Proper Planning Prevents P*ss Poor Performance… Except When It Doesn’t

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We all love a good plan. You set the date, book the tickets, get everything lined up – and then, life happens.

Twice in the last six months, I’ve been caught in the ripple effects of poor planning and unforeseen delays. First, we were supposed to watch a rugby game at the stadium, but it was cancelled because the Cape Town Country Festival was scheduled for the same weekend. The organizers had simply not factored that in. We still went to the festival – it was a blast, though not well attended – but the rugby match got pushed to February.

When the rescheduled game finally arrived, we went. And what a nightmare that turned out to be. Traffic was chaotic because, on the same day, there was also a school athletics derby at the adjacent Green Point Stadium. Clearly, no one had stepped back to think about the second- and third-order consequences of shifting the match date.

This reminded me of the Springboks Lions Tour during the 2021 season when COVID threw their entire preparation into chaos. The team had planned for the big games, but delays and disruptions in training meant they weren’t quite ready when the big moments arrived. We all saw how that turned out, and we only won out the day because of some extreme and controversial messaging tactics from the then-director of rugby Rassie Erasmus.

The lesson? Things are going to go wrong. And when game day finally comes, you’re going to have to deal with the consequences.

This is where Stephen Covey’s Urgent vs. Important Matrix becomes invaluable. If you’re only focusing on what’s urgent, you miss the important long-term planning that prevents disasters down the line.

AI Prompt: How can I use the Urgent vs. Important Matrix to anticipate delays in my current projects so they don’t derail future plans?

A few weeks ago, I was cycling in the Paarl region during a retreat at Vrede en Lust. I set off early in the morning, looking forward to a great ride – only to find myself stuck in heavy traffic, with no shoulder and roadworks. Everywhere.

Every single main route from where we were staying had road construction. How could the planners not have anticipated this? It was baffling.

Then I found out what had actually happened:

The first roadworks project had been delayed due to a community objection.
The second roadworks project went ahead as planned but then experienced some unforeseen delays during the process.
And the third project, which was supposed to start after everything else was done, was on track… but could have done with some second-guessing, as it made the overall situation worse.

Suddenly, a phased plan turned into a total mess.

The good news? In a year’s time, the roads are going to be brilliant. The bad news? Right now, that area is a dog show for any road cyclist.

This is exactly what happens in business when we don’t plan for delays and unintended consequences. If you don’t factor in what could go wrong, you end up stacking problems on top of each other—until you have a bottleneck that grinds everything to a halt.

This is why quarterly planning sessions should include scenario planning. It’s not just about setting goals – it’s about thinking through:

What happens if a critical project gets delayed?
How will that impact other projects down the line?
What contingencies do we need in place?

💡Implementation Prompt: How can I structure a quarterly planning session to factor in unexpected consequences and ensure we don’t create bottlenecks?

The rugby rescheduling, the traffic chaos, the roadworks disaster – it all ties back to one key question:

What is the bigger picture?

Too often, organizations and teams get caught in the short-term execution cycle and don’t take the time to step back and ask:

What are we actually building?
Why does this matter beyond just hitting deadlines?
What’s the long-term vision we’re working toward?

For the roadworks example, the ultimate purpose is better infrastructure – but because no one accounted for the delays and the unintended compounding issues, the short-term experience is frustration, inefficiency, and a lack of usability.

In business, this happens all the time. We get so focused on hitting immediate targets that we forget to ask:

Are we actually moving toward something meaningful?

💡Prompt: What questions should I ask to uncover my company’s higher purpose so I don’t get lost in short-term firefighting?

PG’s PRO TIP

If you want to avoid self-inflicted chaos in your business, you need to foster a culture that anticipates second- and third-order consequences.

Here’s how:

✅ Encourage long-term thinking – Don’t just focus on immediate goals. Teach your team to think beyond the next quarter.

✅ Stress-test your plans – Ask: What happens if this gets delayed? What are the ripple effects?

✅ Develop a habit of scenario planning – Look at both best-case and worst-case outcomes before committing to major projects.

✅ Embrace agility – Plan for change rather than reacting to it in the moment.

✅ Use the Urgent vs. Important Matrix – Make time for strategic planning so you don’t get trapped in a cycle of constant firefighting.

💡Prompt: What are the best tactics for fostering a culture of innovation and long-term thinking in my business?

Because when you anticipate the unexpected, you don’t just survive the chaos – you position yourself to win in the long run.

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Proper Planning Prevents P*ss Poor Performance… Except When It Doesn’t

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