Project Management

Tackling the Obstinate Executive

From the Vision to Value: Executing Strategically Focused Initiatives Blog
Executing initiatives, and their component projects, successfully means delivering value to customers. The Vision to Value blog focuses on solutions to the organizational problems that inhibit that success.

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Categories: Leadership, People, Persuasion

Does your boss only seem to stand in your way? Is he or she fearful of accountability, grossly indecisive, and never providing enough information to understand their objections? It is more common than most of us would imagine. In fact, this behavior is central to every sales interaction. Even though you may be repulsed at thinking of yourself as "selling" to your boss, that is exactly what the action you are doing—selling your concept. Therefore, it makes perfect sense to employ the same techniques used to sell large systems. If you think this is rubbish, as one of my esteemed readers once eloquently said, I will posit that you are already using sales techniques, just the wrong ones—the ones car dealers use. Changing your approach will subdue your unruly boss

The Answer Is Questions

Normally, when asking we ask our bosses to make a decision, we present them with a list of benefits and then ask for a decision. This is identical to the methods of the car lot's stereotypical slimy salesperson. They list numerous features (whether they are important to you or not) and go for the close—"Would you like me to draw up the paperwork so you can drive it home today?" That technique might work if you were buying a multifunction calculator or some new inexpensive widget for your computer, but it falls woefully short in higher stakes decisions where money, reputation, or both are on the line. Instead, decision makers want to understand the value based on the key benefits to them. In the case of the car, what might be a cool feature to the sales person (a remote control rear window sunshade), may be useless to the buyer. On the other hand, additional backseat legroom may be critical for comfortably transporting clients to lunch. A salesperson will have a much easier time selling the latter.

The simple solution is to ask your boss what is important to him or her. For these questions to be successful, they must be the right type of questions. Author Neil Rackham's research shows that when selling any "big" items, four types of questions must be asked—situation, problem, implication, and needs-payoff. These conveniently condense to the salesy term SPIN questions.

Situation Questions

The first level of questioning is situational. These questions determine the authority of the person to make the decision, who is involved with the making it, and so forth. These are the most basic of questions, and seem too inconsequential to focus on. Although they appear to be trivial and may be annoying to answer, they have an insightful impact on the outcome of the decision. Questions in this category are similar to ones that determine whether there is a preference on make/buy, in-house, or outsourcing. Assuming what these answers might be, though, can have a profound negative effect on the decision maker's reception to your proposal. Many of us have been in the embarrassing situation where suddenly the option of buying a COTS (common off the self) solution was the unspoken preference.

Problem Questions

Problems are in the eye of the beholder. Even though you and your boss work for the same company, each of you may identify problems very different. Problem questions elicit your boss' view of what is important. Your view of the problems is irrelevant when justifying his or her decision. To find out the decision maker's view, ask questions about specific problems and their weight on the organization. Always add the question "Are there any other big problems?" Knowing there is a problem is not enough, executives must have an explicit need for a solution. The following two sets of questions determine the explicit need based on these implicit problems.

Implication Questions

When describing problems we are intimate with, we tend to think that everyone understands the gravity of them. It is obvious to us since we have worked with the issues so long. We need to layout out questions that will guide others down a path of discovery so they may internalize the problems' scope. As the name implies, implication questions drill into the ramifications of the problems. They help the decision-maker comprehend the problem's consequences. For instance, if you are trying to resolve a problem with untimely production throughput reports, then implication questions could address whether late or inaccurate reports cause:

  • Starting the wrong material.
  • Scheduling inappropriate overtime resulting in increased costs.
  • Sending people home early detrimentally reducing production throughput.
  • Missing customer deliveries.
  • Failing to identify quality issues in time to minimize rework.
  • Shipping defective product.

It is not the problems, rather the implications that arise from those issues that creates the sense of urgency. These questions help the listener understand the breadth of the problem and sets you up for the final set of questions—the needs-payoff questions.

Needs-Payoff Questions

The structure of needs-payoff questions shows the listener the need for your solution and its payoff. These questions, as opposed to the earlier questions (which are negative by the fact they are exploiting problems), are termed in a positive tone. Instead of saying that an implied problem is costing a certain amount, the questions take on a positive form focusing on how much would be saved if an explicit problem is resolved. For instance, "Eliminating the accidental scheduling of overtime would save you how much money?" and "How much would you save in rework costs if you could catch issues a few hours earlier?" These questions provide the final piece of data that you and your decision maker need—the cost justification. If the cost savings outweigh the cost of implementing the solution, the decision becomes much easier.

Obliterating Objections

The sequence of questions has two significant benefits of:

  1. The cost benefits come from the decision maker, it will be difficult for them to object to the reasoning.
  2. The conversation ends on a positive assessment of the solution that directly addresses the decision maker's explicit problems.

Will some still object? Of course. In fact, some will realize that you are trying to corner them and will stop answering questions. You may need to resort to asking the questions over weeks in casual conversation and keeping meticulous notes. In the end, you will have an extremely convincing case for supporting a fact-based decision.

Posted on: September 27, 2015 09:17 PM | Permalink

Comments (8)

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Dear Todd.
In my opinion the questions exposed here in your blog make perfect sense, and are (for me) quite well explained. From my point of view much psychology and patience is needed to obtain good quality answers to all the above questions.

Never the less in some ocations it is hard to obtain goog collaboration for this. You mention that these are "sales techniques". Does this mean that I should be selling continuously my project (steps) to obtain the right and constructive answers? Any thoughts on this?
Thanks for sharing.


Yes, I do see us as "sales people" or a better word is persuaders. We should not have to sell our projects internally (the sponsor should be doing that) but we do need to be selling our concepts on execution, resource planning, budget needs, etc. Daily we are selling new concepts. You may note that I tagged this article under "persuasion" as that is a much better word to use. When you think about the concept using that word, you are persuading people all the time (in your personal and business life).

I like Rackham's book a lot in this respect. To the degree that I have developed a "cheat sheet" (now it is all in my mind) for conversations that I have to have that make sure I think about these questions and the timeline on which I have to ask them.

Todd C. Williams

Hello Todd.

Yes I agree, "Persuasion" is a better word than "selling". Never the less I get/see ocasionally some resistence to my questions. Things like: Please come back later, Send me an email to setup a date and time. Especially when I get these kind of remarks from the sponser. Bear in mind that the companies I deal with here in the south of Madrid are small sized companies. And they (the sponser) want me around to do the work, and obtain the goals stated in the project, but they frecuently tell me that there are allways more important things to handle. And as you can Imagine, this can be frustrating from time-to-time.

But based on your website I have seen I belief that you don´t have these kind of issues. :-)

When you get the chance to write down the "cheat sheet" you have in your mind, would you be willing to share it? Maybe it might be helpfull..
Many thanks in advance.

So true. However I prefer to think of it as "stakeholder management" rather than "sales"...

Dear Poco,

I have it written and use that version for large tasks, but I have done this so much that I have it, in large part, committed to memory. I just placed it on our site for free. You can find it here as the Persuasion Worksheet. Please let me know if you have problems getting to it.



Thank you for your comment.

I think of stakeholder management as much more than this. Here we are only talking about persuading someone and not trying figure out what their political bend is, what resistance they bring, how they can promote the project, get funds, control dissenters, etc.

You are right though, that is a more polite way to say it. Persuasion might be more accurate.


Dear Todd.
I have registed on your site and I "placed the order" :-)
And I downloaded the sheet. Will have a good look at it and will come back to you. Will write you an email (if you don´t mind) if more questions arise. Many thanks for sharing.

Todd, you're of course absolutely right, stakeholder management is much more. I should have been more precise saying that I consider this a part of stakeheolder management as your boss is surely one of the most important stakeholders for your career...

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