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Dancing with Risk and the Art of Juggling Uncertainties

Updated: Sep 10, 2023

I've got a well-thumbed copy of a book called "Waltzing with Bears" by Timothy Lister and Tom DeMarco, which shaped my approach to risk management many years ago. If you've ever dipped your toes into the turbulent waters of project management or tried to navigate the maze of software development, this book may resonate with you too.


What has always fascinated me is the compelling concept of risk accumulation. Risk, to me, is a layered entity, stacking up in a manner that's as unpredictable as it is inevitable. Imagine that you have one risk with a 5% likelihood of occurrence, another at 5%, and another at 5%. Sounds manageable, right? But here's the rub: it's not a simple addition. This combination doesn't mean you've got a nice, tidy 15% chance of facing a hiccup. Instead, you've got a festering pot of risks where the overall likelihood of something going awry is becoming more of a 'when' than an 'if.' It's a dance with probability, and too many people are ready to roll the dice with key decisions around it.


Imagine for a moment that you're a juggler. Each risk is a flaming torch you're attempting to keep airborne. But here's the kicker: the torches aren't all the same size. Some are mere sparklers compared to others. The real trick to successful juggling and successful project management is recognising which torches demand the most attention.


And this is where "Waltzing with Bears" really hits home. It teaches us to focus on the recurring risks, the ones that don't just spark but threaten to become raging bonfires. Overly optimistic timeframes? That's a bonfire. Quality issues due to rushed QA? That's another one. Underestimation of complexity? You've got it, another big one. And let's not forget the blissfully naive optimism that blankets the start of every project...


However, my key learning over the years has to be the emphasis on avoiding false economy. Trying to do things on the cheap, especially when they're way outside our expertise, is the equivalent of waltzing blindfolded with a bear. My advice? Find someone who's already danced that waltz. Be it a partnering organisation or an experienced leader, they've been there, done it, and have the claw marks to prove it.

As we approach the finale of our dance, let's clear the floor of one major misunderstanding: risk management is not a one-and-done event. It's about more than compiling a risk log, tucking it away in a drawer, and hoping that by some magic, the risks will manage themselves or disappear if they aren't looked at.


Risk management is a living, breathing project element that demands active engagement. It's about constant communication, ensuring stakeholders, and most critically, the top-tier executives, are well-informed about the risks at play. This dance requires a lead, so every risk should have an owner who can guide it, manage it, and see it through its lifecycle.


As we move towards the project's end, it's important to keep our eyes on the changing landscape of risks, regularly reviewing and updating our risk log. After all, a well-managed risk reduces as we approach the project's conclusion (the "glide path", as the book above refers to it). But remember, the earlier we spot a risk, the better our chance of addressing it before it spirals out of control.


Let's make honesty our dance partner here. We must create an environment where raising risks and concerns is encouraged, not stifled. A project team should never be a place where risks are met with passive aggression, dismissal, or accusations of exaggeration. Because let's face it: questioning a risk-raiser's loyalty or team spirit is unfair and detrimental to the project's success.


In conclusion, remember that "Waltzing with Bears" is more than a dance with risk; it's a dance with honesty, responsibility, and proactive management. So, let's keep those feet moving, those risks under control, and most importantly, keep the dialogue open because every dance becomes more fluid with clear, honest communication.

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About the author

Hi, I'm Alan, and have been working within the IT sector for over 30 years.

For the last 15 years, I've focused on IT Governance, Information Security, Projects and Service Management across various styles of organisations and markets.

I hold a degree in Information Systems, ITIL Expert certificate, PRINCE2 Practitioner and CISMP (Information Security Management).

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