Raise your hand if you’ve ever had a project go 100% to plan.

You’re either a 1) Project Management Mastermind, who can probably see into the future, or 2) Lucky, because the odds of things going to plan are really low.

Or maybe you stripped all the complexity from the job to keep everything under control.

The truth is that project planning is hard.  There are three forces at odds with each other, scope, cost, and time.  Conventional wisdom says you can only control two of them:

Here’s how to use the triangle:

The overall quality of the project depends on how well you balance each of the ideas.

Many plans deal with surprises by surrendering a corner of the triangle or sucking it up and working ridiculous hours to keep everything the same (often, this is an illusion).  Strong project plans counter chaos by creating contingencies.

Contingency Planning 101

A “contingency” is the action you’ll take in response to something happening.  Figuring these things out feels like a lot of work, especially because we’re typically too optimistic that our project won’t need them.  Contingencies provide you with a third response to unexpected events:

  1. Delay the project, remove features, spend money
  2. Work your team to the bone to keep all three corners of the triangle
  3. Use your contingency plan

How to Create A Contingency Plan

From Fergus O’Connell’s, What You Need To Know About Project Management, set time aside once or twice per month as a team and go through the following exercise:

  1. Brainstorm as a team anything that can go wrong.  Some examples:
    1. Lose/gain team members
    2. Requests for new items
    3. Shipping delays
    4. Missed deadlines
  2. Rank each from 1-10 on:
    1. Likelihood
    2. Impact
  3. Calculate Exposure of each
    1. Exposure = Likelihood x Impact
  4. Brainstorm ways to reduce or eliminate the risk for anything scoring above 25

Document your solutions somewhere and revisit them as needed.

Three simple ways to run proactive projects

Create a list of deadlines – real and fake.

Real deadlines are the ones that 100%, absolutely cannot move.  Things like events, contract deadlines, etc.  Everything else can be moved.  It’s almost always in your interest to shift fake deadlines away from the end of the project.

For example, if you have a real deadline of October 31, and an ideal fake deadline of October 15, move the fake deadline to October 8 to build in an extra week of wiggle room.

Parkinson’s Law argues that teams will take all the time they have to finish work.  If you keep October 15th on the calendar, that is the soonest they’ll get that work done, which means any delays will pressure your real deadline.

Slice the project timeline into phases

Work on your project in smaller increments.

It’s easier to figure out what you want to do in the next month instead of the next 6 months.  Phases also let you make small, easy pivots, and it simplifies the project timeline.

Eat the elephant one bite at a time instead of all at once.

Define the “critical path”

Your project’s critical path is the set of work that:

For an event, the critical path might be:

Everything else is work that can be done at the same time or it’s something that doesn’t hold anything up.  Figure this out by starting from the end and working backward.

A critical path shapes your due dates and priorities by revealing the most important branches on the tree.


Being proactive lets your team respond with strategy instead of stress when surprises emerge from the woodwork of your project.