8 Questions Every Sales Coach Should Ask

“Coaches who can outline plays on a blackboard are a dime-a-dozen. The coaches who win are the ones who can motivate their players.” – Vince Lombardi 

Sales coaching – as opposed to the directing favored in traditional sales management – works by bringing out the best in sales reps and motivating them to realize their full potential. Sales coaching emphasizes an optimistically constructive worldview, solutions instead of problems, the accountability of ownership and a holistic approach that focuses on the whole person instead of just their behaviors or performances. The best sales managers serve as guides and mentors, but not hand-holders. This distinction is crucial as managers realize the benefits of switching gears from direction-style conversations to more natural, coaching-focused discussions.

This is why the questions that a sales manager asks a rep during a coaching session are critical in setting the right mentoring and motivational tone. Deciphering the best questions to ask also benefits the coach – by using the right questions over and over again, conversations and coaching sessions will become more natural, be better-received by reps and be more valuable to the company overall. Here are 8 coaching questions that every sales manager should ask in any context.

What are you trying to achieve here / what would it mean to if you could achieve this?

Motivated people work best when they have goals to strive toward. Asking this question at the onset of any session frames the motivation for the individual rep. Additionally, asking what such an achievement would mean to them helps reps visualize the reward or end-result, which can be a powerful motivating tool.

What are your short-term and daily activity goals?

Long-term visions are just unrealistic and unattainable fantasies unless there are demonstrated short-term steps undertaken to reach that final goal. Convey to your reps the importance of setting short-term daily goals by espousing the rewarding nature of being able to regularly check important items off your list. Most importantly, give reps a way in which to track their daily activities and short-term goals so that they always feel this sense of accomplishment – or know where they need to pick up the slack.

What exactly is going on in this situation?

Try and coax as many specific details out of the rep as possible. It will be easier for both parties to discuss meaningful progress if they can figure out exactly where they’re starting from in the first place. Additionally, getting reps to break out of their shell will foster a more collaborative working relationship, which is ultimately a great byproduct of coaching.

Why do you think this is happening?

Why questions can come off as initially accusatory – putting you in the position of a manger demanding an answer – but they make good follow-ups. Asking a rep why something is happening empowers them to diagnose the problem on their own, which is a great step toward solving their own issues.

What could you change about yourself that would bring out the best?

Throughout the coaching session, try to help the sales rep remain focused on the things that are within his or her control, namely their own attitudes and behavior. Framing the question in this manner establishes a sense of taking responsibility and accountability.

What stands in the way of achieving your goals?

Obstacles can’t be hurdled unless they are first identified. Clearly establishing the problems on the road ahead – while reiterating that this journey will not be seamless and easy – will gird the rep for what he or she will face in trying to accomplish their goals. Obstacles can also seem less daunting when they are explained and talked through, in the same way a monster under a child’s bed seems silly when you talk rationally about it.

What do you think is the best option for solving this?

Again, this empowers reps to take ownership of their own self-improvement. Their first instinct and natural inclination might be to look to you, the sales manager, for help in solving all of their problems. However, asking this question shows that you have the confidence in their abilities to solve their own issues, with the right coaxing and mentorship.

When should we meet to look at your progress?

Once you have put reps on the right path toward improving their own performances, let them know that you haven’t left them completely to their own devices. It is essential to convey to reps that you are always there to help them stay on track toward achieving their self-improvement performance goals.