Transition from Waterfall into Agile with outsourced development company

I've got 4 Milestones for this quarter from the CEO

Just a few questions to get you thinking about ways to potentially work more Agile-ly:

1. What is your CEO using to validate that his 4 milestones for this quarter are all valuable?
2. Of the 4 milestones, has your CEO provided an order that they be completed in?   
3. If for some reason your company is only capable of completing 2 of the 4 this quarter, is there clarity around which 2 are preferable to complete, and which 2 can be deferred?
4. What can be done to involve your Software Development company earlier in the process?
5. Is a 9-page Word document the best way to capture either a preliminary plan or requirements?
6. Of all the items included in the 9-page requirement doc, are there any items that can be started immediately, without any need for "signoff"?

I've read a few articles on how to transition but they don't mention our remote / outsourced setup.
How could a transition look like to get faster results in the future?

Why not start with a Definition of Done, and whether or not the Development Team can meet it?

@Timothy: 

1. It's mostly coming from his experience and our roadmap (we are planning to do user interviews later on)
2. The order of work / priorities came from me with hints from the CEO
3. There is kind of clarity, which milestones have higher priorities, yes.
4. Thanks, very good point. I've talked to them and they'll provide some further details on their Agile process
5. I don't know. It seemed to be good and detailed at the beginning. Then there have been changes, questions etc. - now we have 2 big word documents, the CEO wants to avoid reading both (too time consuming) and an Excel project plan. We keep on adding ideas, even though we wanted to look at this project as an individual project at the beginning to be able to define whether it has been achieved or not.
   
   I assume all those issues sound extremely familiar for someone who has done the transition.
6. Yes, there have been. Reading this question, it feels silly that we have postponed everything, until the whole project was planned (and then we figured out, the whole plan won't work out and we simply started at 90% in the planning stage).

@Ian:

How would a definition of done look like, especially if the CEO keep on adding / changing ideas? (It's all reasonable additions and I can see how it's difficult to impossible to predict those additions)

I guess, the problem starts even earlier, where the CEO and I are setting those milestones.

How would this be done?

How would a definition of done look like, especially if the CEO keep on adding / changing ideas? (It's all reasonable additions and I can see how it's difficult to impossible to predict those additions)

The Scrum Guide says: "If 'Done' for an increment is not a convention of the development organization, the Development Team of the Scrum Team must define a definition of 'Done' appropriate for the product." 

So why not work with the CEO on crafting a Definition of Done for the organization, which teams can then use as a suitable basis for their own?

It isn't enough for a CEO to add and change ideas. Ultimately the CEO bears responsibility for what happens in an organization, including any risk to corporate reputation. He or she ought to have a keen interest in helping teams assure that their deliverables meet an appropriate production standard.

Hello Ian,

we had some discussions, with CEO and the dev company.

From the CEO side, it would be possible to change.

What I found online about the Definition of Done is mostly .. code or software related. 

That's what the CEO doesn't care about. He'd simply care about features.

An example:

If we have a backlog story like: As a logged in user, I want to see a dashboard with recent data records.

All good, we'd plan the dashboard and create mockups.

The CEO sees the mockups and asks:

Can we add summarized data and stats on the top, additionally to the dashboard?

Sure we can, no, we didn't plan for it and we don't have it in the mockups and our deadline might be missed.



Where is the problem here?

Would that be a new user story, that I'd need to estimate and push back on the CEOs ideas?

Or was the initial user story not precise enough?

Or anything else?

Shouldn’t the Product Owner be the one who is managing product scope, and the CEO’s expectations? Does the CEO acknowledge that the PO has authority over the work articulated on the Product Backlog, and that he must liaise with the PO regarding any changes that are made?

If the CEO is filling the Product Owner role himself, shouldn’t he have an interest in assuring that work is of “Done” standard, and that Sprint Planning is conducted effectively?

I understand you point.

It seems like, we still have quite a bit work to do.

Thank you for your questions - they really helped in understanding our situation better.

What would be the 1 thing to do, that could help Chris and his CEO the most in their current situation?