
Whenever I teach new graduates how to transition into the corporate world, I get asked for advice on how to stay on your boss’s “good side.” I won’t call my answers “words of wisdom” because that sounds pretentious. More like “stuff I wish I’d known beforehand instead of being forced to learn it the hard way.” That is to say, “lessons-learned” in corpo speak.
A topic always makes my list of good advice is take everything a project manager says with a grain of salt. I know that position is going to rile some folks. Heck, if my column still had a comments section, that statement would “generate some content” before folks finished reading the article. Thing is, I don’t mean it as disingenuous rage bait. I’m not out to troll anyone when I caution new hires to be politely sceptical of all estimates, reports, and plans, no matter how earnest the teller.
For the record, I don’t hate project managers; hell, I’ve been one myself a bunch of times. There’s a lot of good PM doctrine out there that serve as practical and effective planning tools. I’d’ honestly advise every corpo to spend a year in a PM role so they can understand what life looks like on the other side of the status report. Learn some empathy. The trouble is, discovering the good stuff often only makes itself known after either (a) a catastrophic screwup or (b) chewing through the intellectual hardtack that is formal PM doctrine. It seems only fair to teach these lessons to the greenhorns up front rather than force them to fight for the knowledge.
Along those lines, I’ve always project management concepts too often presented as an exact science for my liking. As far as I’m concerned, PM skill it’s an art, full stop. Sure, there are a lot of neat scientific tools at a PM’s disposal, and their formal techniques should be used when they’re appropriate for a situation. Almost of the planning parts of the doctrine, though, are a matter of experience-driven guesswork. Complex formulae outputs might as well be dice rolls. No matter how many times you’ve done a specific task, each new implementation brings both expected and unforeseen problems that throw things off.
I believe strongly that it’s crucial for brand new corpos to understand that inescapable limitation as swiftly as humanly possible. The sooner a new hire accepts that plans and status reports and estimates are all based on incomplete and flawed information, the better they’ll be able to adapt and recover when their complex plans go all pear shaped. Getting mad at the PM for not possessing perfect foreknowledge like a mystic seer is both unproductive and insulting. Nobody can prognosticate with perfect accuracy, especially not when people are involved.

A good corpo needs to be able to roll with the changes. Things will always go wrong, so it’s wise to have contingency plans, schedule buffers, reserve supplies, on-call backup, and all the other tricks that talented PMs leverage to mitigate the nonsense that threatens every good plan. A PM is more of an air traffic controller than a manager, in that they’re constantly monitoring the zone around them, but they can rarely force any of the many moving parts to do as they’re told.
A good — if small scale — example of this took place in my yard last week. I’ve been concerned that the fence segments walling off our backyard have been decaying. Since we don’t own any of the fence lines ringing our yard, we couldn’t demand that their owners repair or replace them. Still, one section has been rotting badly since the winter. Braces and stakes have been falling off and the whole thing looked like it was about to blow down in the next windstorm. Thinking ahead, we saved up for months and got an estimate on what it would take to replace just the worst run of fencing and the two gates attached to it: the one on our side and the one on the owner’s side.
I pitched the plan to our neighbours, and they were thrilled … especially when I explained that we’d pay for the entire job, supplies and all. They’d get a new fence line and gate and weren’t required to do anything. This wasn’t an appeal to greed by my neighbours; they’ve had just as many exhausting and expensive home repairs to manage as we have over the last few years. They’ve wanted to fix their fence and even had the job on their list of repair priorities, but they hadn’t made it that far down their list it yet. I empathised; we hadn’t either until this spring.
Once we had the neighbours’ agreement to move forward, I green lit our favourite contractor — Edgar from Royalty Contracting Remodeling, and Paint [1] — to start whenever he was ready. Edgar’s initial estimate for tearing down the old fence, installing new wood bits on the existing poles, building the new gates from scratch, and installing a “dog window” so both families’ pups could socialize ought to take him between one and one-and-a-half 12-hour workdays. We smiled and said, “good luck.”
We knew that Edgar had done fencing before. We also knew that he’s experienced, disciplined, and professional. We’ve seen him work on lot of jobs around our house over the years and trust him at his word. Still, we also know how Murphy’s Law intrudes into every plan, like it or not.

Sure enough, it took longer than expected for Edgar and his team to start work because of spring storms interrupting his existing projects. No big surprise: a Texas weather forecast is subject to random change every 30-ish minutes, just like our feckless politicians’ policies. [2] We lost about a week and a half to delays and interruptions before Edgar got around to our job.
Edgar and his crew weren’t finished with the whole job on the first day. First off, one of his workers didn’t show, leaving his team understaffed. He didn’t have a standby, so the team made do. Still, tearing down the old fence was easier than expected, even with an unexpected tree removal. Unfortunately, one of the existing metal scaffolding poles needed to be replaced a pole that had been installed with a massive load of concrete that all had to be dug out. The original concrete blob looked about the same size as a compact clothes washer. I couldn’t imagine what the danger thing weighed. That unforeseen (and literal) roadblock cost Edgar a bunch of time.
The next day, almost all the vertical stakes went up without any drama. Even taking extra time to be meticulous about the spacing and alignment didn’t throw his crew off schedule. No, what clobbered them on day two was an unprojected need to bring in better power tools to fabricate the gate components. They tried using what they had, decided the results were simply not up to their standards, and asked if we would approve an extension. Of course, mate.
Day three saw my back porch turned into a woodworking shop. My side yard turned into a debris field while my driveway was completely blocked off with debris and fresh materials. It was worth it; the gates turned out fabulous. Unfortunately, the gates also wound up needing all new hinge assemblies once we discovered that the old ones were unacceptable by Edgar’s standards. He and his team did a fabulous job getting everything build and tested but ran out of daylight before they could finish policing up the sire. They’ll be back out Monday to finish the cleanup. Hopefully. I have a backup plan in case they don’t make it.

Were we upset by the job going more than twice as long as projected? Not in the least. Edgar is an old-school builder: he painstakingly reported every setback, revised his estimates, sought permission for every change, and showed us everything he thought might potentially cause us to be upset so we could require it to be redone. He’s honest to a fault. That’s why we keep hiring Edgar and his company; we can trust him and his people to be transparent, detail-oriented, and responsible. So, no. We expected his gung-ho best-case estimate to be a goal, not a guarantee. We knew exactly why each delay happened and sympathised with Edgar’s frustration at being behind schedule … but we never once blamed him for getting his plans wrong. They weren’t wrong, so much as best-case estimates.
This is I teach what new corpos: if you want to succeed in business, you need to always be prepared to calmly expect and adapt to unexpected delays. As we joked in the Army, “no plan every survived first contact with the enemy.” A less martial version of the aphorism for the white-collar crowd might go “no project roadmap every survived first contact with the job site.” No matter how brilliant the plans were, Murphy always gets a say. Things will go wrong, and getting bent out of shape about it never helps. If anything, railing at the PM is very poor form. It shows immaturity, lack of self-control, and a dangerous misunderstanding of How Stuff Works™.
Sure, a sloppy PM is a liability. So is a cowardly PM who tries to blame everyone else for their own mistakes. A good one, though, is expected to be honest, forthright, and transparent. They know that their plans are likely to change and will faithfully report both what’s gone wrong and what they’d like to do to mitigate it every step of the way.
Your job as a new leader, I explain, is to create a healthy culture where your PMs can be honest with you. An environment where the team can flexibly adapt to issues rather than melt down. Learn that early on, I teach, and you’ll earn a reputation for dependability and maturity. This is what convinces a sane boss to trust you and lead without micromanagement. That’s what you want. You’re happy, your boss is happy, and your PM will follow you into Hell.
[1] For once that is a character’s real name. Edgar is a darned good contractor and we’re happy to recommend him.
[2] But that’s a rant for another day.
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