Three simple tips to improve your Sales Coaching

What makes a great sales manager? Much has been written about the topic of coaching, in this post I’ll rationalize two approaches for coaching and provide 3 steps to improve your coaching conversations.

Defining Coaching

The word coaching tends to be overused and usually carries several connotations. Michael Bungay Stanier, in his best seller “The Coaching Habit” suggests that there are two main categories: Coaching for Performance and Coaching for Development.

In the first one, the manager plays the role of advisor and tells people what to do. For a sales manager, this approach seems to make sense in a situation where a very important deal is at risk and urgent action is needed. The expertise that sales managers bring to the table can help unlock deals to a fast and efficient conclusion.

However, this first coaching approach while sellers are in the performance zone, doesn’t help them develop the right selling skills because the sales manager is not creating the space for them to figure out a plan on their own. Also, as a sales manager, when you switch to advising mode, you could enter a dangerous zone playing the role of the Seller which can put you in a tough situation to manage performance if things go wrong. In addition, you may also be overwhelmed with the number of action items and problems that need to be managed and solved on behalf the seller.

Another of my favorite books, the Challenger Sales, groups top sales manager attributes into two categories: Management Fundamentals and Sales Management. For the Sales managers, this is about integrity, reliability and in particular, active listening.  In typical 1o1s, sales managers must avoid jumping into “solution provider” mode and try to overcome issues by themselves truncating sales people creativity and their ability to learn. Author Keith Rosen calls this Soapbox management.

A Better approach to coaching

Coaching for development is more what I considered real coaching. Sales managers play a more passive role in listening and being curious about seller challenges. Sales managers avoid jumping in to tell sales people what to do, instead, Sales managers guide the seller to find the solution and to strategize jointly how to close the deal.

So how exactly do you start? The sales manager will guide the Seller through a set of powerful questions that will open the door for alternatives to remove obstacles and allow sales people to feel accountable for their own actions. In general, sellers have a full understanding of the deal context and sales coaching can push them to think differently to move the deal forward. In the case they don’t have the right connection or understanding of customer buying cycle, sales coaching can also create the awareness on what else needs to be done before a clear action plan is defined.

Here is a 3 step process I learned to use in my past experience coaching sellers in complex deals (and also discussed in Michael’s book) which you can put in your toolkit when you participate in any pipeline management or deal coaching process.

Diagnosing the problem

The first step is to get to the bottom of what is the main issue. The goal is to let the seller articulate all the real and perceived challenges in a particular opportunity, and get to the one issue that is affecting the seller and is within his/her control now. You want to filter out external issues you can’t act on or really long term problems you address today. Start by asking a simple question: “What is going on in your opportunities?“. After you let the Seller present all possible challenges/problems in his/her mind, follow up with: “I think I understand what is going on with this [the challenge], but what is the real challenge here for you to win this opportunity or to commit this opportunity in your forecast?“.

Explore all possible solutions

Once the real problem has been identified and internalized, then you have a chance to help the seller build a plan with as many ideas as possible. I would tease the conversation by asking: “What is the obvious thing to do soon?“. But don’t stop with the first proposal, encourage the seller to provide at least 3 possible solutions. To uncover these options, ask the seller: “And What Else?” After exhausting all the seller’s ideas, you have a couple of options:

1.- If you gut feeling tells you that they need more info before jumping to a plan, then tell him/her to investigate more, highlighting clearly the gaps and come back with more comprehensive alternatives, or

2.- You follow the coaching with these set of questions: “From all your possibilities, what would be the easiest solution to implement now? and What solution would have the highest impact?”.

It would be silly to keep asking endlessly like a robot. If you have a great idea to offer, then try to incorporate it while he/she is sharing theirs. Be prepared, if they explicitly ask you for your recommendation, you can say: “I have a great idea to share but first I would like to hear yours”. Definitely, this second strategy is an important learning moment for both the seller and you.

Drive action

This third strategy will be crucial in driving change, and this is all about getting their commitment to executing. I would ask: “What do you really want to do here?” You will improve accountability if you go deeper and ask: “How and when are you going to implement [solution]”. Finally, ask the lazy question: “How can I help?” or a version of that: “What do you think I should do about it? How do you want me to participate?“. This is the last question that you should ask without getting in advising mode. Depending on the answer, then you can compromise with your suggestion, or you can always say No and the reasons, or you can buy time, by saying: “I need to investigate few things before I commit with the action/funding/etc.

Create a Habit

Coaching for development is not a one-off meeting happening once a year, but an ongoing process during weekly/monthly 1:1s with your team. In order to make this a habit, you need to understand what triggers the action to jump into “advising mode” and recognize that behavior (for example, fulfill your ego or problem-solving mindset). Write down what actions will drive you to change and start using an approach like those surrounded by powerful questions, laziness and curiosity.

There are many great books and tools available out there, and it’s certainly an area not short of content. For that reason, I want to acknowledge three authors I recommend if you want to go deeper into this fascinating subject. One book is the Challenger Sale from CEB authors, this describes the transformation needed in your sales organization to take control of the customer conversation, and it has two chapters dedicated to Sales Managers in how to build or evolve your organization to the challenger sales model. The second book is the Coaching Habit from Michael Bungay Stanier, which provides the 7 questions to develop coaching skills for managers and leaders and finally, the Power of Habit from Charles Duhigg that describes how habits are created and how can be changed.

Please, provide your comments. I’m curious of knowing your point of view and any new insights are welcomed. As Michael Bungay states, “Ask more questions and give less advice”

About the Author



Michele Lanzara is CoFounder at Convercio