Winging It in Sales is Expensive and Risky

Is Winging It Your Sales Downfall?

Whether I’m working with a fresh-faced new seller or a seasoned pro, one thing that almost every seller does is “underprepare” for meetings and calls.

Even when they know I’m going to join them, listen in, or attend the meeting with them, they grab a blank notepad and dial or walk into a meeting. I’ve even had to round up a pen for them to use and encourage them to jot down notes in meetings. True story! (And don’t get me started about being in a sales coaching or training session and watching sellers walk in without anything to take notes on. Grrrrr.)

Some sellers are slightly more prepared than others with a brief check over of their notes – but most are just winging it.

“Winging it” is another term for “improvising.”

The funny thing about those improv masters is that they practice and prepare to be good at improvising and winging it.

They prepare for the unknown by sharpening their skills, practicing, and working through various scenarios. What looks so easy, unprepared, and off the cuff – is actually the result of their preparation.

Meetings or sales calls – aren’t they the ultimate Improve Stage?

WHO KNOWS how a phone conversation will go down or what will happen in a meeting!?!

I don’t.

Do you?

Do your buyers follow tight scripts and respond in predictable patterns?

Nope. No one does.

So, while I’d like to imagine that most seller’s lack of preparation is because they are mega confident, I think it’s more likely they’re not prepared because they’re not thinking about WHAT they want to get out of the meeting or the call. They just do it and hope for the best outcome.

Experienced or fresh to sales (or business, or fundraising, recruiting, WHATEVER) – you know you need to reach out, make calls, go on meetings, and bring in business … but doing it with thinking and planning for the end result is a lot like showing up for a race but not knowing where the course is or how long you’ll be running.

Prepare for calls and meetings based on the outcomes and next steps you’re trying to move to.


Write down your questions, talking points, and potential next steps for various outcomes.

This ONE simple act – thinking our meeting/call through and writing down our talking points or questions – is a huge differentiator in a seller’s success.

I can tell you without a doubt that a seller that prepares this way is going to come out of a meeting knowing where they stand and what the next moves are …

Compared to those that wing it – who lose the path, lose focus, and don’t always get what they needed out of the meeting.

Look, our brains were actually NOT meant for holding on to information. They’re meant for thinking and feeling and doing. We consistently overestimate the amount of minutia and detail we can hold onto. You think you’ll remember what to say, what to ask, or how to respond when you’re in the moment of that meeting … but you’re wrong.

Unless something has reached the “habit” stage, you’re overestimating your ability to remember in the moment.

Thank goodness for our subconscious brains that run us on autopilot the majority of our waking day.

We’re overstimulated, overstressed, overextended, and being OVERCONFIDENT that you know what to say or ask in a meeting is costing you potentially better outcomes.

Put any ego aside you have at thinking you don’t need to prepare and bring a prep sheet into a meeting.

I still prepare for meetings, run through potential outcomes – where to zig, when to zag – on phone calls. And, my outcomes are 1000% better for it – and so yours can be too!

Until next time, stop hoping and start SELLING!


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Straightforward, practical and perhaps slightly cheeky, Shawn Karol Sandy's innate gift is helping people find new ways to solve old problems, unique ways to approach new problems and helping businesses re-invent themselves and their sales strategies. With Bold and Brave thought leadership and Clear Action Plans, her impact on business is Measurable and Meaningful and will lead your sales revolution to growth and revenue goals.

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