Try On Their Shoes To Become A Better Salesperson

Author: The Humble Sale
Posted: July 7th, 2021

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Looking at the world through the eyes of your prospects or customers can strengthen business relationships and improve Sales outcomes. Forgive the cliché, but it really is a case of trying to put yourself in their shoes!


Recently I was asked about the one piece of knowledge I wish I’d had passed to me at the very start of my sales career. One of my thoughts was to recognise that every single person I would be selling to is a complete individual. A unique human, with their own pressures, likes, anxieties, comfort factors, flaws, strengths and so on.

Over the years I’ve worked hard at trying to treat everyone in my professional life as a true individual, especially customers and prospects. As a result, my business relationships have been lengthy and built on mutual understanding and trust. Sometimes even friendship.

It takes practice, but when you really start to look at the world from someone else’s perspective, sit in their chair or try on their shoes, you find better ways to shape your approach and get to a successful outcome. Here are some ideas that have worked for me over the years.


Consider Their Working World

Many times I’ve heard salespeople curse what they describe as a difficult prospect or prickly procurement person. Sometimes there may be an element of truth in this, after all not everyone is decent. However, it is more often the case that the salesperson hasn’t taken the time to truly understand their working world and the environment they’ve stepped into.

So try and look at things from their perspective. What is their job role and what type of company is it? What does this mean their likely time pressures or priorities may be? Do they manage a large team or a small team with a lot on its shoulders? Are there any pressures on their work at present (other large projects to juggle, business performance, etc)? What are their company goals and what role does their department have to play in them? Once you understand these things it’ll put the problem you want to help them solve in context. You can then empathise, take a realistic view on how much time they can dedicate to you or it and shape a plan that supports (rather than battles) them.


Research Them

Not their professional self – them as a human. In addition to understanding their working world you also need to take the time to understand factors at play from their personal life. This take sensitivity. Some things they’ll reveal to you through conversation, other things as you build trust over time. Further facts you can glean from their online presence or finding out about them from mutual connections.

It could be that the buyer who was short with you yesterday was worried about being late to pick their kids up. They could have been juggling a health crisis. Especially during 2020, everyone’s worlds have become a little more fraught, so cut people some slack and be considerate and patient.

Research can also tell you things like their interests to help find common ground for discussion or identify topics they know about which could be useful to frame a conversation or analogy around. You may even have shared interests which can help your professional bond grow stronger.


Display Curiosity

I talk about this a lot I know. Being curious and both preparing and asking meaningful questions is key to Sales. Really work at this. If you ask a barrage of questions it’ll do damage without a decent conversation around it. Show interest, genuinely. Listen actively. Then remember things. Don’t find out the name of someone’s children and then forget next time you meet them. Make notes to ensure the knowledge goes in. Then as you build up this more and more detailed picture of their professional and personal lives – try on their shoes.

Imagine yourself in their world again, but now what you know is more detailed, you have better context and it’ll help you provide better help. You’ll be a better salesperson. One who displays empathy and a genuine desire to do good.

(Interestingly all of this applies to Sales (or any) Leaders too. If you take the same approach with your team, you’ll better understand their motivators and be able to provide more useful coaching and development to get them to their goals.)


Offer to Share the Burden 

As you understand more about where your prospects or customers need help you’ll discover more opportunities to take away the pressure from them. Your deeper understanding of everything they are juggling will enable you to see what is holding them back. Therefore, it can be really effective to offer to share their burden. If you know they need to complete several tasks before the sale you are working on can progress, offer to do some for them.

If you know they need to gather opinions or perspectives from other colleagues regarding the problem or your proposition, offer to do this for them. You could meet several people in the organisation, learn more, get more entrenched and report back to your contact when done. It’ll help you build trust, look professional and credible and you’ll have done them a favour. There are many ways you can help, from a simple task of compiling a spreadsheet to standing alongside them to help deliver change. Whatever it is, roll your sleeves up and get involved.


Look at Your Proposition Through Their Eyes

Finally, if you get really good at looking at the world through someone else’s eyes, eventually you’ll glance over at yourself. You’ll be able to get a sense of how they might view you or respond to your proposal or solution.

It takes practice but it should help you hone your ability to judge whether or not you really have a chance of helping them and thereby securing the sale. If your evaluation through this new super-honed lens is that you can’t, it’ll give you an early exit. You’ll save time to move on to the next opportunity faster and they’ll respect your honesty when you identify that actually another person or company may be better placed to help. Why not even suggest a couple? That is utterly selfless and they’ll remember you for some random future day at the same company or beyond as someone who just wants to help them. Your phone may ring when you least expect it…


For more information, please visit The Humble Sale.


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Curiosity , Research, Relationship