Selling with Attitude: What do I mean by Attitude?

Dec 17, 2024

9 min read

Attitude means a lot of different things to different people, and most of the time it is in a negative context. I actually think some attitude, as I will review in this blog, is a good thing and will help you navigate the complex sale.

Are you crazy? You want sales reps to have an attitude with their prospects and customers? We can't upset the customer. What if they complain to my boss? What about the saying that the customer is always right? I am here to advocate for my customer and make sure I am taking care of them, answering their questions, giving them a good experience.

I have heard all of this many times. If you want to follow along with the customer and take care of them, go into services. If you want to sell big deals and by definition, add a ton of value to your customer, then cop an attitude.

Most of the time, people define attitude as slightly aggressive behavior, willingness to fight or argue, and a general lack of respect that makes someone difficult to deal with. While that is one way to view attitude, I view attitude in a much more positive light and along 4 major dimensions:

Be Fearless and Confident
Embrace Conflict and Confrontation
Show Sexy Indifference (Care, but not that much)
Mindful (loaded word, I know, but I mean process driven, present, and calm)

Reps who do not want to upset the customer, are constantly worried about what their manager thinks about their behavior, and are not able to have a confrontation, however large or small, with the prospect, will never gain the control and respect they need to run a successful sales process. We cannot just follow the customer through the buying journey, since the buyers simply do not know how to research, evaluate, and buy enterprise software.

Be Fearless and Confident

The nicest thing ever said about me was a founder from my first executive job, who said, "John, the thing I love about you is that you have no fear". He went on to say that I stand up for the value of our solution and company and do not back down in the face of adversity. I was probably dropped on my head a few too many times growing up, and this is very hard to teach or train, but fearlessness is critical in enterprise sales. How do we react when we get punched in the face. Are we worried one of our buyers will get mad at us? Are we constantly trying to make everyone happy? Do we do everything the client asks from us?

Of course everyone has fear at some level, me included. But the customer should never see this, and our actions should come from strength and confidence, not fear.

I remember one of my first large deals. I proposed $18m and my competition proposed $3m. (yes, I am dating myself here, since it was a perpetual deal in the 90s.) When the prospect called to give me a chance to reconsider, I declined. When they asked why we were so much more expensive, I simply said, "our solution works". Of course we negotiated later and won the deal for a more reasonable $12m, but the confidence and fearlessness of my response to that first price objection was critical in setting the stage for the negotiation. We were not going to cave in to a lesser competitor. Someone once told me that successful reps always act like they are 200% of quota. Imagine you treated every deal like you had already made quota. I bet your would act much more confident, waste less time, and be a little less agreeable to actions that do not help your cause.

To help increase my confidence in each deal, I would only pursue accounts where I was absolutely convinced in my own mind that we can add tremendous value. And then I would take a very consultative approach, not a sales approach. That way, any time they pushed back on my suggestions, I fell back on the line "hey, I am just here to help. There are many other companies who need my help, but I would like to help you!". When you honestly believe you are there to help, your confidence increases dramatically.

Embrace Conflict and Confrontation

The late, great Rick Page, author of "Hope is not a Strategy", had a ton of quotes, but one of my favorites was "you need to be able to handle all of the small confrontations throughout the sales cycle to avoid the big confrontation at the end, which is a loss". Just following along and agreeing with the prospect is order taking, not selling. As an introduction to this blog series, I talked about no more hoop jumping. The hoop jumping stops when we become fearless and are able to handle the confrontations that will inevitably come up.

Just recently, I was working on a very large deal (largest in company history), and our pipeline was thin, to be kind! We finally got traction from the executive, and since his team was remote, he suggested a series of video calls to run through our solution. A demo would be a great way to start, he said. Long story short, I wanted some in person time and thought that if I could get him to fly his team to a central location, it would prove they were serious and would allow us to have very good, focused discussions. He pushed back initially, said that would take a few months to arrange, and I said, great, we can wait. We did have to wait a month or so to schedule, but it gave us tome for some good discovery calls and he got everyone in one place for focused time from the team, and then we had a great dinner with everyone. We were off to the races.

There are many other examples of conflicts, or potential disagreements, in an enterprise sale. Too many to cover in this blog. Prospects always ask for demos too early. How do you handle that? They ask for references too early. They hate discovery. Etc Etc Etc. How we help the client understand why their asks are either early or will not help them understand our solution, takes the ability to stand tall in the face of conflict. One of my favorite lines is "I have seen how this movie ends and neither of us will like it". I also use the statistic that 70% of all enterprise sales cycles result in no decision, and go on to say that is not good for either of us.

This is not promoting an aggressive attitude, or being disrespectful. It is simply working hard to collaborate with your prospect to set both parties up for success, and not backing down when there is a come conflict or pushback.

Find out the 3 or 4 things that you have done in your successful deals and figure out how to get them into your current cycles. In one company, when we were able to connect with the CFO and also conduct a data analysis (value assessment), we would win 90% of the time. When we did not get those things, we lost 90% of the time. We would be very focused and work through all the conflict to get those events done, or we would not continue with the deal.

Show Sexy Indifference

I hear so much about speed, efficiency, reaction and response time being critical to sales success. For large, enterprise sales, I just don't agree. Do you reply to your prospects email in seconds, or minutes?? Do you agree to the first time they suggest for the next step? Do you try to set up the next meeting time before you get off the current call? (I may write a whole blog on how bad I think that practice is).

What does it say to the prospect when we respond too quickly? It says we are not that busy, and it puts us in a subservient position with the prospect. How about waiting a day or so to respond to emails. I love it when I get 2 or 3 emails asking if I got their email or when I am going to respond, since that means they are into the deal. If a day delay is too uncomfortable, maybe you are in the wrong role. At least try to wait a few hours. Obviously it depends on the request and where you are in the cycle, but hopefully you get the message here. Don't show desperation.

I love Jason Bateman's podcast, "Smartless". On one episode, they talked about Sexy Indifference, and I thought it was the perfect way to describe the attitude I am talking about. Remember when you were dating and responded too quickly and showed too much interest, too early? It probably did not go well. Same for enterprise sales. These are 9-18 month cycles, with a lot of emotions and conflicts along the way. The rep who shows a bit of indifference, who wants to help the prospect, but will not be pushed around, will be in a much better position to shape the deal and the cycle to their advantage.

It is not just the speed of your response, but how you respond as well. How do you respond when the prospect disagrees with your suggested next step? The prospect can sense your anxiety through your tone, facial expressions, body language, etc.. Having a bit of indifference will signal to the client that you are serious about helping them and that you are not going to just cave into their requests and demands.

My motto was always, "I care, but not that much". The prospect has to know you care, a lot, about their situation, their well being, the value you want them to achieve. But caring too much is a dangerous place to be. In fact, I would argue that by not just following their orders, "buying process", or misguided asks and requests, we are showing our prospects that we actually care more than the average rep and do have their best interests at heart.

Be Mindful

You can't do anything I talked about above without being calm, in the moment, and emotionally regulated. Many reps are under so much pressure to show progress and activity they agree to things that they know won't help, and will probably hurt their sale. I have been doing this for a long time and here are some of the things I have heard from my bosses and peers as I work through a sale.

What do you mean you are not going to do another demo?
They asked for pricing, great, give it to them.
They want to do a technical deep dive? Awesome, we have the best product, we will kill it. What? you aren't going to do that?

If I have found it hard to deal with all the outside pressure to show activity, imagine a rep just starting out with less experience. I believe anxiety and stress are the real killers of sales effectiveness. Reps who can hang in there, stay calm, stay in the moment, in light of all the stress and pressure, will have the best chance for success.

But how? This is easier said than done. Of course this is super hard, and unfortunately, there is no quick fix. My point here is to simply understand the importance of staying in the moment and letting go of the outcome. If you don't like the "mindfulness" craze, then use "process driven". For the sports fans out there, Nick Saban's "process" is all about being mindful and in the moment. He does not want his players thinking about the score and the outcome. I have been process driven most of my life, and recently learned how I was actually practicing mindfulness.

In Summary, a Little Attitude Goes a Long Way

This was a tough article to write due to the subjective nature of it all. It has been the toughest concept to teach to my sales teams. I had to model it, live it, and let them see first hand that we would not just go with the flow and follow a poor buying process in the name of "the customer is always right". If the prospect was not treating us well, then something was typically wrong and a win was very unlikely. I like to say, instead of ABC (Always be Closing), let's try ABW (Always be Walking).

Admittedly, there is a fine line between being the "concierge" rep, the rep who just does everything the customer asks, and the jerk, who just does not treat the prospect well, but the point of all this is do not be a whipping boy to your prospect. Be equal, be credible, and work with them collaboratively to help them evaluate your solution. Don't let them boss you around, don't agree to things that do not increase the chance of your sale, and be willing to have the difficult conversations when things are just not going in the right direction.

At the end of the day, your prospects will appreciate you taking the lead, offering up suggestions that will be good for both parties and will help them figure out what is truly best for their business.

Check out my profile on LinkedIn at John Huettel and my company at Lighthousesalessolutions.com. You can subscribe to receive the blog directly to your email.