When you see this title, in terms of selling, what comes to mind? How does it make you feel? 

I wouldn’t be surprised if it makes you feel a bit uneasy. You may even think to yourself, “This is exactly what gives ‘sales’ a bad name.” 

Same words, vastly different effect 

If you are having these thoughts and feelings, I can’t say you’re wrong. But I also won’t say you’re right. Whether you are right or wrong depends on how individuals execute the two ideas. 

You see, each of the two words can be used to describe behaviors that couldn’t be more different. Used one way, both challenge and control can be absolutely offensive. Yet, used another way, they can deliver the most respectful conversation and interaction anyone would hope to have. 

Unhealthy challenge 

Salespeople are often stereotyped as “bullies.” They are assumed to use strong-arm tactics and expected to be argumentative. Stereotypes happen for a reason. 

You don't have to look any further than social media to see the negative side of challenges. You don't even have to look for the behavior; the abusers make it very apparent. Many will even say, “Challenging the (fill in the target of the day).”  

Many times, I agree with the spirit of their message. It’s the delivery I struggle with. What starts as a healthy challenge in their mind comes across as an overly aggressive attack of a specific business, strategy, or even decisions made by would-be clients. 

Attacks tend to take an absolute, black or white, position. Left out is a gray area where healthy conversation can take place. 

Nobody wants to be bullied, attacked, or placed in an inflexible position. It doesn't matter how "right" your opinion is if you are losing your audience's attention and respect along the way.   

Healthy challenge 

The description I give above of the "attacking" advisor applies to a small percentage of advisors. In fact, most are just the opposite. They will do absolutely anything they can to avoid any tension with a buyer.  

If they feel tension building in the conversation, the typical advisor will do whatever they can to make it go away. This “appease at all cost” approach may be more costly than the attacking approach. 

Not only do the most successful advisors not avoid tension, they, very intentionally, put constructive tension into the sales conversation. It takes a healthy tension to get the buyer thinking differently. It’s only when the buyer thinks differently that they see their situation in a different light. It is this new perspective that drives most to make a needed change.  

  • Advisors who take a healthy-challenge approach start by asking questions designed to get the buyer thinking differently about their current situation.  
  • They continue challenging with insightful follow-up questions to expand on the new perspective.  

To be successful in this approach, an advisor must understand the paths forward well enough to discuss the pros and cons of each. And they must also recognize this line of questioning may make their buyers slightly uncomfortable with their new level of insight.  

Challenging doesn’t mean telling people they’re wrong. Challenging is about helping them down a path of discovery, so they know, for certain, they’re making the right decision.  

Unhealthy control 

The idea of controlling the sales conversation makes most salespeople uncomfortable. They misinterpret it as aggressive. Being in control is NOT about being aggressive—it’s about assertively leading the buyer forward. Just because you are the one talking doesn't necessarily mean you are in control.  

Control is about determining the terms on which you compete for the business. 

Someone will always be in control of the sales conversation. Because most salespeople won’t take control, they cede power to the buyer and react to their terms. 

Guess what demands the buyer makes when they’re put in control.

  • “Go get me quotes to help keep my current guy honest.”  
  • “Show me the ‘free stuff’ you would give us if we become a client.” 
  • "Give me a list of references so I can find out if you're any good or not."  
  • "Okay, go sit and wait, and we'll let you know what we decide." 

In the end, the in-control buyer just participated in the exact same conversation with every broker for whom they were playing “puppet master.” They received ZERO additional value from any of the advisors—what a waste of their time (and yours). 

Healthy control 

Taking control of the sales conversation from the beginning is the kindest, most respectful approach a salesperson can take. If a prospect is willing to take a meeting with you, it should be safe to assume they’ll give you a reasonable chance to earn their business. If they aren’t willing to give you a chance, figure that out as soon as freakin’ possible! 

Here is how I see advisors respectfully taking control.

Step One

Define the target that, if you hit it, will likely earn you the business. For example, “We won’t ask for your business until and unless two things happen during our conversations. First, we must find an opportunity for meaningful improvement to your current program. Second, assuming that opportunity exists, we must earn your confidence in our ability to address those needs and deliver better results. Seem reasonable?” 

Control trigger (to move the conversation forward) – “How do you feel you could potentially benefit from taking a broader look at your program? Let’s set up a time to evaluate your current situation and determine if an opportunity for improvement actually exists for you.” 

Step Two 

Have a conversation focused entirely on evaluating their current situation and whether or not they have problems you’re capable of solving. Assess the areas you can address – insurance strategies, compliance, technology, HR resources, etc. This isn’t a conversation to offer solutions, only to determine if they have the “opportunity for meaningful improvement” you already discussed. 

Control trigger – “Based on our discussion, it is apparent you have areas that aren’t working as well as they need to. What would it mean for you to address these issues? Let’s set up a time for me to show you the solutions we have used to address the same needs for other clients.” 

Step Three 

Have a meeting focused entirely on the solutions you would recommend putting in place to address the needs you identified. Include examples of the results you have delivered to others, as well as the steps you would take to put them in place.

Control trigger – Use this for each solution you introduce to a specific need. “Can you see how this solution, when put in place as I’ve described, will address your need and ensure you get better results?” As you use this trigger for each solution you recommend, their confidence in you (remember the second part of the initial target agreement) will build. 

Which is a more respectful and valuable process of control? Is it forcing the buyer to lead you through the same dog and pony show as everyone else? Or is it breaking down the buying process step-by-step, ensuring they learn along the way and feel more confident in their decisions?  

It’s a no-brainer, right?  

Find the sweet spot 

Finding the sweet spot of challenging and controlling in a healthy manner is a game-changer. It changes the game from selling to one of ensuring the buyer makes the best buying decisions. 

When you can challenge buyers' thinking and bring a new level of enlightenment, when you lead (control) them down a path to better results, magic happens. You move from the dreaded "stereotypical salesperson" category into the coveted role of influential advisor. 


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Photo by ra2 studio.