Implementing a sales coaching program can be a daunting task. Many challenges can arise – gaining buy-in, facing uncoachable reps, and deciding on a coaching framework to name a few. 

This article covers each of these challenges to help you create your sales coaching program with confidence. 

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Working with frontline sales managers

When implementing sales coaching within your organization you can get a lot of objections from sales management. One of the most common objections is: making time for it.

Kate Philpot, Vice President Global Sales Enablement at Getty Images, shared her response to this objection:

“If it's important enough, you will make time.”

While your efforts to get buy-in at all levels will naturally include the sales managers, you need to collaborate with them a little bit closer to ensure reps are actually coached enough

What is “enough”?

Statistics have shown companies with reps who receive less than 30 minutes of coaching a week have a win rate of 43%, while reps who are coached for more than 2 hours a week have a win rate of as high as 56%

The more time your sales managers can spend one-on-one with reps, the better. If they understand coaching to be one of their primary responsibilities, they will be more inclined to commit meaningful time to it. 

And it’s in any sales manager’s best interest to coach – especially if they want their team to hit quota. 

Sales coaching and training | Sales Enablement Collective
Your one-stop shop for sales coaching and training. Discover sales onboarding, coaching, training, and skills tips and more in SEC’s sales coaching and training hub.

Training sales managers to coach effectively

However, not everyone is a naturally good coach. Some might not even know what good coaching is if they’ve never received it themselves.

Often, high-performing sales reps are promoted into management positions because of their excellent sales skills, even if their coaching and management skills leave a lot to be desired. 

That combination means that part of your enablement team’s rollout of a new sales coaching initiative must include training and resources for managers to teach them how to coach effectively. 

Essentially sales coaching for managers, if you will.

On our Sales Enablement Innovation podcast, RingCentral’s Senior Manager, International Channel & Strategic Programs Enablement, Alan McIntosh explained how any enablement initiative must be rolled out with synergy between rep and manager in mind.

At RingCentral, Alan launched a coaching certification program for managers in tandem with a rep sales skills certification for that exact reason.

“In parallel to the rep certification, we launched a ‘Coach for Growth’ certification for the sales managers, and that was designed in such a way that ensured we’re delivering really strong coaching skills for managers - I have a real passion for that. 
“We launched that certification globally to around 150 sales managers and leaders across a few weeks, and included in that a number of elements that drove adoption on both sides. 
“We trained the managers and provided them with a playbook that gave them coaching tips and coaching questions which aligned to each of the modules we delivered to the sales reps in the rep’s certification. 
“Right away, the managers can lean in on those skills we've trained the rep on and coach them to take them to the field and execute. 
“The conversation we had was: ‘We're training the reps to execute, and we're training the managers to coach that execution’.”

If your coaching strategy neglects the sales managers and focuses exclusively on the reps, you’re ignoring the vital infrastructure around sales reps which makes coaching them possible. 

Creating a formal coaching strategy can help sales managers engage with reps in ways they previously couldn’t. 

Challenges of remote working

With hybrid and remote working remaining as popular as ever, sales managers face a distinct challenge: they can’t overhear or drop in on their team’s sales calls while patrolling the office. 

However, a formal coaching strategy allows sales managers to leverage technology like conversation intelligence to make purposeful time to coach reps one-to-one, rather than relying on ad hoc office moments. 

Kate sees hybrid working as both a challenge and an opportunity for that exact reason:

“What presents both an opportunity and a challenge for a lot of organizations is that so many of us now are working in a hybrid way. Back in the day, when sales teams were office-based, managers could spontaneously overhear calls or at least have conversations with reps and use that as a jumping-off point for coaching, saying ‘I just heard X’. 
“You're not having that opportunity now because oftentimes your team is somewhere else, so formalizing your coaching is a great way of getting managers to check in with reps and make sure that the things that you thought were happening are actually happening.”

Even if you can’t invest in a conversation intelligence tool, try to get creative and remember that there are ample opportunities to replace office-style, ad hoc coaching with a culture-led formal coaching strategy even if you’re a hybrid or remote workforce.  

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Coachability and dealing with “uncoachable” reps

Something every coach needs to be aware of is coachability, why it’s easier to teach coachable students, and just as importantly - how to deal with “uncoachable” reps. 

Coachable reps are open to feedback, eager to self-analyze to improve, and willing to put the time and effort into bettering themselves. Uncoachable reps are the opposite - resistant to change, feedback, and constructive criticism. 

Coachable reps ✅ Uncoachable reps ❌
  • Open to feedback
  • Eager to self-analyze
  • Willing to spend time and effort to
    improve
  • Possess a positive attitude to learning
  • Resistant to feedback
  • Don’t like change
  • Don’t make an effort to break bad
    habits
  • Unable to take constructive criticism

Mark Garrett Hayes, Author of ‘Sales Coaching Essentials’, believes that understanding coachability is an important aspect of your role as a sales enabler. 

“I think many people are not coachable, because they don't have that willingness to change and willingness to learn. You have to recognize as a manager, as a leader of people, that some people will just not get coaching. 
“I'm reminded often of that skill/will matrix. Where are your individual contributors or members of the go-to-market team going to benefit from coaching? As an enabler, you have to ask yourself tactically and strategically, where are you going to invest your time and get results? 
“I think you have to ask: ‘Am I coachable?’ as well, because if you aren’t coachable, you will not succeed. Being coachable means being vulnerable and open to being coached.
“Good coaches see coaching as a two-way street, you have to coach people, but also be open to feedback. And when your team sees that you're exposing yourself to being coached by them through being on the receiving end of feedback, that really helps.”


Senior Director of Sales Enablement at LinkedIn, Kira Pollard-Lipkis, speaking on Let’s Talk Enablement Season 2, told us that identifying coachability in reps can begin right from the interview process.   

“Marshall Goldsmith has a framework for looking for coachability that I really love. He believes that there are three main criteria to somebody who's coachable: Courage, humility, and discipline. 
“I think you can design an interview process to test for each of those three things, to at least give you a good pulse check on those areas. 
“I like to give feedback in real-time at the end of an interview process. I don't believe in holding a poker face and letting the candidate wonder how they did. I typically try to give some quick, ‘here's what you did really well, and here's some of the things that I think you can improve and focus on for next time’ feedback. 
“I tell that to the person who's doing the next interview, and then ask them how that person actually implemented the feedback that I gave them in the subsequent interview. I think coachable people take the feedback to heart and they adapt quickly, whereas people that are less coachable tend to stick to their patterns and are habitual.”

Building a coachable team through your interview and hiring process makes it easier to instill a coaching culture and reap the benefits of coaching - if your sales organization is full of reps with an eager, enthusiastic attitude to coaching you’re less likely to face hurdles when implementing your coaching strategy. 

Questions like, “Tell me about a time when you received feedback from a manager, what did you do with that feedback?” can help you understand whether a rep is coachable before they even join your team. 

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The GROW model

Understanding coachability is great - but without a coaching framework, it can be a challenge to apply a formal structure to coaching sessions and ensure consistency between sales managers. 

That’s where coaching models and frameworks come into play. 

While there are countless different models and frameworks to choose from, we’re going to run through the popular GROW model, used by both Jocelle Sarenpa, Director of Sales Enablement & Training at Field Nation, and Kira as they explained during Let’s Talk Enablement Season 2. 

What is the GROW model?

GROW is an acronym which covers the four steps of this coaching model. Each letter stands for a theme or set of questions you should ask the coachee to understand where you should focus your efforts as a coach. 

G stands for Goal. The first step is to understand what the sales rep’s goal is. What do they want? What do they hope to achieve through this coaching session? For example, a rep may lack confidence in the negotiation stage of deals - their personal coaching goal could be to improve in this area. 

R stands for Reality. The subsequent step is to understand where they are now, and what circumstances have led to that. This is about understanding what factors are standing in the way of achieving their aforementioned goal

O stands for Options. This is where you explore what the rep could do to achieve their stated goal. What options are available to the coachee to get them from the current reality to their goal? In our example with the rep, this could include one-to-one coaching sessions, using conversation intelligence to study good negotiation calls, or reading a book on negotiation skills. 

W stands for Will. This final stage is the plan of action. Which option will the coachee take? It’s about committing to an action plan, a series of steps which will lead them to their desired goal. It’s important to set a date to review and assess progress and success, in order to create a sense of accountability. 

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Benefits of the GROW model

Jocelle explained why she likes to use the GROW model for sales coaching: 

“I usually gravitate(s) towards the GROW model, as it's super simple, but very effective. 
“What I like about it is that it's really anchored in the goal, and through identifying where you would like to go and where you're at today, you can explore different options that could help get you to the goal, while also acknowledging and preparing for all the obstacles that could potentially stand in your way.”

Kira also uses GROW in her role at LinkedIn, but believes the secret to a successful sales coaching strategy is to use any model or framework.

“I'm a big fan of frameworks. I think anything that is clear, simple, and gives people a mental model to learn is really helpful. 
“It's just like an enablement, anytime that you're able to train people via framework, I think it increases recall, and it helps build muscle memory a bit faster.
“Why I love GROW is its simplicity. I think that it gets to the heart of everything that matters in coaching in a clear way. 
“What do you want to do? What's preventing you from doing it? And what are you actually going to commit to doing and how do you want to be held accountable to doing it? That's the essence of coaching!”

Whichever model you decide to use, it’s key that sales leaders, managers, and reps are trained on and understand how to use it effectively so that they can start working towards their coaching goals. 

Much of GROW’s popularity stems from its simplicity and effectiveness as a sales coaching process, so it might be the right choice if you’re getting your organization started in the world of sales coaching. 

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