Inside Swip
Inside Swip

December 2017
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18 Tactics To Win Against A Deadline

A tactical guide to handling a deadline


It’s a burning sensation

Have you felt it? The inner fire from the approaching deadline. I’ve found out (through some research, cough, cough) that the strength of the fire is very correlated with the readiness I have to meet my promised deadline. I bet you can testify to that too.

It totally makes sense to be like that – our credibility, authority and image would be more or less damaged if we don’t meet the expectations we’ve set and agreed upon.

This time, I will give you handy points to think about before setting your next deadline and while trying to meet it.

Before we begin let’s talk triangles

Everything we undertake can be classified as a project. No matter if we are freelancers, entrepreneurs, employees we are constantly in a project – and projects have deadlines. There is, however, one other characteristic every project has, that we can leverage to get the best of every project situation. This characteristic is called the project management triangle. Here is how this triangle looks:

Project Management Triangle

Every project has a fine balance between time(deadline), Cost(resources) and scope. Trying to leverage one of them means impacting the other two. Keep this triangle in mind as it will come handy in some of the upcoming tips.

1. Clarify Outcome

Before agreeing to any deadline, make sure you and the other parties know exactly what is expected for this deadline. Do not leave anything ambiguous. This tip is first as I deem it most important. Not only it will save you sleepless nights. It will make sure your clients do not leave this project with a sour taste in the mouth and no good recommendations for you.

2. Clarify The Deadline

Just like the previous one do not agree to a deadline worded as “next week” or “next month”. This again plays with your client expectation. You would be planning to deliver on Sunday and your client will be expecting it as early as Monday. Imagine his/her feelings and frustration for the following 6 days. Be strict and clear.

3. Small Buffers Are Good

Expect the unexpected. No matter how good you are at what you do, there is always a chance of something weird happening and if you are on a strict tight deadline, this will spell either sleepless nights or penalties. Make sure you have some small buffer to account for that.

4. Buffers Are Bad

On the other side of the spectrum is setting too big of a buffer. Not only you are going to lose business due to a ridiculous timeline, but there is a common human trait that causes us to take as much time as we are given to complete a certain task.

5. Break the project into small-ish parts

One of the biggest mistakes I’ve seen in regards with estimates is forgetting that something small is still taking time. Don’t think that, because you’ve done something hundred of times, it suddenly takes no time. Break your project into small-ish parts and calculate them too. You fill find that your project is a good 30% bigger, or should I say – accurate, because of that.


6. Don’t look too far – take the first step

One downside of the breakdown to small tasks is that you can now be feeling overwhelmed by the sheer quantity of work that needs to be performed. Don’t let yourself be tricked by your own mind. Focus on the next step only.

7. Ensure no interruptions

Do you know that once interrupted, our minds need about 23 minutes to get back to the level of productivity it was before the event? Ensure you have a distraction-and-interruption-free environment or you might very well throw away 20 min on every hour (or 1/3 of your schedule).


8. Recheck daily if you are on track

One of the upsides of breaking a project into tasks is that you can very clearly track your progress. If you break your project to a day, half-day or hours work, you can easily estimate how far ahead/behind your schedule you are. This way you can be transparent as early as possible.

9. Stay transparent

Give your client, accurate and up-to-date status. It will improve your relationship and can even save you from an upcoming deadline. Give your client heads up about hardships you’ve encountered or little victories you’ve accomplished. Transparency involves your client emotionally as much as you. Both of you will be emotionally involved in the situation, no matter good or bad.

10. Recognize that deadlines matter

I’ve seen many people just not caring about their deadlines. Do you want to keep your relationship good, your word-to-mouth flowing and your own credibility high? In that case you need to make it unacceptable for you and your team to miss a deadline. This is what separates the best from the average.


11. If you run multiple projects, make sure you don’t need a clone

Okey, so you are popular now and many people want to work with you? Make sure you have your schedule sorted out straight. Understand that you and your team have limited time and you either need to extend the time of the parallel projects you are offered to work on or do them one after the other. There is just no other way, yet.

12. Don’t promise too much

There is always the case where we want a deal so bad, that we promise the world and the moon together, delivered yesterday. Make sure that your promise is possible and achievable by you and your team.

13. Don’t be Too Optimistic

When taking on a project there is always some amount of uncertainty. Unfamiliar technology, a new client or some other new event can cause you to give an estimate for something you are not familiar with. Make sure you are not optimistic on these matters. Better safe than sorry.

14. Prepare to give your all

No matter how well you have planned your work, you will sometimes be caught out of time with some deadline fast approaching. This is the time where you need to roll up your sleeves and show your client that you are committed – pull off an all-nighter and finish the work before the deadline. Just make sure it does not become a habit.


15. Leverage the scope

Remember the Project Management Triangle. If you are seeing that your deadline is impossible to meet try to leverage the scope by offering to cut some parts of the feature set. It’s rarely looked with a good eye, but when there are mitigating circumstances you can pull this one off.

16. Leverage new resources

If you’ve spilled the beans, think about hiring someone to help. You will earn less, but you will save your credibility thus enabling you to account for the loss on the next project.

17. Try for a new deadline

Similarly to leveraging the scope, if you cannot meet your deadline, try splitting the remaining feature set to two deadlines. This way you will show your client that you are serious about delivering what you’ve promised.

18. Learn from your mistakes

Make sure you take some time and reflect on both successfully met deadlines and unsuccessfully met ones. Try to take lessons from both and improve your game. This is how you stay on top of your game.


What now?

Enjoyed this list? It was compiled through our experience and the experience of the teams using Swip. Some of these tips can and should be automated by your task management system. Still using a spreadsheet? It’s time to go to the next level. Try Swip the only project management with embedded AI Lean assistant and become more productive in less time.



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Hi! I am George Spasov - Growth guy at Swip. I simply love creating things! I've created many articles for sites like, Swip, etc. I've been part of the creation of three startups. I love hearing creative electronic music and I love the brain-shattering creativity of mystery/crime novelists. Like my creations? Follow me and Swip around in social media!

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