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Why do executives hate project managers?

Regardless of whether you’re working on a waterfall, agile or hybrid project, building a great project culture presents unique challenges.  No relationship matters more than that between the Project Manager and their Executive stakeholders.

And yet, Project Managers and Executives can often find themselves at odds, due to differing styles, differing focus, and competing priorities. Executives are often juggling both their leadership demands as well as trying to communicate the priorities top-down. Project Managers are often focused on the bottoms-up details with their team, the nitty-gritty project management basics of task management, resource management, and cost management.

The following questions can help you frame and remediate the common concerns, from recognizing the problems, to addressing common challenges and transforming your project culture before it’s too late.

1. How does Executive/Project Manager friction develop? 

The first step to addressing this friction is to recognize the problem. This takes fortitude, stamina, patience, and a keen eye for communication gaps.  It’s helpful to trace back your whole relationship and understand ground rules, communication preferences, and even job descriptions.  Getting a sense of the terrain is a key part of navigating through the thicket of potential misunderstanding.  

A key part of Microsoft partner training 20 years ago was a curriculum called Solution Selling.  It was a discipline that asked at every level of decision-making: what are your pain points and how does this solution (possibly a project or product) provide you with relief?   The same questions should be asked between Executives and Project Managers at every opportunity: What are your constraints and what can we do – together — to remove them?

For Executives, some of those pain points might be reaching sales or production quotas, providing timely status to the CxO level, or working to reduce cost. For Project Managers, it may be making sure your team is producing quality output, providing timely status to your Executive stakeholders, or working to reduce the cost of project execution. Or maybe it is just slowing the pace of cost growth.

If Executives are working top-down, taking direction from the CxO level, and Project Managers are working bottoms-up, making sure their teams are productive and sustainable, what can we do to make sure they are actually synchronizing?  

2. What is the risk of not addressing Executive/Project Manager rifts? 

As project velocity increases, so does the speed of change.  And that change is happening at both the Executive and Project Manager levels. If the CxO is responding to quarterly earnings pressure, they may decide to curtail projects, and the fallout descends directly on the Project Managers to respond.  Likewise, requirements analysis at the Project Manager level invariably uncovers execution surprises and challenges, whether it be staffing or costing or supply chain. All of these challenges directly impact the other levels.  

If the Executives and the Project Managers aren’t constantly assessing the team’s ability to react, change, and perhaps forecast change and proactively adjust, the latency of change increases, and with it perhaps missed market opportunity, not just missed milestones.

3. How severe a problem is Executive/Project Manager challenges? 

There are several benchmarks to gauge project dysfunction.  Some of my favorites are contained in the article The 6 not-so-obvious reasons a project plan fails.  And PMI’s Pulse of the Profession makes an excellent case for power skills defining project success.

There are literally dozens of metrics associated with project success or failure, so many in fact that I get tired just thinking about it, and I’ve long since tired of listening to other people talk about project failure.    

But when you have numbers like 70-80 percent certainty of projects busting through the time / cost / quality guardrails, you can leave no stone unturned in finding a solution. We have to do something. I find solutions a lot more exciting than challenges.

Because the Executive/Project Manager junction is critical to making projects perform, we have to pay attention to building up those capabilities, whether they are navigation of the power structure, improving public speaking, or just simple recording results in a database. We can and must strengthen our resolve to support the relationships on which great project performance is built.

4. What can the Project Manager do to address Executive angst? 

The Project Manager is so good at managing downwards, they often have challenges managing in the other direction. Fear, intimidation, and lack of attention all contribute to a degradation of the key relationships for project governance, so I would suggest some key steps to relieve the pressure.

Project Managers should regularly meet with their Executive stakeholders.  Project Managers need to understand each Executive’s pain points and work to resolve them for their projects.  Increasing the frequency of the Executive / Project Manager communication cycle reduces the pressure for each interaction, making the dialogue safer for all involved.  

Project Managers must also understand the preferred communication styles of the Executives they are interacting with. It may not be enough to have a half-hour one-on-one meeting on a monthly basis. Texts and emails may help, but there is no substitute for a shared understanding of common metrics. Understanding the specific effective communication cadence and method for each individual is crucial in assuring understanding and decreasing decision latency.


5. What can the Executive do to address Project Manager angst? 

The Executive is often very skilled at managing upwards and may not have a lot of time to manage their Project Managers. Lack of patience, detail orientation, or available time are all contributors to a breakdown in the Executive/Project Manager relationship. How can Executives help by stepping into the breach?

Executives can resist the urge to step in to assert authority, but rather seek ways to reinforce the Project Manager’s control over the project and the team. The Executive can work with the Project Manager to mutually remove constraints like cost, time, and resources to clear the way to project progress. The Executive must make regular communication a priority, so that there is a safe forum where the Executive can hear the unvarnished truth in a productive manner.

6. What are the benefits of improved Executive/Project Manager relations? 

When the Executives and the Project Managers are operating on all cylinders (and yes, I’m dating myself with that phrase, but given the state of PMO maturity, maybe not so much), there is incredible value unlocking opportunities. When there is open communication, issues are addressed sooner (bad news doesn’t age well), budget growth is understood, and resource issues can be addressed in a cadence aligned with recruiting realities.

The stress-test of quality Executive / Project Manager relationships is a downturn. I’ve seen my share of business and economic reversals, sometimes as simple as a business structural problem, or as momentous as a global recession or pandemic. Something goes in reverse, and projects need to be spun up, shut down or severely altered at a moment’s notice.

One of my favorite Warren Buffet sayings is “Only when the tide goes out do you discover who’s been swimming naked.”  When projects go wrong, having a strong Executive / Project Manager relationship will find you BOTH better prepared for the tide coming in, going out and any other eventuality.

7. Who needs to take action on Executive/Project Manager relations? 

In a word, everyone. I think the place to start is at the CxO level, where expectations of a high performing Executive/Project Manager relationship are kindled, stoked, and constantly reinforced. It takes time to create the space for creativity, safety, and growth that this relationship needs.

At the Executive level, work on productive communication, better metrics, and a cordial yet mutually beneficial relationship can be had with some effort. Everyone can improve and Executives can lead the way.

At the Project Manager level, constantly refine modes of productive communication, and get away from manually collecting and preparing status (you can and must automate this, the tools have only been available for DECADES), and get on with the interpretation and qualified actions resulting from good metric tracking.


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