Don't win the battle to lose the war!
- cgreen1609
- Apr 9
- 5 min read

Sales is about listening and it is about psychology. The end result must be that your prospect trusts you to the point where they feel comfortable enough that even if they don’t buy your product now, they will come back to you as opposed to others when they do need it.
Unfortunately, sales and sales people suffer from a bad rep. This is entirely down to the small section that not only believes that you should say anything to get the deal done but also in the pressure sale. As I wrote in my last blog Spot the gorilla playing basketball! | LinkedIn you should get to the point where your pitch/script and the answers to the objections are all embedded in your implicit brain. In other words, you don’t need to think about what you’re saying. All of your brain power is busy watching and listening to how the prospect is responding. Ultimately with enough practice this means that you will eventually get very good at selling what you offer. This is usually a good thing until it starts to lead to bad behaviours. The first of these is forgetting how to handle an objection properly.
It is not uncommon for a salesperson to get good enough at handling objections that they start to see it as a competition between them and the prospect. The objection becomes a challenge to be overcome and turned into a close so that the salesperson can ‘win.’ This line of thinking is disastrous for all salespeople but especially so for bootstrappers as it creates a state of conflict - a battle between you and the prospect.
An objection is often presented as an opportunity to close and it is- eventually. It is also an opportunity to further build your relationship, develop a greater degree of trust and help the prospect become more comfortable with you.
Any objection can be handled in 5 simple steps: agree, empathise, overturn, close and leave the door open. Most salespeople only attempt to do the third and fourth – overturn and close. By just doing these steps is where you win the battle and lose the war.
You have to remember that you are not the first person to sell to a prospect. This is not their first rodeo, especially in b2b sales. This means that they have heard similar pitches to yours before and are just as practised as you. They’re human beings and don’t want to be rude so as opposed to saying just an outright no, they will give you their standard objections; it’s not a good time, it’s not their decision, it’s expensive, they haven’t heard of your brand/ product, they don’t see how it works, etc
When they use these objections they are fully expecting you to move into overturn and close mode. They know from experience that it’s what most salespeople do. Just doing these two steps, overturn and close, immediately creates a state of conflict whether you like it or not. You and the prospect are now in conflict - you are in a battle over who will win the argument. This is why the first two steps are so important. They avoid a state of conflict
Step 1- agree with them. It will surprise them. Just as experienced sellers are only using their implicit brain to sell, experienced buyers are only using their implicit brain to object. They are expecting you to disagree and to overturn. They are not really paying attention to what you say as they have heard it before. By agreeing you surprise them. You have done something different, something they weren’t expecting and so they start listening.
Step 2 – empathise. Now that you have got their attention you have an opportunity to develop their trust and further build comfort with you. No-one buys when they are in a state of conflict. No-one buys when someone makes them feel stupid. You can avoid both of these potentially fatal feelings in your prospect by empathising. You’re just saying that you understand why they have their objection and that they’re not stupid for thinking or saying that. You’re making them feel comfortable with their objection. This stops any feeling of conflict. It starts to build trust. It further engages them. Most importantly it opens them up to listening to what you have to say in a positive as opposed to negative way.
You can then move through steps 3 and 4 but you must remember step 5. When a salesperson just does step 3 and 4, they inevitably create a feeling of conflict. When a salesperson skips 1 and 2 and step 4 doesn’t result in a successful close then the feeling between salesperson and prospect is by this stage antagonistic. This means they couldn’t do step 5 even if they wanted to and any attempt is a token gesture by both parties.
Step 5 is crucial in all sales but especially when you’re bootstrapping but it only works properly if you’ve done steps 1 and 2 at the start.
When you’re bootstrapping you are often in product development at the exact same time as you are selling. You are trying to get cash in and put food on the table as you look for product market fit. Step 5 is key. As you get direct feedback from prospects you are working with product builders to use this primary market feedback to further develop the product. You and your product person need this direct feedback from potential customers. once you get it you can iterate. This means that quite quickly you can go back to the prospect with new product features an developments that hopefully overcome their objections. In the early stages these can be quite significant and fast changes – the prospect will not be expecting either. people are trained to buy a certain way and you need to allow for this.
Imagine you go to buy a car and decide that despite the fact you like the car it doesn’t go fast enough and hasn’t got enough legroom in the back. You never imagine that the next day or week the salesperson will call you to say that the car now goes 10mph faster and has an extra 20 cm legroom. This exact situation is what happens when you’re bootstrapping and iterating quickly. This speed of product iteration is your superpower. The prospect will not be expecting it and therefore you have to make sure that you leave the door open for such a conversation. If at the end of step 4 you are locked in a gladiatorial combat then this won’t happen. This is why you need step 1 and 3 to set up a successful step 5. When bootstrapping never go for a hard yes / no close. It slams the door shut and means you can’t use your superpower – speed of product iteration.
Handling objections properly is key to both successful selling and bootstrapping. Ensuring that you correctly work through from step 1 to 5 will ensure you get better and faster sales results and applying the correct techniques in step 3 increases that even further. Next week I’ll look at these objection handling techniques like third party stories, political dodges and red towel vs blue towel but in the meantime remember- never win the battle to lose the war!
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