Sales Execution

1:1 Sales Meeting Formats to Increase Sales Effectiveness

Headshot of Alex Kremer, Sales Manager at Outreach

Alex Kremer
Sales Manager, Outreach



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Photograph of two sales reps having a one-on-one sales meeting
Photograph of two sales reps having a one-on-one sales meeting

As a rep, I used to dread my one-on-one sales meetings. Every week I’d show up and my manager would ask me, “So, Alex, what’s up?” And that was about it. He seemed to completely forget the previous week’s conversation and action items.

If he wasn’t taking our one-on-one sales meetings seriously, why should I?

If you’ve ever been a rep, you know working your deals can sometimes feel like you’re stuck in a corn field. You’re head's down in execution mode moving forward and rarely do you stop to look up and ask, “Am I going the right direction? Am I even in the right corn field?”

Effective one-on-one sales meetings remove your reps from that tunnel vision and force them to ask themselves the right questions.

The question remains, how do we do this?

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Weekly Pipeline Reviews

During pipeline reviews, I make sure my rep and I have clear next steps on what’s necessary to move the deal forward. We’re constantly reaching back for the “arrows in our quiver” as we like to refer to it. What are arrows in your quiver, you might ask? It can vary from things such as sending the prospect swag, gaining executive alignment, or inviting them to an event/dinner we’re hosting in their city. We’re always looking for the best plays to make sure the sales process is moving forward and we’re continuing to establish a strong partnership.

Even if next steps have been established, let’s say a demo is already on the books, we’re asking ourselves what needs to happen between now and then to make sure they are excited for that demo. Or it’s brainstorming future action items — if we crush that demo, what’s the ideal next step?

It’s not enough to just think about what’s right in front of us, but instead to think of what’s to come. Always be one step ahead of where you can go with the deal.

Bi-weekly Coaching Calls

Most reps crave the opportunity to be coached. They’re desperate to know how to close better, demo better, ask better questions, negotiate stronger, and much more. We take the time to do that in our call-coaching one-on-one sales meetings.

We use a coaching journal to document a) what they want to work on and b) what I think they need to work on. During our call coaching, we’ll look at what we documented in our previous meeting, then listen to their calls in Chorus to see if they’ve improved.

For example, one action item might be to have a stronger opening statement and establish a goal of the conversation, while another might be to make sure they’re booking the next meeting while on the call (if possible). We’ll listen to calls two weeks later and specifically pay attention to both action items to see how they’ve improved. It becomes a running list that’s constantly evolving and growing. It’s amazing to look back and see how far reps have come.

Mentorship Meetups

Mentorship discussions are the one-on-one sales meetings I always wanted to have as a rep. These are proactive conversations to check in on the heart and soul. It’s important to take the time to ask how they’re feeling about their current state, where they’re trying to go, and make sure they feel they’re an integral part of the team.

Many reps are taken aback, saying, “Wait, you want to know about how I’m doing? You don’t just want to know about how my biggest deals are going?”

It’s these sorts of questions that make reps not just want to work harder, but also make them feel part of something bigger than themselves. As leaders, we’re here not just to create incredible sales professionals, but also to invest in our people beyond the workplace.

Stop Just Checking the Box

My one-on-one sales meetings are opportunities to provide legitimate value for my reps and stop just checking the box. I want my reps to expect to come out of our meetings with something tactical they can implement immediately. Now I’m not perfect (no, I don’t always have a well-thought-out agenda beforehand), but I always try to make sure they go back to their desks feeling stronger than they did before our one-on-ones.

These tips were originally captured in our webinar with Clari, Chorus and Outreach: Don’t Let Fake Sales News Distract You: How to Run an Effective One-on-One Sales Meeting

Author Bio: Alex Kremer is a Sales Manager at Outreach, a Sales Engagement Platform company that helps organizations drive efficiency and effectiveness for sales organization. In this role, Alex leads, trains, and mentors a team of 15 Account Executives as they work with organizations across the world. As a proven and successful sales leader always looking for the new challenge and opportunity to grow, Alex was previously a high-performing Account Executive for 6 years at both Outreach and Microsoft.

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