Advice on Struggling with Making Sales?

Hi, I am very frustrated because I have not hit my quota in over a year. I am working extremely hard, but the numbers don’t show it. I have the worst numbers of all the sales reps at our company, but I can’t figure out why this is happening and why it has been happening for so long. I am a pretty positive person and have been trying to keep a good mindset about it, but I am afraid of losing my job. Everyone at my work likes me, including my boss, and my boss just keeps telling me to keep at it and that I’m doing the right things. Has anyone been through something similar in their sales career? Do you think I should leave sales completely? Thanks in advance.

Before you decide to completely switch careers, I suggest you take steps to reexamine the sales process and how you are going about it. I also suggest asking questions like “is your product of good quality?”, and “are you selling something in high demand i.e. what is the market like surrounding your product?”. I suggest doing this because it simply might be the case that you should switch the industry you are selling in, maybe to software or something with high returns and relative ease to sell. However, if you are already in a high profit industry where it is clear other sales reps are making money, then I suggest you examine your sales technique down to the basics. Tom Hopkins “How to Master the Art of Selling” places heavy focus on the 5 basics to being a great sales person. Next, you need to examine what you are focusing on during your sales pitch, is it your product or the customer?. If you said the former, you’ve already got the wrong idea. The game of sales has changed drastically thanks to buyers having more and more access to information, so the old idea of talking up your product is gone because they probably already know the gist of its features. So, now you have to focus on the customer and their pain points, what’s keeping them up at night. Maybe something is costing them money and time. Focus on what’s causing them pain and then slowly moving toward how your product can solve that. This method makes you seem genuine in your desire to simply help the customer rather than sell your product. Another good strategy is to try and catch customers when they realize they have a problem but have yet to start looking for solutions. Good books to reference for more info on how to do this are SPIN Selling by Neil Rackham and Shift! by Craig Elias. The former focuses on discovering the customers’ pain to sell, while the latter focuses on timing and trying to leverage what stage of the buying cycle the customer is in. Good luck!

Take a deep breath, and remember why you got into sales in the first place. If that motivation is still there, then continue on! Sales is full of rejection and failure, but the only way these things can hurt you is if you let them (by not learning from them). If you aren’t already, I suggest keeping a record of your successes and failures, how each of them happened, and where you could’ve done something different that might have resulted in a better outcome (even for the deals you close, because there is always room for improvement). Keeping this record will shine light on overarching struggles you’re having and reveal patterns that may not be allowing you to hit your quota.


Both LordByron and Samantha gave you great advice. Remember the number one quality in a good sales person is persistence and it sounds like you haven’t given up. I’m in my early 50’s and having the best success in my career within the last couple of years. I had to change my work habits and how I talked to younger customers. Here are a couple of points that work for me:

  1. If you want to be the number one guy, work like the number one guy. My personal goal was 1 million in sales per month, so I starting working like I did a million per month and it’s paid off.
  2. Identify your resistance. Once you confront whatever keeps you from doing your job will make you overcome anything (I’m not suggesting you’re not doing your job). This helped me a lot.
  3. Customer Service- let your prospects know you will take care of everything they need. Be responsive and proactive. The best customer service always wins.
  4. Treat everyone the way you want to be treated. If someone turns you down, send a thank you note for at least talking to you. After meeting someone for the first time, send a hand written note. Ask them questions about them before you pitch anything.
  5. Everything positive you do will pay off.

You will be ok.

How long have you worked there? If you’re selling anything beyond your cost to the company, the manager will keep you. What do you sell and do you feel a sense of fulfillment? Do you feel a purpose and meaning on your job? These questions begin the conversation.

Remember you’re unique. We all have our own ways of doing things. My way may not be yours. But we can explore the link that gives you career contentment with your career.

Thank you all so much for all of your encouraging words and advice. This helps me so much and I really appreciate it. I really like sales, and definitely wouldn’t want to leave unless I had to, but I’m determined to give it more of a shot and use these tips to try different approaches. I am pretty young, and to answer your question @AntonArtaud, I have been working in sales for 5 years. @JobSiteSafety It is very inspiring that you have gone through something similar and that you are so successful now later in your career. The 5 things you listed are great. I think you are all right in that I need to be more patient and trust the process. Thank you all for taking the time to reply to my post and offer your advice!