Software estimation is a nefarious art at times - no matter how hard you try, or how small you break up tasks, there will be times where the unforeseen adds up past your deadline.  Of course, when this happens to you as an individual contributor, there are lots of things you can do to compensate - you can work more hours, ask for help, or negotiate to cut scope.  But what do you do when this happens to someone on your team?Imagine this situation (likely familiar for most software dev managers):There is a project to build Feature Sphinx.  Developer Max (which is also my dog name, being used a proxy - any semblance to real person is just coincidence) is assigned to build this feature, and as part of sprint planning the team assigns story points to Sphinx and its subtasks (because we like to break things down small) and the resulting estimate is that this feature should be about 5 points (and for this example, let's say that should correlate to 5 days).  Max agrees to this estimate and commits to the tasks and gets started.Max starts work on Monday and dives into the feature.  At the end of the day he isn't through the first subtask so he stays late.  Then on Tuesday, he works tirelessly all day and into the evening again.  On Wednesday Max enlists form his other team members, and again stays late to try and get through this difficult task.  On day 4, Max is still not through the first subtask and things are not going well.   However, Max is tenacious and convinced he can get things done if he works the weekend.  If you are Max's lead, what do you do?As his manager you there are several things you need to consider:

1. Sphinx is going to be late, so planning will need to be adjusted accordingly.
2. Max has been working 4 days and hasn't made progress.  He has asked for help, and it is unclear if it would be better to assign this task to someone else at this point.
3. Max has been working really hard (which is commendable), but isn't getting results (which is ultimately what the team is judged on)
4. Max is demoralized.  Despite his hard work he hasn't been able to achieve the results and knows he is letting his whole team down.

In this situation there is obviously no "right" thing to do, but one tactic that has worked well for me is to engage with the employee (in this case Max) and have him *recommit* to the project.The first part of this is a conversation.  You want to give Max a chance to explain, vent and provide a picture to you of where things are with the project.  One of the most important aspects of this conversation is to be empathetic, actively listen, and reflect on ways you can help ensure the success of the project.After this conversation, comes what I call the recommit email.(BTW, I encourage most managers to follow up difficult conversations with emails not just because it will help everyone stay on the same page, but also because some people just absorb information better in writing; so writing it up can really help hammer or reinforce a point or direction)The recommit email has 5 parts to it:

1. Summarize the situation.
2. Say something positive about the person involved - what has gone well.  Despite being hard on people and coaching them, you also want to inspire them and motivate them.
3. Reiterate the changes/actions/next steps that were discussed in the conversation.
4. Ask the person to confirm the next steps or new deadline.
5. Thank them again for their hard work, and offer help or guidance.

So in Max's case this email may read something like:

Dear Max,As we discussed earlier Sphinx is going to be late because it has taken longer than anticipated to complete the first task. (1) I know you have worked really hard to try and get this done quickly, and I appreciate your tenacity and dedication. (2)For the next steps - we are going to assign the other 2 subtasks to Gizmo, and you are to finish subtask 1-3 by next Wednesday.In the future, it would also be helpful that if you are past the estimation of a task that you let me know sooner so we can enlist more help if needed. (3)Can you confirm that you are comfortable handing off subtasks 4-5 to Gizmo and completing yours by Wednesday?  Please let me know by the end of today. (4)Thanks again for all of your hard work on Sphinx, Max.  And remember, I am here to help you, so don't hesitate to grab me or let me know if you hit any additional roadblocks. (5)Kate

This sort of email reinforces the good things the employee is doing right, let them knows you are here to help, and at the same time outlines a clear plan of action and what needs to change.Obviously, this isn't something you would want to use for a "repeat" offender, but for the times when great employees slip up - this sort of email allows you both to press the rest button and recommit to the project/situation.Do you have other ideas that help with these situations?  This has worked well for me, but I would love to hear other thoughts and ideas in the comments :)