Every sales manager we talk to says, "I coach my team all the time." But their idea of coaching often means quick hallway conversations or phone calls, pipeline reviews focused on opportunities that can close right away, or ride along coaching calls where the manager dominates the conversation and the salesperson just watches. Rarely do sales managers have structured, focused, consistent coaching conversations focused on development rather than production. That’s where we step in to teach them a better coaching methodology. And the sales managers who implement our coaching methodology can make tremendous progress almost immediately. They get better at asking coaching questions and the whole sales team starts gain momentum as a better coaching rhythm is established. And then - usually around three or four months into establishing that rhythm - they hit a wall. Usually we hear something like, "I think we're losing momentum. It's not working as well. "
Almost always, it turns out 
that the manager has fallen into a rut. They've become predictable. They're going through the motions and their sales team knows it. What happens is, they start to ask the same handful of questions and use the same format week after week. They start every coaching conversation the exact same way, the salespeople know what they're going to ask before they ask it, and they're absolutely sure which direction the manager is going to go. Your sales team can just go through the motions and think, "Okay, he's going to ask about this, this, and that. I'll have those answers. We can be efficient." When that happens, the manager will say to us, "We're losing momentum. The coaching calls are getting shorter."
The way to avoid falling into a coaching rut is to make sure your sales managers mix it up. Change up what they're asking. They've obviously got to cover similar topics week to week. For example, in a weekly, structured coaching conversation, they know you should take a look back and say, "Tell me about the week that just passed. Tell me what's going on with your sales pipeline. Tell me about your calendar. Tell me about any challenges you have." A lot of sales managers will ask the same backward-looking questions instead of mixing it up, so coach your sales managers to be more intentional and change the question focus. Have them try asking more specific questions such as:
- Tell me about the call that you were most excited about that didn't turn out like you expected.
- How about a call that you had no hopes or expectations for that actually turned into gold?
- Which meeting are you most excited about from last week? And why?
- Tell me about a call where you met another key decision maker or influencer.
- Tell me about the call that was an absolute disaster. What did you learn that you can apply going forward?
In these examples the sales manager is still looking back at the week that just past. They're asking the salesperson, "Hey, tell me about your week," but instead of being generically predictable they're keeping the salesperson on edge by asking very specific questions about their week and what they learned. And when your sales managers do that consistently, slightly changing the focus of their questions from week to week, the coaching conversations stay fresh and the team keeps making progress.
If your sales leaders ask generic "how did your week go?" questions they'll get generic (and unhelpful) answers like "pretty good." Instead, the coaching conversation should explore potential areas where a salesperson may struggle and make mistakes. And speaking of mistakes, if you have salespeople who aren't making mistakes fairly regularly, they're probably staying in their comfort zone. They're probably not trying new questions or new techniques. They're just going through the motions. When your sales managers have regular, consistent coaching conversations that discuss mistakes salespeople make (and lessons learned), disastrous sales calls (and lessons learned), calls that the salesperson thought would be easy that turned out to be quite hard (and lessons learned) as well as calls they expected to be difficult that turned out great (and lessons learned) they create an environment where making mistakes (and learning from them) is not only acceptable but regularly encouraged.
The second part of that conversation - the "lessons learned" part - is crucial. It has to be, "Tell me what you learned from it. Tell me what you're going to do differently next time. Tell me how that made you better as a salesperson." Then, if it’s a good example and your salesperson is comfortable with it, "Hey, would you mind sharing that at the next sales meeting?" is the next step.
A great way for your sales managers to reinforce the "lessons learned" in their coaching conversations is to ask about future goals as well. It sounds like "Tell me about the week or the last two weeks, and then let's look forward a week. Looking at your calendar, what call are you most nervous about, and how can I help you?" Or, "Looking at your calendar, what are you most excited about next week, or what deals absolutely have to move forward next week?" Mixing up your conversations in this way does a couple of things. First, it makes it more interesting for the sales manager. You're going to explore different areas and find different weak points in what that salesperson is doing or not doing. Second, it's also going to keep it fresh for the sales person. If they come into a meeting and they're not exactly sure what direction the sales manager is going to go, it's not predictable for them. They have to stay on their toes a little bit, and they have to be ready to go whichever direction the sales leader takes them.
If your sales managers are getting in the habit of establishing a consistent, structured, coaching conversation – which every sales manager absolutely should do – ask them how they're mixing up their questions and what they focus on from call to call. Make sure that they're not just following the same agenda week after week after week, because you will absolutely find them in a sales coaching rut and they'll be less effective as a sales leader.
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