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Updated: May 21



If sales were described as the childrenโ€™s story โ€œThe Three Bearsโ€, then Goldilocks would likely avoid the Aggressive and Passive bears but find the Assertive bear โ€œjust rightโ€.


OK, that analogy may be as good as warm porridge, so letโ€™s run away from this analogy and concentrate on the business lesson.


For clarification, assertiveness is both confident and forceful. Itโ€™s not overbearing (excuse the pun) because you respect and understand the other person.



Plan in Place โ€“ The more you consider all the possibilities of what can go well and what can go wrongly, the better you can keep things moving forward. You want to effectively and quickly respond to difficult questions and potential complications, so you can engage in the moment. Even the most detailed plan will not cover every contingency, but a plan prepares you for common objections and concerns.


โ€œI see your point, can I explain how weโ€™ve helped other companies with similar challenges?โ€


Keep it Moving โ€“ No one likes to carry a conversation or be dominated in one. Keep the discussion moving forward by adding useful, relevant points. Simultaneously, you should be introducing the next steps each time. Enter every conversation with a clear sense of what you want to accomplish and what is the next step. It may feel daunting at first, but eventually this will form a habit of progress.

โ€œIt sounds like we can help. When is a good time to show you how the product works?โ€

Focus on Value not Price โ€“ At its best, sales are about helping customers create benefits through efficiency, quality, conveniences, etc. Throughout discussions, it should be clear how working with you will help the prospect solve problems and grow the business. Regularly position the value of your offering based on what the customer will gain in the future. If the discussion gets stuck on price later, revisit the value proposition.

โ€œWhat are you looking to achieve with a 20 percent reduction?โ€

Go Heavy Early โ€“ While itโ€™s tempting to be placating and ask light questions until closing a deal, asking tough questions early will not only help to screen the right prospects but also sets the tone for later hard questions. Making sure the prospect has the budget, technology, and resources to work with you. You donโ€™t want to discover a deal-breaker after weeks or even months of conversations.

โ€œBased on the size of your company right now, will the team have the budget to implement a solution?โ€

Take a Stand โ€“ The passive person may focus only on listening, and the aggressive person may only want to dominate with their ideas. Assert yourself around your business expertise and industry knowledge. Add to the conversation in ways the customer can benefit. In some cases, you may not have the information needed โ€“ acknowledge that and come back with the right information soon. That builds reputation.

โ€œWeโ€™ve seen great success in companies like yours, can I show you some of their results?โ€

Face Risk โ€“ In their mind, the customer is risking everything by trying something new: reputation, time, energy, budget. It helps to acknowledge their point of view in discussion. Sometimes, you may even want to call out the obstacle and address any concerns directly and collaboratively.

โ€œI understand your budget constraint, can we discuss some creative ideas which may work for both of us?โ€

Target Customer โ€“ While you want to do business with a lot of people, you know that not everyone will benefit from what youโ€™re offering. Understand the right demographic for success. Over time, measure your effectiveness across industries, roles, regions, departments, etc. to determine the best fit for your offering.

โ€œWe help employees with young children working from home, do some of your employees fit that group?โ€

Be Direct โ€“ You canโ€™t wait for a door to open itself, and you donโ€™t want to slam it open. You want to find that Goldilocks approach between a bull in a glass shop and never entering the store. After you introduce how you can add value, clearly ask for the next step by building on the value just offered.

โ€œDo you have five minutes for me to tell you how we can increase your leads by 15%?โ€


Accept โ€œNoโ€ โ€“ If you are in the middle of asking questions and hear the word โ€œNo,โ€ itโ€™s tempting to dig in with more ways of asking the same question. Confidence is the fortitude to accept that answer and move to the next question. Sometimes, being willing to speak concisely and then remain silent lets the customer provide more context and color to their question.


If you have reached the close and they say, "Actually, we're all set," you could reply, "If you reviewed what I sent you and you feel that way, then you're right" and pause. By waiting on their answer, you may get more insight into their thinking.



Play the Long Game โ€“ If itโ€™s not worth pursuing, ask if you can follow up in a few months to see if anything has changed. Itโ€™s possible that over time their needs have changed, the vendor they chose was not a good fit, or you have additional products or services to offer.

โ€œI appreciate all your time so far. We are constantly adding new features / services, could I reach out in 3 months and give you an update?โ€


The assertive approach focuses on solving problems and moving forward in a way thatโ€™s beneficial for both sides. It starts with a plan and results in honing your message to better reach valuable prospects.


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Ideas in this post come from the great book, The Challenger Sale, by Matthew Dixon and Brent Adamson and from M. Jeffrey Hoffman



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