Sales Execution

4 Tips for Successful Sales Coaching — and 4 Traps to Avoid

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Michael Lowe
Director, Content Marketing, Clari



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Photograph of mouse traps on a wooden table
Photograph of mouse traps on a wooden table

One-on-one sales meetings are a standard part of managing your team. But how often are they truly effective? As Grace Tyson, Sales Manager at, shares: “As a manager, you don't want to be one of someone’s 90 different managers or mentors who haven't been impactful. You want to be one of the few that have a huge impact and transform your teams’ careers.”

In a recent webinar, Tyson, along with Alex Kremer, Sales Manager at Outreach, and Anthony Cessario, AVP of Sales at Clari, discussed the 4 building blocks of effective one-on-one sales meetings, as well as the 4 biggest pitfalls that teams face.

Cracks in the Sales Coaching Foundation

No matter what level of experience your reps have, the best ones are always looking to improve. This is where valuable and consistent one-one-one sales meetings come in. Unfortunately, most one-on-ones don’t live up to expectations.

“How many managers, coaches and mentors have you had in total? What percentage of them were actually transformative to your career?” Tyson asks. “You can probably count the ones that have had a huge impact on one hand.”

There are 4 key areas where the majority of one-on-one sales meetings fall apart. Do any of these sound familiar?

  1. Too much time spent reporting the news;
  2. Lack of accountability and follow-up;
  3. Lack of value to the rep;
  4. Having an interrogator instead of a coach.

Trap #1: Reporting the News

Anthony Cessario from Clari has termed this the “Ron Burgundy effect,”referring to the fictional TV anchorman played by Will Ferrell in the Anchorman movies. “Ron Burgundy's either being asked to show up to these one-on-ones or just showing up uninvited, and all he was really doing was reporting the news.” In other words, he comes in, sits down, and just reads off his teleprompter.

In one-on-one sales meetings, Cessario says “reporting the news” means a rep will show up with a list of deals and go through each one, line by line, giving the manager an update on every deal. It can be a painfully grueling process.

By the time the rep and the manager get through the list (if they're even able to), the 30-minute call is over and there is no time left for strategy or discussion of next steps.

“You certainly don't want these one-on-ones to be like that,” Cessario continues. “Unfortunately, because of the lack of visibility most frontline sales leaders have, they're being forced to ask the rep to report the news. That gives you such a small window to actually focus on more strategic coaching.”

Further, without solid data to ensure accountability, you can end up with the entire one-on-one sales meeting taken up by storytelling. Alex Kremer from Outreach says, “You ask a sales rep about a particular deal and where it's at, all of a sudden, you realize that they've been just telling a story for 5 minutes that's not necessarily relevant to the deal.”

Instead, employ some tips to use one-on-one time more productively.

Trap #2: Lack of Manager Accountability and Follow-Up

It’s not just reps who need to come prepared to one-on-one sales meetings. Managers also need to be accountable. Kremer recalls dreading his one-on-ones with a manager at a previous company because each week his manager would simply ask him “what’s up?” — having seemingly forgotten what their conversation was about the previous week. “He’d forgotten what my action items were, and it was very apparent he was not taking this seriously. Why the heck should I be taking this seriously?” Kremer says.

Trap #3: Lack of Value to the Rep

In order to be effective, one-on-one sales meetings need to provide real value. Otherwise, you’re just “checking the box,” as Kremer puts it.

Even experienced reps want value from their one-on-ones, Tyson stresses. “When I was on that side of the table, I was extremely hungry for coaching and feedback every single week,” she says. “I was a top performer but that did not mean I was satisfied with hearing the response of ‘you're doing well; you're on track.’ I knew that I could go further. I wanted to learn more. I was really hungry for that sort of feedback.”

Trap #4: Auditor vs. Coach

The fourth trap that many managers fall into for one-on-one sales meetings is taking on the role of an interrogator rather than that of a sales coach.

The more experienced the rep, the less time they want to spend discussing transactional details and weekly progress. According to Cessario, “They just want to call me and get coaching. So, for me, the major crack is that managers are coming to these meetings without a point of view.”

4 Key Components of a Successful One-on-One Sales Meeting

While these traps may be all too common, there are solutions to these pitfalls. According to our experts, there are 4 key components of a successful one-on-one sales meeting:

  1. Review the (right) data;
  2. Deep dive into the deal;
  3. Drive deal strategy;
  4. Develop skills and coach.

Tip #1: Review the (Right) Data

The first part of a successful one-on-one sales meeting starts with reviewing the right data.

Cessario explains that his team leads with the forecast: “Our forecast is in real time. We have the real roll-up in front of our eyes,” he says. “So, I spend just a few minutes making sure I understand any changes in numbers with my team. Maybe 5-10 minutes, at most, making sure we're on the same page with how we're rolling up our forecast.”

Instead of spending time reviewing numbers and processes that can be automated, look at relevant deal data or, even better, look at it ahead of time so you can come to your one-on-one sales meeting with a point of view instead of waiting for the meeting to inspect it.

Tip #2: Deep Dive on Deals

After reviewing the right data, it’s time to dive deeper into the deals, particularly when coaching newer reps. “We do a rigorous, streamlined, consistent framework for diving deep into a deal,” Tyson shares. “And I highly recommend doing something consistently so that you can cut right to the heart of the matter rather than hearing the story or hearing the news.”

She continues, “We look at things like op creation, pipeline value, lost deals, the reasons why deals are lost, activity metrics. And then we also look at leading indicators of success, like talk-time ratio on calls, engaging questions.”

We’re partial to the 4-point deal inspection, which is a tried and true process for quickly seeing the health of a deal.

Tip #3: Drive Deal Strategy

Deal strategy should be a huge focus area for both new and seasoned reps. This involves taking a step back and asking the right questions to look at the macro view, or big picture, such as:

  • Are we driving the revenue bands that are important to us?
  • Are we creating pipeline?
  • How are we tracking against our longer term deals?

The focus is not only on next steps, but also on what the end goals are, and how to get there down the road.

Tyson uses what she calls the AAA plan — answers, action and attitude — to help drive deal-strategy discussions. “Answers: What answers do you need to get on this next call? Action: What action do you want the prospect to take coming out of the call? And Attitude: How do you want the prospect to feel coming out of that next call?”

Tip #4: Develop Skills and Coach

“Reps crave to be coached,” Kremer says. “They want to know how to close better. They want to know how to demo better. They want to learn how to ask better and stronger open-ended questions.”

But it’s critical not to overwhelm reps, he adds. “If you give them like 5 to 6 items that they need to work on, that they could improve, at the end of the day they're not going to do any of it. So be very prescriptive and specific in one thing to work on. Once they prove that they've mastered it, we can move on.”

Cessario shares that development is just as crucial for enterprise reps. “Twice quarterly we focus exclusively on development,” he says. “We'll get together live in a one-on-one sales meeting, and we'll spend that entire one-on-one focused on developing for performance as well as career development.”

More Tips

For more valuable tips on how to improve your one-on-one sales meetings, check out the full webinar here.