Be Prepared & the Charlie Munger test

May 27, 2025

 In my last blog Don’t be like Scott- be like Shackleton | LinkedIn I wrote about the difference between the failure of Scott of the Antarctic and the success of Roald Amundsen in reaching the South Pole and bringing all his team back alive. It came down to two key things: preparation and the 20 mile march. I’ll look at the latter next week but preparation is absolutely key and is often forgotten, ignored or deprioritised. This is always a mistake. The last time you want to be trying something for the first time is when it really matters.

One of my favourite sales trainers, Jack Daly , frequently  starts training sessions by asking why US football coaches often talk with their hand in front of their mouths or with a piece of paper screening their mouth. The answer is so that no one can work out what plays they are calling. His point is that for every single play, offence or defence, there should be a tried and tested counter play and the same should be true in all sales. This doesn’t just apply to sales but to pretty much everything. Whether it’s a conference keynote, an after-dinner speech, a product presentation, an investor meeting or a sales conversation, practice makes perfect. While it’s clear what the benefits are to practice when it’s a one-way presentation or monologue, like an after dinner speech or a keynote, the benefits of practising an interactive dialogue are often ignored. Nowhere will this hurt you more than in business and especially in sales.

By failing to prepare, you prepare to fail is a well known cliché and like all cliches it is also true. Imagine you have a big deal that you are hoping to close. Maybe as a bootstrapper this will provide the cash flow funds you need for the next six months. Maybe it will get you out of an existential hole and stop your business going under. The pressure is on. I have personally been in this situation many times and witnessed others going through it. The best approach is to apply what I’ve always called the Charlie Munger test. Charlie Munger was Warren Buffet’s business partner and famously said that if you want to best work out how to defend something then first work out all the different ways to attack it. This will invariably lead to working out the best way to counter the attacks and successfully defend it. This is key.

 You need to work out not just every objection that you are likely to get but also what the answer should be to the questions or objections you really don’t want to be asked. Once you have worked out your answer to the worst and most difficult ones then you need to practise them and not just practise them but do so out loud with another person. This is really important as you will be amazed at how different words sound when spoken out  loud as opposed to when just run through them in your head. Once you have practised the answers so you can say them without thinking Spot the gorilla playing basketball! | LinkedIn then you will be in a place where you have a chance.

 Invariably the meeting or conversations are rarely as bad as your worst fears. However, by making sure you have an answer even for the most difficult ones you put yourself in a good position to be able to handle all the objections confidently, assuredly and leading to the outcome that you want. When it’s a big deal that will enable your business to survive then usually there is a chance that this will happen as a matter of course but I am always amazed about how this is not common practice even then.  What I find shocking is that whether through laziness, arrogance, over confidence or simply not thinking its really necessary , this is rarely done as standard in sales conversations.

 This should be mandatory for every single sales conversation that you have and should be run through on a daily basis. Think back to Jack Daly and his point, correctly, is that there should be no objection that you get that you have not been able to anticipate and have an answer ready for. There is simply no excuse to be caught unawares. The entire point of a scripted pitch is that you know exactly what you are going to say and as a result should know or be able to anticipate every single possible response and objection you are going to get. These can then all be practised on again and again until they are embedded in your brain and ensuring that you stand the best possible chance of success. As I said at the start the last time you want be doing something for the first time is when it matters.

 This isn’t just for sales either. When you’re bootstrapping and still tyring to find product market fit this is a really important team practice. Involve the product people. As you work through all the objections you’re getting as well as the potential answers this gives them a chance both to understand issue with the product, what is a must have vs a nice to have feature and to also understand what the sales process is. This is crucial for your team culture. If product and sales don’t understand clearly what the other does then you will encounter problems and misalignment especially when the stress levels and workloads increase, which they inevitably will. Misalignment of goals will lead to at best a stalled business and at worst a business that no longer exists.

 As Scott of the Antarctic found out there is no excuse for lack of preparation and the consequences can be dire. After every sales or business conversation and meeting you should be asking yourself a number of key questions:

1.      Did I do everything I could to prepare and practice? Was there anything I could have practised more? Did I fail to anticipate anything?

2.      What dd I learn from that? How can I improve?

If every day you’re not learning and hence improving, then you’re just wasting your time. Preparation and practice is key- success won’t come without it.unger test ( May 27th)