How to turn hostile deadlines into helpful assets.
Nolan Bushnell, the founder of Atari is credited with this quote. I am not sure though how many of you feel this way!
The origins of the term “deadline” actually come from prison camps during the American civil war. It referred to a physical line or boundary. Guards would shoot a prisoner who crossed the “dead line”. Later, the word was adopted in the publishing world to denote a time limit before something had to be completed.
At one point, honouring deadlines was considered sacrosanct. But over time, as our lives have become busier, we have become sloppier with deadlines. Just look at the pre-reads before any review meeting. Nowadays, they come at the eleventh hour – not giving the meeting participants much time to read them in advance. Or for that matter, many of our planned launches last year and the many delays we encountered.
Frankly, not many of us find working on deadlines to be fun and grudgingly learn to live with them. And if you are among the many at work who struggle to meet deadlines, stop and ask yourself. Are deadlines really the enemy here? Or are they just symptomatic of other issues – like poor planning, unclear expectations, procrastination, an overload of projects, insufficient bandwidth, changing feedback or a lack of structure? Is the problem with having deadlines or with how they have been determined?
So, my message this week is on why you should stop dreading deadlines and, instead, use them to your advantage.
Figuring out how to leverage deadlines effectively helps you define priorities, plan properly, flag mid-project concerns, and streamline accountability.
Setting deadlines forces you to think about bandwidth and staffing and better stakeholder management.
It makes you ask yourself questions that you probably wouldn’t have otherwise.
And of course, there is the sheer excitement of meeting deadlines and successfully closing a project, which can be hugely motivating.
Here’s how can you start approaching your deadlines more effectively:
1. Figure out what is going wrong
Try figuring out what isn’t working. Where do you get stuck on deadlines? Is there a misunderstanding on expectations? Are you not being able to get buy in? Is there too much other stuff that keeps coming up? Are your deadlines not realistic to start with? Do you need more help? Is this an issue you face with all projects, or some in particular; what is common to them? Talk to people you work with, for their thoughts as well. Anticipate and solve for specific problems if you can.
2. Get the details you need
Get your briefing on the project right. Ask more questions. What is the scope? Who are your stakeholders? What would success look like? What are the expected timelines? What are possible derailers? Get into the specifics. So, for example, instead of settling on “in a few weeks”, or “first thing next week” as directions, narrow down on a specific date to deliver on. The more details you get, the better you will be able to plan. Don’t commit to final deliverables unless you have all of this information.
3. Stretch, while keeping it real
We absolutely want you to stretch yourself and raise your personal bar at Ndiema. To take up more challenges, look for new ways to add value, both to yourself and our company. And be an example to others. But at the same time, in your enthusiasm to do more, be careful about over-promising and under-delivering.
As many of you would probably agree, this is usually a problem which you see your more highly engaged, high performing team members grappling with. So, the answer is not to lower standards on delivery or do less. It is more about prioritisation and being okay with making choices. Some of this comes through practice – getting better at estimating the time and effort that this will require, asking more questions, so that you can pace yourself better.
4. Break it down
One of the first things that you should do with any project, once you have deliverables laid out, is to break it down. Smaller, bite-sized plans are always easier to deal with. Not only are they less daunting, but they force you to think about the steps you have to follow to complete the larger task. Try to use your understanding of working on similar projects in the past, to help plan. Put down these interim timelines, create bandwidth for the deliverables and use them to track progress. Find a good way to integrate enough reminders on what you need to do and when. Focus on what you need to deliver now, rather than worrying about the bigger picture. That, your plan should take care of.
This is particularly helpful when you are working on multiple projects with overlapping timelines. Agreeing to deliver on something two months down the line may sound possible at first, but until you create these interim steps and place them on your calendar for the next few weeks, you won’t get a real sense of how you need to plan for it.
5. Build in enough buffer
Things change. That’s just the way it is. Priorities can change, stakeholders can change, the critical nature of a project can change. Not just that, your project is probably one of many, both for you and the stakeholders involved. So, what happens in other projects and the larger organisation, can and probably will impact this project too. I’m sure there are several times when you are probably progressing well on a project and then, suddenly, you have to divert your attention to something else that has come up. And the truth is that there will always be these unplanned things that crop up and need your immediate attention. Even the best laid plans can’t accommodate them. But we don’t end up accounting for them when we set deadlines. The problem with this ‘planning fallacy’ as Heidi Grant Halvorson calls it in her Harvard Business Review article Here’s What Really Happens When You Extend a Deadline, is that we tend to work basis best case scenarios. We don’t pay enough attention to past experiences and what could go wrong.
So, build in a realistic buffer for unexpected contingencies. Don’t squeeze your deadlines so tight that there isn’t some room to move around things, should they not go according to plan. And closer to the final date, carve out focused time for last minute emergencies.
You can’t do everything at once. Everything can’t be equally important. You have to prioritise. You may feel that everything is important. Is that truly so? Break down how you are spending your time. And allocate disproportionate time to the most important tasks. Aaron Radomsky had written a great piece a few months back on this. Do read it for some useful tips.
7. Ask for help
In the rush to either prove that we can do it all or maybe just because we have miscalculated the time required, we don’t end up asking for help when we should have. We make do with what best we can. That doesn’t work. If anything, you’re taking away from the value you can deliver on the project. Being able to reach out to the right people for help and to do so well in time, can be greatly enabling. Don’t wait for things to become a crisis to reach out. Remember that other people are probably as strapped as you are on priorities. Call out where you need help. It could be with your manager when you need to prioritise or staff for a project, your team members who need to chip in, the project sponsor who needs to get you more input.
This is probably equally, if not important, for how you approach your family and friends too. They can be of tremendous support, enabling you to bring your best to work every day.
8. Pushing deadlines isn’t always the answer
Asking for an extension on a deadline may, more often than not, seem the most obvious solution to you. But that isn’t really the answer, not unless the only issue you are facing, is the need for more time. As Halvorson points out, most research actually suggests we end up finding it quite difficult to use this ‘newly-found time’ effectively. That, once the much welcome initial relief of having extra time is over, more often than not, we find ourselves back to square one, under the same pressure to deliver. Why does this happen? Because we are more driven to deliver on immediate, looming goals. If we push one back, then with it, we usually end up pushing the need to prioritise it too. We probably haven’t solved for the real problem here – like perhaps not being able to estimate how much time this required in the first place.
9. Flag concerns as soon as you can
If you think you can’t realistically deliver on time, flag it at the start. Don’t wait to be closer to the deadline to raise it. And instead of saying no, try to find a workaround that suits both you and your stakeholders. Suggest an alternative timeline. See what you can move around on your calendar – or theirs. Perhaps you could, together, find a way out. Perhaps you can’t. Either way, people will appreciate you being upfront sooner, rather than later. It goes the same for if you realise that the project will get delayed because you have something more pressing that has come up. Have a frank conversation with your stakeholders and give them the heads up on this change. It may not be the easiest conversation, but at least you will allow them the option to rework their own plans or make alternate arrangements, if necessary.
10. Keep stakeholders posted on progress
Plan for regular check ins with your stakeholders. Step up communication with them, if you haven’t already. Share updates against the timelines you had agreed on. Let them know what is and isn’t working. Get as much feedback as you can, especially early on, so that you can incorporate it without it throwing too much off track. Don’t wait to share everything right at the end, only to find out that it requires significant rework. Keeping your stakeholders regularly updated also ensures that they stay involved and are likely to feel more accountable about making this successful, should you need them to step in and be of greater support.
I am sure that this is something that you can relate to. Even as we get into discussions on priorities and deliverables for the year ahead, think about your approach to deadlines. What can you do better? And what is it that you’re passing on to your teams? The bigger question here is also, what is the kind of culture on deadlines that we want to build at Ndiema? This isn’t about just setting deadlines to get things done. It is also very much about getting it done right.
What is it that we need to do to make this possible? I look forward to hearing your thoughts.