart your LPM journey.

  • Associating lean business case and value hypothesis with portfolio investments help us in decision making when it comes to building the stuff that matters the most.

  • Creating relevant Portfolio Objectives and aligning them with the work items helps in tracking value delivered and being focussed on the outcomes.

  • Conveying the strategic intent to the execution teams along with Portfolio vision helps keep the teams motivated and aligned.

  • Close collaboration & sync sessions with strategy & leadership in order to be effective in portfolio prioritisation and setting portfolio vision.

  • Moving away from looking at Portfolio as a group of projects and rather looking it as a way of funding initiatives which enables value streams to deliver value to the end customers.

In this writeup I have shared activities and learnings which I have seen working well with customers of almost all sizes.

What are the ceremonies/practices that you think can provide great value as well without large change management.


Mark Cruth
Atlassian Team
Atlassian Team members are employees working across the company in a wide variety of roles.
February 22, 2022

Absolutely LOVE this article! It's so important to build upon a strong foundation (at each level of scale) - if not you're bound to have lots of pain on the journey. Thank you for sharing this @Tarun Sapra !!!

Like Tarun Sapra likes this
Christoph Piotrowski _catworkx_
Marketplace Partner
Marketplace Partners provide apps and integrations available on the Atlassian Marketplace that extend the power of Atlassian products.
February 22, 2022

Hi @Tarun Sapra , thanks a lot, great article! :-)

Like Tarun Sapra likes this


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