“How long will this take?”

The dreaded question. The one that no team wants to answer.

People think this question is about time. It’s not.

The currency of estimates are confidence & trust. And this is how your answer is measured.

Everything you say can, and will, be used against you in the court of Delivery.

How can you answer with conviction, when the only thing you are certain of is that the number will be wrong?

Your shoulders tense up. Possibilities race through your mind. So many unknowns. Your stomach is in a knot. You want to get out of answering.

So, you do the dumbest thing possible: blurt out a big range.

And, just like that, you lit the bat-signal that your answer can’t be trusted.

To avoid this, first understand why you’re being asked.

Does the stakeholder want to know:

“Is this worth the investment?” (scope is fixed)

or

“Can we make it to the deadline? “(time is fixed)

Estimates are educated guesses. They are inherently tricky yet can be beneficial when we know why we need them. But remember, they are more about confidence than time.

When someone asks you, “How long?” the unspoken question is:“How certain are you?”

So before answering, separate the things you are sure of from those you are not. Your goal is to reduce this uncertainty as quickly as possible.

In a fixed scope situation, write down the process end-to-end. If the plan is well understood, construct Story Maps¹ based on Jobs To Be Done². If you information is scattered between stakeholders, gather the key people for an Event Storming workshop and locate the unknowns.

The next step is the crucial one: Regardless of what agile or project delivery framework you follow, make all tasks visible through boards or tickets. Ensure that they are broken down to the smallest practical size.

(As a rule of thumb, aim for 1-3 days of work or less)

When you are at the mouth of the Cone of Uncertainty³, estimates may be off by a factor of four. This lack of certainty affects both your confidence and others’ perception of your reliability.

Breaking down work allows you to progress from low confidence to informed forecasting. The missing ingredient for you to do this, is using data instead of guessing.

Methods like Monte Carlo Simulations⁴, allow you to project the likelihood to deliver before a certain date, based on past performance and variance.

And as your team progresses through the work, observe how the confidence lines move. Your job now is to inform the stakeholders about the likelihood of the outcome.

In the fixed scope scenario, focus on the projected date and communicate its updates.

For the fixed timeline case, ensure that the work left to do has a 95%+ chance of being delivered before the deadline. If the projection slips over the target, cut down the scope to bring it back under control.

In the end, your success with “How long will this take?” depends on your ability as a leader to communicate with confidence:

You got this.

References

1. User Story Mapping https://jpattonassociates.com/story-mapping/ ↩︎
2. Jobs To Be Done Theory https://online.hbs.edu/blog/post/3-keys-to-understanding-jobs-to-be-done ↩︎
3. The Cone of Uncertainty https://www.construx.com/books/the-cone-of-uncertainty/ ↩︎
4. Quantifying the Uncertainty: Monte Carlo Simulation https://getnave.com/blog/monte-carlo-simulation/ ↩︎

Photo by Casey Horner on Unsplash