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A Best Practice Guide for Sales One-On-One Meetings

Meeting individually with your team members is essential for guiding their professional development. Yet many sales representatives report that they receive little value from their one-on-one meetings.

There’s a reason for this: many sales leaders simply don’t know how to run coaching meetings effectively. Oftentimes, the meeting will be too unstructured to provide real value. Other-times the meeting can turn into the sales VP talking at a representative with little reciprocal dialogue.

To provide your team members with real value, you need to understand best practices for planning, executing, and following up on one-on-one meetings. Here’s a guide to get you started:

Priming meetings for success

1. Schedule regular meetings and stick to the schedule.

One-on-one meetings are most effective when they happen on a regular basis, allowing both parties to follow up on the conversation. Determine whether you want to have meetings weekly, monthly, or quarterly. Create a schedule that everyone can consult easily so you can avoid back-and-forth email chains about scheduling.

Then, you need to follow through. Once a meeting is on the schedule, it should be treated just as important as a meeting with a client. Although emergencies happen, cancelling meetings on a regular basis sends the message that you don’t really value your team members or their time. Similarly, establish a cultural expectation that team members attend all meetings as a scheduling priority.

2. Establish a cultural norm that the meetings will be about growth, not simply job evaluation.

Many sales representatives come to dread one-on-one meetings because they believe that the meeting is little more than a report card on job performance. To counter this perception, you need to demonstrate to your team that the meetings are to help them grow professionally. Establish separate meetings for performance evaluation, or devote only one meeting per quarter for evaluation. Otherwise, meetings should be focused on how you can help team members grow in their roles.

To ease team members’ nerves, it’s oftentimes helpful to begin on a positive note. Plan to begin the meeting by discussing a recent win. When people feel as though their accomplishments are recognized, they will be more open to frank discussion about their difficulties.

3. Use a planned structure for the meeting.

Some sales managers like to keep things casual. Perhaps they’ll begin with open-ended questions like “tell me how things are going” and see how things go from there. This is often mistake that will hinder the meeting’s potential.

Your employees like having a general idea of what to expect when they walk into a meeting. Establish a typical meeting structure and stick to it to the best of your ability. For example, you might structure a 45-minute meeting like this:

  • First 10 minutes: Overview of recent deals and other relevant information.
  • Second 10 minutes: In-depth discussion of important business items, such as a deal in progress.
  • Following 15 minutes: Discussion of long-term career goals and professional development.
  • Last 5 minutes: Recap meeting and go over the next steps.

While you may find yourself deviating a little from the structure on occasion, having a structure in place will facilitate smooth, productive meetings.

4. Plan to coach during the meeting.

Ideally, the one-on-one meeting should be an opportunity for managers to provide individualized coaching for team members. Most sales representatives—especially those with high drive—want coaching. In fact, more than 60% of sales reps say that they are more likely to leave their job if their manager is a poor coach. As a sales manager, you need to seize any opportunity to provide quality coaching. When done correctly, the one-on-one meeting can be a great opportunity to provide coaching that is tailored towards their needs.

While you may not be able to delve into in-depth sales coaching during the meeting, you should go into every meeting with one point you want to impart. You may decide on a single take-home point for all team members or, if your team is small, devise a unique coaching agenda for each sales representative.

If you can show sales representatives that one-on-one meetings offer coaching, they will come to see meetings as a valuable part of professional growth.

5. Prepare discussion points for each meeting.

Managers should go into every meeting with a basic list of bullet points that you’d like to cover. Coming in with a plan will help you to run a productive meeting that really touches on the most relevant and pressing issues.

More importantly, preparing for individual meetings shows that you are invested in team members as individuals. When you can talk intelligently about specific deals and situations, you can establish yourself as a credible coach and partner. Preparation also helps you lead by example. Sales representatives who see that you prepare for the meetings will start preparing questions and discussion points of their own.

To prepare your discussion points, review recent deals, KPIs, and your notes from previous meetings.

Conducting an effective meeting

6. Be fully present during the meeting.

Few things are more irritating to an employee than sitting down to meet with a supervisor only to find that the manager is pretty much checked out. If you’re going to hold one-on-one meetings, commit to being fully engaged with the meeting. Turn your phone off and mute any notifications from your computer.

Besides eliminating distractions, you need to go into every meeting with a clear focus. Don’t think of meetings as just another hoop to jump through. Try to look at it from your employee’s point of view: this is a rare opportunity for them to receive undivided attention from their supervisor. Get yourself into a headspace where you can be really excited about helping this person to improve their skills.

7. Ask open-ended questions that delve into team members’ genuine experiences.

Although questions that are too open-ended lead to general and unproductive conversations, you shouldn’t try to exert too much control over how the conversation progresses. The questions you ask should be specific enough to spark a discussion, but still give sales representatives room to elaborate on the issues that concern them most.

If you really want your team members to speak honestly, ask questions that allow them to air concerns that might otherwise remain unspoken. For example, you might ask questions like these:

  • What’s the most challenging part of this job?
  • Which part of the sales process do you think could work better?
  • What are your favorite/least favorite parts about what you do?
  • What problems with our product have you noticed?

By asking open-ended questions, you can develop a deeper understanding of what your team needs from you and help them to resolve problems constructively. Communicate to team members that these meetings are designed to help everyone improve, managers included. No one receives value out of an “everything’s great” meeting.

8. Give sales representatives the opportunity to voice their own questions and concerns.

During every meeting, you should create opportunities for your sales representatives to ask questions. Encourage your team members to come in with questions, and establish a cultural norm of “no question is a stupid question.”

If a team member wants to take a meeting in a different direction based on a situation they’re dealing with, be open to the change. The fundamental purpose of one-on-one meetings is to provide sales representatives with the guidance they need, not to follow an exact formula. You might even encourage your team to email you ahead of time with questions or concerns they’d like to discuss during the meeting.

9. Express appreciation for team members’ contributions.

Sales representatives are more receptive to constructive feedback if their successes are recognized. Even if you’ve already congratulated the team member on a recent triumph, it never hurts to provide additional positive reinforcement during your one-on-one.

10. Discuss long-term career development.

The day-to-day grind of sales can be so overwhelming that it’s easy to lose sight of your team members’ long-term goals. To be proactive about long-term career development, build time for this topic into your meeting schedule.

You should learn about your team members’ goals in their first few months at your company. Keep in mind, however, that their goals might shift as they gain work experience. Continue to ask questions about career plans and take the conversation from there. By asking direct questions about long-term career development during your meetings, the topic remains at the forefront of their minds.

11. End the meeting with an action plan, including next steps.

In a good meeting you’ll constructively discuss issues—but a great conversation is useless without a clearly defined action plan. During the last five minutes of your meeting, make sure you discuss what needs to happen next. What follow-up actions does the team member need to take? What actions are you responsible for completing? How will you measure your success?

By ending with a plan, you ensure that the work you do in one-on-one meetings carries through and set yourself up for the next meeting.

Making meetings stick afterwards

12. Follow up with an email summarizing the meeting, including the plan of action.

Within one or two days after a meeting, send an email to your sales representative that summarizes all issues discussed during the meeting and what comes next. This will help the team member remember everything that happened during the meeting and follow through on the next steps. It also creates a handy cheat sheet for future meetings. Create special email folders for follow-up emails from each team member.

13. Get ready to resume the conversation during the next one-on-one meeting.

Once you’ve established regular meetings, they shouldn’t be treated as isolated events. Keep track of your records so that you can better integrate your meetings. If you discussed lead generation in detail during one meeting, the topic needs to be at least touched upon in the next meeting.

Over time, you can develop a sense of how team members internalize information discussed during meetings and what form of coaching works best for them. Use this knowledge to set the agenda for future meetings.

By following these best practices, you can make sure that one-on-one meetings aren’t just another item on the to-do list. When done well, one-on-ones can form the backbone of a strong management and coaching strategy.

James Meincke

James is the Head of Marketing @ Demodesk, the intelligent meeting platform for remote sales. Previously he was the Director of Marketing at CloserIQ.