A 'dog with a bone' vs. "obnoxious" seller

The common maxim suggesting only the hungry survive and win applies exponentially to selling. The hungrier you are as a seller, the more you’ll get fed. The more persistent and aggressive you are, the more you’ll sell. 

Check. We get it. Table stakes. 

Yes, only the strong survive. Yes, you got to go get what you want. Yes, competitive times call for strong and deliberate measures. 

But that doesn’t make it okay for being dumbly aggressive. That begs the question: what is the difference between “assertive selling” and being “too aggressive”?  

I recall a long-ago meeting with a client who reacted to my gentle, proactive probing about not getting more of her budget by calling me “obnoxiously aggressive” and then storming out of the room. All I said was, “why would you make a stupid decision like that?”

Wait-what?? Was that not smart?

OF COURSE I DIDN’T SAY THAT…I wasn’t any more aggressive that day versus any other. I was only guilty of consistently pushing with direct questions that challenged her buying decisions. But isn’t that what we sellers are trained to do? Was I guilty of being "dumbly aggressive"?

The client’s embarrassed associate, who witnessed the exchange, assured me “it’s not you” after her manager stormed out. But inside, I admitted that some of it was me. I had to look in the mirror and re-appraise my approach and how my calculations were wrong about “the line”.

“The line” is really “the issue”. The area across the line representing the “obnoxious zone” is different for every client. (No duh.) The area representing comfortable behaviors for a seller is different too. Given my belief that most B2B sellers could use a bit more oomph to get to the “red line” on the assertive selling dial, you can see the challenge here. 

Years ago, as a sales manager, I remember pushing my sellers to push harder, but in retrospect, I should have provided more specific guidance by discussing both lines with them. I should have explored their comfort line – how much calculated strength, directness, and skill application they were capable of - and how to better understand their prospect’s line. 

The burden is on both sales manager and seller to identify and manage the real estate on both sides of the line. 

The following three suggestions will help define what pushing means in the quest to be a more assertive and thoughtful seller. These recommendations underscore how selling assertiveness is not measured by your verbal intensity in meetings, or how combative or truculent your behaviors are, instead it’s about how you thoughtfully prepare for and execute during your prospect/client interactions. 

1. Focus on gathering information, not confrontation.  Be crystal clear on interaction objectives and focus on the information, not the person who delivers it. Your goals for client interactions never include creating frustration or friction, so focus on getting the info you need and deeper understanding. If you think you’re not getting your share of the budget, or you didn’t get the business, focus on how the prospect’s buying process and decisions are made. And of course, probe to determine buyer perspectives and possible bias too. 

2. Prepare your “probing” and “impact” questions ahead of the meeting while you’re calm and methodically constructing your strategy and meeting goals.  Your sales career will be filled with uncomfortable client conversations, but you can prevent runaway emotions by preparing and following your script.

3. Proactively identify client personality types and moods.  Certainly, you’ll need to appraise the type of partner you have sitting across the proverbial desk. In situations where you are face-to-face with your clients, pay extra attention to how your questions are landing by observing body language. Why not replace the standard “How’s your day going so far?” with, “So, on a 1-10, how open are you to go a bit deeper today on the recent decisions regarding your spend?” At least with that question you’re preparing them for a bit more intensity to your agenda. 

While the above story is true - a client did walk out of a meeting with me - I don’t feel at all sheepish about it. I have a loving wife and family, two fantastic Vizsla dogs who also love me, and plenty of friends, so my goal isn’t to “bestie” every client I meet. At the same time, I’m never trying to tick off a client. Yet, I have a job to do. My motto has always been to get as close to the “red line” as possible while still maintaining respect and trust. And hey, I have a long history of getting results. It’s inevitable I miscalculate “the line” at one time or another. 

Pushing yourself to get the most from your selling activities and behaviors should be top of mind at all times. Don’t forget, pushing yourself to intensely apply effort and skills is different from pushing clients.