Coaching Skills: Ask a Few Questions Before You Speak… and Your Style Really Matters

By David Szen on Jul 14, 2014

4 Minute Estimated Read Time

The role of a sales leader/coach, regardless of industry, is not an easy one. The sales leader/coach is living day in and day out with the skills and abilities of the team they are putting on the field. Depending upon a ton of variables, the experience a sales rep gets from coaching may be wildly different from coach to coach. Let’s face a few facts right up front:

  • The sales leader has a great deal of responsibilities and limited time
  • Some sales leaders may never have been taught anything formal about coaching style
  • In the heat of the moment, a sales leader may rely upon instinct
  • Sales reps vary widely and come in all varieties of skill sets, to say the least
  • Some days it is just easier to tell people what to do
  • Style and the “softer touch” take time and discipline
  • You will get farther with sugar than you will with salt – but sometimes using sugar is painful for the coach when it would just be easier to thrown some salt.  HUH?

Now that you may be totally lost let me translate a bit. I get to coach sales leaders from a few different industries, and one of the consistent challenges that I hear is this one: “I feel like I have to watch my tone of voice, over-engineer e-mail, and walk on egg shells when I coach these people.”  Let’s first look at the source of the issue from both sides of the coin.


The leader: They have a job to do. That job is clearly outlined in most sales organizations. It is to get results, hit budgets, drive sales, grow the client base, drive revenue from strategic clients, retain talent, hire talent, and last but not least – develop talent. More on that in a moment.


The sales rep: They also have a job to do. That job is also clearly outlined in any sales organization. It is to win clients, prospect, drive customer relationships, sell the right mix of business, make presentations, communicate, landscape the decision process, research, be prepared, plan a territory, overcome customer objections/obstacles, manage the sales process, and hit the sales targets! All of this while being willing to be “coached.”


Try not to take a side on which role is harder. It is not the point. Here is the point – Sales reps are PEOPLE!  People would rather be engaged and developed in a positive and uplifting manner than a cold and abrupt manner. Sorry – this is the truth! This does not mean that you have to send flowers and gifts and have conversations that feel like Mr. Brady talking to one his six kids from the Brady Bunch.


It does mean these simple concepts:

  • Ask at least three good questions before you tell them what to do
  • Do not forget the small stuff when communicating – regardless of how busy you are

Asking Questions

I know, this will sound incredibly basic, but asking questions is fundamental to developing sales talent. Try to ask three good questions before you suggest any direction to the sales rep. Why?  Because it helps you to assess what their logic was and how they got to where they are right now. This is critical. Let me show some examples of typical things a sales leader would be coaching and what types of questions to ask in order to provide better direction. 


Rep has a sales funnel that is very weak

Questions to ask:

  • Tell me about your sales plan for the coming week.
  • Which of your target companies seem to hold the most promise?
  • Talk to me about your overall sales goals for the quarter.
  • How much opportunity do you feel needs to be in the mix in order for you to hit your goals?
  • What things, if any, are in your way that I can help you with right now?

Sales rep has a difficult time closing deals that are in late stages of the sales process

Questions to ask:

  • Talk to me about the types of questions you like to ask in order to advance the deal.
  • What are the final objections/stalls/obstacles you get the most often?
  • Talk to me about the level of decision makers you have engaged at ________ deal.
  • What other competitors have been identified in these deals you are pursuing?
  • In what ways would you describe us as different/same/better than our competition?
  • What value do you feel the buyer has placed in making this decision or working with us?
  • How do you feel we can advance the process?

The science of this approach is to truly understand what your rep is doing and thinking as it relates to both of these issues. You can’t help them until you know what they are thinking, what they know, and what they are doing. What stops many a great sales leader from asking these questions? Put simply, time. My advice is to step back from the problem and think about 3-5 questions to ask that will help you to better uncover how to help.


The small stuff is not small… IT IS HUGE! 

Ok, brace yourself for this one. People like to feel as though they have been treated fairly and respected along the way. These are all adults – quantified as over 21 and in the professional workforce. Here are the things we should all consider as the small stuff that is HUGE.


Tone of voice and delivery of your questions

Look at this question again please. Tell me about your sales plan for the coming week.”  This question, if asked wrong, can blow up in your face. You could kill it all together by changing a couple words and not using an open and non-intrusive tone. For example – “What exactly is your sales plan for this week?” Say that out loud in the wrong tone right now and listen to how bad it sounds.


Common courtesy

Some people call this “the softer touch,” and I can tell you this for sure – it matters! These are things like: “How was your weekend?” “I have a couple of things I’d like to chat about, please.” “Let’s grab a cup of coffee and talk about the upcoming quarter.” “I am flexible to schedule our time when it fits you tomorrow.”  And then the big ones – PLEASE and THANK YOU.


Body Language

People read and understand your messages primarily through body language during conversations. Here are the dealmakers:

  • Making eye contact
  • Taking a few brief notes while they are talking shows interest
  • Having a relaxed posture, but not too informal
  • Being focused on them – not your phone, e-mail and other things

E-mail Tone and Friendliness

I know… How can your e-mail have a tone? It does, and certain types of people sit there, stare at the screen, and can’t even fathom that someone has typed these words to them. If your style includes using few words that get right to the point, recipients will perceive it as cutting and demanding. Sorry, these are the cold facts. Whether it is through e-mail or text, it’s all the same, and they do read between the lines.

Include things like:

  • “Hope you are well today…”
  • “When you can call me, please do. I would like to get caught-up on ________ “
  • “I know you are really busy today. This report requires attention, and I need some information from you. Please take a few moments later in the day and call me if you want to chat about it. Thank you.”
  • “Thanks for all of the hard work. Let’s get together Monday and talk about the next quarter. I am sure you have it under control but would like to plan with you.”

In summary, take the time to ask more questions and do sweat the small stuff, regardless of how busy you are.

David Szen

Written by David Szen

David Szen is a contributing author for Symmetrics Group and a sales effectiveness expert. Having delivered numerous sales and leadership training programs for companies across industries, David understands the nuances that can impact sales team performance. David explored generational impacts on sales team effectiveness and co-authored the book The Multigenerational Sales Team with Symmetrics Group's founder Warren Shiver.

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