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Simple tips to rejuvenate how you schedule projects

How to do project management and schedules in a way people will actually enjoy it. (Bold claim, I know)

April 11th, 2023

by Michael Karampalas

in Productivity

When people think of project management, their minds typically jump to long lists of tasks, droll meetings, or that one person that just didn’t do what they were supposed to. With so many pre-existing negative connotations, how do we transform people’s attitude about project management and planning into something people relish rather than just mildly tolerate?

It comes down to one key concept: creating and maintaining a workable schedule. It reduces stress for the team, it improves the quality of work, it enables people to take responsibility, and it opens up lines of honest communication that otherwise wouldn’t exist.

For anyone that has ever managed a project, you know what bad scheduling looks like. Missed deadlines, milestones slipping, scope creep sets in, and before you know it you’re in a conference room explaining to the leadership team why the project that you promised would only take 4 weeks is now going to take three times as long. So begins an inescapable cycle of lost productivity that most teams never overcome.

It doesn’t have to be this way! Whenever it’s time to start scheduling a project, there’s a few key concepts to keep in mind that will revitalize the way your team runs and ensure you achieve your goals.

Constantly Communicate With Your Team

Stop me if you’ve heard this one before: a great team full of A-players, an executive team that’s fully bought in, and a product that people are really going to love. Day One: Excitement. Day 30: People are bolting for the doors. What happened? In almost every case, it was a lack of proper communication.

Learning to be a more capable communicator is a process, but there’s a few areas that you can begin to change immediately.

First, you’re scheduling a project for your team, so don’t be a dictator. Your team will be delivering based on their roles, so creating estimates should be collaborative. You may think that writing the copy for a landing page will take an afternoon, but they might know something you don’t, and they’ll be able to tell you about it ahead of time rather than weeks later.

Second, you need to specifically define the scope of a project and make sure everyone knows what it is. Unless every member of the team is bought in on what the project is about, you’re not going to succeed - it’s as simple as that. This could mean sending an email, or holding a meeting, or talking about the scope in 1-on-1’s. How you communicate can be based on your personality. However, what you communicate is based on your team’s needs.

Third, you need the right tools in place to foster communication. Whether it’s Slack, Basecamp, and/or Status Hero, communication doesn’t matter unless your team knows it’s happening. Whatever the tool, it needs to be lightweight, it needs to be approachable, and it needs to be something everyone is comfortable with. As the project manager, it’s your responsibility to enable quick communication and status updates.

If you start with these three things, you’ll be well on your way to communicating more effectively. This will immediately impact your team, and things will begin to move much faster and with a higher degree of quality.

Scheduling Never Finishes

Many companies approach scheduling like a task: there’s a project coming up, you need to properly allocate resources and time, and so you need a schedule that you can share with people. Once ready, you move to running the project itself, and watch as the schedule slips into irrelevance. Then you repeat the cycle.

The biggest mistake here is that scheduling isn’t a task you check off, it’s a process that’s constantly changing and never stops. You create the first draft, and then the team begins working on delivering results. Then, as things evolve and the work required becomes clearer, you reevaluate the schedule. It’s about constant iterations.

In practice, this means that the schedule is a living document. So, begin incorporating the idea of flexible time. Timelines shift and estimates are often wrong, so it’s smart to insert a day or two of unallocated time to allow flexibility while still hitting your next milestone date. This keeps your team on track, while also allowing you to more accurately predict when the next milestone will be reached. Best case scenario? You’re ahead of schedule by a day. Worst case scenario? You just saved yourself a tough conversation where you have to explain why your project was behind. This sort of mentality is essential when shifting to a new mode of working where schedules are constantly being reevaluated.

Never Rush to the Calendar

So you’ve got a project, and you’ve written down your goals. Congratulations! Now, before you rush directly to the calendar and start guaranteeing release dates: Stop. Think.

If you rush to the calendar, the best you can hope for is that people begrudgingly agree to what you’ve decided. Much more likely, however, is that you’re going to have to talk with your team to get more information, meet with the leadership team again, and end up revisiting the schedule a dozen more times. All before ending up with a calendar that looks nothing like your first draft, and with many hours wasted.

Since we know this is going to happen, let’s try to avoid it. Before even considering the calendar, make sure that you’ve got all your ducks in a row. Do you know the final goal of this project? What about how many team members are available and what else they’re working on? Have you spoken with Marketing and Sales to ensure that they’re in sync with your project?

There are so many variables to consider and they’re different for every company. The key, though, is that the time you spend actually filling out your team calendar should be a minuscule fraction of the overall time you spend planning for your project.

Team Responsibility Starts with Estimates

If you’re not planning on micromanaging your team at every step of the way, you need to entrust them with responsibility from the beginning. You work with smart people and need to be able to trust them with the schedule you’re creating.

In practice, this simply means that you base estimates off of what your team member is saying, and not about how long you think it should take.

For example, say you need to create a credit card entry form for a website. You think it should take three days (and you might even be right). However, if you go to the engineer that’s going to be working on this, when you tell them that it will take three days, the very best response you can hope for is, “you’ll get it in three days.”

What would happen if you went to them with a different attitude, and trusted them with the responsibility of working efficiently? Well, you might just find out that when you bring up the question of a credit card entry form, that your engineer knows of an open source project, and it’ll only take an afternoon. Two whole days saved!

By being more open to contributions from your team and entrusting them with the responsibility of estimating time, you’ll find yourself with far less to worry about, a more motivated team, and more-often-than-not, quicker turnaround on projects. Your worries about scheduling? A thing of the past.

Learn. Then Learn More.

If you’ve followed the tips so far, you’re taking an iterative approach to scheduling, you’re being more thoughtful in your planning, you’re communicating clearly, and your team has taken much of the burden off your back, there’s one final thing to do: don’t stop.

Scheduling is a dynamic skill that changes depending on the team, the company, and the project. As it’s changing so often, you need to be changing your practices just as often.

To start, at the end of every project, look back at your original schedule and see how closely you matched it. Did one team member’s estimates turn out to be way off? Or did the scope drastically shift? Or perhaps you didn’t account for the new weekly all-hands meeting?

Whatever it is, something always goes wrong. The important thing is to see that truth with eyes wide open, and then change your plans accordingly. Once you begin to critically evaluate your past, you’re going to see what needs changing. And if you do this every week, month after month, you’re going to look back and see unimaginable improvement.

In addition to looking at what you are doing, make sure you’re also listening to people at other companies. They might just be facing some of the same problems you have. With that in mind, tweet us some of the best lessons you’ve learned with scheduling projects at @statushero so we can spread new tips and tricks to as many people as possible.

What’s next?

Imagine a team that has a open and honest communication every day, that takes responsibility for their tasks, is smartly evolving their plans, and learning from past mistakes. Doesn’t sound like your team? It can.

For your next project, just start testing things. Communicate more openly, focus on learning from your mistakes, and trust your team. Start with one or two of the tips we’ve outlined and see how it goes. Once you begin to move from the mindset that nothing can be fixed to the mindset that things can constantly be improved, you’ll begin to see a whole new world ahead.

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