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I think for each of us THE greatest challenge we face is to know ourselves, so once I started forming a sense of my priorities and values, and set out to build buildings, I discovered the elements of Project Management and the job that can put us to the test:
THE PROJECT SCHEDULE is one of the pillars of Project Management, and one of the most fundamental elements that needs to be understood and managed.  Along the way, as it became clear how important a well put-together schedule is towards making a project a success or failure, I was part of great schedules, messy schedules, impossible schedules, but usually schedules which were described as 'aggressive'.

On the surface a large dollar-value project appears challenging by virtue of its dollar value;  certainly large dollar value projects involve comparatively large quantities of resources:  people, materials, equipment, land.  But you' can't buy time, and a schedule with no 'float' time - no buffer time to rely on if a critical path step is missed on its deadline - is daunting.

In my career, the Harrah's San Diego hotel and casino was a very challenging project because of the scope fit into a 12 month schedule:  21 stories of hotel - AFTER existing casino structure was removed to make room for it, and AFTER the huge pit was excavated for driving the piles which supported the pile caps which supported that hotel.  We also built a wastewater treatment plant for the new hotel and expanded casino, we also built a 4 story parking structure, 30 acres of underground utilities, paving, grading....5 new utility electrical services, and very exotic finishes throughout.

A tough Schedule has been one of my greatest challenges.
CHANGE is very disruptive to a project.

When change happens, all items triggered by the changed item are impacted, and their trajectory moves and costs generally rise.  Administratively, the change must be understood by all affected, and estimators must price the impact.  Overhead costs like management salaries continue to accrue, and the specifics of the scope change cause their effects on everything downstream.

Personally, the impact of the economic downturn caused great change in my life too.  When the large project I was on in 2008 finally started winding down, I got my layoff with no work for me in my employer's hands in May of 2010.  I incorporated as Keystone Resources and went to Nashville, TN to consult for Piedmont Natural Gas as they renovated their LNG plant during litigation with a fired contractor.  The process of incorporating taught me much about legal and tax issues for a corporation, so while change is uncomfortable, it can teach us much, and most importantly, it never stops.

MANAGING PEOPLE and all the things that involves remains the biggest challenge to me, and to most Project Managers who excel in their work.  Cultural, communications style, conflict resolution, learning, and many other differences among people mean each individual and each situation requires adaptation and full attention.

Without proper management, interpersonal relationships and team morale suffer;  in my experience, high morale can compensate for many deficiencies from inexperience to lack of resources, and low morale can sink the best planned and staffed projects.
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