Skip to main content

Transition from Waterfall into Agile with outsourced development company

Last post 07:20 pm May 24, 2019 by Tom Ottmann
8 replies
02:11 pm May 13, 2019


we're a 15 ppl company across 3 countries/remote, with 1 person/project manager in IT (me), the CEO and the team (working the daily tasks, not IT related).

Currently, we're customizing our CRM system. I've got 4 Milestones for this quarter from the CEO.

So I've started planning (I wrote kind of user stories and elaborated on details - 9 pages Word document) and have sent the plan towards our software dev contractor.

They got back to me with some clarifications, discussions on individual points etc.

After a max. of ca. 6 time back an forth (some details back to the CEO, some input from the team and their feature requests), we're finally ready to start.

Ca. 6 weeks of planning with back and forth.

The Software dev company quoted around 4 weeks of development time.

From our experience, there will be some more weeks of testing and bug fixing etc.

I've broken our 4 milestones into ca. 8 sub tasks / features which might make it possible to do testing for those individually.

What didn't work well was the long planning process with back and forth with the team and the CEO and their busy schedules.

And I'm not sure, whether our software dev company is used to, or would be able to transition to a more agile approach. (quite a big company in India, not bad, but with some people remote as well.)

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?



08:13 pm May 13, 2019

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"?

09:36 pm May 13, 2019

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?

12:40 pm May 14, 2019


  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).


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?

02:44 pm May 14, 2019

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.

08:52 am May 19, 2019

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?

10:39 am May 19, 2019

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?

10:59 am May 19, 2019

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.

07:20 pm May 24, 2019

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

By posting on our forums you are agreeing to our Terms of Use.

Please note that the first and last name from your member profile will be displayed next to any topic or comment you post on the forums. For privacy concerns, we cannot allow you to post email addresses. All user-submitted content on our Forums may be subject to deletion if it is found to be in violation of our Terms of Use. does not endorse user-submitted content or the content of links to any third-party websites.

Terms of Use may, at its discretion, remove any post that it deems unsuitable for these forums. Unsuitable post content includes, but is not limited to, Professional-level assessment questions and answers, profanity, insults, racism or sexually explicit content. Using our forum as a platform for the marketing and solicitation of products or services is also prohibited. Forum members who post content deemed unsuitable by may have their access revoked at any time, without warning. may, but is not obliged to, monitor submissions.