7 lessons learned from Challenging Projects

Eilis Gregory
6 min readJun 9, 2021

There are some projects that dredge up nightmares from the darkest corners. You wake up in a cold sweat in fear of those conference calls with that client that somehow paid you to do the job but refuses to listen to expertise. The gauntlet is about to begin. How will you ever complete what seems to be an impossible project?

Here are 7 lessons learned from Challenging Projects.

1. Establish a Working Agreement

Often, a contract, statement of work, or standard operating procedure may dictate the norms in which you may have to work to fulfill a client project. Even there are specific requirements. You should also set some norms with the client that is a Team Working Agreement. This is especially important when you have clients and teams across the globe. Some key things to include: Working Hours, Response Times (Especially Outside of Work Hours!), Collaboration & Communication Methods/Tools, Level of Engagement. By establishing a team agreement, you’re able to better focus and deliver. It also sets the boundaries on how to interact between you and the client that are often assumed and not spelled out in contracts.

2. Maintain a Constant Feedback Loop

When working with a client. Often they are eager to hear about the progress or have a conversation to verify your work. Having a regular feedback loop is good. You can incorporate a client into a regular demo of the work progress to solicit for feedback. This works really well in the product and software development space. Giving the client insight always puts them at ease. Keeping open lines of communication to request feedback or information gives the client transparency. Make sure it’s not an overabundance of communication that could be a little too much. Decide what is the right balance of conversation.

3. Be Consistent In Your Work Flow Stream

Being consistent in your workflow provides clients with a scheduled cadence of what they can expect from you. An example of this could be, we always deliver status updates on Wednesday morning at the same time and date. The reason for this would be if you needed to adjust a schedule or pivot on a deliverable, you’re mid week versus finding out on a Friday later afternoon where rescheduling your team may become a challenge. Thursdays are when demos and feedback are solicited. Having a regimented schedule allows you to deliver consistently.

4. Manage Resource Availability & Control Projects

It seems like a given. However, when there are issues with the schedule or delivery for whatever the reason may be. Emphasizing resources are only available based upon a agreed upon time box is crucial. Your team may have commitment to other clients. And while it is important to finish work you promised to your first client. If the impacts are on the client’s end. It’s important to put into writing that if it’s not possible to commit to providing information or feedback in the agreed upon time. The resources are released from the project until they can be docked back into a new schedule. I know that this is more nuanced than that. Sometimes it’s as simple as conveying this reality that the client will prioritize giving you and your team the information to complete the work within the schedule. Providing alternative project plans to be as close to the original baseline that both your company and the client may find amicable is helpful in achieving success.

5. Provide Accessible Information

While we often think that email is the primary vehicle for communication. You can provide access to your progress updates, design documents, business requirements in a secured collaborative tool you can provide links to your client. This provides them with a way to find information on demand without feeling the need to dig through emails. If you are maintaining your documents and labelling folders and files meaningfully. I often find it particularly useful to upload key project management artifact documents here too. It’s an efficient way to have all your information in one central location for both you and your client to have a single source of truth. Keep in mind, as a PM, I also have a folder that may not be part of this link that is where I create my draft documents that may not be ready to be shared just yet. This is a little different that living documents. Living documents can be requirements, RAID Log, or other types of artifacts that are collaborative.

6. Step Away For the Weekend

I know that sounds counter-intuitive when the stakes are high and there is an endless amount of work. Stepping away allows you to recharge and to focus on the upcoming weeks. Working hard and persevering are important. However, not giving yourself time to recuperate and not be at your best self could be equally damaging. It makes feel stressful to not do work on the weekend. Crashing a project and spending as much time as possible to get ahead of the work can only take you so far. After that you may find a deprecating return on the areas you have borrowed from your personal life. It’s fine to work extra on the weekend or weekdays to make sure a project is successful. Doing it on the regular will be a slow road to burnout and other unintended consequences.

7. Show Gratitude to Your Team When a Milestone is Reached

Major milestone are something to be celebrated. In this current pandemic a pizza party or high fives aren’t really the way to go. And while virtual happy hours aren’t exactly the same. Showing gratitude can come in different ways. Sending Teams/Zoom call to say thank you. Or a handwritten card you send to express thanks is one of the few ways to show appreciation to your team. If appropriate, finishing a work day early on a Friday is a nice way to close out a big week. Create that exciting positive environment.

Final Thoughts

There are many lessons learned from challenging projects. I can share all the battle scars gained through projects I’ve worked. The thing is, they drudge up some terrible feelings and memories. I went with sharing the lessons learned because you can use these different lessons to evaluate how you want to approach that beast of a project. There are many reasons that projects can be extremely challenging. Sometimes you go into them feeling like your hands are tied behind your back. Many of the project managers that survive and have years under their belt will attest to that you’re not alone in that fight. We’ve all heard or shared similar stories before. Having a few lessons that help you manage your project will be one of the many factors to success. The rest comes down to you, your grit, and your ability to inspire your team to take that mountain that seems beyond reach. When you come through on the other end, it’s not the work you remember but the people that you took that journey with.

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Eilis Gregory

Millennial, Lover of Memes, YA fantasy, video games, and sometimes trying to be an adult.