Here's the Next Uncomfortable Question to Challenge You
In our previous blog post, we left you with a simple but pointed question:
How confident are you that if you asked each of your key executives to run the same thought experiment independently, they would come up with identical answers to yours? [link to that blog post]
Wouldn't you want to know?
That experiment was about achieving objectives: the vision, the direction, the destination. But there's something else you'll want to know. Something equally important, and considerably more uncomfortable.
What traps are waiting for you on the way there? And how deep, dangerous, and imminent are they?
The Part Nobody Wants to Have…But Everyone Needs
When we guide clients through our execution system implementation, the section where we delve into risks and obstacles is the one that, ironically, generates the most enthusiasm and the most satisfaction. Our clients consistently tell us it's their favourite part of the process.
Ironic, you ask? Yes, and for reasons that will sound familiar:
Nobody enjoys thinking about everything that can go wrong.
A successful business runs on positivity and optimism. Cataloguing roadblocks feels like a negative mindset.
In a team meeting, nobody wants to be seen as the “Debbie (or Danny) Downer”.
And who relishes walking into their boss's office to announce there's a big problem? Pretty much nobody.
So naturally, people don't talk about issues until there's a five-alarm blaze, at which point telling your boss becomes less risky than having them find out you didn't. By then, of course, the damage may already be well underway.
A Current and Very Real Example
Consider what's sitting on the table for companies on both sides of the Canada-U.S. border right now. The "America First" and "Buy Canadian" movements, buttressed by tariffs, are forcing some genuinely difficult strategic questions.
Do you move production across the border to stay competitive in that market? It sounds logical. But what if you invest millions to do it — and then everything reverses over the next six to twenty-four months?
Plus, while you were repositioning, a competitor quietly sailed in on the winds of the new trade corridors opening with Europe and the rest of the world. They set up one efficient operation, establish economies of scale from a single location, and when the cross-border disputes start to ebb, they have a structural cost advantage you can't easily close.
These are not hypothetical concerns. They are live, high-stakes decisions that belong in a frank risk conversation at your leadership table, and not in a series of private worries that never get named out loud.
What Happened When Our Client Got the Ghosts Out of the Attic
One of our clients, Avasta, was a well-funded financial services startup with ambitious growth plans. The senior team was excited. However, there was also an undercurrent of trepidation that nobody was quite naming.
When we guided them through the risk and obstacle section of our process, a lot came out. Because each executive sees the business from their own unique vantage point, they each perceived risks and issues that others hadn't fully seen. Or they weighted them very differently. Working through it together got all the ghosts out of the attic. And together, they were able to realistically size them up, and more importantly, prepare for them.
For the CEO, the experience was, in their own words, hugely impactful. They discovered roadblocks they hadn't considered, and re-calibrated their assessment of others they thought they understood. It was one of the sections of our process that generated the most positive feedback we've ever received.
There's something deeply relieving about naming the things everyone was privately worried about, and finding out the team can handle them together.
Your Next Thought Experiment
The first thought experiment was about where you're going; this one is about what's in the way.
Same format as before. Three executives, independent answers.
Start with your COO. What are the biggest risks and issues keeping them up at night right now in their area of the business? Write down what you think they'd say.
Do the same for your CFO.
Then pick one more executive of your choosing and run the same exercise.
Now the familiar question, but with a new edge to it: if you asked each of them independently, would their answers match yours? And here's the scarier follow-up question —
What are they actually doing about those roadblocks right now?
We'll expand on that in the next post.