Coaching the Self Doubter

Meet Joe.


Jow is a successful district sales manager who could work in any industry and for any company. In fact, there are many Joe’s in all companies. Each month Joe is put to the test with different sales reps he must coach to success. 


Joe has decided to start the year by building development plans with each of his reps. Joe is a strong believer that his role as a district sales manager is to help each rep develop their skills as well as ensure that the district achieve their sales numbers. With the economic down turn, the market place is becoming increasingly more competitive. Baltic senior sales management feels that new business will help them a reduction in business from existing clients. The company has had good growth over the last 5 years but there is an overall sense that the sales force is composed of many gathers and there is a need for more hunters. 

In our follow up coaching session Joe singled out a rep he felt was his biggest challenge. In Joe’s own words:

Tom has been with Baltic for 10 years. He has been through the company selling course and has also taken the CPSA Professional Selling course. He is the district “go to” person in terms of his product knowledge. He has been an above average performer with lots of potential. Tom’s success has been built on his existing customer relationships.


Joe has been Tom’s manager for the last 2 years. Tom is a hard worker; “every time I go out with him we have a full and busy day”. Tom has an excellent understanding of his products, his customers like him and appreciate his technical ability. Not only does he doubt his value, Tom constantly apologies to customers and rarely asks for the business.”

Every time Joe provides feedback it is taken negatively and Tom becomes very defensive.


  1. How can Joe coach Tom and help him develop into a STAR?
  2. What is the best approach to help a Self Doubter become a better sales rep?

Here are my thoughts …..

Dear Joe,

Reps who are Self Doubters can be challenging to coach. If you provide direct feedback it may be met with “I already do that” or reasons why they don’t. The Self Doubter perceives any critiquing as weakness and personalizes it as confirmation that they are doing a horrible job! The trick with this type of individual is to lead them through a process of self-discovery and improvement.

Here’s how:

  1. You need to ask a series of questions (listed below), 
  2. Guide Tom to write out his own course of self-discovery and improvement.

Ask Tom:

  1. What are the key elements critical for effective closing? Write out a list.
  2. Which elements of closing do you excel at? Write in order.
  3. Are there opportunities for growth? Write them down.
  4. Which of the elements would he like to work on?
  5. What is in it for you to grow your competencies in these particular elements? Have him write those down.
  6. What are you committed to doing? All commitments should be written down.
  7. When should I follow up with you? Put a follow-up date at the bottom of the paper. Sign it.
  8. Congratulations now you have buy-in from Tom and a high level of commitment.

Let me know how it goes,


Steven Rosen, MBA

Sales Executive Coach