5 ways sales leaders can improve their coaching skills

Posted November 3, 2021

Sometimes as a sales leader you may wonder why the things you tell your reps don’t stick. You say, “Hey, I need you to do this on your next call,” and yet they don’t do it. Why? Consider the difference between feedback and coaching.

Telling them what you need them to do is feedback. And while we do learn through observation and feedback, we get behavior to stick by doing it repeatedly. That’s where coaching comes in.

We recently hosted a session between two of the industry’s top sales leaders on the do's and don’ts of real-time coaching. It was a lively discussion with more first-hand knowledge sharing and best practices than can fit in this post. Here we’ll dive into the top five takeaways. Of course, you can always listen to the full discussion too. Let’s dive in.

1. Create an environment for execution

In our school days, we were taught how to regurgitate information. We held onto something for just long enough so we could pass the test. As adults working in the field of sales, that’s not always helpful, especially when the amount of information salespeople must remember is astronomical.

If you remember your best teacher in high school, and if all you did was go to that person's class and listen, you wouldn't have passed the exam. You have to listen, take notes, have a study group, a little practice test. And when you do all that and put it all together, that's how you get a good grade
Mark Kosoglow
VP of Sales, Outreach

Rather than regurgitating information, we need salespeople to recall it in the moment and apply it within the context of the conversation. That means as leaders we must create an environment for execution that triggers recall. Prompts are effective tools for that. Of course, several prompts are particularly important.

  • Discovery prompts: What are the core seven or eight questions they must ask and why?
  • Objection prompts: What are the most common objections your reps hear, and how do you handle them?
  • Pricing and packaging prompts: What are the key details specific to your organization?
  • Competitor prompts: Do your reps really know what makes you different from your competitors? Do they know how to engage buyers on it by asking the right questions?

Prompts, not full demo scripts, help reps recall the right information. It looks different for every team, too. Some sales teams have placemats they can keep handy. Some sales reps use sticky notes all over their desk. Others may have sales decks saved to their desktop. The information is there somewhere, but the part that gets tricky is getting to it at the right time. We've all experienced that dreaded silence as you ask your customer to hang tight while you try to search for the answer. 

Technology like Kaia makes sure that’s not an issue. Content cards contain the same small bite-size bits of content with the information reps need. The difference is that it’s served up to a rep in the moment within the same pane and triggered by the context of the conversation. There’s no breaking your train of thought or asking to hang tight.

2. Establish your process, then document it

“Here's the thing that no reps want to tell you. They're waiting you out. They know if they don't pay attention for four to six weeks, you're moving on and they don't ever have to learn it and do it.” Mark Kosoglow, Outreach’s VP of sales, dropped this harsh truth during the discussion. However hard it may be to hear, it’s the truth. And the consequences result in an unscalable, inconsistent, unfixable type of sales process because no one rep is doing things the same way.

Instead, Mark suggests paying tribute to the process. Be the broken record and teach the habit of coming back to your tools and processes day in and day out.

Process is only one part of it, though. “Process makes you great, documentation makes you legendary. Because in the process of documentation, you learn so much,” says Mark.

Documentation means you can plug new reps in quickly. It also means you can enable your reps to find the answers for themselves. More importantly, you can add the element of continuous learning. Like how a rep handled an objection and it’s better than what you have in your documentation? Great! Capture, document, and everyone benefits.

Every quarter we do something called scaling greatness. How often are you studying the positive outliers to see what's going right? Who has the highest close rate on your team? Who's booking the most meetings? Who has the best response rate? Have you studied them and documented what they do?
Kevin "KD" Dorsey
VP of Inside Sales, Patient Pop

If all that greatness is bottled in your team’s playbook, imagine how powerful that could be.

This is another area where Kaia can come in to help. Kaia makes it easy to keep content accurate, up to date, and available when it’s needed most.

3. Focus on the right things, not all the things

Too often in sales, we look at the macro and try to make a fix by boiling the ocean. The problem is that it can lead you in a direction entirely different from what the true problem is.

For example, let’s say a manager says their reps’ show rate dropped to 65% and they’re trying to help that rep bring it back up. Is show rate the problem or is it that the rep only scheduled four meetings in the last month? In fact, the schedule is the problem. Sometimes it’s about focusing on the metric behind the metric.

In this case, Mark suggests taking a different approach by specifying your leading and lagging indicators. The leading is the measure of effort and the lagging metric is the execution. For example, at Outreach for an initiative like prospecting, meetings booked is the leading indicator and pipeline created is the lagging.

4. Coach in practice, not right before the call

Often, managers start coaching a rep right before the big meeting. Don’t forget! Don’t do this again! Stay away from this! The next thing you know your rep’s confidence is down at a time when they need it the most.

Instead, it should be about putting reps in the mind frame to execute during customer calls. There are no warnings and there is nothing new thrown at them. It’s just those simple prompts and reminders around the things you've been practicing.

One of the fundamentals of coaching is 'we don't beat up on people in games.' Practice is where you let them have it. The game is all about building them up. And I think that's a really important concept that a lot of coaches don't do.
Mark Kosoglow
VP of Sales, Outreach

Kevin drove that point home, “If you're giving them new things to consider right before the call, it either means you've been practicing the wrong things or you're just not prioritizing well.”

Being in the mind frame to execute also means being able to engage entirely in the conversation. Yet, our reps must take detailed notes during customer conversations. Whether we like it or not, our reps' listening ability goes down so that processing of what they’ve heard and then writing it down can increase.

Here’s another place where Kaia can step in to make every moment count. Live transcription captures the conversations, but reps can bookmark key moments so they can stay focused on the customer and not on taking notes.

5. Remember to coach the coach too

The truth is that few managers are taught to coach. They likely were top reps before being elevated into the role of manager. Without the right training, they end up coaching on the wrong things. It’s time we coach the coach.

Part of that is helping them prioritize what to focus on, defining the metrics you want to measure to see growth, and giving them the resources to do it.

Taking a level deeper, it’s also about helping them understand those metrics. “If you understand the metrics, you'll be able to find and fix what's wrong. If you don't understand the metrics, you're always going to be guessing,” shared Mark.

And when it comes to coaching the coach, the final thought Mark and Kevin share is to talk coaching plans, not results. Managers don’t need to report their reps’ results. Why? There are dashboards for that. Instead, managers need to share why the results are what they are and what the coaching plan is around it.

Want to dive further on how to guide reps to take the right actions? Watch Do This, Not That: How to Coach Sellers in the Moment on-demand to hear more sales coaching insights from Outreach’s VP of Sales Mark Kosoglow and PatientPop’s VP of Inside Sales Kevin “KD” Dorsey.


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