Optimism Isn’t a Strategy
“I didn’t see that coming.”
How many times have you said that? Or heard another manager say it? Your project derailed because a dependency wasn’t tracked. A launch failed because someone forgot about a compliance requirement. The deadline slipped because a key person went on vacation.
None of these are bad luck. They’re predictable failures that didn’t get predicted.
The best managers I’ve worked with aren’t luckier than everyone else; they’re more paranoid in a productive way. They spend time asking “What could go wrong?” before things go wrong.
The Preparation Most Managers Skip: The Pre-Mortem
You’ve heard of a post-mortem — the meeting after something fails where everyone figures out what went wrong. A pre-mortem is the opposite. Before you start something important, you ask: “It’s three months from now, and this failed spectacularly. What happened?”
It’s a root cause analysis before you’ve actually suffered the incident. You’re looking for all the ways things could go wrong before they do.
Let’s discuss via concrete examples.
Example: We Missed the Client Delivery
The first question is how you missed it. Did you miss the date, or did you deliver the wrong thing? These are two completely different problems.
If it’s a date problem, that means you don’t have enough resources or capacity to get the work done. So how do you get that capacity before it becomes the reason you fail?
If you delivered the wrong thing, that means you didn’t understand what your stakeholders actually wanted. Have you asked them — in a way that’s well-defined and, equally important, documented? If what you need to deliver isn’t concrete and written down, now is the time to get concrete. Then build checkpoints along the way to make sure you’re still delivering the right thing. That way, in three months when someone says “You didn’t deliver what we needed,” you can point to six different check-ins where you showed your progress and asked if you were on track. Since nobody said you were off track — and in fact confirmed you were on track — the conversation is very different. Hopefully you don’t even need that conversation because you actually delivered what they wanted.
Example: The Performance Review Surprise
You know you’re going to have to give somebody a low score. Their effort has been poor. They deserve it. But nobody should be surprised by a low score. They shouldn’t get to their end-of-year review — after a good midyear — and be blindsided.
The pre-mortem here is simple: if this person acts shocked in December, what did you fail to do between now and then? The answer is almost always the same. You didn’t have the hard conversations early enough or often enough.
You should be meeting with them every two to four weeks, being direct about where they stand. That way, when they get their review, you can point to six to twelve different conversations where you said “You’re not performing well” and laid out exactly what needed to change. Sometimes people will only hear it if you make it unavoidable. I’ve told people: “This isn’t your end-of-year review, but if I had to give you one right now, I’d give you a low score.” That drives the message home. Even then, some people will claim they didn’t understand, but if you’ve documented it, you have a strong argument.
Example: Burning Hot on Budget
You’ll get close to the finish line and realize you’re running out of money. The number of managers who are surprised by this always surprises me.
Build checkpoints. A quarter of the way through, you should know: have we spent a quarter of the budget? If yes, you’re on track. Have we spent 50% of the budget? You’re burning too hot, and this is going to be a problem.
All of these examples are about the same thing — having checkpoints along the way that show intermediate progress. Not as a CYA, but as a way of actually having time to correct course before you run into the rocks.
The PACE Framework
With the pre-mortem, you work backward and address the top risks before they become problems. It sounds simple. Almost nobody does it. Because it feels pessimistic, and managers are trained to be optimistic.
Be optimistic in your goals, but pessimistic in your planning.
There’s a good action drama on Netflix called Rebel Ridge where the main character talks through PACE planning — a military framework for planning around disrupted communications. More importantly, the acronym makes it easy to remember:
- P = Primary — What is your main plan?
- A = Alternate — What’s a quick pivot if your main plan is blocked?
- C = Contingency — What’s a backup if both Primary and Alternate are offline?
- E = Emergency — What’s your last resort?
This means you’ve thought through four different ways to handle an outcome. Your mind is much more ready to pivot when it’s already explored other options.
If you’ve only thought of your Primary as your only plan, you’re unprepared the moment something goes wrong. This aligns with Eisenhower’s line: “Plans are useless, but planning is indispensable.”
It doesn’t take a lot of time to build these plans. It does take the understanding that you need alternatives and need to think through them ahead of time. When one of these scenarios actually hits, you’ll look like a genius — because you’re able to pivot quickly while your peers are caught flat-footed.
See you next week!
-Frank
