This week we continue with our 5 Top Challenges for Digital Leaders series, looking at Agile Angst Part 3 - delivery date drama!
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(Here’s Part 2: The Dreaded Annual Budget Bun Fight if you want to catch-up).

​Even if you’ve been leading agile projects for years, there’s always uncertainty about teams meeting delivery dates.
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In our work, talking to NZ’s leading CDOs and CIOs, we’ve heard two main complaints:

1. I have no certainty that my agile project is going to deliver when my team tells me it will.
2. Somehow we got committed to a date that’s really not achievable

​In a perfect world agile teams would not have to commit to a delivery date. Features would just ship to users when they were ready.

But unfortunately in corporate life if you want your project funded then usually the quid pro quo is that you have to promise to deliver something in return. And preferably this year!

This can be super-stressful for a transformation leader. Does my team really understand the work involved to deliver the promised feature? Do we know enough upfront about how we will solve the technical issues? Are the right sort of resources available to help the project?
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So, what can you do to reduce delivery date uncertainty and the emotional angst this can cause?

A reader recently pointed out to me that it doesn’t matter how technically good you are, if you don’t have the culture you need in your team, you’re not likely to be successful beyond the short term. He’s absolutely right. Underpinning any high performing team has to be a desire to deliver great outcomes for users; curiosity and thirst to continually learn and improve; and strong collaboration, respect and trust within the team.
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This is the place to start and it’s on you and your people leaders to develop the culture you need for your team to thrive. 

One of my favourite sayings is “you can’t eat the elephant in one bite” and this is so true for large or complex agile projects. Is your minimum viable product really and truly the minimum or have you introduced additional scenarios that aren’t needed for day one? Be ruthless about your bite-sized chunks.
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If your project is complex or has multiple deliverables then your team needs to develop an upfront roadmap showing their current best knowledge of how they will phase the project, which can be continually refined as the project progresses. 

There are at least two schools of thought about this – on the one hand doing the easy things first gets runs on the board for your team and success breeds more success. (And please do celebrate that success).

On the other hand, if you start with the hardest stuff first then you’ve got the most time to figure it out. And you’re more likely to de-risk your longer-term delivery.

Whichever way you decide to sequence your work you can future-proof your project by having some of your most talented people working to solve the biggest issues up front.

Is integration with your customer system likely to be a problem? Get your best folks on it now and stand up a proof of concept for how you will manage it.
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Will your sales staff need a lot of training to learn this new feature? Get your change people on it right away so they have enough time to develop their thinking and content as the project progresses.

Work with your teams to help them identify areas where they need improved or additional skills.
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A team that consistently under-delivers each sprint may need help with their estimation process. Or maybe dependencies outside the team are causing delays and you need additional skill-sets within your team or a new way to manage dependencies.
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Ask your agile coach, experts within your wider organisation or external advisors to spend time working with each of your teams on the issues that are impacting delivery.

​Once a team has broken their work down into sensible phases, ensured they’ve tackled the hard stuff early, have the right resources and are working on the things that impact them, then the team needs to set and own a targeted delivery date. 

An agreed team date means:

1. Everyone in the team is responsible for the date, not just the product owner or the person who presents to the execs.
2. “What’s getting in the way of us hitting the date?” is a common conversation at team ceremonies and all voices are encouraged to participate (and are listened to).
3. Metrics are in place to honestly track project progress and this data is shared widely.
4. Urgent action is taken if a part of the project goes off track.

​You can foster this sense of accountability by ensuring a culture where speaking up about schedule is rewarded and by helping teams overcome hurdles that get in the way of delivery.

Most of us are not (literal) rocket scientists or involved in life or death situations. Strong discipline around meeting delivery commitments is unquestionably something to aspire to for high performing teams but don’t do it at the risk of your or your teams’ mental health and well-being.
 
Sometimes stuff happens that derails you and you just need to re-group and get on with it.
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And if team well-being is an issue then go back to step one and work on your culture some more!

​Good luck!

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