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The Sales One-On-One: Best Practices for a Critical Conversation

The sales one-on-one (1:1) is a hard conversation to do well. Too often, it just becomes a “how can I help” moment with little long-term value for the direct report. That is a huge wasted opportunity, as a 1:1 is one of the most effective tools a sales manager has to impact outcomes (that is, sales).

Let Them Guide the Meeting

The expectation should be that the direct report prepares for the 1:1. When run well, it is “their time” and the direct report should feel comfortable setting most of the agenda. It can be easy for supervisors to start directing or “managing” reps, but it’s important to let them focus the conversation on their needs and concerns. However, there should be a clear expectation that they come in with a set agenda. No one should be “winging it.” For a deeper dive on structure, check out former Intel CEO Andy Grove’s High Output Management, a classic on the art of getting the most out of high-performing teams.

Review Important Deals

Go through each major account, focusing on the next steps. “Trust but verify” that deals are moving forward by asking detailed questions about the near-term plan for each account. Don’t let reps get away with generic platitudes like “we had a great meeting.” Dig for specifics and let reps know that you expect them to come in prepared to discuss all of their deals. Keenan’s Gap Selling has a good discussion of 1:1 deal reviews and suggested questions to ask to uncover those missing details from your reps.

Track What’s Discussed

This seems simple, but it is critically important that both parties have a running record of the topics and goals being discussed in your 1:1s. (Pro tip: it’s nice to have a shared cloud-based agenda and set of notes to keep you both on the same page). Looking back on previous 1:1s is critical for accountability and guiding long-term growth in a rep. Check in on areas that need improvement and review rep numbers vs. benchmarks in each meeting.

Remember Professional Development

The 1:1 is a great time to discuss career trajectory and the skills needed to rise to the next levels. What do direct reports need to learn, to accomplish, or to demonstrate to do well in their current roles and move up to the next? Keep reps accountable by checking in on their progress toward those goals.

The sales 1:1 is often one of the most important ways managers interact with their team members. It’s a great opportunity to practice both data-driven coaching and the human element of sales mentorship. Being mindful and prepared for these conversations will go a long way to helping your team be successful.

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