How Overcoming Obstacles in Life Applies to Sales Blog Feature
Steve Bookbinder

By: Steve Bookbinder on March 23rd, 2017

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How Overcoming Obstacles in Life Applies to Sales

Sales Tips | Sales Training

Today’s salespeople must be versatile.

On one hand, you have to be great at classic sales skills like prospecting, verbal and non-verbal communication, as well as time management.

On the other hand, you have to be willing to adjust and reinvent your approach to incorporate new skills and technology. Your own company’s products, services, marketing support and competitive advantages will continue to evolve in order to keep pace with the rapidly changing marketplace.

Everyone is now selling more complex solutions and they are selling across many platforms to a growing number of influencers and decision makers.  And guess what? Your competitors are working hard to beat you and they are targeting your customer’s budget. 

So, this means we have to be innovators and pioneers too, especially when it comes to reaching bigger goals and overcoming obstacles along the way.

That’s why I’m sharing my story about how success in sales is a lot like successfully swimming the English Channel, which is the world’s hardest open water event.

In 2008, I successfully swam the English Channel as part of a 4-man relay. In 2009, I had my next English Channel. This time it was to launch a successful company in the middle of a recession after losing my job. In both the real and metaphorical English Channels, I was determined to succeed, but had an even stronger desire not to fail. 

Selling is filled with English Channel challenges. And it’s a metaphor you can apply to any challenging goal that you don’t want to fail at achieving.

Here are the 3 things I learned about overcoming English Channel challenges and how it applies to sales:

How to overcome obstacles in sales and life

#1 Getting in Shape

As soon as I agreed to join the 4-man relay, I knew I was out of shape but I wasn’t quite sure what type of “in shape” was needed?

What I learned was the importance of crafting the right description of your goals. Anyone can get “in shape” but if you’re going after a specific goal, then you need to be as descriptive and specific as possible.

Lessons applied to sales

Know Your Starting Point

Be honest with yourself by assessing your current position. What are your strengths? What are your weaknesses? Are there risks involved in going after this goal? Or are there more opportunities available? Your starting point will help you determine how to take your next steps.

Commit Yourself to the Goal

When you’re committed to a goal with relentless focus and determination, it makes the inevitable roadblock more bearable. This is because if you hold yourself accountable, then you will take responsibility to think of every possible idea or path to make it to the finish line.

Organize Yourself around a Task

If you’re focused on achieving a big goal by a certain deadline then you have to align and organize your time, your activities, and your resources. If you’re trying to get X number of appointments each week, then you need to ensure you’re organizing yourself around this goal or task.

Develop a Dashboard to Track Progress

If you want to improve, then you have to establish benchmarks. This is so you can compare your current position to your progress along the way. Let’s say you want to improve your customer retention rate, then you need to track how many clients renew at the end of each contract. When you see yourself improve, you are more motivated to keep going.

Leverage the Power of Negative Thinking

Imagine you’ve missed your goal. You’ve failed to successfully cross the Channel. Now what? Well, when those feelings of disappointment creep into your mind, they will trigger ideas and insight. All of a sudden, the things you should have thought of or didn’t know become clear. This is especially helpful when applied to sales because you now know what you would have done differently. But usually it’s too late. So, before a situation like this occurs, consider leveraging your feelings of disappointment to generate ideas about what you “should” have done in advance of missing the goal.

#2 Jumping into Cold Water

The thought of it is worse than it actual is, but fear of the unknown is an element that often stops people in their tracks. When you’re navigating obstacles, you will experience a lot of cold water that you’ll have to dive in head first. But when you prepare and anticipate you’ll be well positioned to face this type of obstacle and overcome it.

Lessons applied to sales

Take Small Steps

Break down your goals into small steps. No matter how unpleasant the thought of doing something may be, if you break down a bigger task into smaller steps, you can think in terms of minutes or days instead of hours or months. Adding one more minute of training, or one more prospecting call to the end of the day, you’ll be one step closer to reaching your goal.

Do Your Research

The more you know, the better off you’ll be. When you do your research and consider the information available, you can interpret and apply what you’ve learned to inform your decisions. In sales, it’s now standard operating procedure to be knowledgeable and prepared prior to every meeting.

Know Your Weaknesses

Mostly everyone would succeed in an ideal setting under perfect conditions. But what matters is how you react under pressure or difficult circumstances. In sales, there are many instances that lead to stress or uncomfortable situations that need to be dealt with professionally and proactively. That’s why you must acknowledge your weaknesses and work towards improvement.

#3 Avoiding Jellyfish

What is your personal kryptonite?  When you fear failure, what does that fear look like? When you brain is yelling: DANGER! How can you stay relaxed enough to recognize the fear while remembering and practicing your new reaction.

Lessons applied to sales:

Reinvent Yourself

When you’re set in your ways and have established patterns or habits, nothing short of shaking things up by trying something new will help you face your personal fears. Everyone has a fear of change, to an extent. But when you’re on a constant mission to break old habits, you begin training yourself to change. This takes time, but once you get started you’ll have renewed energy and enthusiasm for the goal you’re trying to accomplish.

Keep Training

When you’re constantly training and engaged in ongoing development, you become very good at absorbing information and then applying it to your own situation. If you stop learning, just like exercise, your muscles will atrophy. Consider finding yourself a mentor or coach who will advise and guide you on an ongoing basis.


Both life and sales are full of uncertain obstacles and rough waters, but when you have a willingness to learn and reinvent yourself as well as make an effort to prepare, anticipate, and hold yourself accountable you can pioneer your success.

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About Steve Bookbinder

Steve Bookbinder is the CEO and sales expert at DMTraining. He has delivered more than 5,000 workshops and speeches to clients all over the world and has trained, coached, and managed more than 50,000 salespeople and managers. Steve continuously refreshes his training content to reflect his latest first-hand observations of salespeople across industries and regions. Through him, participants in his workshops and coaching sessions learn the best practices of today’s most successful sellers and managers across industries. Steve understands that sales is a competitive game. To outperform competitors and our own personal best results, we need to out-prospect, out-qualify, out-present and out-negotiate everyone else, not merely know how to sell. Through his specialty programs in Pipeline Management, Personal Marketing, Great First Meetings, 2nd-level Questioning, Sales Negotiating, and Sales Coaching, Steve trains sales teams to master the skills they need to overcome the challenges they face in today’s world… and keep improving results year over year.

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