Dealing with Very Complex Projects

complexity-630By their very nature, projects can be complex entities. They can be multi-faceted, with deliverables and resources spanning both local and global geographies. They can consist of numerous stakeholders (both internal and external), large-scale dependencies and different phases of execution. Whatever the mix, a project can become quite daunting to even the most seasoned project manager as additional complexity is added.

While project management in general has numerous process methodologies and options for project managers when they are contending with an extremely complex project or program, oftentimes, rigid adherence to a particular methodology can often introduce more complexity than intended. The end result can often be a bureaucratic nightmare which ends up causing more problems than it solves.

With that in mind, what might be the best tactic to employ when attempting to tackle a complex project?

Start from the Ground Up

When staring at the various pieces of a complex project, it is easy for the project manager to become quickly overwhelmed. It is akin to looking at a Jigsaw puzzle splayed out across a coffee table, with all its component pieces in disarray. Yet as we all know, within that maelstrom of confusion lies the eventual solution. With that in mind, it is important to organize your project into manageable ‘pieces’. Going back to the Jigsaw example, people often start working on various sections of the puzzle individually before attempting to consolidate their work. In the same sense, try to look at how your project is structured and see what common denominators exist. Often times, functional areas will make this a little more obvious as well as the different deliverables that make up the project as a whole.

Organize Project into Manageable Parts

Following from the above suggestion, once you start seeing the component parts of your project a little more clearly, begin to organize the project into manageable parts. Usually, the best solution is to create an aggregate ‘program’ that will function as the overarching placeholder for all the component pieces. Once that is in place, you can begin to organize the various parts into functional projects of their own. By doing so, you can start to determine how the various pieces coalesce with each other, how the various resources working on your project are distributed and which stakeholders align with which functional project area.

For more information on projects and programs, please access the previous post: Program Management – When a Project Should Become a Program.

Devise a Solid Communication Plan

With complexity will come multiple individuals working in multiple roles within the overall project (or program) structure. This can include team members in multiple different locations and functional areas, different stakeholders that may only be involved in portions of the project while others are involved more holistically as well as potentially more than one project sponsor. With that in mind, how you disseminate information effectively will be crucially important to the project as a whole. Note everyone needs to be apprised of every change, so metering out information in a targeted fashion will be much more effective. Trying to encapsulate all pieces of data in more amorphous project status report may make it too unwieldy, thereby making it more likely that certain individuals will not be able to determine aspects of the project easily. What works better is to create separate communication zones that align with the individual project components, as they were structured. Each of these communication zones will disseminate communication relevant to the project it is aligned with. For a more holistic communication mechanism, have a program-based communication plan that leverages drill down into the component pieces of the projects. This will allow individuals to get a ‘summary’ view of the program as a whole while allowing them to link to additional details as needed.

Leverage PERT Analysis

One of the most important aspects of dealing with a complex project is handling dependencies. Nothing makes the job of a project manager trickier than trying to determine how and when various aspects of a program need to be completed to ensure everything is on track as a whole. As one tackles the various component pieces of an aggregate program, there will be instances where certain work needs to be performed first before other work can commence. Examples include laying the foundation for a home, installing hardware for use in a new software effort, or even getting various licenses and legal agreements signed and ratified before a project commences. All these must be considered and organized efficiently.

From the standpoint of techniques used to handle dependencies, one of the most well-known is the PERT analysis, which is an acronym that stands for Project(Program) Evaluation and Review Technique. A PERT analysis will yield a chart that will provide an excellent visual representation of how a project or program needs to be set up in order to maximize productivity and ensure all dependencies are factored in correctly. The PERT can then be leveraged to create either a GANTT based schedule or can also be used to assist in Sprint planning if one is leveraging Agile process methodologies.

As a sidebar, there is one massive benefit from performing an adequate PERT analysis: the ability to discern the ‘critical path’ for the project. For those who may be unfamiliar with the concept, the critical path is a way to determine the longest route through a PERT chart that will allow you determine the timeline for the completion of the entire project or program. Depending on the outcome, contingency tactics can also be employed by the project manager and stakeholders to ‘fast track’ aspects of the overall program if they determine the completion time for all deliverables exceeds their comfort zone.

For more information on PERT analysis, please access the following posts: The PERT Analysis – Part 1 and The PERT Analysis – Part 2.

Utilize the Correct Tools

As project managers, we are very familiar with leveraging various tools to make our job easier. Whether it be MS Excel or Project, Agile Backlog and Task software utilities, dashboarding programs to convey project status, and so forth. Knowing which tools to use and when is an important component of how we perform our day-to-day duties.

One thing to note: tools are there to help make our jobs easier, not get in our way. As such, it is important for the project manager to know when they should leverage a particular tool and when to avoid doing so. In some cases, especially when a learning curve is involved, a tool can become a hinderance, making things more difficult in the long run. And when contending with a complex project, one does not need to inject more complexity just for the sake of using something that happens to be there. In some cases, less really is more.

For information on how to effectively select the right tools, please access the following post: Project Management Software – Making You More Efficient.

Never Be Afraid to Ask for Help!

This may seem like a no-brainer, yet it is not uncommon for project managers to attempt to deal with all problems personally. While that may get them by with smaller, more manageable projects, it will make their lives a living hell if they attempt to deal with every problem and every contingency personally. With that being said, as part of the overarching communication strategy outlined earlier, the project manager should set up specific communication conduits with certain stakeholders and team members to reach out to when in need of assistance. Keep a list of these individuals and their functional roles handy, even if it’s a postit note on your computer screen. Know when to ask them for feedback or assistance and do not be afraid to call a meeting if an issue has manifested and you require input from your peers. In the end, it is far better to tell people something has arisen up front rather than having them find out when the problem has spiraled into something that could have potentially been dealt with earlier in the cycle.


Complex projects are no picnic. Anyone who has work on one can attest to that. Yet with adversity comes opportunity. We all strive to better ourselves and being the project manager of a complex project can be both daunting and rewarding at the same time. You will stress and you will sweat, but you will also learn a great deal. And ultimate benefit comes with the successful completion of a complex project and the praise and admiration you will feel for yourself, along with (hopefully!) the respect of your peers.

One final note: the suggestions above provide a rudimentary framework to leverage when tackling a complex project. There is a more formal technique available called, ironically, Complex Project Management. For those that may be interested, there is a fair amount of literature on the topic on the internet. Simple search for the ‘complex project management’ keywords in your favorite search engine. For those in the software space, there is a derivative of this technique referred to as ‘Extreme Project Management’, which is meant to function in tandem with Extreme Programming. You can learn a little more about that concept at the following Wikipedia article:

Project Management and Working With Executives

photo_corporate-executive-board-meeting-evaluationAs project managers, it is within our remit to be able to communicate effectively. Dealing with people on a day-to-day basis in part in parcel with our job description. However, how we communicate and interact is often heavily predicated on who the individual is that we are speaking with. Dealing with resources or ancillary team members is one think: dealing with high-ranking individuals in the company is quite another. The nature and type of information to be shared can vary greatly as well as to how it is disseminated.

To understand communication with executives requires a fair amount of flair on the part of the project manager. More often than not, your time is limited and scrutiny is high.

Types of Executives

Within the corporate ranks, there are varied levels of individuals who are generally the ‘big cheese’, so to speak, or at least hold some high level status within the company. In certain cases, depending on the nature of the project, one or more of these individuals may want to be kept apprised on how the project is progressing. This can include an executive delegated as the project sponsor, or even executives who are defined as stakeholders. As a quick overview of varied executives that can exist in a corporate structure, here is a brief synopsis.

  1. Sr. Director – The highest ranking ‘middle management’ level on most organizations. Can have a varied staff which includes individuals contributors, first and second line functional managers as well as other directors. May periodically function as a project sponsor but more often than not will be more akin to a stakeholder.
  2. Vice President – First line executive in the upper branches of the corporate structure. Will generally be responsible for a specific business unit or organization within a corporation. Generally has Sr. Managers, Directors and Sr. Directors reporting to them. Very common for a Vice President to act as a project sponsor.
  3. Sr. Vice President – Second line executive, also usually responsible for a specific business unit or several business units. Usually will have Sr. Directors or other Vice Presidents reporting to them. Can also function as a project sponsor.
  4. Executive Vice President – Third line executive, which often holds some of the most senior ranks within a company, usually responsible for many high level lines of business that function in common spaces. Often times, individuals like Chief Operating Officers, Chief Technical Officers and Chief Financial Officers will have an Executive Vice Presidential rank. May act as the project sponsor for very high level projects.
  5. Chief Executive Officer – The highest ranking executive in the corporate ranks. Essentially the de facto leader of the corporation. All other senior and executive level vice presidents will be reporting to this individual in one way or the other. It is highly unlikely that he/she will function as the project sponsor, but they may ask for regular updates on the project status, depending on how high-profile the project may be.

In addition to those listed above, there may be other derivations of the above ranks. Chief Information Security Officer, Chief Marketing Officer, Chief Legal Counsel, and so forth. But for the most part, those titles will generally be aligned with the ranks in the aforementioned list.

Suggestions on How to Present Information

As project and program managers, we are very used to both collecting and distributing information. Generally speaking, the majority of our engagement will be at the team level, coordinating resources, dealing with low-level project priorities, and so forth. However, there are also those circumstances whereby we are tasked with presenting information to the upper brass.

As most can probably surmise, executives are busy people. They spend copious hours in meetings per day, either in person or on conference calls. As such, they have become very accustomed to a high level of meeting efficiency. With that in mind, executives will have very little patience with an individual who appears ill prepared or is struggling with his laptop and PowerPoint deck. In addition, executives have a very high level view of the organization and may not know (or frankly care) about some of the finer details.

With the above in mind, here are some presentation tips that the project manager can utilize in these circumstances:

  1. Speak Clearly and Plainly – As alluded to, executives have little patience for long-winded banter or tangents. They want to quickly understand the information being presented so as to be able to absorb it and make cogent decisions. So avoid too much dialog. Get to the point as quickly as possible. Be terse in your answers and do not go into overly long detail unless otherwise asked. It is better to let the executives drives the dialog by asking questions as opposed to trying to lead the meeting.
  2. Your Slides Should Be Easy to Understand – As indicated, executives want information quickly and easily disseminated. A single slide with twenty bullet points on it will not go over well, as it will appear too busy. Try to minimize content to three bullet points per slide. Additionally and whenever possible, use graphs or charts to drive your point home. It may sound corny, but a picture truly is worth a thousand words. Also, keep your slide deck at manageable levels. Move details into the appendix and keep the actual deck as short as possible. Remember that your back and forth dialog with the executive should be the primary facilitator of information. The slide deck is just there to provide context.
  3. Make Project Progress Easy to Comprehend – In a similar fashion to keeping your information simple and terse, actual project status and progress should be as simple to comprehend as possible. Utilize color codes to denote project status (i.e. Green=Good, Yellow=Warning, Red=Problem). These are simple concepts that anyone can easily understand at a glance. If you are also using charts and graphs, which is recommended, make them simple in concept and type. A line graph or a basic histogram is pretty easy to interpret for just about anyone. Make them look professional, but don’t get overly fancy, as it may make your charts look too busy.
  4. Allow for Ample Time for Questions – As indicated, the Q&A between yourself and the executives should be the primary driver of the presentation. As such, ensure you provide enough time in your overall presentation for questions. It is also important to stop periodically as you are moving through your presentation to ask if anyone has questions. Do not leave all the Q&A to the end. It is not always easy to budget your time, but you are far better off ensuring you can get through your presentation with ample time for questions rather than having to leave information behind because you did not budget your time effectively.
  5. Dress Appropriately – This one may seem like a no-brainer, but in the tech world, many of us have become accustomed to being able to wear what makes us comfortable. However, when you are dealing with executives, especially in person, how you present yourself will go a long way towards providing a good first impression. If you show up at the meeting looking like the frat boy who just woke up from a huge kegger party, it will probably not be well received. One does not necessarily need to wear an Armani suit or be dressed to the tees. But keep yourself presentable and as refined as possible.

The Dos and Don’t of Dealing with Executives

How your communicate with executives often requires a little bit of flair. It can be as simple as knowing which words to use and which to avoid while also ensuring that you give the executives the respect they deserve. Or, at least, think they deserve. Here are some additional pointers when it comes to your engagement with senior leaders.

The Dos

  • Be Honest – Nothing will irk an executive more than attempting to be deceitful about specific information. We all have a natural tendency to think executives don’t want to hear bad news. But that is just placating to human nature. Nobody wants to hear bad news. But executives understand that it can happen and would much rather know about it so they can come up with some contingency as needed.
  • Be Confident – Once again, how you present yourself will go a long way towards gaining respect from your leaders. We all have a natural tendency to be intimidated by those who hold higher positions in a company. But remember; most of them were once in your shoes. Once you understand that, you can better relate to those to whom you are presenting.
  • Be Receptive to Their Views – The last thing an executive wants to hear is outright disagreement to their opinion or stance on a subject. With that in mind, if an executive raises a point during your presentation that may be counter to what your opinion may be, acknowledge it. You are not necessarily correct, afterall. If an issue is raised, start a frank but professional back and forth on the issue. If necessary, that can always be offlined for further discussion depending on the topic.
  • Be Cognizant of Their Knowledge – Despite what many of us may think, most executives reached their level of success because they were good at what they did. As such, consider them to be a good source of suggestions. An executive may give you a particular response to an aspect of your presentation whereby they suggest an alternate course or a simple change of how the information is conveyed. Be appreciative of that feedback and acknowledge it. For the most part, they understand how things operate at that level and are just trying to be helpful.
  • Be Funny – This one may heavily depend on the type of presentation. But in many cases, executives can appreciate a little levity as much as the next person. So don’t be afraid to show your whimsical side. That doesn’t mean turning your whole presentation into a standup routine. But a good-natured bit of humor here or there can go a long way towards making the presentation a little less dry while also making you more comfortable in the environment.

The Don’ts

  • Leave your Ego at the Door – As mentioned above, the executives you are presenting to probably have a lot of credentials and success under their belt. As such, they are not going to be too receptive or patient with someone in the lower echelons of the org chart showing off like he is some rock star. Keep yourself in check. Perhaps you may have some more intricate knowledge of this particular project area, but it is highly unlikely you have the comprehensive knowledge of the executives.
  • Try to Avoid Saying No Outright – This goes back to the terminology and how you use words in your dialog with executives. In many cases, the word ‘No’ or the words ‘We Can’t Do That’ do not sit well with the upper brass. No that is not to mean you should never use those words. But in cases where the answer it not entirely obvious, let the executive know that you will get back to them after you have conferred with the team. (And make sure you do so after the fact) At least that will give the impression that you are exercising due diligence rather than appearing dismissive.
  • Don’t Expect Specific Instructions – As mentioned, executives are used to efficient meetings. As such, they are not going to spend time trying to guide you through the presentation. Be prepared and don’t expect them to carry you. You will have to carry your own weight. You can always welcome them to provide suggestions on how the material should be presented, but more often then not, they will assume you know what you are doing.
  • Don’t Air Dirty Laundry – When presenting to executives, the last thing one should be doing is bringing up issues that are either tangential or irrelevant to the presentation at hand. If the company is having issues, the executives don’t need you to tell them. They are fully aware. Additionally, if you have had issues working with certain teams and some of the executives in that room have these teams in their reporting structure, the LAST thing you want to do is starting the finger-pointing game. Those types of conversations should be done privately. Any executive whose team is being bad-mouthed in front of his/her peers is not going to appreciate you bringing up the conversation at that time.
  • Don’t Take Things Personally – This one may be one of the most difficult things to contend with. However, it is imperative that you keep your cool and do not take criticism in a negative way. There is always going to be situations where you may be the brunt of a slight or perhaps a direct recrimination of some sort. Once again, you will earn far more respect keeping your cool in such a situation rather than devolving the presentation into an argument. We are all professionals in the end.


Working with executives is a challenge many of us may face in our working lifetime. While intimidation or dread can be the emotion many of us will feel in that circumstance, you are far better off looking at it as an opportunity. One that will allow you to showcase your talents and earn the respect of those at the top. You never know. A good presentation here or there in front of the top brass, and perhaps one day you will have that cherry parking spot next to the main entrance of the head office.


Get every new post delivered to your Inbox.

Join 51 other followers