TALKING SALES 92: “Are you a Square Peg Sales Manager?”

Square Peg          “Don’t be a square peg sales manager in a round hole” – Discussion with John Smibert


In this conversation Tony Bonanno uses a word picture to help us understand the issues that many of successful salespeople have when we become a sales manager.

TB Pic 300x300 Sept 2015Tony explains that sales skills (the square peg) are important for a sales manager to possess. However when we put that square peg into a round hole – i.e. the sales management skills required – the peg will fit if the round diameter is the same as the square diagonal. however there will be lot’s of gaps around the hole. This depicts the many skills that are required in order for the sales manager to be rounded out in order to successfully manage sales people.

Tony goes on to emphasise that the motivation of a salesperson to move into sales management is critical. Get the motivation right and the skills and attributes to manage well can be developed.

Salespeople need to think very seriously about whether they really want to move into sales management, and if they do, they need to understand it’s a very, very different role. They’ll need to develop different skills to make sure they develop a round peg set of management skills

See the interview below for more.insight from Tony on developing  sales management capability.

Tony Bonnano is a thought leader in sales management, sales growth and behavioural change

See more of the ‘TALKING SALES’ series here


John: Hello, I’ve got Tony Bonanno with me again – welcome back, Tony!

Tony: It’s good to be here, John!

John: Tony, we had a nice discussion offline about square pegs, round holes, and we were talking about the skills of salespeople and sales managers. Could you share some of your thoughts with the audience on that subject?

Tony: Happy to. The concept of a square peg in a round hole is a nice word picture that we can work very well with, and if you think of a square peg trying to fit into a round hole, it can fit.

John: Provided the peg’s small enough.

Tony: Yes, if you’ve got the diameter of a hole and the diagonal of the peg, it’ll fit, but what you’ve got missing are some bits around the peg where there’s something missing, something’s not there.

John: Sure.

Tony: And in the case of sales management, a salesperson moving into sales management, those could be the missing skills, the skills that they don’t have when they are in a sales role that they need when they are now in a sales management role.

John: So taking them back to the sales role, they’ve probably been a very successful salesperson and it really was a round peg in a round hole; now they’ve been taken out and they’re in sales. And it’s a classic issue, isn’t it?

Tony: It’s very common.

John: Okay. So, what’s the point of talking about square pegs and round holes then? What do we do about that? What’s the issue?

Tony: Well, there’s two ways of looking at it. For some salespeople the desire to go into management may not have anything to do with their ability to sell, it may not have anything to do with their success, and perhaps their path should be to stay in the sales role because that’s what they do best. But if they are going to make that transition from sales into sales management, they need to think very carefully about what has to change, what conversations have to change, what skills they have to develop. In essence, when you’re talking about selling there’s a given set of skills, and it’s about managing the sales process; when you’re talking about sales management, it’s about managing people who manage the sales process, and that’s a different ball game.

John: And you’ve got to be a leader, you’ve got to be a coach, you’ve got to be a manager of spreadsheets… [laughs]

Tony: Unfortunately.

John: And CRMs and data, and manage up as well as manage down, all that sort of—totally different to selling, isn’t it?

Tony: And a lot come undone when they go there.

John: And it’s really interesting that we build this… I think it’s less now, but we used to encourage people to go up the hierarchy in organisations, and the reality is those people would be a lot more value, both to themselves and to the organisation and their customers, staying as salespeople – I agree with that. So we really need to look at the aptitude of people, and whether they’re suited to be managers versus salespeople.

Tony: I think the salespeople, John, need to look at their motivation for wanting to go down that path before we look at their aptitude, because if their motivation is the right one, then we can work out how to skill them up appropriately, but if their motivation is, “Well, I was a great salesperson. I can go and make other people great salespeople by copying what I do,” that won’t necessarily work.

John: It’s not going to happen, it’s not going to happen. I can tell you now, it’s not going to happen.

Tony: That’s right.

John: In my experience, they have to learn how to be good coaches and managers, and just because they think they can do it it’s probably not going to happen.

Tony: Yes, that’s right.

John: Okay. Square pegs and round holes, and basically if I’m a sales guy and a really good sales guy, think very seriously about whether you really want to move into sales management, and if you do, you need to understand it’s a very, very different role, and you’ll need to develop some skills to make sure you do have a round peg management set of skills.

Tony: And salespeople should put their hand up and say, “I need help.” if they want to go down that path.

John: Great advice – thank you very much, Tony!

Tony: Pleasure, John!


More interviews with Tony Bonanno:


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John works with companies who are striving to grow high margin revenue by retaining customers, creating value for customers and strategically acquiring new customers. He loves successful and happy sales teams who are driving positive change for their customers. He coaches sales professionals who are keen to enhance their career. He helps them develop their skills and capabilities and enhance & leverage their personal brand.

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