Experiencing Deadlines Throughout My Career: Reflections of a Long-Time Worker by Brandon Chu

Using Deadlines: A Debate in the Tech Industry

People in the tech industry have been debating whether deadlines should be used in projects for a long time. Some individuals strongly oppose the use of deadlines, citing that they are simply a bunch of “bullshit” created by business-minded individuals who do not understand the technicalities behind designing and building great products.

While some might agree with this sentiment, others believe in using deadlines, not because of the date itself, but because of the powerful influence they have on the behavior of a team.

The Power of Deadlines

At present, the team at Shopify is getting ready for Unite, their annual partners and developers’ conference. The preparations for the conference have been six months in the making, starting when the team committed to launching a bunch of products at the event.

Despite the stress and draining chaos that comes with planning such an event, no one forced the team to do it. They imposed the deadline on themselves knowing that it would make them better at what they do, and ultimately improve their product.

Why Deadlines Work

Deadlines force critical thinking by adding constraints. When a deadline is set, teams are compelled to work backward from the launch date, which forces them to confront what needs to exist at launch. The by-product of this is a realistic list of all the work that needs to be done.

Deadlines also force teams to prioritize ruthlessly since there is a fixed time to complete the work. The team must decide how much time they are willing to allocate to each task.

Open-ended projects mean that progress cannot be measured efficiently, but with a deadline set in place, teams can track their progress and know if they are on pace.

Deadlines also prevail over human nature. People may not be lazy, but they do not default to urgency. Parkinson’s law explains this best, “work expands so as to fill the time available for its completion.”

Additionally, deadlines compel teams to ship faster than they otherwise would have. Most teams dream of their product in a perfect end-state, which can create an inertia to ship. Deadlines combat this by providing an externality to help teams justify shipping an imperfect product.

Using Deadlines Effectively

There are two types of deadlines: those that matter and those that don’t. The deadlines that matter tend to relate to either a short-lived opportunity or a company’s survival. The day a startup runs out of cash is a deadline that must be met.

More interesting (and common) are deadlines that do not matter. Missing an arbitrary launch date might attract some moans from stakeholders, but it may not have any significant business impact. In situations like this, delaying the launch by a few weeks could hardly cause any damage.

However, the date’s meaning is often irrelevant to its usefulness. The behavioral benefits can be achieved by simply having a deadline in place, even if the date itself does not matter much.

Using Deadlines When the Date is Irrelevant

As a leader, setting deadlines when the date is irrelevant can be challenging. To get the behavioral effects to work effectively for the team, the leader has to genuinely care about the date, or the team will see right through them.

Instead, the leader can rally the team around the deadline by making it a point of team pride to achieve it. Everyone should be motivated to meet the deadline, not only for the impact it will have on the customers but also for the challenge it presents and what it says about the team.

How to Avoid Using Deadlines Disastrously

Leaders must be wary of deadlines negatively influencing their decision-making as the ship-date approaches. When leading a team, one must not beat the “we can do it!” drum everyday for seven months. Emotional investment in meeting the date may lead to irrational decision-making.

Here are a few reminders for leaders as deadlines approach:

– Do not ship a “shitty” product for the sake of the deadline
– Never punish missed deadlines
– Celebrate met deadlines

No More Debate

Deadlines work because constraints foster creativity and resourcefulness. They push teams to do more than they thought they could and give them a challenge and something to prove. Deadlines make product teams better, and that’s why they are useful.

Conclusion

Deadlines are a double-edged sword, and while they can be powerful, they must be used cautiously and in service to good products. A good leader will use deadlines to enhance the team’s performance and not use them in priority to the product. A well-managed deadline can bring about a productive and successful project, but an ill-planned deadline can result in disaster.