Why Playing It Safe Is the Fastest Way to Lose in Sales: The Top 5 Risks Every Salesperson Should Consider Taking
In sales, success often favors the bold. The best salespeople know that calculated risks can lead to breakthrough results, stronger client relationships, and real career growth. Playing it safe might feel comfortable, but it often leads to missed opportunities. The top performers in this field understand that taking the right risks can unlock growth, higher commissions, and long-term success.
Here are five meaningful risks that can elevate your sales career:
1. Pursuing Bigger, More Complex Deals
It’s easy to focus on smaller, faster wins, but the most valuable deals often come with more decision makers, longer sales cycles, and higher stakes.
These deals may seem intimidating, but they offer bigger rewards, stronger partnerships, and the chance to build your reputation at a higher level.
*The risk: You might lose.
* The reward: You could land a deal that defines your year or your career.
2. Being Authentically Honest
Telling prospects the full truth, even when it’s uncomfortable, can feel like you’re risking the sale. But real honesty earns long-term trust and repeat business. This means admitting when your solution isn’t the perfect fit or when a competitor may offer something better in a specific area.
*The risk: You may lose a deal in the short term.
*The reward: You build credibility that leads to future deals and loyal customers.
3. Walking Away from the Wrong Clients
Not every opportunity is worth pursuing. Some clients drain your time, strain your resources, and prevent you from focusing on better opportunities.
Learning to recognize when a prospect is not a good fit, and walking away, is one of the most valuable skills in sales.
*The risk: Immediate revenue loss.
*The reward: Protecting your time, energy, and reputation while creating space for better clients.
4. Challenging the Status Quo
Many clients get stuck in what’s comfortable. Proposing a new solution or suggesting a different way to solve a problem can feel risky, but this is where you move from salesperson to trusted advisor. Bringing creative, bold ideas can open new doors and deepen relationships.
*The risk: Resistance or initial pushback.
*The reward: Becoming a valuable, long-term partner rather than just another vendor.
5. Investing in Yourself
Top salespeople actively invest in their own growth. This might mean seeking out advanced sales training, attending conferences, learning new technology, or developing leadership skills.
Waiting for someone else to develop you is a bigger risk than stepping up and doing it yourself.
*The risk: Personal time, effort, and sometimes financial investment.
*The reward: Long-term career success, higher earning potential, and lasting expertise.
The biggest risk in sales is standing still. Smart, calculated risks are often the difference between an average career and an exceptional one. If you are looking to grow with a company that encourages bold moves, let’s connect and explore your next opportunity.
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