5 Valuable Skills You Need to Tackle Complex Project Like a Pro

Managing complexity like a pro

I still remember the day I was assigned a project that I thought would kill me.

I was 25 and working as a Senior Project Manager for a small gaming company in NYC.  I was asked to oversee the full development of a 2MM contract.

The video game would be used in over 400 classrooms throughout the US to educate high school students on business and accounting. We planned for over 100 unique characters, were slated to write a six-week course curriculum, and provide players with custom-build avatars.

This was the most complex project we had ever tried to tackle, and we realized we had bitten off more than we could chew.

As the PM I began to ask myself, “Why me?”

In an instant I had the answer to that question: I thrive off of complexity. I enjoy untangling the most complex project and making it tangible.

What makes a project complex?

There is a difference between a complex project and a difficult project, and it is important to understand the difference.

A complex project isn’t necessarily a difficult project. Projects can be difficult due to reasons such as cost or performance, but this doesn’t automatically mean the project is complex.

Complexity refers to projects that include ambiguity or uncertainty. They are surrounded with unpredictability.  Other indicators of a complex project include:

  • Involvement of many teams & stakeholders
  • Numerous moving parts
  • Project timeline
  • Budget / restraints

After identifying the complexity level of your project, it’s time to use your skills to tackle the beast one bite at a time.

The essential skills you need to manage complex projects

Managing a complex project requires more than the ability to herd cats and spin plates.  This is just one of the many skills needed for project management. Others include:

  1. Adaptability
  2. Collaboration
  3. Communication
  4. Expertise
  5. Leadership

To be successful you must be adaptable. A project is constantly evolving and project managers have be evolve with it. This means not always thinking in black and white terms. There will come a time when you have to adjust and flex you project management style when the situation changes.

Communication is probably the most important skill of a PM. Over 90% of a PM’s time is spent communicating. It is essential that PMs can effectively convey vision, ideas, goals and issues, as well as producing reports and presentations.

Communication goes beyond documentation. It also requires building a relationship with your client and your team. If they don’t trust you, the project will fail. You must be willing to collaborate with your team. Working with others to get things done is important on all projects and never more so than on something that is really challenging. You cannot be successful by yourself. Work with your team and client to achieve success.

Lastly, leadership and expertise go hand-in-hand. If you can lead, you can deliver. Leadership is all about guiding, directing and motivating your team to do their best work and understand how their tasks contribute to the overall vision.

Leadership comes with experience. Neither skills can be taught. They develop overtime from real-life, practical experience.

Having these essential skills is the backbone for identifying what makes a project complex and how to navigate the water.

Let’s now put these concepts into concrete action.

1. Document. Document. Document.

A project may be broken down into the most perfectly manageable mini-projects, but without clear documentation on the individual pieces and how they relate to the whole, the project remains opaque and complex to anyone aside from the main project manager.

Clear, up-to-date documentation is the insurance against this issue. It defines everyone’s roles and their deliverables and ensures that the overall vision isn’t trapped inside someone’s head. If someone new needs to come on board at any stage of the project, in any role, there is a clear roadmap outlining where the project has been and where it’s going. To ensure your team is up to speed, create a high level timeline in Powerpoint to show the team’s overall process as well as a detailed gantt chart with individual tasks using a tool like TeamGantt.As the project manager it is your job to document everything. Every week send out a project status to the full team. By providing clear documentation, both your team and your stakeholders can stay informed throughout the entire project lifecycle.

2. Continuously clarify your goals.

If you do not understand the “why” behind your project, you will not be successful.

Understanding the why brings clarity to the goal(s) of the project. It allows the entire team to find ways to innovate and bring their own areas of expertise to the table.

Project Managers tend to focus on delegating tasks. Our minds fall into a divide and conquer mindset.  As the leader, you are expected to paint the bigger picture of the project for your team.

Don’t be afraid to push your team outside of their comfort zone, but also remember that people aren’t machines.

If we are constantly delegating tasks without clearly defined goals, our team will fail. It is important to pick our heads up and continuously clarify project goals. When your team understands their roles and the task at hand, they are able to dive directly into execution mode.

Clarifying your goals to ensure your project works remained aligned with the initial premise – not just once, but continuously. Remember and accept that you will not know all the answers, but push to explore all possible outcomes and what that would mean for the project.

3. Create more visibility.

When navigating complex challenges, teams often find themselves bogged down in the project details. It becomes a struggle to move forward when you’re buried under too much information.

To create more visibility within a project, adapt a project management tool that works best for you, your team and your client. This tool will allow everyone on the project to stay informed and see what is happening. Use this as your single source of information. This type of tool will provide real-time insight into the decisions and activities that are relevant to each member of the team.

Additionally, our teams have adopted process mapping for our complex projects.

The process map is a visual representation of the forecasted project roadmap. It allows both our team and our client to know where we are in the project and what activities are planned. Having a physical copy printed and hanging on a wall helps our teams facilitate huddles and planning meetings.

We are able to point directly to our current status and identify dependencies and risks in real time. This keeps us on track and the client informed.

4. Be flexible.

The only constant in complex projects is change. I don’t care how amazing you think your project plan is, it will change. If you are not willing to adapt and be flexible for the sake of your client, you risk losing them.

Plan for unknowns, pivots and adjustments early on and set up processes that allows your team to remain nimble and respond to changing demands.

“The single biggest problem in communication is the illusion that it has taken place.”—George Bernard Shaw

There is no such thing as over communication as project managers. We have lots of ways to communicate and the most popular methods don’t require you to open your mouth. Find out what style of communication works best for your project and stick with it.

If digital communication works best, go with it, but never assume your team is reading everything you write.  If you are not getting results, be proactive in your communication. There are times when it is necessary to have face to face conversations. It will help ensure the message is not loss through back channels and that the team is clear on the objective.

Moral of the story

Remember why you do what you do. You may waffle and second guess a decision that you’ve made, but at the end of the day every complex project needs a PM.

The short answer is this: The Project Manager either adds value (making stuff more efficient and effective) or reduces risk (without a project manager, bad things are going to happen).

The PM takes care of communication. He or she is the human shield between you and the development team, ensuring the team can work effectively without too many interruptions.

Never settle and never accept the constraints imposed upon you.  Remember that you have more power than you think.

At the end of the day, everything turned out alright at the 2MM video game.

We realized we couldn’t be everything to everyone. We hired additional help. Had a lot of tough conversations, but we launched the game.

We ended up creating a high school course curriculum that ran for 6 weeks in over 400 schools nationwide.

We wowed the client.

What would you say…you do?

What would you say you do?

For over a decade I’ve dedicated my professional life to being a project manager, yet to date, my parents still have no clue what that means. They look at me with a confused face and mutter “bless your heart” under their breath when I try and explain. If you’re southern, you know that bless your heart is not a good thing. My parents think my job consists of making lists and answering a lot of e-mails. The more I thought about it, the more I realized that a lot of people just don’t get it. They have no idea what it means to be a project manager.

Let me climb up on my soapbox for a moment. Project Managers are not babysitters. We are not glorified note-takers. We are badasses. We go to war for our team. We walk into every meeting with confidence. We are not afraid to have a difficult conversation. We are the conductor leading the orchestra. We are our team’s biggest cheerleader, while also being a shoulder to cry on. We do our jobs every day without any expectation of a thank you. <Mic dropped.>

Today, digital project management (DPM) has become a rapidly growing profession. Thanks to people like Brett Harned and Nancy Lyons people like me have finally found a voice. Hell, we’ve even started our own conference.  However, there still aren’t enough of us sharing our own experiences as DPMs. It’s my goal to use this blog as an avenue to help educate people on what it means to be a DPM. Hopefully, my parents will read this and finally get it.

Web Education: Preparing for GenZ

Gen Z


I remember the first time an AOL CD-ROM appeared in my parent’s mailbox. It promised me thousands of minutes to connect with others through our computer. A computer, that up until that moment, had been used primarily for solitaire.

I patiently waited for the program to load. Nothing happened. Where was my Internet? I didn’t realize I needed a phone line to connect. I “borrowed” a phone cord from my parents room and figured out how to connect the computer’s modem to the phone jack. For the first time, I heard the strange sound of dial up, and the word “Connected!” appeared. I was online.

Learning to use the web has changed slightly since then. While everything in the past had to be self-taught, we can now get degrees or go to bootcamps to learn all kinds of Internet technology. Indeed, staying abreast of the latest techniques is a must for developers to do their jobs. Learning more about the latest technology trends led me to attend ConvergeSE, where I heard a keynote that blew my mind—Pamela Pavliscak’s talk on Gen Z and the Future of Technology.

As Pamela Pavliscak explained, GenZ is the first generation who are truly digital natives. They make up 25% of the population, representing how future technology users will navigate the web and expect applications and interfaces to work. By paying attention to how GenZ uses the Internet, we can both improve the quality of our own work and make future technology more accessible and useful going forward.

The Future of Community

The definition of community for GenZ is different from what I grew up with. My idea of a community was going to the park and seeing kids on the playground. Today, kids have fewer physical hangouts. Instead they hang out online in spaces like Twitch. These digital communities allow teens to have their own identities and play around with their social presence. Because GenZ uses the web to create a vast social community and develop real relationships online, their communities have the power to be both local and global.

What does this mean for the future of technology? It means we can control the context. This means allowing and encouraging GenZ to participate in grown-up conversations through technology. We also need to know how to protect ourselves and GenZ from turning toward Dark Social–the social sharing of content that occurs outside of what can be measured or tracked by web analytics. Because everything in Dark Social is anonymous, it often leads to bad (even illegal) behavior. To combat this, we have to promote a digital culture of openness that shifts how we identify ourselves and others through the web.

Communicate in All the Ways

GenZ’s communication style favors immediate, diverse, and ever-changing connections. For GenZ, phones are no longer for talking. GenZ spends more time texting and talking to Siri than they do talking to real people. They do not email. Why would they? An email isn’t real time. Emails don’t offer instant gratification or connection like text messaging or Snapchat. GenZ wants to create a memory and experience something together. This means they want to re-frame, reshape, and re-experience the moment. For them, a memory isn’t something that is set in stone. It’s a moment in time that is captured and built on.

The future of technology allows us to communicate in all the ways: to convey a mood, to show rather than describe how we feel, to constantly stay connected, even when we have nothing to say. We have to learn how to incorporate all kinds of technology into our communication, from voice to texting to video capture. GenZ communicates in bite sizes. They communicate in symbols. They speak in emoticons and emojis. The symbols provide context and create subtext for their private conversations. If we can understand what these symbols and shortcuts mean in our language, we can use the right visual and textual vocabulary in our technology and design.

Default to Private

GenZ often uses technology as a way to escape the everyday. This explains why they are usually the early adopters of new social networks. For them, new tech trends are like new wearables. For example, when I was a kid, everyone had slap bracelets. If you didn’t have one, you weren’t cool. For GenZ, being connected to the latest tech trend is their slap bracelet. They don’t want to be the only kid in school who isn’t on Twitch. GenZ is constantly online, but that doesn’t mean they want you to know everything about them—they understand how to hide and limit who can see their posts using privacy settings.

What’s our lesson? Educating yourself on how to use privacy settings is imperative. We are stepping away from wanting everyone to know everything to only wanting to share with those that we know. This trend will lead to more social networks adapting stronger privacy settings. Besides affecting how we advertise and communicate on these networks, this also means we need to learn how to protect ourselves from what we share. As we continue to create our own social brands using technology, we need to know how to portray ourselves without losing our privacy. And when we design new communication technology, we should make user information private by default.

Leave it Open

Being creative and playing is about combining off-screen and on-screen. GenZ wants to be able to create. They want to to see what they are creating on-screen. Zs want to do anything but read on a device. They want to tell stories and they are using their devices to do this, by creating art with their screens. They create short animations through different apps. They build entire movies out of photos. They do this, not for themselves, but for their family and friends.

When designing for the future, we need to leave our platforms and technology open. GenZ doesn’t want the story to end. They want to make their own choices. If there is an ending, it doesn’t appeal to them. We need to design for GenZ’s short attention spans, allowing them to operate multiple screens at the same time.

We also need to learn how to build for the worst case scenario. For example, GenZ cares less about having the latest technology than just being connected. Growing up, they typically inherited older devices from parents or siblings, so they became experts at connecting with slower tools. Our lesson? If you’re building for mobile, you need to develop apps that work well on older devices instead of focusing entirely on state-of-the-art smartphones.

Understanding Our Future

I thought back to my first online experience. No one showed me how to connect to the web. I was lucky to have a computer. I had to teach myself everything that I learned about technology.

This is not the case for GenZ. They will never need to figure out a dial-up modem or wait to connect. They were born with online technology, and navigating it has become primary for them. And one day, GenZ will be the ones who provide us with our future web education. Zs will be our teachers and we will be their students. But before that happens, we can learn from how GenZ uses the web: making our technology more secure, more connective, and more open.

What are your experiences with how GenZ uses the Internet or web-based technology? What are you learning from this new generation’s preferences and practices? Let me know in the comments below.

Compromise. Balancing Project Needs with Internal Ideals


Projects, like life, are never perfect. No matter how detailed the plan, it’s inevitable something will go wrong. The struggle becomes real—something has to give, but how and what?  It comes down to compromise and finding the middle ground.

Not long ago, I experienced this firsthand when I acted as both the client and the project manager for a renovation project at my house. Imagine it—the perfect oasis for your home. I could envision every detail. The windows, the wrapping deck, the BBQ pit, a bar for our bourbon collection, and finally a table large enough to seat loads of friends.

Early construction

Like any other project, I attacked this renovation by first addressing the scope. My husband and I outlined what our requirements were for the room, and once we had an idea of the size, layout, and floor plan we felt ready to articulate our plan to a contractor.

Next was the timeline. We wanted the room to be ready for football season, so we started meeting with contractors—a lot of contractors. Eventually, we settled on one and that’s when our first roadblock occurred. The result: our timeline was shot. I had to learn my first lesson in compromise.

Agree to be sensible

Setting a deadline that isn’t rooted in sensibility will almost always equal failure. It’s important to understand the full scope and intricacies of a project before setting an arbitrary date, so if there’s not a fixed event driving the deadline be sensible with your timing. For our expansion, it took a month just to settle on financing. We found ourselves beginning a build-out during the middle of winter, leading to additional delays. Fortunately, our contractor was up front with us over the timing and found a compromise for the completion date that still met our project’s needs.


Once our contractor was selected, our last step was the budget. This was my biggest sticking point for our project. We took out a home equity loan to pay for the expansion and we couldn’t exceed the loan cost without pulling from our own savings, which lead us to our next compromise.

Listen to opinions.

Every project manager has heard the saying, “Good, fast, or cheap. Pick two.” I couldn’t budge on the budget, but I didn’t want the room to look cheap either. I expected quality. To keep our expansion within our allocated funds, I had to listen to the opinions of others. As a client, this can be difficult.

I was dead set on having our new room constructed a certain way. I wanted to mount a television on a particular wall, have the table centered in the back, and the bar along the side. I knew this was the best layout for the room and the best fit for the project. I was wrong. I listened to the opinions of my contractor and my friend Lizzie, who happens to do interior design (Side note: everyone needs a Lizzie in their life, or at least a great designer friend.). They explained that for the flow of the room, the layout should flip. I made these adjustments without sacrificing quality or spending additional budget.

Building a new room was thrilling. During the first few weeks, so much came together. We watched as the framing went up. Then the walls. Suddenly, there was a space that you could walk into. The project continued to move forward seamlessly. We were still on budget. We saw changes every day. Then, it stopped. Suddenly I’m staring at an unfinished space wondering when will it ever be completed. This takes us to our next compromise.

Remind Them Why They Hired You.

You are hired by your clients because you are the expert. You and your team have the skills and ability to make a project come to life and every project needs the confidence of their team to keep the trust of the client. Never give the client a reason to doubt.  There will come a time when the client will ask you to make an alteration you do not agree with. For the sake of the project, it is imperative you use your experience and knowledge to protect the integrity of the project. Establishing trust with the client will make it easier for them to remember why they hired you and to defer to your judgement.

When I stopped seeing movement on our expansion, I lost faith. My builders brought me back around. They explained to me that it may seem like nothing is happening, but quite a bit really was. My non-builder eyes couldn’t easily see the progress. They took the time to walk me through the changes which reminded me why I hired them in the first place.

walls up and furniture in

It took longer than anticipated, but our new room is basically complete. Sure, we’re still picking out the right furnishings, but it’s usable. Stepping back, I now have a better understanding of how to balance project needs with my own internal ideals. When I look back at everything we went through with this room, it opened my eyes to what it means to be a client and the final compromise.

Put yourself in your client’s shoes.

I had to step into my own shoes as the client for this renovation. I balanced what was the most important for me and my husband with the space. I learned how to compromise. The outcome? Our dream room.

New space

From the very beginning of the project, make it a priority to truly understand where the client is coming from.  We are all passionate about our craft and sometimes this passion leads to forgetting the client’s needs. But it’s understanding what drives your client which will lead to a successful project.  So be flexible and allow for exceptions even if it falls outside of your ideal project scenario. Finding the right compromise between your internal ideals and your client’s needs will consistently lead you to mutual success.

This is the first in a monthly series prompted by Sparkbox to bring more thoughtful conversations surrounding the web industry. A new topic is announced the first Monday of every month. Everyone who chooses to participate will publish their post on the last Friday of the month with the hashtag #startYourShift. This is my first of hopefully many articles for #startYourShift.

Why Your Meetings Suck

Meetings Suck

Meetings. I have a love/hate relationship with them. The last thing I want is to have my time or my team’s time wasted due to a poorly planned meeting. We’ve all been there. One person shows up five minutes late. No one knows why they are in the room. The dial-in number for the conference room doesn’t work. The list goes on and on. As project managers, we control the pace and tone of the room. It is up to us to identify when a meeting is going down the wrong path and bring it back around.


When was the last time you walked out of a meeting thinking, “Wow. That meeting was incredible!” Most likely you’ve left feeling drained and with an action item of a follow up meeting. Patrick Lencioni stresses the importance of a well structured meeting in his book “Death by Meeting“:

 “Bad meetings start with the attitudes and approaches of the people who lead and take part in them.”

You are the project manager. That means you have the power to change the attitude around meetings. Walk in like you own it; because you do. It’s up to you to pick up on cues. It’s also up to you to not be the main culprit of bad behavior. If you’ve ever set up a meeting and did/thought any of these things, your meeting will suck:

  • Who needs an agenda? I’ve got this.
  • I don’t need to explain why we’re meeting, that’s what the meeting is for.
  • Hmm, I can squeeze a one hour meeting between my 2 o’clock and 4 o’clock. It’s not like I need to prep the room.
  • Time’s money. It’s cool if people use their phones/laptops during the meeting. I know they’re busy.
  • This collaborative meeting is turning into a one man show, but I really can’t interrupt him. That would be rude.
  • Oh crap, I think she just hijacked my meeting.
  • Is this thing on? Why is no one talking, and why are they all looking at me?


Scheduling a meeting shouldn’t be taboo. Your meeting shouldn’t be unproductive or uninspiring. It should be to the point, drive results and get things done. You can make this happen. You just need a checklist. What project manager doesn’t like a checklist?


If you walk into your meeting and you don’t have an agenda, slap yourself upside the head and walk out. Without an agenda your meeting will not be productive. Instead of getting things done, you just charged your client a lot of money to talk to your co-workers about their weekend plans. Create a firm agenda and send it out with your meeting request. Remember that you can be flexible, but plan for it. Your agenda should focus on a desired outcome and how you can achieve that goal.


When putting together a project plan, you know there will be demos with the client. You also know that weekly check-ins lead to success. Plan for these meetings. Schedule your demo for the same day and time. This gets both your team and your client into a rhythm. It also guarantees that your developers will always have their next release in mind. They may even want to kiss you for planning ahead so they can avoid unexpected disruptions of their work. For your client, it helps them plan their day. Remember, working with you is not your client’s full-time job.


Follow the scout motto and always be prepared. Never assume things will just work. If technology always did what it’s suppose to, we wouldn’t find ourselves constantly updating our devices with the latest release. Don’t book yourself in back-to-back meetings. Give yourself enough time to set up the room, and make sure you can start your meeting on time. If you are using a conference line, dial in early. If you need to walk through a presentation, have it on screen as people walk in. Set out copies of the agenda on the table. Allow yourself a moment to breathe.


Yes, we’re all super heroes, but that doesn’t mean we have to do everything. If you are running the meeting and doing all of the talking, then assign someone to help you take notes. If you are operating as the facilitator, then assign yourself as the note taker. Just make sure you take notes.  Do not be afraid to pause the conversation to let everyone know you’re jotting down what they said. Repeat back key points. At the end of the meeting, share out your meeting notes. It’s a lot easier to go back and reference notes than trying to remember every decision that was made.


If you scheduled a meeting for 30 minutes, start wrapping it up at the 25 minute mark. It’s up to you to control the pace and respect everyone’s schedule. Use your agenda to time-box the meeting and set a end time. Time-boxing will cut down on mindless chatter and stop the group from wanting to ramble. It will also help identify if a topic is too large to cover in one session. If a topic starts to run long carve out time for a micro-meeting. This allows you to stay on schedule.


Messing with your cell phone during a meeting is disrespectful. We understand how busy everyone is, but I promise the world will not end if you go for 30 minutes without a phone. At the start of the meeting, ask everyone to toss their phones into the center of the table. If there are a lot of laptops, go around the room and ask everyone to identify how they will be using their laptop. If it’s not being used to bring value to the meeting, ask them to close it. If someone continues to play on their computer or phone during your meeting, ask them to leave. Obviously, they are not bringing value to the conversation.


If you called the meeting, you control the pace. Go over the rules of conduct at the start of the meeting and enforce them. We’ve all experienced the meeting hijacker. The person will interject their own agenda. Speak up. You can diplomatically interrupt to get the meeting back on track. Listen to their point, express appreciation and then suggest you table that topic for another time. Engage with the group and be a facilitator. You have to read the room and pick up on the cues. If the meeting isn’t going as planned, it’s up to you to bring it back around.


What project manager doesn’t love action items? The most successfully meetings are those that end with actionable tasks and a clear understanding of what’s expected. At the close of the meeting, recap what was discussed, address each person by name who has a takeaway, and get their confirmation that they understand what is expected of them. After the meeting, send out a recap e-mail. Don’t forget to thank everyone for participating.


We all have our own style and rules to live by when it comes to meetings. Some of these techniques may not work for you, but they should give you new ideas on how to transform your meetings. Do you have any unusual tips or suggestions you’d like to share? The DPM community would love to know!