I’ve lived in the project management trenches for nearly 3 decades. I decided a few months back to pen a “survival guide” of sorts called “Burn That Project Down.” 

I decided to conduct some field research by sanity testing my own grizzled wisdom with project management professionals around the world. I turned to the LinkedIn PMI Project, Program and Portfolio Management Group, and asked a few simple questions:

What’s the most painful lesson you had to learn that wasn’t covered in a book?

There are plenty of great books about specific methods, tools, and frameworks. But what about the OJT you had to learn on your own?

What advice would you give your younger self?

The responses were so high-value and so much wisdom was being shared, I decided to capture each commenter’s advice in a single post (in no particular order, edited for clarity):

Wael Maksoud

Investing in planning and thorough risk analysis exercises are key to success.

Warren L.

If it’s not in writing it’s not true. Reporting and status are key. Ensure stakeholders are informed throughout the lifecycle and ensure you include financial reporting in your communications. Tightly manage deliverables in a project to ensure it doesn’t spiral into chaos.

Bridging the gap between project technicals and financial measures involves integrating financial literacy into project management, fostering a value-oriented mindset, encouraging cross-functional collaboration, utilizing financial metrics in decision making, and clearly communicating financial impacts. 

PMs should shift focus from solely technical achievements to how projects contribute to financial health and strategic objectives. This approach enhances project management’s strategic value, ensuring projects align with broader business goals and financial success. 

This is not so much about a CYA, but rather a strategic partnership as opposed to merely project execution through a project management methodology (insert any methodology). 

Being on track against the budget of a project is 1 communications consideration, the investment into the build and knowing why whilst tracking execution against value of a feature is key.

Max S.

Vendors lie.

Dennis Dubberley

Customers do too.

Revenue is way more important to organizations than cost. I saw this too many times where sales sold something that couldn’t be delivered and operations was left picking up the pieces. And attempts to engage early during the selling process rarely improved things. Sales is typically 100% focused on hitting their short term quarterly numbers and the system incents them to do so. I spent 30 years of my career in a love/hate relationship with sales.

I’ve often considered that adding project gross margin performance to the sales compensation equation would be very beneficial, but I don’t want sales telling operations how to deliver either so enforcement would be a challenge. The best sales people I ran into either came out of or spent considerable time in operations. They understood that profitability was just as important as growth to the shareholders.

Omar Lieves

Beware of those project managers that say they have never failed.

Narothnee J.

Never assume, always repeat everything, and get decisions in writing.

Jason Cohen

The more people involved in decision making, the higher the risk of failure. Delegate authority for decision making as close to the people responsible for doing the actual work as possible.

Bill Jackson

How to deal with obtuse people on projects.

Dawn Rose

Even if they seem inconsequential at the time, keep a decision log or a running list of decisions. Stakeholders change what they say or refuse to admit they said something they shouldn’t have. This is more than meeting minutes. It is a consolidated place to find all decisions made for a project so you don’t have to go searching for the information later.

Arnót Terblanché

On project communication, always keep in mind “no news is NOT good news”.

Bryan Kern

Be sure to have an issue escalation path clearly defined at the very beginning with all the participants in that path signed off on their role, responsibilities and expectations set. Too many times issues had no where to go for resolution. I learned this one, for sure.

Richelle L.

Trust but verify. There were times on several big projects that I relied on someone else’s opinion, only to find out at a critical juncture that they were wrong.

Bobbie Calhoun

Listening to current PMO leaders to truly understand their pain points is “step zero” when joining a new organization or team… don’t solve what’s not broken. Also, bring leaders together in a constructive consortium to share best practices!

Jason Orloske

There are 2 pieces of advice I’d give my younger self:

1. Take the time to uncover all impacted stakeholders. My first, and biggest, project failure was due to not identifying a team of 4 key people in a company of 17,000.
2. Learn how to deal with difficult personalities that will suck the morale out of a team. Narcissists, bigotry, entitlement, and more have been experienced in my 20+ years and each is damaging. It takes courage and experience to deal with these.

Jerry Russell

First, you must plan–always. Second, the day you publish your plan, it will change. Embrace that.

Mark E. Geres

1. Dealing with covert behaviours/processes in the workplace;
2. don’t sell your soul for ‘golden handcuffs’; and
3. understand why people lie.

John Wigant

Develop a thorough transition plan to the operational teams to ensure they are comfortable assuming ownership going forward. It’s bigger than retrospectives or lessons learned. The work done in this phase will be as key to project success as any ROI.

When your project includes any sort of year over year configuration or testing, not clearly identifying ownership, budget, timing as part of the project transition places the Organization in a bit of a scramble and as such, the project was not fully implemented. I call it the drop and run approach.

Kiron D. Bondale

Never take your eye off the business case or rationale underlying the project’s existence. It is too easy to get tunnel-vision on delivering to the triple constraint and satisfying key stakeholders, all of whom are delighted to continue delivering a project which will not provide the returns expected.

If external factors change or underlying assumptions have been invalidated, the team might execute the project with excellence within approved baselines only to end up delivering scope which doesn’t address the business need.

Adapt to conditions as they change which includes being willing to recommend to “the powers that be” that your project needs to be terminated to avoid throwing good money after bad.

Ahmed MUSTAFA

Communication: The proper timely communication is an essential and crucial between the project team and stakeholders in order to execute and deliver the project with client satisfaction.

Alexander Merkouris

Learn to live in ambiguity cause a plan is easy to follow.

Irina Korolenko

Check for any missing requirements on your own; don’t rely on others to catch them. It’s a common occurrence for subject matter experts to focus on their specific areas without giving much thought to how everything integrates. Critical things at the edges of these functions can easily be missed.

Edward Murphy

While you are and have always been 100% customer centric because it’s the correct thing to be, don’t assume others are and have the same customer’s best interest in mind. Nothing worse than dealing with those who only serve themselves, believe mediocracy is acceptable, and do not believe it takes a real team to deliver. Faster you can get the right people on the job, the better, and don’t feel bad about leaving the others behind. They will drag you, the rest of your team, and the customer down.

Being a successful Project Manager or Director is a people skill far more than any other skill such may have. My OJT people skills were honed working public facing blue collar and construction jobs for 10 years before I entered the technology world. It’s natural to learn, to lend a helping hand, and to be attentive when heavy physical objects are being lugged around. And when something does not get moved or moved incorrectly, it is physically seen and obvious. Not so much when pushing around 1’s and 0’s from a keyboard. So, experience, environment, and values naturally occurring or gathered over time, are all important. “Coach Up” may be the WEAKEST link. It doesn’t work well if it is the “blind leading the blind.” If I had a nickel for every time I had to get on a plane to put out a fire created by a SME … And if you want to bring people “up to speed” quickly, nothing wrong with tossing them right into the fire, but done so that the calvary is always there to help if need be. Coddling is a poor option and used too often these days.

Michelle O’Brien

That sadly it is possible to go through an entire collaborative project designing a service to make people’s lives better….only to have it killed for implementation by a sponsor who had zero intention of implementing….just wanted to look good.

Karthik Chamy

Stay close to the sales people and try to get as much information about the ‘prospective’ project before it becomes one. Raise all the red flags early so it doesn’t solely become your responsibility to deal with them later.

It’s definitely a challenge to start with as we often operate in silos (departments, business units, etc.). We tend to think, “It’s not my job,” or are told “it’s not your job,” and avoid involvement until a project is official. 

But the bigger picture is projects can’t be delivered in isolation and as an organisation we’re building a narrative to the customer (from pre-sales to project to customer support and so on). There NEEDS to be an overlap – especially, when sales are making a promise on your behalf that a project CAN be delivered (but you’re not part of the conversation!). I find the concept fundamentally flawed. Just a few hours of early intervention pays dividends during delivery & handover. 

As a PM you do try to build that relationship anyway. After a few successful projects + happy customers, everyone in the org realizes it’s a win-win for all. All this holds true only if you work for a company that’s in it for the long term.

Chris Schleich

I prefer to be part of proposal process for this reason. Sometimes it doesn’t feel sustainable to have operations folks in proposal and estimating, but I like it much better than starting a project with a bad proposal.

Glenn Egan

As part of navigating the stakeholder maze, find the ‘people behind the people’ and look to build a project relationship with them. 

It’ll be natural for them to look at the WIIFM (what’s in it for me) factor, but if you can connect in a good way with them, they will likely help to open the doors that need to be opened for the project to have a better chance of success. 

Also crucially important to get the governance structure and forums established early in the project lifecycle.

Ronald Vaughan

Shut up and listen.

Jeff B.

Figure out your project organizational structure at your company. This will save months of headache while you figure out how to best manage based on processes and culture.

Sultan Alshardi

Stakeholders management is the real challenge as it can change the direction of the project completely if not managed well.

Omeed Adham Sindy

Stakeholder management is def covered in the books, but how to deal with overbearing or overly demanding stakeholder isn’t and you only get good at dealing with them through experience

Michael Lewis

If you’re new to a company, identify who the important people are immediately. Some projects require frequent check-ins with ‘power people’ in the company, even if they aren’t involved in the project. Whenever a decision is made, management may ask “Have you gotten input from person X?”. This will prove extremely frustrating, but is a reality. These are ‘hidden stakeholder’–not part of the project, but management may be hesitant to buy off on anything if this person didn’t give the go-ahead.

Moitreyee Das

Convert all verbal communication into written format. Extreme documentation and archival of all artifacts as evidence. This is a boring thing to do, but trust me, it can be your saviour. Use the same email trail every week to report status/meeting notes/risks etc, so that you don’t lose anything because of organisation’s email retention timeframe, even if the project runs for years.

Ensure that monkey is not on your back, because no one’s responsibility is project manager’s responsibility.

Mustafa H.

Be open about communicating risks and collaborate for solutions. You will thank your past self later!

Mia Martins

1. Keep learning outside of your project. There’s a lot of info to teach you, no matter how experienced you think you are.
2. Learn how to manage all types of personalities & what motivates them.
3. Focus on the goal, not what others tell you is the goal.

Zaid Hamed

1. Don’t assume that your team or your client is on the same page with you; make sure you ask the right probing questions to have them speak up.
2. If you call yourself a mentor, make sure you put in time to actually show the work not explain on paper or screen. You will be pleasantly surprised that you won’t be redoing the work as much and you will delegate work more confidently to your team who will deliver top tier quality.
3. Don’t think you are the smartest one in the room. If you do answer – back it up – or just politely say, “I don’t have the answer now but I assure you I will get you an answer by a certain time and stick to it.”

Jamie Andrews

Your RAID (risks, actions, issues, decisions) log should be your best friend. If it’s not the most updated, the most accessed, and the most referenced artifact for your project then you’re doing it wrong!

What advice would you tell your younger self?