Answer “when can we release it?”​ under pressure — Timeline Abstract à la Heily

Heily Hindrea
7 min readMar 24, 2021

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The Singles’ Day

It is 14th October 2020 and I have been forwarded an email with a question from the senior management — can we get an important change done by 11.11 sales day?

For the audience members who are not familiar with the significance of 11.11 — “Singles’ Day is a holiday celebrated in China on November 11. Unmarried people commemorate the occasion by treating themselves to gifts and presents, leading Singles’ Day to become the largest online shopping day in the world, by quite some margin.”

As I am checking the calendar I realise — we are just 20 working days away from the biggest sales day of the year and the change requested has not been mapped out yet. How would you answer? What would you do?

Here is how I went about it…

Keep Calm!

The situation feels tough and my “reptilian brain” (aka amygdala) wants to run away without even looking at any of the facts — just say “NO!”.

Let’s see why and what is at play here:

  • The uncertainty is high as we have not started the refinements = scary.
  • The timeline is very short to go through the full cycle — plan, refine, develop, test, release, stabilise = even more scarier.
  • The stakes are high because of the risk we might be taking when releasing too close to the single most important sales day of the year while not having almost no recovery time if anything were to go wrong = through the roof scary.

Even though it looks like good enough reasons to reject the request almost immediately — I have been long enough in this game to know that I need to force myself through the “why, what, how, when” process before I can give an answer.

Every “no” (same way as a “yes” or a “maybe”), needs hard core arguments in order to evaluate the situation and back up the decision. As I have learned — in the moment of feeling rushed, the best thing to do, is to slow down.

Starting the process from the beginning while ignoring the big red countdown clock in my head, is the way to go here! Even when it feels like every delayed minute, hour and day can become fatal for the release, I tell to myself: “Just forget about it for a second and keep calm!”.

Know the “why” before you storm the troops

Firstly, I look at the “why” — making sure I am asking all the right questions from the stakeholders. Why is this release important to be done before sales day? What is the business impact and significance of it? What happens if we do not release it? What do we gain, if we do? How is customer impacted by the success or failure of this particular move? What other business risks may be at stake here? etc.

Without me taking the time under the heat to understand the situation I might be setting myself up for failure in conveying the importance of the topic to the development teams later. I need to be convinced by the worthiness of the interruption before I throw the “bomb” at them as I need their buy in, if we decide to execute.

Take the pressure out from the situation — unhook the deadline from the jobs to be done

As I have understood the significance of the topic at hand, now is the time to storm the troops. Knowing already from my own amygdala default reaction, I need to help my team to see past the pressure of the deadline. I tell them to forget about the deadline as at this given moment it is not important — we need to get the answers to the “what” and “how” first.

  1. What are all the jobs needed to be done for it? Every team representative will start listing out the tasks.
  2. How much time and effort is needed for them to successfully and confidentially finish this job. Here we are using actual man days for the estimations as eventually we need to answer the question about “how much time would it take” and “whether we can make it for 11.11 or not?”.

As I am writing down all these notes I have set the corner stone for something called “Timeline Abstract a`la Heily”.

Timeline Abstract is a way to create a timeline without actual dates. You can think of it as a blueprint overlay which you can put on top of a calendar in order to determine where you might be landing with your release date.

For this Example — let’s say Team X needs 8 days, Team Y needs 5 days. The team with the longest time will be taken as the total time needed, which is 8.

For the above to work, it is very important to manage the room and really make them feel that I am not trying to squeeze this release out of them, but I am listening to them and just mapping out the situation. I know we are not yet there to answer the question from the senior management, and that is ok.

Listen to our team’s worries

Now I can start addressing the hypothetical deadline of 11.11 release by asking questions that help me to see what they are seeing and what they might be worried about. Worry creates cortisol in the body and blocks the mind to think, thus it is important here to give the space for the team to speak openly.

  1. If we were to want to release for 11.11 what other risks are you seeing? The team is listing out different obstacles — from the code freeze timelines, stabilisation period etc. All these find their way to the Timeline Abstract.
  2. Next comes one of the most crucial questions — “Tell me, what else is currently on your plate and would be fighting for your time and effort? If we were to prioritise this new emerging topic, what else would needed to be sacrificed? What do you need to compromise with? Who do you feel you would be disappointing?

This is a gold mine as the team starts to answer — this gives a clear list of items and impact areas that can be used in discussions with other managers and the senior management. This would give them the understanding on what will be “delayed” as per previous plan if we would shift our gears to support this new topic. All time related items mentioned by the team find their way to the Timeline Abstract as well.

I have expanded the Timeline Abstract with the information I have gotten — we need to be live at least 7 days before the peak day to feel comfortable. This brings the total time needed to 15 days.

As we have listed out all the influences to our timeline, it is time to do a reality check agains the deadline.

On the paper and with this simple math exercise it looks like we are in the “green” for the 11.11 deadline! Whohooo! We could go back to the management with the following statement — if we start the work now, or latest by 19th October, then it looks like we are able to make it. Right?

Well…

What looks good on paper, does not mean every aspect is reflected!

The golden question about confidence

Thus, I ask one final question from the teams:

  1. How confident do you feel with the plan, taking into consideration every aspect we have spoken about — select a number from the selection of 0, 30, 50, 80, 100%.

This question works like magic, because suddenly the teams need to put everything we have spoken about into an evaluation — they need to give a number that represents their mixture of worry and confidence.

Most of the team members give the evaluation of 80%, which is acceptable as no-one under these circumstances would say 100% — there are still risks and unknowns hidden in this journey. 80% is totally acceptable and appropriate evaluation and I am interpreting it as high confidence. However, suddenly one of the team members answered — 50%, which gets me a bit off guard. In order to unfold the 50/50 confidence I follow up with a question:

  1. What needs to be true, so that you would be able to raise your confidence to 80+%? From this, additional aspects emerge that we would need to address.

Lucky, I asked this confidence question, right ;)!

Since the 11.11 release is still a bit shaky, then I play around with an alternative scenario by asking the team about sacrifices and confidences if the deadline would be extended and would land just before 12.12 (another upcoming peak sales day). Everyone gives a green light and an 80+% confidence for that particular date.

By now me and the team are equipped with all answers — we know “why, what, how” and we can also give a clear break down for the “when”. We can tell about how big the job is, what sacrifices need to be made, what are the risks, what do we need etc. We can continue to make an informed decision whether to execute the move or not.

Can you guess what we decided to do ;)?

For the Timeline Abstract template I have put it into a GSheet and you are welcome to make a copy out of it if you would like to give it a go.

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Heily Hindrea

Solutionist on the kitchen side of fashion e-commerce. I ignite the mindset changes to transform teams from feature teams to real product teams.