TALKING SALES 78: “5 coaching questions for sales managers”

coaching questions3          “The correct coaching questions a sales manager should ask.” –   interview by John Smibert. 

In an earlier discussion with Dean Kelly we discussed how sales managers – who want answers to “when the deal will close” and “how big it is” – should not directly ask those questions of the salesperson – these questions can lead to poor behaviour with customers. Dean said sales managers need to have a more customer focussed conversation with their sales team  – one that will coach the salesperson to have the correct type of conversation with their customers..


I asked Dean if he could discuss each of the key 5 sales management questions.

He outlined each question, the reasons why it is important, the outcome it should elicit, and how each should encourage good sales behaviour by the salesperson.


This interview is likely to be valuable for sales managers, sales leaders and the CEO, COO and CSO. Salespeople are also likely to get value by asking themselves these questions

See the full interview below to learn more.


Dean Kelly is the Sales Deal Mechanic.



John: I’m here again with Dean Kelly, the ‘deal mechanic’ – welcome back, Dean!

Dean: Thank you very much for having me, John!

John: Hey Dean, we’ve talked a lot about things sales managers should be doing to coach their people, and make sure their people are focused on the customer and not on our own internal needs. You’ve mentioned the five key questions that sales managers should be asking their salespeople.

Dean: Yes.

John: Can you just quickly go through those five? And then let’s share that on the Strategic Selling Group.

Dean: Certainly. So, the five questions that I start looking at is all about reinforcing the right conversation that the salesperson needs to have with the client. So, it starts with: What is the business problem we’re trying to solve? And obviously, as a manager you can coach to uncover more or less, and really gauge how good the conversation must have been that the salesperson had with the client, given the amount of information they can recall.

John: Sure.

Dean: The second one is: Who is that important to, what is their priority, and how will they measure success? That’s getting the salesperson to start thinking outside the box, that they may have been meeting with one member of the client organisation, but start thinking broader. Who else might benefit from that? Because that’s another value that you might be able to create in the mind of the client; that’s the second question. The third question is: Every organisation has an alternative to buy from, if it’s not you. Who are those? They could do it themselves, they could actually do nothing, or they could go with a competitor.

John: So, “who are those?”

Dean: Yes.. And working out, as a salesperson, or you testing the salesperson, what is their strategy to beat those, to nullify the advantages, the alternatives provide, and in order to get your value on to the table, which allows you to get more security that the deal will happen. So, that’s a critical one and number three.

John: Alright. Question four?

Dean: Number four: what is the value expression – or, in your language, the compelling event if you will – What is the value expression to compel the client to do a deal quickly? A lot of us give out this generic value message, and it’s around actually writing down what is the value message we want to give the client. It’s got to be relative to the alternatives, so showing our incremental, real-time value. It’s got to be expressed relative to the client’s business objectives, coming back to question one. And thirdly, it’s got to be expressed in the client’s measurement. How are they going to measure success, not how we’d normally measure success ourselves; very customer-focused messaging.

John: And really, is it compelling?

Dean: Absolutely.

John: And I like the concept of having an event that you’re also going to be in. Whether it’s a board meeting, or whatever it is; an event with a compelling driver, and an event that’s going to get it across the line.

Dean: Absolutely. It could be Christmas, it could be a rush time, it could be a holiday – there’s all sorts of things that you can tie into that, to make it…

John: End of financial year.

Dean: Absolutely. And then the last one – which I have been caught out myself on a number of occasions, not asking question number five – is: What are the buying steps the client must go through, and how are you managing them to turn this opportunity into revenue for our organisation?

John: Yes, it’s so important, because so often we focus on our own sales process and forget about understanding what the buyer’s journey is, what steps they’re going to go through.

Dean: Big time. Have they got budget? And it’s not asking them the question “What’s your budget?” because we all know that’s an unreliable answer, but it’s what are the steps they need to go through to either raise the budget, or perhaps even get more budget, if they haven’t got enough. And what are the steps, and how are you managing them? Who are you meeting with? Is there a cost justification? Is there a hurdle rate for ROI? It’s getting inside the head of your salesperson. How well have they really gone down that path, and understand.

John: And making sure they’re in the head of the customer, because…

Dean: Oh, absolutely!

***  Download Den Kelly’s guide to the 5 sales management questions here  ***

John: Then you’re asking the sort of questions that they should be working with the customer, and getting answers to them.

Dean: Now, these questions are ideal right at the beginning; these are qualifying questions. And quite honestly, if I’m meeting with you in the first two or three meetings, I’m within my rights to challenge the client and say “If there’s real interest here, what are the steps you’d have to go through in order to take this forward?“ And so it’s actually a good question that says to the client “I’m serious about this, and we’re in business to do good business for our clients, but I’m not going to be here begging for the deal.”

John: “And I’m here to help you go through those steps. I’m here to work with you as you go through the steps.”

Dean: Absolutely.

John: Dean, I love those five questions, and I know they do lead to lots of other questions. But if a sales manager, sales leader has got those five in their mind, and that’s where their focus is, on their salespeople, they’ll have their salespeople focused in the right context with the customer.

Dean: Absolutely – most important.

John: Love it. Thank you very much, Dean – look forward to the next time we talk!

Dean: Thanks, John!


More of Dean Kelly:


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John leads three related organisations, Custell, Strategic Selling Group and Sales Masterminds APAC. These help B2B selling organisations, who recognise the need to transform their sales capability, to respond to the tsunami of change that is starting to wash over us all. He works with people who recognise that to survive they must more strategically support their customer in their buying journey - and understand that they must become specialists in the customer's domain in order to be of value to them. He also helps sales teams build differentiated personal brands and leverage the digital and social worlds to engage to create trust and value.

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