Often deals go sour, and we don’t know why. Maybe the prospect mysteriously goes quiet right after the demo. Perhaps it is wild demands that emerge suddenly at the negotiating table, or your champions go MIA at the big presentation.

All of these are symptomatic of mistakes made much earlier in the sales cycle, and it’s not just rookies who make them. Deals are simply more complicated with longer deal cycles, more “decision makers,” increasing competition, and greater solution complexity. Even the most seasoned sales professional can get caught by common errors.

To help navigate these challenges, here are ten of the most common mistakes made during a complex sale:

1) Focus on product, not solution

It is so easy to lead with product. All you have to do is show the product. The problem with this approach is you get reduced to features and functions, bypassing the opportunity to speak to business value and tangible results that differentiate your offering.

Instead of product features, focus on the stories of other successful customers.Lead your discussions with these vignettes. This forces you to talk about the pain points experienced by similar companies and show the value of your solution.

2) Selling to unqualified prospects

Qualifying well is hard to do. We are generally too lenient on those “lost causes.” Make sure you have clearly established qualifying criteria, and qualify those poor fits out of pipeline as soon as possible. And continue qualifying on a continuous basis — deals can change quickly, so be prepared to alter your strategy.

One tip is to reconsider strict BANT (budget, authority, need, timing) criteria as the answers can often lead you astray. Define your own set of questions based on winning deals and your unique solution fit to quickly establish whether an opportunity exists or not.

3) Not targeting buyer need

We often have this monolithic view of the customer and people we interact with. However, people’s motivations are highly nuanced, and different people will come with different agendas, needs, and expectations of the sales experience.

Frame your solution’s value to what matters most for that person. This means the messaging, approach, and solution benefits need to be tailored based on the person and her role in the organization. Link your solution to operational, cultural, financial, political, and strategic benefits so you are prepared to cover all ground for each person you meet.

4) Doing the demo dash

The easy approach to sales is to lead with the demo, but that is a trap that sticks you in the feature / function frame. You want to perform a needs analysis BEFORE any demo. If that is not possible, use the beginning of the demo to invite the prospect to talk about her needs and ONLY focus on product capabilities that link to those needs.

Another point to mention is to keep your pitch to no longer than 20 minutes. Why? Research shows that attention drops precipitously after that and introduces feelings of fear, anxiety, and disengagement in your audience.

5) Lack of executive engagement

Selling high is a necessity to create “energy” for your deal. This simply means that when your solution gets attention by a senior executive, there is momentum in the organization to expend resources towards your solution. When you sell to middle managers, you solve middle manager problems which are tactical and non-critical. Executives have higher order needs that require higher urgency and have greater organizational impact. This translates into greater deal momentum.

You do not have to start off high, however. Call low first to get the lay of the land and develop some facts to reframe your message and tailor a more relevant pitch to the executives you want to target. That way your message will have more immediate impact in the context of their specific needs.

6) Mismanaging your champion

Champions are great until they become a major liability. Understand where the political influence exists in your account and see where your champion sits in the frame of organizational power. Remember, titles only connote structure; they do not necessarily map to power, authority or influence.

Make sure to build multiple champions. By building many relationships at once across the organization, you mitigate any minefields that might stall your deal due to political sabotage or competing organizational initiatives.

7) Negative competitive selling

In the heat of a deal, we often share a missive or two about the competition with prospects. Done in the right way, you create subtle landmines that your competitors cannot easily overcome. If you are too blunt, though, and bad mouth the competition, you look petty and potentially anger your prospect.

Plant your competitive landmines by aligning your capabilities with the needs of the customer. Then align those needs with your competitors and highlight deficiencies with their offerings. Also consider solution delivery, risk factors, company strengths, customer references, service levels, and key personnel to give you multiple ways to create distance between you and the competition.

8) Talking price too early

Price is never important in the early stage of deal. Price can be a gate, but higher order problems have higher urgency and impact, thus there tends to be less price sensitivity (which is why you sell high). The real price negotiations happen after you become the preferred provider.

Never mention discounting upfront. It puts you in “vendor” mode and shifts discussion from value to price. It also puts you at a significant disadvantage because the discount becomes the new base price during the negotiation phase. If pushed early in a deal, state that discounts are provided based on the commitment level and value offered and leave it at that.

9) No team sales strategy

Sales is a team sport and no major deal happens on the back of one hero rep. The best reps are a lot like a conductor who brings the orchestra together and ensures they are in sync. Make sure account executives understand that a key responsibility is to communicate deal strategy clearly and regularly.

This goes against the grain, but deal strategy should not be in the CRM. Create a template with the key questions and qualifiers during a deal and use this as an ongoing checklist for the team.  Make sure that all team members have easy access and can collaborate on it.

10) Believing in assumptions

Hard questions are hard to ask. That is why we put on the proverbial “Happy Ears” to sweep away any hint of doubts about our deals. This is exactly when you need to apply critical thinking and have the guts to ask hard questions with prospects to confirm or adjust your deal strategy.

Because it is so easy to slip into Happy Ears mode, schedule regular deal review sessions with the sales team to discuss objectives, milestones, and actions. The goal of these sessions is to create actionable output to follow up on that improve the optics on deals and uncover assumptions.

If you found this post useful, there is a companion presentation that you can download and share with your sales team.  And let me know in the comments below if you have other sins you see in enterprise deals.


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