Can Bold Business Moves Pay Off?
When your company isn’t making the progress you expect toward your ambitions, it’s tempting to consider a bold move. Can such bold business moves pay off?

Written By: BOSS Editorial
Reading Time: 5 minutes

When your company isn’t making the progress you expect toward your ambitions, it’s tempting to consider a bold move.
This might be exploring completely new markets or changing your brand identity. Whatever the focus is, it can be a daunting prospect. Can such bold business moves pay off? Well, yes, they can. But as with so much in business, your success isn’t guaranteed. Let’s explore some of the various factors, practices, and attitudes that can impact the process.
The Boldness Mindset
Making bold moves doesn’t come naturally to everyone. This is often the case when you own your business. After all, you’ve dedicated a huge amount of time and resources to getting it to where it is now. A risk-averse attitude can feel more natural.
So, what goes into the type of boldness mindset that enables entrepreneurs to take big steps forward?
- A sense of where your company is: One of the common attributes of bold move-takers is that they have an innate sense of whether it’s time to initiate risky steps. This tends to come from having a deep connection with your company and its journey. It enables you to recognize when things are becoming stale, if you’ve achieved everything you can with your current practices, and if change is right for the company and its stakeholders.
- Boldness without being callous: There’s a misconception that the best business leaders have a callous attitude to business decisions. This is certainly something the public has been sold by people such as Elon Musk. This isn’t quite the reality, though. Being callous is not required or even preferable for making bold moves that pay off. Risk is a part of business but there’s a responsibility to pair boldness with caution.
Just like any new skill, these are traits you may need to work on. Changes in mindset are often prompted by changes in behavior; the “fake it till you make it” approach. Acting in ways that appear bold can start to develop a genuine mindset over time.
Making Informed Decisions
Making bold business moves that pay off isn’t about storming into the situation with no knowledge of the potential consequences. Boldness isn’t recklessness. Instead, it’s about pushing forward to try something different with your business based on informed and balanced reasoning. There’s still risk, you’re still stepping out of your comfort zone, but it’s tempered by pragmatism.
So, what does this involve? Well, you need to be a little courageous, assess the circumstances, and apply some strategy. In this way, bold business leaders can be similar to experienced card players. Card players read competitors to get a better understanding of the moves opponents are likely to make. As a bold entrepreneur, being observant of consumer, market, and competitor behavior can help you be a better predictor of needs and where you can best direct your bold behavior.
So, how can you best gain information on the risks before moving boldly forward?
- Analyze the potential risks and benefits: Get a good understanding of what the worst-case scenario is should your bold move not pay off. What does it cost your company financially and reputationally? Be realistic about what the potential payoffs are, too. How have similar projects benefited others in your sector?
- Perform a risk versus reward calculation: This involves dividing your predicted profit from your actions by the maximum potential cost if you fail. Consider whether the resulting ratio represents the level of risk to reward you think is acceptable for your company.
Some moves — such as cultural changes — may not have solid quantitative data available. You should still seek to get qualitative data to help inform your choices. The point is to gather information that empowers you to calibrate the balance between boldness and caution before acting.
Gaining Stakeholder Buy-In
Unless you’re a sole operator, you’re not the only person your bold moves will impact. Even if you’re the primary decision-maker in your business, it’s not wise to push ahead without the approval or understanding of most of your stakeholders. These might be investors whose capital you’re gambling with. It could include employees whose jobs might be at stake and who are expected to implement the changes. The more buy-in you get, the more positive your change process is likely to be and the greater confidence you’ll probably have in your choices.
What can help here?
- Use visuals: Simply talking to your stakeholders about the changes you want to make and the risks involved isn’t always effective. Using visual tools to create and demonstrate the strategy for your changes can make things clearer for everyone. For instance, RAID (risks, assumptions, issues, and dependencies) logs are a simplified way to help stakeholders see the potential problems and influencers of success in your plan. Product roadmaps can communicate the key steps in the project and the timeline they need to be completed on. In essence, you’re making your data supporting and driving your bold moves more consumable.
- Explain your risk management approach: Each stakeholder will likely have concerns about the risks you’re taking. Don’t just explain how you’ve assessed the potential for risk and why you’re proceeding anyway. Show them what solid risk mitigation measures you’re putting in place. Demonstrate that you’re not recklessly playing with their well-being.
Remember that buy-in isn’t just an agreement. In the best scenarios, you want active participation in change. Therefore, invite stakeholders to provide suggestions related to your bold moves to give them greater ownership of the project. Besides, their perspectives might highlight potential issues or solutions you hadn’t considered.
Conclusion
Bold business moves can pay off, but it’s important to find a balance between caution and courage. This comes from your mindset, your strategic approach to the hazards, and your interactions with stakeholders. In the end, though, the final decision is likely to be yours. Sometimes the best you can do is give yourself the tools to gain the confidence to move in the most positive direction.
By Indiana Lee, BOSS contributor
