From Pre-mortems to PM Tools, Follow These Tips for Better Project Management

 

By: Nick Sonnenberg
Founder, Leverage

In March, I had the honor of joining Kara Austin at the PMXPO Virtual Experience Series for the Book Club presentation (which you can still see on demand through January 31, 2024). I spoke about my book Come Up for Air, and continued the conversation in this blog in May when I answered some questions about changing “free for all” meeting attendance, work management tech systems, and getting your inbox to zero. Now it’s time for another round of Q&As that came from my session, where I address passion projects, overcoming obstacles, skill development and more!

1. What project have you worked on that you were most passionate about? 
The project I'm most passionate about is actually my book that just came out. We've been working on it for the last four years, and there's been so many moving parts. If we didn't have a work management tool to track all the different milestones and tasks, and collaborate with all the different people involved, this book wouldn't have happened.

We had projects for marketing, and then within that we had all the different marketing activities and initiatives like blogs and podcasts and ink articles; and then for actually writing the book, that was a separate project. So all of these various projects had all these milestones and tasks in there, which is where we collaborated. 

All those ultimately lived in a Come Up for Air portfolio, which housed all the projects. So in one place, we could see everything that needed to happen, all the milestones that we were going to hit. And yeah, it took a village to get this done, but if we didn't have it organized, it probably wouldn't have gotten done.

2. What obstacles did you need to overcome for this project to be a success?
So many obstacles. I would say time was the biggest obstacle. I'm the CEO of Leverage full-time, and working on a book is a full-time initiative in itself. So finding the time to be writing a book and working with the team on the book, as well as running a company, I think was the biggest challenge.

3. How did you overcome those challenges?
I would say one, we're all very efficient—we're not wasting time going on a scavenger hunt for information. By keeping things organized and not wasting time looking for something (”What's Aiden supposed to work on today?”), that saved a lot of time. 

I also have a fantastic team. I probably spent over 1,000 hours on this book, but if it weren't for having a full-time head of content on my team that wrote a lot of the book…I might have been able to still write a book, but it definitely wouldn't have been to the quality that you see it today. So I would say have a great team, have great systems. Ultimately, I think it's that simple—but it's not easy all the time to execute on.

4. What advice do you have, or what key lessons have you learned that have helped you manage projects better?
I would say the way that a project is kicked off is critical. So many people don't spend the time to kick it off properly. It could be over a text message or an email, or even in a work management tool, but it's not properly kicked off—meaning you don't establish clear owners or worlds and responsibilities. You don't spend the time to explain: Why are you doing this project? What does success look like? 

You know, a lot of people do post-mortems after projects where you reflect on what went well, what didn't go well, what was learned for the next time. But you might even want to consider a pre-mortem, where you sit down and say, “Okay, we got a book coming out February 2023. The goal is to hit the bestseller list. Now let's imagine that we don't.” And we start analyzing why we don't. You start having that conversation on the front end.

Across companies that we've seen, some teams do this—thinking through what the risks and challenges are, why we might not succeed. And having that conversation up front is so valuable. And having a project manager on the project, or someone that's responsible for making sure that the project's hygienic and that there's not a bunch of things past due, I think is critical as well. 

So in summary: Have you established roles and responsibilities to really kick it off properly with why are you doing this? What's the success criteria? In general, I like to think through the milestones that we need to be hitting before starting to think about all the minutiae, all the tasks. So on that kickoff call, we'll go through the high-level stuff, and then we'll start going from like 30,000 feet to 20,000 feet to 10,000 feet. Meaning, what are the milestones that we need to start hitting and laying out in order to achieve that bigger goal of completing the project? Once you get that, then we start thinking about what tasks we need to hit those milestones. 

5. What skills do you think are most important for project management?
A project manager needs to be organized. I think that you need to be technical, too. In this day and age—look, you could project manage off a piece of paper and a pen. But the future of project management is really about knowing how to use these more modern tools like Asana or ClickUp or Monday, because even if you are really well-organized and you have good follow-through and all of that, if you're not taking advantage of some of these really powerful tools—sure the project still might move forward and things will get done and you'll be on top of it, but these tools are built for a reason. They have functionality to make your life easier. They will allow you to move faster, not have to work as hard, maybe you can manage more projects. 

So you need those qualities of follow-through in an organization, but in the future it's gonna be more and more critical that you know how to use these more modern tools.

6. How would you recommend acquiring skills that someone might not have yet?
Read my book, Come Up for Air! Not to plug my book, but I wrote it because you need to know how to use the functionality of these tools. You could also go on YouTube to learn about how you do various things for whatever tool you need to use. What I found missing—and why I wrote the book—was there's not really best practices. Like, what's the purpose of the tool? When should you use one tool versus another? 

But there's a lot of free stuff online that people could just start Googling, honestly—Google is your friend. There are books out there. There's my book. PMI has some fantastic books, too. So, you know, there's some cheap solutions out there to really get started and inexpensively accelerate your learning.

7. What is your moonshot idea that you would love to assemble a team around and make reality?
Hmm, that's a great question. So this stuff that we do at Leverage, we do operational efficiency training and consulting. So regardless of whether you're a financial advisory firm or not—we've worked with companies that do poop spray, we've worked with some of the largest tech companies—everyone has very similar issues. And what we've established are best practices of when and how to use all these tools. 

And so in the future, what I envision Leverage doing is building technology. So imagine a bot that's living in your Slack or your Microsoft Teams or whatever your internal communication tool is, and that tool is connected to all of these other core tools that you use to collaborate—all these modern tools that kind of fit into my CPR framework that I talk about. Well, there's some common best practices that we teach that we could code and have a bot ping you and say, “Hey Kara, we notice that you have this many past-due tasks…”; or, “We notice that you haven't been getting to inbox zero in your email”; or, “Here’s a little video to remind you of what we've talked about before. And if you need some help, you could read this article or watch this video.”

So I think building some SaaS component to how we're training and consulting that connects to all these tools and tells you exactly where you’re missing the opportunity to be more efficient is the direction that we're going in.