What Should I Talk To My Manager About?

Most sales managers in complex B2B sales believe they are coaching their teams. Most salespeople don’t feel like they are being coached. Often, salespeople feel like it’s up to them to get the help they need, but they don’t really know what they need. It’s a no-win on both sides, and leaves many salespeople asking: “What should I actually be talking to my manager about?”

The good news is that it doesn’t have to be a mystery. What you need is a structured cadence of calls, based on the types of coaching your people need, and the right questions to ask in each. With a consistent structure, sales managers can focus on zooming in and zooming out on the right areas to genuinely help salespeople improve.

Your cadence will be different depending on your environment, but in most situations, the types of calls can be divided into employee development (personal goals, skills, and challenges), strategy, pipeline, deal, win/loss, and account planning and management.

Individual Development Calls

Every individual on your sales team has different strengths, weaknesses, goals, and motivations. Individual development calls help managers understand who each person is and create individual development plans that work for them. This is a “zoom in” on the individual and a “zoom out” on that individual’s larger perspective.

Good questions to ask include:

• What is your purpose in life? How does that align with what you’re doing now? Is there anything holding you back from that?
• What are your personal career goals? How does that align with what you’re doing now?
• Is there anything holding you back from that? What do you need in order to take the next step?
• How do you feel about your performance inside this position? What do you need in order to improve it?
• What skills and knowledge are you strong on? Where would you like to do better? What resources and support do you need in order to do that?
• What motivates you to go the extra mile? What do you want or need in this position that you don’t already have?
• What could you do more or less of and why?
• What beliefs do you have that may be holding you back?

Strategy Calls

In order to execute on it effectively, salespeople need to understand the company’s sales strategy as well as their own, and learn to align and take ownership and responsibility for them. This is a “zoom out”  Asking these questions can help sales managers help salespeople to get this right:

• What are the main outcomes you want to achieve in your role?
• What would success look like for you and the company?
• How will you know you’ve achieved that success?
• What needs to happen in order to get there?
• What’s standing in the way of that?
• Which clients do you find most valuable, and why?
• Which deals and accounts should you have stayed away from, and why didn’t you? How will you do that in the future?
• Interesting… tell me more about that.

Pipeline Calls

Pipeline coaching zooms out from the deal level, and zooms in on the individual’s pipeline. Without a structure, they often devolve to the manager saying: “You need more pipeline. Do more prospecting.” That’s not coaching, that’s just dictating. Instead, coaching should focus on asking open-ended questions that help the salesperson identify and solve their own problems. Questions like:

• How is your pipeline doing? Are you happy with its size and health?
• How would you like for it to be different?
• Why does your pipeline include these specific deals?
• Which opportunities in your pipeline seem the most promising to you? Why?
• Which ones seem less promising than you initially thought? Why is that?
• What has to happen in order to put more opportunities in the pipeline?
• What assumptions are you making that might be in your way? Could another assumption be valid?
• What happens if this large deal goes silent?
• If we look at your win rate, deal size, and sales cycle, what would you most like to improve?
• What can you do to improve them?
• Which stage of the pipeline is hardest to maintain momentum through? Why is that? What can you do to improve that?
• When should we meet to look at your progress on this?

Deal Coaching

Deal coaching zooms in from pipeline to specific opportunities and what needs to happen to move them forward. Good questions to ask include:

• Why should the prospect even care about our offering? Why should they care about the problem?
• Who are you talking to? Who should you be talking to?
• How can you reach the people you want to talk to?
• Who would you really like to have on your side? How can you get them on your side?
• What do you need from me or the company in order to move this deal forward?
• What would cause the prospect to do nothing?
• How will the competition try to take the edge? How can you prevent it?
• How strong is the status quo?
• What would make the customer leave the status quo? What might cause them not to? What can you do about it?

Win/Loss Call

Win/loss coaching can zoom in on specific wins and losses, or zoom out to the trends across the board. They can zoom out on the whole sales team or zoom in on individuals. During win/loss coaching, sales managers can ask questions like:

• Which of these winning deals are you proudest of? What did you do well? What do you want to repeat in future deals?
• Which of these archived deals did you think you would win, but didn’t? What went wrong? Was there anything you could have done differently?  Did we lose because of perceived risk or lack of value?

Account Planning Calls

Salespeople who manage larger accounts benefit from coaching calls that zoom in on specific accounts. Good questions for these calls include:

• What is the main focus for this company at the moment and how are we aligned to help them with that?
• What do we need to know bout this account but don’t?
• Who are our biggest champions and influencers within this account? Do we have any blind spots?
• Who would you really love to have on your side? What can you do to make that happen?
• Where are the biggest areas for potential growth in this account?
• Who are you talking to about those opportunities? Who do you need to be talking to?
• How can you reach the people you want to talk to?

Great sales managers don’t leave it up to salespeople to know what to talk about. They structure their coaching to touch on each main area, and structure each call to keep it focused and useful for the salesperson. When the manager is doing their job effectively, the employee won’t have to ask “What should I talk to my manager about?” They’ll already know, and be prepared to do it productively.

What are you doing to help your salespeople have productive conversations with their managers?