Powerful words.
This week, while traveling, I encountered a Waymo self-driving car. Less than five minutes later, I saw an autonomous delivery service robot out for a delivery (pictured).
A few minutes later, I saw another self-driving car.
I walked by someone talking on their Apple Watch.
I rode a Peloton in the hotel fitness center.
I used a tablet in my room to order room service.
As I reflected on these technologies, I realized that most of them either didn’t exist or were still in development in recent memory.
Somewhere along the way, an innovative person inside an organization had a “what if we…” mindset.
None of these things would have been invented if someone hadn’t worked in a business environment that valued innovation and new thinking.
It reminded me how important it is for leaders and organizations to identify people who push the envelope – and then encourage them to take the time to think about what could be.
You can also look around and see businesses that once dominated their industries but no longer exist because, instead of imagining what could be, they rested on their laurels and focused on past successes.
Few things are more damaging to an organization’s long-term success than remaining anchored in the past.
Here are a few examples:
- Blockbuster – Dismissed streaming and online rentals while Netflix leaned in.
- Kodak – Invented the digital camera but failed to embrace it for fear of hurting film sales.
- Borders – Passed on e-commerce while Amazon redefined how people buy books.
- BlackBerry – Ignored the shift to touchscreens and app ecosystems.
- Sears – Failed to modernize operations and customer experience despite massive brand recognition.
In my industry, professional speaking at conferences and events – I’ve often noticed that my association clients have a tendency to repeat their meeting format year after year.
Sometimes the schedules are nearly identical: two and a half days, two keynote speakers, 30 breakout sessions, followed by an awards banquet or dance.
Very few really push the envelope.
While this may work well for some, it raises an important question: Could one reason attendance is declining – particularly among younger professionals – be that they are yearning for a “what if we…” mindset?
My friend Russ Webb, CAE, CEO of the Bay Area Apartment Association, put it this way:
“Time poverty is real, and associations are competing for our members’ time more now than ever. There has to be ROTI-Return on Time Investment. Gen Z and Gen Alpha are looking for experiences, and copy-and-paste programming won’t get it. Mixing it up gets attention and engagement.”
Russ also suggested identifying a “sacred cow” event that continues out of tradition – even though it struggles – and replacing it with something bold and fresh. He shared that they rarely repeat the same event, and if they do, it’s never exactly the same.
“We did an Amazing Race last year and they loved it. They’ve been asking when it’s coming back. We’ve done field days, walking tours of member sites, meetups at the zoo, and more. It’s about creating FOMO.”
The reality is this: failing to change is a sure-fire way to join the list of defunct companies above.
Here are some ideas to consider:
- Encourage innovation and intentional thinking pauses within your organization.
- Reward new ideas-even if they aren’t immediately implemented.
- Ensure your board or advisory committees include people who challenge the status quo.
- Create your own advisory board – or what I call a Circle of Six (which I’ve written about before).
- Build a culture where people feel empowered to ask, “What if we…”
Innovation doesn’t happen accidentally. It happens when leaders create space to think differently.
The organizations that will thrive in the next decade won’t simply work harder – they will pause strategically. They will question assumptions. They will challenge sacred cows. They will empower someone in the room to say, “What if we…”
The question is simple:
Will you be the organization that disrupts – or the one that gets disrupted?

