22 March 2023 |

How to shadow your reps

By Gabrielle "GB" Blackwell

I’m a big believer that the golden nuggets of sales success happens behind the scenes – how research is done, how reps prepare for meetings, how reps prioritize and select accounts, etc. So I really appreciated this question that came  from a VP of Learning & Teaching:

On the advice of shadowing your reps in their work – do you have some concrete examples of how to do that when it’s not something like a call or presentation? Is it asking them to talk through their process? Or share their screen while they go through their process to watch?”

When I’m shadowing reps, I like to consider a few scenarios to inform shadowing purposes:

Scenario 1: The rep who has a high conversion rate but low activity

For this rep, I’ll want to understand how they prioritize their accounts and do their research. I’ll set up 45 min and ask the rep to work as they usually would but instruct them to focus solely on one process. Using the account prioritization example, I’ll ask the rep to show me what they look for when choosing their focus accounts.  

In observing their process, we can usually find a way to:

1) Speed up some part of their process so they can move quicker from one task to the next (usually includes giving them a dashboard to find info faster or enablement on how to use the tech stack more effectively).

 2) Find ways to operationalize what works for them and roll out to the team. 

Scenario 2: The rep who is high activity but low conversion 

You’ll have an opportunity to guide them towards higher converting activities +/or identify what’s blocking them from converting more effectively. 

For example, let’s say you have a rep who has great first meetings with prospects but seems to lose out at getting the next step scheduled. This could be a great time to shadow how they manage their “follow up” work. In this example, I’d ask a rep to walk me through how they keep a pulse on follow up tasks + how they organize their calendar to keep on top of their tasks. 

Scenario 3: The rep who is new / early on in role 

The shadow sessions for this rep are purpose built for direction, correction and validation. 

Being new, even if someone has experience in the position, can easily lead people to feeling insecure about if they’re doing things right. You being there to shadow and affirm they’re doing the right things can be SO helpful in building confidence.

On the other side of that coin are the reps who are new but who bluff about what they know or overestimate how much of a handle they have on the new role. Shadowing these reps can help you correct and redirect them before poor habits set in. A great example of a shadow session for these folks is having them walk you through the end to end process – from research to send – of crafting a prospecting email.

How to intro a shadow session (and ease anxiety)

The best shadow sessions are the ones where people feel comfortable to share how they work because they know you’re there to help them get better and feel better about their work. 

To have the most productive shadow sessions, you’ll want to set specific objectives for your shadow sessions, i.e. identify process bottlenecks that hinder productivity. 

You’ll also need to define the scope – or focus – of the shadow sessions. For example, if your direct report is struggling with finding which leads to work, you focus only on what views, dashboards, and reports they use to see their leads.

Assist: Let’s say you have a rep who is falling behind on their activity and you want to suggest a shadow session. Here’s what the set up could sound like:

“Hey, I noticed that activity goals for calls made haven’t been met. You’ve mentioned that it’s been difficult to know exactly who to call and what to say when you get to your calling hour. To make sure you’re set up to be successful, how about we find a time where you can walk me through your process for building your call list? From there, we can figure out what adjustments can be made to support your activity goal attainment”.

In being specific about your objectives and your scope of the shadow session, you’ll help your rep anticipate what to expect. If they’re able to understand and have clear expectations around the shadow session purpose, you’ll also settle some of the anxiety your people may feel about “being watched” while working.

Where to have your shadow sessions

If you and your team are remote and/or unable to meet in person, all you need is access to a video conferencing solution with screen sharing capabilities. You’ll ask your rep to share their screen so you can follow along with their workflow. 

If you and your people work in the same office, I’d recommend doing shadow sessions where your people do their work. If one person works primarily at their desk, do the shadow there. If they work predominantly out of conference rooms, do the shadow session in a conference room.

Getting the most out of your shadow sessions

The work of a shadow session doesn’t end once the screen share ends. There may be dashboards that need to be built to support your reps. There may be training and enablement needs to satisfy. And there are accountability checks you’ll need to do with your team members to make sure progress is being made against the shadow session objectives.

Follow through and hold people accountable to making the adjustments needed to improve.

Bringing it all together

If you’re able to get a better understanding of how your reps work and what their specific bottlenecks to performance and productivity are, you’ll put yourself and your reps in the best position to find appropriate and timely solutions. You owe it to yourself and your reps to shadow where needed.