Ask the Hard Questions – Quickly!
December 2013
Tim Lindner

“Time is money” is an old cliché we’ve all heard and probably used in the course of our adult lives. It has been applied to just about every business activity known to man. The meaning is clear: The more time something takes to do, the more it will cost. If you have a fixed cost for the effort you are making, more time doing it leads to unprofitability. The implication of the phrase is motivational. Do it in less time and you are more profitable. 

When it comes to selling complex technology, such as middleware platforms for M2M ecosystems, software that can voice-enable work processes like putting away, picking, and loading products in a warehouse, or embedded devices that transform payment methods, long sales cycles are common. A long sales cycle is defined as more than three months from the initial qualification of a prospect to the close of the sale. In a recessionary marketplace, the minimum could exceed six months. Typically, the average sales cycle is six and 12 months, respectively. That represents a considerable financial commitment from you and your company. Simply, time is money, and the longer the time involved, the greater the risk that the financial investment you are making to support the selling process may not be recovered if the sale is not closed. 

Why is it so long? The simple answer is there are many “moving parts” to the complex technology sales process. It should involve the participation of many people representing different functions and corporate perspectives to assess the impact of the proposed technology on the prospect’s business objectives. 

First, let us understand why it is so important to engage all of the prospect’s stakeholders as early as possible in the sales cycle. As we do this, let’s continue to keep in mind the “time is money” cliché. 

How do you know this is not just a fishing expedition or a science project on the part of the prospect’s team? The rank and function of the team members provides an insight to the risk level. If they are director level or below in operations, and no other function (such as IT or finance) is represented, then your internal alarm should be ringing. 

Is there a defined and approved project, or is operations looking to find a “straw man” with which to show senior management they are focused on the bottomline? Have they looked at the technology within the past year and taken no action? While it is typical for operations to identify technologies that could have a positive impact on operational efficiencies, the “best practice” assessment should be conducted by a cross-functional team from the start of your engagement in the process. 

Is there reluctance on the part of operations to bring IT into the discussion in the early stages of the process? If there is one thing you can count on, technology adoption will require the involvement and approval of the CIO. Too many times, the sales lead fails to push for the early involvement of the prospect’s IT team, resulting in the commencement of a second sales cycle when IT finally arrives. 

Because of the complexity of the technology, selling it requires a structured plan. The best companies use one, and it is an inherent best practice in what is called “Value Selling.” 

As the sales lead for your company, once you have initially qualified the prospect, you should introduce the process plan, which I will call the JPP ( Joint Project Plan). The JPP lays out for the prospect the necessary collaborative steps required to assess the “fit” of the technology for the business objectives. It identifies all of the stakeholders within the prospect’s company appropriate for determining the technology’s value, and when they will be engaged in the project. It ends with contract review and signing. 

By positioning this working document with the prospect early in the sales cycle, you have established the means by which you can ask the hard questions that will further qualify the prospect, or qualify you out of the opportunity. As the sales lead, you are under pressure from management to forecast the close and qualify the likelihood of that close. If you forecast a close too soon, it becomes a liability to you. Management is using your forecast to make revenue projections to shareholders if the company is publicly traded, or to the owners if the company is privately held. Forecasts based on the adoption of a JPP are more realistic and can be more quickly updated based on benchmark attainment or slippage. 

In my experience, introducing a JPP changes the dynamic of the relationship between you and the prospect’s team. First, you are making clear the fact that your company is process driven, and will not take shortcuts to attain a thorough understanding of the prospect’s business requirements and how your solution can help them attain them with a high return on investment value. 

You are also taking the first critical step to control the agenda and the course of the sales cycle, putting any competitor not following a process plan at a disadvantage. 

Most important, in your initial review of the JPP, you are penciling in benchmark dates for each of the steps in the process. It requires the prospect to put dates on paper and agree with them. While in the normal course of the process, some slippage is typical because of scheduling conflicts, everyone understands the process timeline. A JPP should have the written acceptance of both the prospect’s team and you. This is where the opportunity to ask the first hard question arises. 

If they do not want to agree to a JPP, why not? Objections will either be vague or, if they are honest, specific, such as this is an exploratory effort, there is no approved budget this fiscal year, and so on. The answers will give you a firmer basis to make the “qualify in or out” decision. You will save your company unnecessary resource expenses if you determine there is no commitment to a process plan, thus qualifying out of the situation. 

Let us keep in mind the JPP is a visual roadmap to the resources your company will bring to bear to support you in the sales process. You will need to deploy your company’s resources to parallel the function and rank of the prospect’s participants at every benchmark you have defined. 

In your plan, you will have laid out the requirement to meet with senior finance, operations, IT, and general management stakeholders in the prospect’s hierarchy. Each participant has a scheduled meeting (for you, a useful “touch point”) and an agenda. Following through on each of these meetings helps you to identify potential conflicts among the prospect’s team members, and which member could be favoring a competitor. 

Early in the process, you will want to schedule a meeting to review the ROI and value proposition with the CFO (chief financial officer). If the payback period does not meet the CFO’s expectations, then a successful close is clearly at risk. Identifying this risk will save you wasted time and continued resource investment. 

If the prospect’s team does not agree to bring in the other functional resources according to the JPP’s timeline, you must ask the next hard question. Why not? Especially for technology adoption, IT’s early participation in the project is mandatory. If you are given answers such as “IT is a roadblock” or “IT has no available resources to spare for this project at this time” then you are guaranteed two outcomes. 

First, if you accept this explanation and continue on, you will have only deferred the participation of IT while spending your company’s money on resource commitments. Second, once IT becomes involved, you essentially will have to repeat many of the meetings to educate them and understand their issues. This is in effect starting a second sales cycle. Imagine the impact to your forecast, and your credibility. 

Successful value sellers have learned two lessons through experience. While they have “learned” these in training, they have typically taken them to heart after experiencing failure because they have not applied them. 

The first lesson is to put in place a detailed project plan with the prospect at the start of the sales cycle. If the prospect balks at having a plan, the probability of a long, but unsuccessful sales cycle is high. The longer the failed sales cycle, the higher the cost in resources that supported the effort. 

The second lesson is it takes courage to ask the hard questions and make decisions based on the answers given. New, inexperienced sales people tend to avoid asking the hard questions because they think it will jeopardize the sale. The pain and frustration of a failure to close due to the fact they allowed a flawed process to continue longer than it should have will drive home the mistake. A sales lead’s available bandwidth to manage more than a few prospects’ sales cycles at a time is limited by the complexity of the technology. Wasted time is wasted bandwidth that could have been devoted to another opportunity. 

The best sales leaders have learned to ask the hard questions quickly. They make the most in commissions, and give the best closing forecasts to management. Time really is money, as they wisely use value selling techniques to optimize their sales cycles.

Tim Lindner is a seasoned technology selling strategist, and can be reached at

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