Hey there! I’m Sonya Siderova, founder & CEO at Nave and I help managers hit their targets consistently while growing happy, engaged and motivated teams. This week’s topic is all about managing deadlines effectively and the data-driven approach to making reliable delivery commitments.
Do you ever notice that sometimes when you’re about to leave a friend’s place, you meander towards the door and suddenly there’s this burst of conversation?
It’s like you’re trying to squeeze in everything left unsaid, now that there’s a clearly established time limit.
With your hand on the doorknob, intuition takes over. You want to say everything because this is the only time you have left.
Creativity thrives within parameters and the most important parameter is time. The presence of a deadline forces us to trust our instincts and become more efficient with how we manage it.
The same principle applies in the project management world. Setting and managing deadlines is paramount. Delivering results within the set deadlines is crucial for our business outcomes.
Now, how can we put realistic project deadlines in place while preserving our teams’ creativity, efficiency and well-being at the same time?
In this article, we are going to challenge the traditional project management practices.
Making Reliable Project Delivery Commitments
Arguably, a better question here is how can you make reliable delivery commitments without asking people to estimate each individual task in the project scope?
Let’s explore the concept of probabilistic forecasting. This is an approach that uses your past performance data to produce reliable delivery predictions. The tool that will serve you best for that purpose is the Monte Carlo simulation.
The simulation runs a large number of random trials to predict the delivery of your project. You define your scope, and the simulation provides a range of delivery dates and the probability that comes with each date.
Let’s say that the scope of your project is 40 tasks. The simulation above tells us that there is an 85% probability that you can finish all the project items by Nov 21st. It also says that there is a 95% chance to complete all work items by Dec 2nd. The further you go in time, the greater the certainty of completing all tasks.
So what makes this approach reliable? The fact that it eliminates all the guesswork from the equation.
It doesn’t matter how advanced your team’s capability to estimate their work is. Knowledge work is notorious for its unpredictable nature. There is always risk involved.
The Monte Carlo approach lets you manage that risk in an efficient manner.
Did you notice that we didn’t commit to single certain delivery date? We came up with a range of outcomes and the probability of hitting each target. It’s up to you now to decide how much risk you’re willing to live with.
A word of caution here! Just because you have 40 stories in your backlog, this doesn’t mean that these exact 40 stories will be delivered on the date you’ve committed.
That’s not what the Monte Carlo simulation promises. What Monte Carlo is telling you is that you have 40 free slots to deliver on your commitment. You have to decide, in a continuous manner, how to fill these slots to meet your customer’s expectations.
Why Teams Miss Deadlines
The main reason why teams miss their deadlines is not that they are over-committing.
Teams miss their deadlines because they don’t recognize the importance of managing their work effectively.
Very often, the focus is on the actual end date, and if that deadline isn’t approaching soon enough, there is little to no attention to team efficiency or speed of delivery.
Here is the thing, managing deadlines effectively is a continuous process. It’s not something that has to be brought up once the end date starts to draw near.
Putting your finger on the pulse of the work, eliminating the obstacles that hinder your performance and enabling your team to do their job in the most efficient manner should be your highest priority from the very beginning when your project is initiated.
Now, let’s say you’ve committed to the 85th percentile and your goal is to deliver your project by Nov 21st. How do you stay on schedule to meet your deadline?
How to Stay on Track and Deliver Your Project on Time
Managing deadlines effectively becomes really easy when you have the visibility to make reliable data-driven decisions. The secret here is to start tracking the status of your work in progress.
We want to make sure that we keep the delivery times for each and every task in the project scope within a reasonable timeframe.
This is where the Aging Chart comes into play. The Aging Chart uses the same visual format as your Kanban board, with each column representing a state in your workflow. It shows how many days a task has already spent in progress.
The colored zones in the chart are called health zones and they represent a timeline. They visualize the amount of time that your completed work items have spent in progress, as the work was moving through each process state.
If your dots go into the red zones at any point along the workflow, this means that they are taking significantly longer than your previous work items (85% of it to be more precise!) and you are going off track.
It only takes a couple of individual items to get delayed to throw off your whole project schedule!
By managing your work in progress on a daily basis, when something goes wrong you know exactly what’s going wrong and in which activity it’s going wrong.
Now, you can start the conversation about how the team can collaborate effectively to resolve the issue.
Follow up with every single item that goes in the red zones. Tackle the problem head-on and make sure you move these items across your workflow with a priority.
By resolving the issues promptly, you will preserve your delivery speed and finish your project on time.
How to Manage Your Long-Term Deadlines
Now, your initial forecast is just that – an initial prediction you’ve made at the very beginning of your project. Don’t fall into the trap of assuming that everything will go as planned.
Knowledge work is complicated; a lot of unexpected and surprising things happen and you have to account for these changes as you are working on your project. In order to meet your long-term goals, your plan has to adjust as you collect new information.
Even if you resolve any obstacles along the way, your forecast will change as you deliver more work. Your delivery rate will vary based on any changes in your Kanban board, the scope of your project, your team or the efficiency of your workflow.
All these factors will affect the base you used to perform your initial prediction. That’s why continuous forecasting is essential – to be able to manage deadlines effectively and deliver on time, you have to reevaluate your initial project deadline.
Run Monte Carlo on a regular basis (ideally, every 2 to 4 weeks!) and adjust the course of action accordingly.
And even if it becomes obvious that you won’t make it on time, you’ll be able to communicate that to your customers and stakeholders early so they can react on time. Acts like this build credibility and shape our reputation as professionals.
Here is your action item: Start analyzing your past performance data right away. If you haven’t registered at Nave just yet, you can do it here. It comes with a 14-day free trial, no CC required!
Use Monte Carlo to predict the delivery date of your projects and integrate the Aging Chart into your daily meetings.
Just by doing this alone, you’ll gain so many insights into what hinders your delivery speed and prevent you from meeting your deadlines.
Managing deadlines effectively and staying on schedule is challenging but certainly possible.
By keeping your focus on managing the work instead of workers, using your past performance data to make reliable decisions and consistently reevaluating your delivery commitments, you’re setting yourself up for success in the long run!
I hope you find this article helpful and if you do, share it on your social media channels. I strongly believe that this message is important and I’d be grateful if you spread the word.
I’ll see you next week, same time, same place. Have a productive day ahead!
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Meet the Author

Sonya Siderova is a passionate product manager and a driving force behind Nave, a Kanban analytics suite that helps teams improve their delivery speed through data-driven decision making. When she's not catering to her two little ones, you might find Sonya absorbed in a good heavyweight boxing match or behind a screen crafting a new blog post.