How to prioritize programs to drive clarity

There is always more work to do than resources available – both for individuals and for teams.

To solve this, let me introduce how I prioritized my work at Microsoft and Okta – creating a backlog and cutline. A prioritized worklist makes it easy validate you’re working on the most important tasks, and it helps you communicate your priorities to your management and peers.

This approach has four steps:

1. Create a list of the work that needs to do- this can be an initial brain-dump
2. Enrich the tasks with data that helps you make decisions
   • Assign three attributes to each row on the table, using t-shirt sizing (S, M, L, XL):
     • Level of effort – how much work does this require?
     • Business impact – how impactful is this on the business?
     • Cost – how expensive is this work?
   • Add the following data points, to help clarify how this work drives impact
     • Primary KPI – what outcome does this drive?
     • Own/support – are you the primary owner of the work? or are you supporting someone else?
   • Sort the list initially by business impact (XL -> S) and level of effort (S -> XL)
3. Add a Priority column and ruthlessly assign one of four values:
   • P0 – Required/committed work; you can’t avoid or cut this stuff
   • P1 – Critically important; supports your OKRs/KPIs
   • P2 – Drives significant business impact, but has a smaller impact on your OKRs/KPIs
   • P3 – Areas that could drive business impact or work that is no longer a priority
   • P4 – ‘Nice to have’ work that is probably not formally committed
4. Review your prioritized list and revisit it until you have a list that you are comfortable with:
   • Sort: Resort the list by priority (P0 -> P4), business impact (XL -> S), and level of effort (S -> XL)
   • Evaluate: Review the order of the list and determine how much you can actually accomplish with the time and resources that you have available – that’s your ‘cut line’
   • Iterate: Repeat this step until you are comfortable with the prioritization and your cut line!

For example, a DevRel team may have a prioritization list that looks something like the below image. At a glance, it’s easy to understand exactly what the team does (top-of-funnel outreach and technical content), and where they support the business. It’s also clear what business outcomes that they are driving, and which ones are not a priority.

With your prioritized list in hand, you can socialize this with your management/leadership, your peers/stakeholders, and with your team members. These lists are fantastic to drive clarity of what you are (and are not) doing, and they enable trade-off discussions to align scope.

A few tips from my experience building these lists:

• List order – The order of the list matters – even within a given priority level.
• Colorization – I like to mark ‘at risk’ items orange and ‘below the cutline’ items in red.
• Notes – I add a notes column for budget and KPI changes, and other assumptions baked into sizing.
• KPIs – Ensure that your most important workstreams track the KPIs that you are accountable for.
• Strategic projects – If you are doing a strategic project (a big experiment or new investment), call it out with its own color.
• Owned vs Supported – I like to track my ‘owned’ and ‘supported’ lists separate. And it’s important that you have a healthy set of workstreams that you own (the outcomes that your uniquely driving) and that you support. If you find that you are not listing many workstreams that you support, it’s a sign that you aren’t capturing everything or that you may be living on an island – both are bad.
• Owners – If you have a team, write down the name of the individual who is the owner for that work. And, yes, it needs to be a single name – who is the individual that feels most accountable for the work and who you would call to understand how the work is progressing.

Once you have your priorities set, get to work!

And as you execute, I find it useful to revisit this list on a monthly basis – both to validate that your T-shirt estimations are correct and to verify that your priorities are…well…being prioritized. If they aren’t, reflect on why they aren’t and update the list to reflect your reality.