Why These Complexities are Stalling your Deals

May 9, 2018 | Closing, Complex Sale, Sales, Sales Leadership

Is your sale complex? Are there multiple buying influences and long sales cycles? Does it seem like these deals are getting more complex and harder to close?

Not every B2B sale is a complex sale. Some sales are merely a transaction. One phone call to ask a few questions and then buy the product. Some initial sales for lower dollars, don’t require much more than a salesperson from your company talking to the person who has the budget. But for some of you, the larger deals, with companies much bigger than yours are complicated and painstaking. It’s hard to predict the dollars that will be spent and even harder to predict when they will close.

Not sure if you have a complex sale or just salespeople who can’t get a deal closed?

Defining the Complex Sale

I researched the definition of the complex sale and believe it or not, I didn’t find much. The definition from my father Steve Heiman and his partner Bob Miller, from the late 70s is, “A Complex Sale is one in which a number of people must give their approval or input before the buying decision can be made.”

According to their definition:

  • The buying organization has multiple options.
  • The selling organization has multiple options.
  • In both organizations, numerous levels of responsibility are involved.
  • The buying organization’s decision-making process is complex – meaning that it is seldom self-evident to an outsider.

I believe this is still relevant today and there is more.

Googling, I found this from George Brontén:

“Interchangeably used with Enterprise Sales, a complex sale is typically a long sales cycle deal (sometimes longer than 12 months) that requires an RFP (request for proposal) and then winning that proposal against a sea of competitive sellers. Complex sales have large contract values and contain multiple decision-makers and stakeholders.”

His article is quite good, but I decided I needed more, so I asked a few experts and of course got different answers:

Lisa Magnuson, CEO of Top Line Sales and author of ‘The TOP Sales Leader Playbook: How to Win 5X Deals Repeatedly’ says, “Complex sales, or what I call 5X opportunities, have many unique characteristics including the imperative for executive sponsorship both within your organization and within your prospect’s company. The financial value of the opportunity is large (5X means about five times your average contract size.) as well as the strategic value. Stakes are high for both the selling organization and buyers organization as complex sales demand a heavy resource load over a longer period of time. One more critical element is the commitment of the opportunity team to maintain a high level of focus over the long term to develop and close the deal.” you can format it to follow the others if it is too different.”

Kendra Lee, President of the KLA Group says, “A complex sale involves multiple layers of contacts, multiple decision makers, multi-faceted needs that must be fully understood. It involves a solution that must be customized in some way to meet the needs of the organization. As a result, it typically has a longer sales cycle and is more expensive. I don’t feel like competition is a key factor although it’s very common because of the size of the opportunity.”

Anthony Iannarino, Speaker, and Best-Selling Author of The Only Sales Guide You Will Ever Need and the Lost Art of Closing says, “Difficult problem, high-value strategic outcome, multiple stakeholders, transformational change, serious implications for failure, high risk, high reward, significant investment, variable outcomes possible.”

Janice Mars, Principal and Founder of Sales Latitude says, “Complex sales are B2B sales where there is involvement of many people on both the buyer’s side and the seller’ side since there are many different people/job positions that are affected if/when change occurs.”

Regardless, there are some similarities and I believe some elements we all need to be aware of, several of which I feel are being overlooked.

Elements of a Complex Sale

Long Sales Cycle

Is your sale cycle getting longer? Would say your sales cycles on average is 3 months? 6 months? 1 year? More than a year? Are you not sure? Most of the companies I work with don’t measure consistently and don’t really know. Think about how you are measuring the length of your sales cycle. Could you fine-tune?

High Dollar Stakes

The deals are 6 and 7 figures. What is a complex deal worth at your company, $100K or less? Over $250K? $500K? $1 million? For many of you, these are the largest deals you close. Could they be larger? How many of the deals under $500K could be more if you were better positioned?

Multiple Buying Influences

Besides the obvious players, there are many that you will never know about. In fact, according to CEB/Gartner, there are 6.8, which is up from 5.4 just 2 years ago. How many of the decision-makers are your salespeople working with 3, 4? Where are the rest and how are they getting to them?

Perceived Risk

This is a tough one for most salespeople. They find it hard to put themselves in the shoes of the buyer and truly understand the risks involved in making a decision. Not just to buy your product, but to make any decision. Buyers are afraid they will be fired. Knowing that your approach will have to address that. Buyers need approval from their peers and superiors, so they feel secure that they won’t be fired for making a decision. When the buying influences can’t come to a decision your sale stalls or disappears. This is probably why doing nothing is one of our biggest competitive threats these days.

Multiple Solutions

There are so many competitors out there selling solutions similar to yours. Buyers want to make sure they choose the best solution. They take the time to look at many of them and they are trying to compare them to yours. It’s more important than ever to be able to differentiate yourself in the marketplace, and have great testimonials and online reviews.

Technical and Integration Complexities

Even if everyone agrees on everything, can IT make it work? How long will implementation take? How will its use be integrated? What training will be needed? What problems need to be anticipated? Will outside consultants be needed to help with integration? Lots of unknowns here.

Multiple Influencers on the Sellers Team

This is one most of you may not have considered. Think about what it takes from your side to get a deal done. What resources are needed, are there SME’s involved? Do sales leaders need to get involved? Does legal get involved? Is there a sales prevention department lurking somewhere that is actually lengthening the sales cycle on your end?

Other – Unique to Your Sale

What complexities are unique to your sale? How are they making the sale more complex?

What Will You Do?

Knowing all of these complexities exist, what can you do? How can you help your salespeople navigate these complex deals?

I recommend putting a process in place for mapping the players and information to better position yourself. Insist that your salespeople use that to plan their strategy and their sales calls. Then debrief with them. Ask them a series of questions to find out how they are positioned and help them uncover where they have gaps in information that could stall the deal.


Ask each member of your sales team to map one complex sale and assemble a team to help them think through the opportunity and share ideas on how to advance the sale and shorten the sales cycle. Put 2 or 3 members on each team and give them a format so they stay focused. You don’t have to be at every strategy meeting but you do have to make sure they happen and hold them accountable.

Sometimes, we have to slow down to speed up. Complex sales require strategy. Salespeople are busy and don’t want to slow down to map out or discuss a strategy, but, if they could win more deals would you figure out a way to get them to do it? I’m betting you would.

Want a bit more on this topic? Watch this now!

Alice Heiman

Alice Heiman

Alice is nationally known for her expertise in elevating sales to increase valuation for companies with a B2B complex sale that have exceptional growth potential. She’s originally, from the widely known Miller Heiman Group. Spending her time strategizing with CEOs and their leadership teams to build the strategies that find new business and grow existing accounts is her passion.  Her clients love her spirit and the way she energizes their sales organization.


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