Every organization reaches pivotal moments—those times when staying the same might lead to stagnation, while making a change feels risky and uncertain. Pivoting is never easy, and it’s no surprise that organizations often struggle with it. Over the years, I’ve seen these challenges show up consistently in three key areas: people, products, and technology.
Here’s how I approach each of these areas and why I believe tackling them head-on is essential for growth.
The People Problem: Acting Decisively – One of the hardest pivots to make is when it involves people. As a leader, I’ve learned that these decisions often take longer than they should because they’re so personal. You’re not just dealing with performance metrics—you’re dealing with real people, their livelihoods, and the relationships they’ve built within the organization. But here’s the reality: the longer you avoid addressing an issue, the more it affects the entire team.
Over the years, I’ve embraced a simple yet powerful philosophy: hire slow and fire fast.
When it comes to hiring, I believe in being deliberate and thoughtful. It’s about more than just filling a role—it’s about finding someone who aligns with the organization’s culture and values. That means taking the time to thoroughly vet candidates, ask the right questions, and dig deep during reference checks. A rushed hire often leads to long-term headaches.
But even with the best hiring practices, sometimes it just doesn’t work out. When that happens, acting quickly is critical. Holding on to someone who isn’t a fit doesn’t just hinder their growth—it holds back the entire team. I’ve seen firsthand how a single misaligned team member can drain morale and productivity.
It’s never easy to let someone go, but doing so with clarity and compassion is vital. When you address the issue promptly, you protect the health of the team and keep the organization moving forward.
Let’s also not forget, sometimes the pivot might need to come from you. If you find that you’re no longer aligned with your organization, it’s okay to make the choice to move on. Recognizing when it’s time to pivot in your own career is just as important—it can open the door to new opportunities, better alignment, and greater fulfillment.
Products: Letting Go to Move Forward – Letting go of a product is one of the toughest decisions any organization can face. I’ve been in the room when these conversations happen, and they’re almost always dominated by the same thought: We’ve already invested so much. It’s human nature to want to hold on, but that kind of thinking can keep you stuck.
I’ve learned to approach this with a different mindset. The focus shouldn’t be on what’s already been spent—it should be on whether continuing makes sense for the future. Is the product solving a real problem? Are customers embracing it? Sometimes, despite all the effort and resources poured in, the answer is no. And that’s okay. What’s not okay is continuing to push forward out of fear of failure.
Pivoting in this area doesn’t mean giving up on innovation. It means redirecting your energy and resources toward something that aligns better with your market and goals. It’s about having the courage to admit when something isn’t working and the clarity to move on.
Technology: Making It Work for You – Technology is supposed to make your organization better—faster, more efficient, more effective. But I’ve seen how easy it is for companies to end up in a situation where they feel like they’re working for the technology instead of the other way around.
I approach technology decisions with a simple framework: it needs to work for us, not against us. If a system is causing more headaches than it solves—if it requires constant workarounds, endless resources, or a dedicated team just to keep it running—it’s time to pivot.
Switching technology can feel overwhelming. I get that. There’s data migration, training, and implementation to think about. But I’ve found that the pain of staying with a system that doesn’t serve your needs is far greater. I’ve learned to prioritize tools that genuinely make us better, even if the transition feels daunting at first.
The key is to look ahead. Don’t be afraid to let go of something just because it’s familiar. If a better solution exists—one that can help your team do their best work—it’s worth the investment.
So, Is it Time to Pivot? Pivoting is tough. It requires honesty, courage, and a willingness to step away from what’s comfortable. Whether it’s addressing people challenges, letting go of a product that isn’t working, or upgrading technology, the question to ask yourself is this:
Is this helping us thrive, or is it holding us back?
As a leader, I’ve learned that thriving organizations don’t fear change—they embrace it. The decision to pivot isn’t easy, but it’s essential for growth.
See you next week,
Brent, your Rivr Guide
