A Sales Enablement Conundrum: Who’s Coaching the Coach?


Share on LinkedIn

The room (and the online meetings) always become very quiet when we ask this question. Everyone knows the value of coaching, whether they’ve consciously thought about it or not. How many Olympic athletes have a coach, or even more than one? Now that the NFL season has once again kicked off, how many of those teams have coaches?

Answer: ALL of them.

George Leonard, in his seminal work on Mastery, noted having a coach is the #1 key (of 5 he identified). So we get it, yes, having a coach is a key to improved performance. What sales organization in the world is looking for improved performance?

Answer: ALL of them.

Yet, when we survey firms and ask about coaching received from sales managers, not focused on pipeline or deals but rep development, the numbers are excruciatingly low. And when we ask about the coaching managers are receiving, typically the silence is deafening.

Moving up the line becomes even quieter: how much coaching do directors receive? VPs of Sales? Sales Enablement leaders? In short, the most frequent answer to “Who’s coaching the coach?” is no one.

Is this a problem?

In our opinion, the answer is “yes” for two reasons (at least). First, it assumes the VP of sales, Sales Enablement leader, director level, already are fully formed; completely up to speed; have things down pat. This would be unlikely in a complex but static environment and is not remotely possible in a complex, fragile and constantly changing environment (i.e., modern B2B sales).

There is, however, a second reason that the Uncoached Coach is problematic. It is telegraphing the exact wrong message to your sellers. The message being, “Eat your veggies; I’m already a Big Kid (and don’t need to).” Not only does this lack integrity but, since people learn by example, it also takes all the air out of any proposed coaching program. Veteran reps can, by extension, say they are Big Kids in their role and coaching is only for newbies.

State of Sales Enablement

Retreating to our favorite Edwards Demming quote: Without data you’re just another person with an opinion, let’s look at some data. According to CSO Insights 2019 Sales Enablement Study here are the Top 10 Sales Enablement goals:

Anything missing? Increase sales manager capabilities? Improve sales leadership coaching skills?

The emphasis of programs continues to point at results, which is understandable, but not doable. You don’t do results, though you can measure them. It’s normal to track results but you must take an indirect route to obtain them.

You increase EBITDA by streamlining operations, improving processes, and/or providing more timely production feedback. You increase 1-10 above by growing your sellers’ skillset, elevating their ability to execute and manage sales cycles/accounts, creating a data-driven culture of continuous improvement.

To this end, the following model is helpful.

The box represents a system, any system (e.g., manufacturing, HR hiring, sales pipeline). An arrow entering the box on the left represents inputs (raw materials, job applicants, sales leads). The arrow coming out of the box represents output/results (units produced, new hires, deals closed). To the extent the arrow on the right is different than the arrow on the left, something happened IN the box, which is your process. So far, so good.

Except, as it turns out, good isn’t good enough. Look at the list of Top 10 above and each is about improving, increasing, reducing, etc. So what is desired is not process but, process improvement. For this to occur our process model needs one more element: a feedback loop.

We now have a closed-loop system for process improvement. Another point on this worth noting is that feedback equals coaching; coaching is, in fact, feedback. (For more on this see this video.) With this model, it becomes even clearer why there is little coaching of coaches.

First, do you have a coaching framework/process for each level of your sales management organization? The answer, surprisingly, is “no,” even for first-line sales managers. When there is a coaching framework, it typically will cover things such as: reviewing rep pipelines and forecast reporting; mandatory training including sexual harassment; dealing with difficult employees; product training; policy training; etc.

We recently surveyed 125 Sales Enablement leaders to determine the primary services they are/would be providing their companies’ sales managers. 41% listed “Dedicated Sales Manager Development Program” as one of their services. Whether these have and/or will be activated will have to wait until our follow-up survey.

When, and if, enacted will these programs include: career pathing? Goal setting? Scheduled coaching/feedback sessions?

Invest More in Manager Training

Ken Powell, who ran Worldwide Sales Enablement & Learning at ADP, said he often felt the budgeting of sales training should be reversed. Instead of 80% of the budget going to seller training and 20% to manager training, managers should be receiving the lion’s share of training dollars and learning. There are good reasons for doing so. For starters, the leverage of 6-8 sellers per manager. Trained managers can share their learning with their direct reports, whereas, training sellers is essentially a 1-off, singular event. Further, managers tend to be less transient than sellers, so your payback period is longer and, for those that stick around and move up, you’re investing in the firm’s future.

If you think first-line manager level training is scarce, it’s essentially non-existent as you move up. Presumably, directors and above already know everything needed to manage folks. But have they also grown to their full potential? Does knowing how to manage also mean knowing how to lead? What role does Sales Enablement play in this discussion and, finally, who’s coaching the Sales Enabler? Asked another way, “Who’s enabling Enablement?”

We also asked which functional area Sales Enablement reported to.

Nearly half (44%) report to Senior Sales Management and another quarter (25%) report to Sales Ops, which typically reports to Senior Sales Management. It makes sense that with 70% of Sales Enablement reporting up to sales management that the goals will be aligned: increase revenues, add new logos, boost lead gen.

All of these outcomes are important and all contribute to growing the business. But it is also important to grow your people. Like coaching, everyone appreciates the value of this sentiment but, too often, it remains just this: sentiment. How to get beyond good intentions to active coaching?

Like everything else, people lead and learn by example. Vistage is a resource, primarily for entrepreneurs, to receive both individual and group feedback. The Sales Enablement Society (SES) has local chapters and an annual national meeting; they offer some resources but primarily networking for Sales Enablement practitioners. Many consultants are also members of SES. Sales Mastery now has a hybrid model of online resources, group and individual sessions for Sales Enablement and Ops leaders.

Similarly, the Sales Management Association (SMA) and the Global Sales Operations Association (SOPSA), offer resources, courses and forums, for professional development and networking. These can be effective resources but do not replace coaching. Again, coaching equals feedback.

For feedback to be meaningful, and for coaching to be effective, it must meet 5 tests:

  • Timely (annual or quarterly reviews too infrequent to impact behavior changes)
  • Accurate/Objective (data-based observations vs opinion-based judgements)
  • Consistent (picking and sticking with a single area of improvement)
  • Relevant (finding an area of improvement the rep agrees will have high payoff)
  • Individualized (tailoring the selected behavior to a specific rep’s growth)

Coaching Guide

Coaching has a very positive connotation in our culture and everyone seems to see the value of it. Yet, it often doesn’t happen. One company surveyed their managers and more than 80% said they regularly provided coaching to their reps. 85% of the sales reps in this same organization said they received little or no coaching at all, and no regular coaching.

How could this be?

What the managers most often were involved in were deal reviews. Where are we with this opportunity? When do you expect it to close? What needs to happen to make this happen?

All of this may be legitimate sales conversation but it is NOT coaching. Look at the key concept points and see which are missing.

The key to making coaching operational is the same as other concepts: 1) define what better looks like; 2) define how you’re going to measure success; and 3) provide follow-up and feedback.

What better looks like:

  • Having a coaching plan: agreement on 1 skill/behavior to improve
  • Discussing how the behavior is being measured
  • Establishing a baseline measurement and a check-in schedule (at least monthly)
  • Holding both parties (coach and coachee) accountable for meeting/measuring on schedule

Reading this may elicit one of a couple of reactions: A) So what else is new? Or B) I already have more to do than I can keep track of; who has time to track each seller’s coaching plan?

To the first point: nothing. Nothing is new. Feel better? Here’s another bit of truth: The Knowing-Doing Gap[1]. It’s not that your sellers—and you—don’t know what to do. It’s that you don’t do what you know. Why not? Distractions, lack of clear focus, addiction to email, or other time-consuming tasks. It’s especially easy to justify checking email and messages every 5 minutes when working remotely, in the name of being responsive.

A couple of things you might try to better multiply, rather than fragment, your time and attention. First, look at the things you do each day/week and apply the test not only of importance and urgency but, also, significance. Roy Vaden does a terrific job of presenting his time multiplying funnel during this 18-minute presentation. If you’ve heard the greatest time management tool is saying, “No,” Roy’s talk takes this to a new and more precise level.

If you’ve heard of the “Pomodoro[2]” technique, this refers to concentrating on a task for 25-minutes, then taking a quick break. A variation of this is blocking out 2-3 hours each day to make progress on the big rocks (important projects) that you need to move forward. Breaking big projects down to incremental tasks and making regular progress, will help you avoid procrastinating because a task is too big to take on right now.

Writing down these incremental goals at the end of each day and reviewing them at the beginning of your next day can also help you stay on task.

As to the second point, who’s got time to coach? Gut check whether you really believe in coaching. Do you have a coach? Are you working on improving a skill with high payoff? Are you being accountable to yourself and your coach? What’s the payoff/reward when/if you improve?

This last question is worth really considering. If the only reward is getting to pick another thing to improve at, well, that’s not much fun. Where’s my cookie?

If the payoff is you’ll make more money, achieve a target, get some time off, get a promotion, whatever… What will you do with the money? How will you celebrate hitting/exceeding your target? What will you do/not do with your time off? Like, really. In full hi-def, visceral visualization, What’s in it for YOU?!! Asked another way, “Who’s coaching the Coach?”

This is when a lot of folks fall back to the old standby, “I don’t know what I want to be when I grow up.” Well, forget that and Grow Up! There’s no time like the present. There’s no time but the present.

In Closing

In addition to the value of coaching which is generally recognized, and the rigor of coaching outlined above, COVID and remote working from home have added one more layer of difficulty to being a real coach. Not insurmountable but more difficult than when everyone is showing up in the same office or location. Do not be deterred; the effort is worth it and the growth of your players will be reflected in their improved results.

Note: If you’re interested in taking our Sales Enablement Services Assessment survey (6 questions) and receiving the results immediately, click here.


[1]The Knowing-Doing Gap: How Smart Companies Turn Knowledge into Action, by Jeffrey Pfeffer and Robert I. Sutton , 1/15/2000

[2] Named after a kitchen timer that looked like a tomato.

Barry Trailer
Barry has been involved in complex B2B sales for over 30 years and is intrigued with how it's changed/changing and what this means to Sales as a Profession (SaaP). Salesware, the analytics company he co-founded, was acquired by Goldmine Software in 2000 and his next company, CSO Insights with Jim Dickie, was acquired by Miller Heiman Group in 2015. He has twice been published by, and been a keynote for, Harvard Business Review, and is author of Sales Mastery, a novel.


Please use comments to add value to the discussion. Maximum one link to an educational blog post or article. We will NOT PUBLISH brief comments like "good post," comments that mainly promote links, or comments with links to companies, products, or services.

Please enter your comment!
Please enter your name here