3 Ways to Jump-Start Your Sales Career


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I recently moderated a fascinating panel discussion at a sales conference. The panelists were all successful business professionals. One set strategy and vision for a $2 billion IT company; two were serial entrepreneurs, one of whom just sold his company for millions; the last was a CIO at a multinational company. What they said will provide you with valuable insights on how to become a better sales professional.

How do you deal with risk?

The first question I asked was how they made decisions and assumed risk. One panelist took the microphone and said very emphatically, “Very early on I realized I need to have risk. I can’t work in an environment which is risk free.” He was the one of the serial entrepreneurs who had never worked for anyone else. He had always been an entrepreneur.

Would you prefer to take on more risk? Perhaps you already do and are a commissioned salesperson. The amount of risk you can tolerate will determine how you get paid as a salesperson. Just be sure your family supports your view of risk. I’ve seen marriages end when a spouse couldn’t handle the same level of risk.

What size company fits you and your temperament?

Next I asked the panel to describe their first job and how they selected it. One of the panelists said he started out at a large company. He then realized he didn’t like being part of a large organization, and all his subsequent jobs were at smaller and smaller organizations.

You may find it odd and indicative of a career going in reverse. He didn’t. He wanted to try new things, control what he did, and he wasn’t concerned whether he was successful or not. He couldn’t get those opportunities at large organizations where so many people were involved. At smaller companies he would be forced to do a variety of work and make decisions simply because there weren’t other people there to do the work.

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What about your approach to sales? Do you like having autonomy to determine which products you sell? Or do you like having other people determine a global sales strategy of whom you should sell to and how much you should charge? Which of these scenarios makes you happy and which one makes you very unhappy?

Different-sized organizations delegate different levels of authority to their sales teams. You might be better suited to another organization depending on how you answered these questions.

Where’s your planned career trajectory?

I then asked everyone to discuss something in their career that led to their success. One of the panelists said, “I created a career plan when I first started. The first page was where I currently was at the time; page 20 was where I wanted to be over the course of my career. In between I had a document that I modified over the years and used to guide me to make my career decisions.”



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