Building your coaching schedule:
The best managers focus on making sure their team gets better every week. However, getting better doesn't just magically happen, you need a playbook to make sure your team has a structured way of getting better every day.
Here's a weekly schedule you can follow with your sales team to ensure they're getting 1% better every day. This method works best when you're working together on skills as a team but the same process can be followed for coaching your team 1-1.
Monday:
15-min meeting to discuss the key thing they're going to focus on improving that week. It's important to choose one main focus, because any more than that will be distracting, and they won't end up making progress on anything.
Once they choose the skill, have them write it down, along with 3 actions they'll take. Also it's important that the sales rep is choosing the skill they want to focus on, not you as the manager. You can help guide them with good coaching but ultimately they have to own their skill improvement.
Here's an example a sales rep could use:
"This week I'm going to ensure that I have defined next steps on each sales call. To do this I'm going to first, set a silent alarm that goes off 5 mins before the end each call so I get alerted to wrap the call up and ensure there's enough time to agree to next steps. Second, I'm committing to 100% adherence to updating my CRM with defined next steps (and next step date) for every meeting I have). Third, I'm going to message my manager at the end of each day, listing out each of my meetings, along with the defined next steps.
Tuesday:
Read 2 articles on how to improve that skill. You'll always get a few ideas you hadn't thought of and will keep up the momentum. You'll be surprised how quickly you can get great ideas on nearly any skill just by simply googling "How to get better at _____".
This is one of the easiest hacks to get ideas on skill improvement.
Wednesday:
10-minute check in (ideally on the calendar) to just talk through road blocks, challenges, & wins you've had over the last couple days. This is the best opportunity for battlefield coaching because typically the rep will say one of three things:
Thursday:
Thursday is the 'team day'. This is a chance to share with the team what you're working on and get their advice. This typically is best done in one of two ways.
The casual lunch chat: Everyone grabs their lunch and either gets together in a room, or on a Zoom call, and you simply casually go around the room and everyone shares what they're working on, their wins, and their losses. This is the chance for the team to bond and commiserate so it's important that this is a casual conversation and that you stay quiet. If you talk at all, you're just facilitating. After a team member shares a roadblock you could say something like, "Hey Jenn, I know you we running into the same issue a couple months ago, how'd you deal with it?"
Team war room: This can take a few different forms. You can get the sales team together to listen to a call together and then discuss how the rep is applying the skill. Another option is to have people bring a few examples of areas they're struggling with and have a chat around the table. Just like the lunch option, it's important that this is casual so that people feel comfortable enough to open up to their team.
Friday:
End the week with reports and reinforcement. Use the same doc that you used on Monday two write down your weekly goal and plan, however this time you simply recap how you did.
Ideally you take a few minutes to review each team member's results with them, it's important that this is a live conversation (phone or Zoom are fine). They should know they're going to need to report back to you on Friday, sometimes just knowing that you're going to report back will give that extra motivation/reminder to push through.
Here your role as a manager is to help your teammate feel like they made some positive momentum that week. This is a great way to send them into the weekend on a high, feeling great about the work they accomplished that week, and will set a better tone for them coming back on Monday.
Time to celebrate:
Lastly, be sure to celebrate some of the key wins across the team before you break for the weekend. I've seen this done as a casual Friday drinks chat where everyone grabs a couple casual minutes before the weekend to celebrate their wins, sometimes I'll just send a few highlights to the team via email/Slack/etc. I've also seen managers record a quick video to the team, wrapping up the week, and highlighting the wins.
The key here is that everyone feels some great momentum going into the weekend.
I promise you that if you can build a schedule like this your team will become unstoppable over the course of the months, quarters, years. Try it out!