Emily FitzPatrick

Global Revenue Enablement and Training Manager, Showpad

Creating a Coaching Culture with your Sales Leaders

Accelerate: In a few sentences tell us what sales enablement means to your organization?

Emily: Doing Enablement at an Enablement company creates lots of great opportunities to challenge ourselves to ask “are we setting the standard for Enablement?” Which is incredibly fun and unique to this role. Our enablement team primarily focuses on the delivery of new content, assets or tools to the Revenue teams. We have a Product and Corporate marketing team that creates the content hand it over to us and it is our job to ask,

  1. Why do the reps care about this? 
  2. How will they use it? 
  3. What impact does the business expect it to have?
  4. How will we know when it’s been successful?


Accelerate: What is one enablement tool that is a must-have for your team?  How do you measure its effectiveness on your sales enablement efforts? 

Emily:  Showpad! — I’m not just saying that because I work here, I genuinely think it’s the best tool on the market. It combines a content management tool, a learning and coaching tool as well as, most recently, a meeting intelligence tool! Our sellers love it and it really supports my role.


Accelerate: When designing a sales leadership coaching program, who do you work with throughout the company to establish program buy-in? 

Emily:  Sales leadership, it is important to start with Senior Leadership (CRO, VP of Sales, Sr. Directors) but you really need to gain trust and by in with your FLM because they are who have to execute it.


Accelerate: What levels of sales leadership do you include in your sales coaching sessions? 

Emily:  All! Coaching is a contact sport, you FLM’s will mirror the coaching that they receive from their managers so everyone needs to know how to execute a great coaching session and know how it feels to be both the coach and the coachee. 


Accelerate: What are your personal tips for including sales management when establishing your coaching framework? 

Emily:  Keep it simple. Often we think about coaching to sales stage or an entire call vs. one simple, practicable and repeatable action. Sports analogies are helpful here; if you were practicing your golf swing to improve accuracy, you would do the same action over and over making small tweaks to your grip, run drills focused on specific muscle groups to create muscle memory. I often see managers start to big– they will coach on Discovery, so many skills go into making a great discovery call or calls. What SPECIFICALLY do you want to work on? Quality questions, objection handling, active listening, not stacking questions, upfront contacts, outlining the next steps… etc. Focus on just one at a time, bring it to the awareness of the rep (or team) give them the opportunity to practice in the moment and keep it in front of mind for their next calls. You will upskill them one component at a time!


Accelerate: What does a typical framework look like for you when designing your program for sales managers? 


I have learned a few coaching methodologies over the years, GROW, SBI, AID are all good models to build accountability in the rep. The framework I use when setting up a coaching program at a new company is from “The Sales Coaches Playbook” by Bill Bartlett — this is my adaptation of that process: 

  • Identify coachable reps (pay attention to Skill vs. Will, you can coach reps to have a skill gap and the will to improve and grow, if they don’t have the will then coaching is not a fit for them) 
  • Manager observation of calls and real situations 
  • Manager and Rep Identify coaching opportunities/skill gaps
  • Confirm with rep and commit to action & practice 
  • Practice (role-plays or on live calls)
  • Continue coaching cycle


Accelerate: How is a sales leadership coaching session different from a front-line sales coaching session? 


This is an interesting question, I don’t think there is a difference between sales leadership coaching and FLM coaching. The process and intention behind the coaching is the same, what you are coaching on will differ. Always start by identifying what competencies you are coaching on (whether it is objection handling or giving a sales rep effective feedback) observe them in real situations and identify what the gaps are, when and how they can work on them. 

I think it is essential for all sales leadership to receive coaching, as in order to be a good coach you need to have experienced good coaching. 


Accelerate: In your experience, what push-back have you had when putting together a sales leadership coaching session?  


Lots, there are some leaders who don’t want to let an insider into the sales leadership team, some who think they don’t need the help or the old adage that there isn’t time. The funny thing is that there isn’t a need for training/coaching when everything is going well and there isn’t a need never time for training or coaching when things aren’t going well. 

Setting a sales team up for a successful next month, quarter or year is paramount to the continued success of a team. So making it an expectation for sales managers to coach their team is a no -brainer, what takes a little bit more work to show the need for is to get sales leaders or FLMs coaching on how to be a great coach. But coaching is a skill and a practice that takes time and attention and investing in it will really pay dividends. 


Accelerate: Like all of us, sales leaders have a lot going on throughout their day, how do you ensure coaching is a priority for them?  How frequently should you hold coaching sessions? How do you incentivize them? 

Emily: Great question, it goes back to the expression “inspect what you expect” if your sales leadership has the expectation that sales managers are coaching, then they will need to inspect the quality of that coaching. It’s about evaluating your sales managers on more than just quota attainment. They should be evaluated on the development and promotion of their sellers, adoption of new skills or tools and the engagement/satisfaction of their teams. All of these skills require coaching. I think it’s enablement’s role to help make coaching bite-sized. Managers already meet with their sellers weekly to check in on deals, use half of that time for coaching conversations. 


Accelerate: Technology is everywhere, what tools and reporting do you use for your sales coaching program? 


Well… we use Showpad 🙂 We use our MeetingIQ product for managers to observe and give feedback on meetings they are not able to attend. Within Showpad Coach we also have PitchIQ which is a great tool for sellers to practice new skills and managers to provide feedback on their team’s submissions. 


Accelerate: How did you get into sales enablement? 


I was working at Groupon as an Account Manager back in 2013 and there was an opening on the Sales Training team. I have a theater degree and I moved to Chicago to do Improv and Sketch comedy in Chicago and I thought that the sales training role would be a great merging of my two worlds. At the time we were growing like crazy so I would run training sessions for 25+ new sales reps every 2 weeks, and it really felt like a performance a lot of the time 🙂

I really fell in love with OD and Adult Learning Theory and stayed in the L&D world for the next few years always in Training roles and then in 2018, I found my way to Showpad and into the fast-growing world of Sales Enablement. 


Accelerate: What is the biggest misconception of sales enablement you’ve heard?  How do you see this changing over the next five years? 

Emily:  I think the biggest misconception about sales enablement right now is that there is only one right way to do it. Every company and every team is doing Sales Enablement whether or not they have a dedicated team or function for it. The need for enablement tools and teams will continue to grow and grow over the next few years. 

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