How To Get Started With Sales Coaching In 5 Actionable Steps

When sales managers come to the realization they need to take coaching seriously by instituting systematic coaching programs, they have taken a huge step in becoming true professional sales leaders.

But knowing where to start (and how to do) sales coaching can be overwhelming, especially if you don’t already have the “muscle memory” of implementing coaching programs several times in the past.

If you feel the nagging need that your coaching efforts need to be taken more seriously and systematically, but don’t quite know where to start, read on.

First, Start By Assessing your Team In These Five Ways

The first step in starting a sales coaching program is ensuring your coaching efforts are rooted in reality by diagnosing (and validating) the true coaching needs of your team. This ensures you address your team’s sticking points accurately, rather than bouncing between (imagined) coaching needs in a random fashion.

Here are the five steps to doing this.

One: Analyze Conversion Rates Between Opportunity Stages (And Other Key Sales Metrics)

If you have a sales operations team, leverage them here. Your task is to analyze how quickly (and at what rate) opportunities move from stage to stage in your pipeline. This data serves as a barometer, pointing the rest of your diagnostic efforts in the right direction.

For example, if you notice you have a great conversion rate going from the “Discovery” to “Demo” stages, but going from “Demo” to “Trial” is where deals tend to drop off, now you can form a hypothesis:

My reps are struggling with communicating our value proposition.

Notice this is just a hypothesis. We have not yet validated this yet. Hold your horses.

While you’re doing this analysis, take a look at other relevant sales metrics such as sales cycle length, time between stages, and overall win rates to see if any other trends and patterns surface themselves. Take note of each.

Repeat this process for each individual account executive you manage to zero in on each rep’s sticking points.

A great tool to use for this step is InsightSquared, but you can also just add CRM data to a simple spreadsheet if needed.

Two: Cross Reference with Rep Activity Data

Now that we’ve formed our initial hypothesis by analyzing pipeline conversion ratios (and similar metrics), we can take our first step toward validating those hypotheses by analyzing each reps’ sales activities.

Again, if you have a sales operations team, now would be the time to leverage them. If you don’t, time to roll up your sleeves and get this data yourself.

David Duncan wrote a great post about how to do this step.

You should view your reps activities as their own sales funnel, and create benchmarks of activities to compare them against.

The activities included will be different for each sales organization, so you’re going to have to determine that on your own. Include all sales activities that are relevant to shepherding deals through the pipeline. This may include prospecting emails and calls, intro and discovery calls, demos completed, proposals sent, and deals won.

As you analyze this sort of activity data per rep, take a look back at each reps’ pipeline metrics you analyzed in the last step. Take note of any interesting trends and overlap. Some of your initial hypotheses may validate themselves here.

This step should be done at the individual rep level, rather than aggregately across the team. Be sure to compare each rep’s activity metrics to other reps on the team to surface comparative patterns and trends between top, mid, and low performers.

Three: Validate the Coaching Need By Listening to Sales Calls

Most likely, you don’t have a fully validated hypothesis yet as to where you should direct your coaching efforts. The pipeline data pointed you in the right direction, and the activity data may have given you some soft conclusions.

Your next task is to fully validate each reps’ coaching need by listening to sales calls that occur within the opportunity stages that seem to be the reps’ sticking point.

You have two options for doing this: shadowing sales calls live and reviewing call or demo recordings.

I recommend the latter. Sales managers are spread too thin to coordinate their schedules around their reps’ scheduled sales calls. With recordings, you can pump through several of them in a single time block. This is called “asynchronous coaching.”

Also, if you’re sitting in on live sales calls, the rep’s behavior is likely to change. This will make diagnosing their sticking points much more difficult and will possibly lead you to false conclusions.

Reviewing calls is the ultimate way to validate your hypotheses of each reps’ sticking points. You’ll hear exactly what reps do (and don’t do) on their calls, what they’re good at, where they struggle, and what’s working for them.

Remaining blind to how your reps manage their calls and demos will relegate your coaching efforts to guesswork.

I recommend reviewing three calls per rep. Each call should have occurred within the opportunity stage the rep seems to be struggling with based on the earlier analysis.

Three calls sound like too much? Well, who said this money-making thing was easy? Plus, there are technologies that can drastically cut down the time this takes.

If you’ve done the above three steps, consider yourself miles ahead of 80% of sales managers out there.

Four: Understand How Your Reps’ Perceive Their Strengths and Weaknesses by Enabling Self-Discovery

Understanding your reps’ perspective of how they’re doing, what they’re struggling with, and what they’re good at is your next point of leverage.

Have reps review and comment on a couple of their own calls, score themselves, and even prepare the agenda and outline for your next 1-on-1.

Observing how your reps comment on their own strengths and weaknesses will unleash another floodgate of useful information to you.

Five: Hold 1-on-1s That Have a Slight Twist to Them

Remember when I suggested having reps prepare the agenda and outline for your next 1-on-1? There’s a method behind that madness that almost no one understands:

1-on-1s should be regarded as for the rep, not for the sales manager.

This is not a pipeline review meeting. That is for the manager’s benefit, not the rep’s.

As an ancillary reason for this format, when you have reps prepare for the 1-on-1s, they only have to do it once. If you prepared for these, you’d have to do it 6-8x (or however many reps you manage).

Going over the outline they’ve prepared will, again, give you a window into how they think about their own performance, strengths, and weaknesses. This will help you modify your coaching approach to each rep. You’ll also learn things you couldn’t have learned in any other circumstance.

During the one-on-one, let the rep lead most of the discussion by following his or her outline. Begin to address some of the coaching needs you’ve identified in previous steps during the last third of the meeting.

A couple tips in doing 1-on-1s effectively…

First, they should last at least an hour. I know, you’re spread thin, I get it. But if you schedule these for too short of a period, reps tend to bounce around surface level issues they’re facing rather than talking about deeper, important issues.

If you’re a rep, and you have a deep, nagging issue you’re facing, how likely are you to bring it up in a 15-minute meeting? Not likely at all. Surfacing these things takes time.

Second, 1-on-1s should not be recurring. They should be “rolling.” You schedule the next 1-on-1 at the end of each 1-on-1. If you do a recurring meeting, you risk having to cancel due to the rep being on vacation, a previously scheduled sales call, or other obligations.

Third, the frequency of 1-on-1s should depend on the potential that exists in improving that rep, and the level of expertise they have (or lack) when it comes to the area of improvement you’ve identified.

Fourth, use a sales coaching template like this one. It’ll help you focus on high-impact areas where your reps (and your team’s performance) stand to gain the most.

If you have a superstar who’s pretty good on all fronts, you can get away with once a month.

If you have a rep who could be great but seems to be struggling due to shallow discovery skills, you may want to schedule as frequently as once a week.

Maintaining the same frequency with each one of your reps is a big mistake.

Now That That’s Done, Here’s Step Two

Once you’ve gone through this process of discovery, validation, and 1-on-1s, the last task you have in getting started with your coaching program is implementing one (and only one) systematic coaching cadence.

Eventually, you’ll have more than one, but that takes time to build to. Trying to implement too many programs, activities, and routines at once will lead to overwhelm, and eventually collapsing your coaching efforts. Single-mindedly focus on getting one recurring activity off the ground.

The type of coaching cadence you decide on will largely depend on the discovery work you’ve done in the previous steps. But here are some examples to get your thoughts flowing:

• Weekly data-driven coaching diagnostics (same day/time every week)
• Rolling 1-on-1s with each rep, with varying frequency
• Weekly group call recording reviews as a team
• Binge watching demo recordings over 120 minutes once a week
• Reviewing and scoring call recordings
• Having reps review two of their own calls each week, then reviewing with them afterward

Pick one of these, and go all in. Make it a recurring, systematic activity your team adheres to come rain or shine. Ideally on the same day and time to make it a ritual (with the exception of 1-on-1s, which should be rolling).

If you manage to do this, momentum will take care of itself, and getting other systematic coaching cadences going will naturally happen over time.

Summary – The Two Things Needed to Get Started With Sales Coaching

To sum up how to get your coaching efforts started:

• Diagnose and validate coaching needs with the above 5 steps
• Implement one (and only one) systematic coaching ritual

Do those, and you’ll avoid Random Acts of Coaching Syndrome.

Feel free to tell me your thoughts in the comments below, especially if you have insights to add to this process.

Still Need Inspiration?

This sales coaching template has you covered:

High-impact coaching areas to look for on your team? Check.

Actual coaching examples for each of the key areas? Double check.

A copy-paste-win formula to get started easy? TRIPLE check.

Download it here.

If you liked this article you may also be interested in:

• Sales demos – 9 Elements of Deal-Closing Sales Demos, According to New Data
• Sales calls schedule – Find out the worst time
• Remote sales coaching