An important part of your work in software engineering is to provide estimates or level of effort to your stakeholders: your boss, your peers, and your customers. It can be a stressful part of your job since you are held accountable for your estimates, and let's face it, no one likes to be late on a deadline that they've provided.
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A critical part of every Engineering Leader's job, including your manager's, is to challenge the estimates they receive. It's their job to question you on the estimates, ensure that you are building the right thing, that you looked at it from different angles, that you are taking the simple approach to building it, and to push you on shipping it sooner.
This might induce some fear into you. You might feel pressured to reduce the estimate and over-promise on the timeline. This is normal. It's important to take a breath, and not commit on the spot to a new date on the spot. Instead, go back to the drawing board and re-visit your plan with a clear head. You might come to the same conclusion and the same date after all, and that's also okay.
Now is the time to be firm with your estimates. You've done your homework, and you and your team know your project best. If you're still getting pushed on the timeline, make sure to explain how you've come up with the estimate but remain firm. At this stage, the disappointment will be a lot easier to swallow than the future disappointment had you reduced the timeline and not met it. In my experience, the disappointment of over-promising and under-delivering is very unappreciated, and erodes trust quickly, so you should avoid this path.
In fact, your stakeholders will appreciate a well-thought out plan and explanation on the estimates, and their trust in you will grow if you meet that estimate. They will respect the fact that you know your project enough to make well-educated decisions, and that you deliver on your promises.
This is why — if done right — estimates can help build trust with your stakeholders. The more you deliver on your estimates, the more trust they'll have in you.
The same concept applies to building trust through your commitments and how well you follow through with them, but I'll keep that for another time.
I hope you enjoyed this article, and do not hesitate to reach out if you have any questions or comments. I'd love to connect!