Ask a project manager if the glass is half empty or half full and you might get the response, “Either way, in a few minutes, the glass will be totally empty.”

The best project managers use their experience of what has gone wrong in past projects and promise themselves, “I’ll never let that happen again.” The trick? Stay ahead of surprises. In this series, we explore the types of surprises that can derail a project and what you can do to avoid them.

First up: Schedule Surprises.


I remember a project in which my client’s project manager had a family vacation planned well before the project kicked off. Every time we reviewed the project plan and key dates, this person never spoke up. Late in the project, just before the most critical sessions and knowledge transfer, I learned he was leaving for PTO for 2 weeks. At that point, there was nothing we could do. 

But whose fault was that? At the time, I only blamed him, but you can be sure I learned my lesson. Ask the question early and often. Ask your primary contacts on the project to ask others as well. Don’t assume the one key person you’re working with is asking. Periodically review the key project dates with the project team and ask explicit questions about when people have time off planned or when they’re thinking about taking time off.

These things are commonplace and do come up regularly, but they should be noted as project risks to be included in your mitigation plan. In some cases, there’s not much you can do, but in the event things do go wrong, you want to be able to show you had a mitigation plan and planned for it as best you could.

Company Events

Something a little less obvious is company events planned during the project. Whether it’s a sales kickoff, a user community event or a big trade show, these have a tendency to take more time than the few days blocked on the calendar. 

If there is a company event planned, find out who on the project team is participating. It may not be on their individual calendars yet, so ask the question broadly to get people thinking about upcoming events. Just as important, find out each person’s role in the event. Are they just showing up for it, or are they involved in planning? Find out what this means in terms of time away from your project.


“…ask the question broadly to get people thinking about upcoming events.”


Maternity/Paternity Leave

This one is a bit more delicate, as you don’t want to scan the room and call out someone who looks pregnant. Also, paternity leave is becoming more commonplace, so don’t assume this won’t come up. 

On one of our projects, a PM from our client was assigned to our project after a couple of weeks in. Several more weeks after onboarding and reviewing the project schedule, the PM finally mentioned his wife’s due date was in the midst of go-live weekend. This person and others who knew ahead of time failed to mention it. Ultimately, his wife delivered a few weeks early so more than just go-live was impacted.

When you’re reviewing the project schedule, ask a question like, “Does anyone plan on taking any extended leave for any reason? Any major life events coming up you need to plan around? This will also get people thinking about out of town weddings and graduations that may be coming up as well.

Depending on the project role the person is playing, this type of absence can be easily accommodated. Again, what you’re looking for is to ask questions and avoid surprises. 

Finally, when you’re putting your contingency plan together, it should account for more than just the planned due date in the event of an early delivery.

Competing Priorities

On another project I was managing, my client was late arriving for the kickoff meeting. Two hours into the meeting, a key stakeholder arrived late, apologized and asked what she missed. An hour later, she excused herself, “Client escalation… sorry!” This went on with nearly every person. Everyone was so busy with their day-to-day responsibilities, no one was able to focus on the project.

Technically, the project schedule was fine with them, and no one had any issues with the dates for the working sessions and testing sessions. But when those dates arrived, no one had the energy or patience to tackle the project work.

To get ahead of this, set clear expectations of how much time you’ll need from each member of the project and at which points. If you have all-day sessions, make it clear they need to cancel other meetings. Keep an eye out for early signs, like missed calls and early drops. Escalate this concern to the stakeholders and project sponsors and include it as a risk in your status report. Better to address this early and insist it be corrected than to stumble across the finish line and risk project failure.


“…as the project manager, it is your reputation on the line. “


Long after the project is complete, no one will remember the team commitment issues – as the project manager, it is your reputation on the line. 

Technical/Logistical Dependencies

We’re in the business of implementing solutions from and FinancialForce, so we are dependent on a small number of prerequisites: Do we have a sandbox license? Are they approaching platform limits? If so, which ones? Are there enough user licenses? The list goes on.

If you’re in a different business, you may have other issues that can delay the project. Whether it’s hardware, vendors or related concurrent projects that can delay your schedule, identify what they are and keep communicating that list of dependencies as risks until they aren’t. 

The Bottom Line

In every project, there’s always something that goes wrong – usually several things. Don’t pretend it won’t happen to you. Stay vigilant, keep asking the same questions, and have a mitigation plan. With some diligence and some luck, you’ll have a successful project without the element of surprise.

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