leading successful sales one on one meetings sales training toronto

As a leader, your time is already stretched. You’re being pulled in several directions at once, overseeing multiple projects, implementing new initiatives, and ensuring your team is on track to hit their targets. With so much going on at once, who has the time for one-on-one meetings with every member of your sales team?


You do!


That’s right – if there is one non-negotiable fact about leadership, it’s that meeting with each person on your team individually is crucial to the team’s overall sales success. Group meetings, daily chats, or emails you exchange consistently throughout the week cannot substitute for one-on-ones where you can conduct a pulse check, see how they’re doing, and directly set them up for future success. And be sure to conduct these meetings in person or by video call so that you can see each other and pick up on body language cues.


Getting started with one-on-one meetings


From the most successful managers I know, I’ve heard things like this:“These one-on-one meetings have such an impact on culture and performance, that my effectiveness as a manager, along with the team’s sales results, significantly improved once I perfected them.


From my first-hand experience, I completely agree with this. I’ve worked with companies who didn’t regularly have one-on-one meetings with their salespeople, only to be completely sold on the idea once they tried it and saw the results.


Many companies struggle to get started, not knowing how often to hold these meetings, or for how long they should last. With relatively new team members, I recommend holding one-on-ones every week. This helps onboard them to your sales philosophy and activities more quickly, and prevents them from spinning their wheels.


Since new people need more of your time, be sure to schedule them well in advance in both of your calendars – and don’t cancel them. If you get in to the habit of cancelling these meetings, you lose credibility and your positive culture of accountability takes a hit.


After your new team members settle into their roles, you can consider scaling the meetings back to only bi-weekly. However, if you feel that their performance begins to lag, take the initiative to start meeting more often once again. Be flexible as things as constantly changing out there.


More experienced salespeople still need to meet with you regularly, but frequency is impacted by your sales cycle, the complexity of your business and product offering, and the skill, experience and track record of the individual. Bi-weekly seems to be a sweet spot for these one-on-ones, because monthly is too long a span of time, even if your sales cycle goes up to or beyond a year. I think of meetings like this as tuning a radio dial – that is, helping to finely tune the activities of your salespeople, ensure they are on the right track along with showing them your support.


Luckily, we have technology that allows us to conduct meetings from virtually anywhere, so if one of you is unable to meet in person, you can do so virtually through Zoom, Microsoft Teams, or other video conferencing software. Be sure to keep the focus on your team member, and don’t conduct the meeting while on the go or driving the car. Both of you should be sitting in a quiet place in front of your computers with all other apps closed, or face-to-face in the same room.


These meetings should be 45 minutes to an hour to give each person the individual attention from you they need to succeed. However, with a junior team member you may find you need to help them with specific opportunities, which may extend the time of the meeting. And that’s okay – give them the extra time if they need it. The investment will pay off in the long run as your newbies move up to join your roster of “A” players.


Even then, you’ll still need to meet with them, and they’ll be looking forward to it even more. John Wilson of CEO Global Network says, “Your A players want time with you.” I say,“and they need it!”


Start With My 3 Favourite Sales Metrics


So now that you’ve booked your one-on-one, and your team member is sitting across from you, what do you talk about?


I always recommend that you start the meeting with my three favourite metrics:


  1. Sales YTD vs. Goal = to give you the gap that is remaining to sell in the period (month, quarter, year)
  2. Pipeline value to address the gap
  3. Activity to fill the pipeline


Here is how I define the interrelation between the three metrics:


The activity should support (fill) the pipeline, which supports (adds to) the sales.


This meeting is intended to focus on results initially, and by opening with a discussion of these points in this order, you’ll achieve this objective. Conversely, if you start by talking about activities, the discussion could turn into micromanaging the activities themselves, which isn’t conducive to your meeting’s objective.


When you turn to reviewing the activity component of the meeting, you can ask these two questions:


  1. Tell me about the new deals you’ve added to the pipeline since we last met
  2. Which deals have you moved forward since we last met?



Start booking those one-on-one meetings with your salespeople this week and stick to them. After a while you’’ start to wonder how you ever managed without them!


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