Strategic CIO // IT Strategy
11:40 AM

IT Career Advice: How To Sell


In the US today, only about 80 out of more than 2,900 four-year colleges or universities offer a curriculum in sales, yet 50% of graduates from these schools end up in a sales career. How is this fact relevant to those of us in information technology? Well, many tech pros in the corporate world find themselves woefully undertrained in the essential skill of knowing how to sell an idea or a project effectively.

One downside of the fact that sales is not commonly taught in college is the widely held perception that selling isn't a real discipline, the way IT, engineering, marketing, or finance are. It surely doesn't take training, education, or practice to sell something, right?

Nothing could be further from the truth.


[What makes a great IT leader? Read 3 Underappreciated IT Leadership Skills.]

Understanding the complete picture and having a strategy to address all aspects of the proposed initiative -- both as an individual project and as it plays out against other alternatives on the table -- is critical if the CIO hopes to see his or her particular project get the go-ahead.

Remember, this isn't about you
Effective selling requires understanding that this decision isn't about you personally, nor is it about the overall IT function. Effective selling is about the other party -- in this example, the board and the individual board members.

The board wants the company to be successful and is looking for options from management as a means to this end. But they don't want to be "sold to" any more than any of us would. The most common misperception about effective selling is that it's about using tactics and skills to manipulate someone to adopt your point of view or support your project.

Effective selling is really about understanding what is important to a buyer and guiding that person or group down the path that gets them what's important to them. Both individual objectives (what matters to me personally) and corporate objectives (what is important to the company) are part of the decision. In the real world, most people make decisions based on what is best for them personally and then back into the corporate rationale.

Also critical to an effective outcome is that you are genuine and authentic in your approach. Effective selling involves transparency and intentionality -- the opposite of how pop culture often depicts salespeople.

The following questions may help guide you in thinking through your sales strategy. These questions work for a wide variety of situations, from recruiting a talented employee to negotiating a new assignment or convincing a board to fund a strategic initiative.

  • What is important to the buyer, personally and professionally? If the buyer is a group, such as a board, do I understand the full criteria and what's important for each person involved in the decision?
  • Is this decision something that is important? Urgent?
  • Where in the list of the buyer's priorities does this fall? Is it in the top three?
  • Does my proposal fully and completely address the buyer's key personal and professional decision points?
  • How does my proposal compare to other alternatives?
  • What risks does the buyer perceive as part of this process? Do I have a strategy for mitigating these risks, whether they're perceived and real?
  • What is the impact or ROI of a successful implementation of my idea? If the upside is significant, why has there been no action on it up to this point?
  • What is the impact of making no decision or choosing a different alternative?
  • What is included in the decision-making process?
  • What additional information is necessary?
  • If you were on the other side of the decision process, what would you do?
  • Am I, as the seller, completely trustworthy?

You'll gather the information you need from direct questioning, from observation, and from others who know the person or people you're approaching. Mastering the ability to sell effectively is a critical competence for every executive to add to his or her portfolio. Plus it's fun -- just remember that the goal is to help others get what they want.


Daniel Weinfurter consults with many organizations, developing and implementing sales and leadership effectiveness strategies that drive profitable growth. In his his 25 years as a serial entrepreneur, he has built three successful private equity-backed companies, ... View Full Bio
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User Rank: Moderator
7/25/2014 | 8:28:38 AM
Re: How To Sell
Understanding what is important to the buyer and the customer are critical areas to understand. It should be fundamental to anyone's IT career. These practices should be learned early on and separate training would also benefit to the IT staff on how to best handle, approach, deal with such buyers or customers. They wouldn't have to go too in depth but having the basic understanding and of course understanding of the organization's market should be a requirement.
User Rank: Author
7/22/2014 | 11:02:33 AM
Re: Citations please?
The research I know of backs up the relative lack of Sales education. I don't think you can equate Marketing and Advertising. This from Depaul's Sales Leadership Center:  

"In 2011, sales education curriculum was offered at a total of 101 United States universities and colleges. At the undergraduate level, 32 offered a major, minor or concentration, while the remaining 69 provided some level of sales curriculum in their offerings, but not a degree. At the graduate level, 6 offered graduate degrees with a sales concentration (and 9 provided some level of sales curriculum in their offerings)."

User Rank: Ninja
7/22/2014 | 7:27:05 AM
Re: Selling IT
Sometimes rejection in general is hard not to take personally.  I know that early on in my career I had times where I was very frustrated when budgets were cut and I took it as a personal attack.  Luckily I've learned to look at the big picture and understand that a business has to function outside of IT.  The end result is good and bad I guess.  I've been asked to negotiate for other departments because of my ability to disconnect personally from the transaction to the point that co-workers commented that they'd never want to be on the other side of a negotiation with me because I have "ice water" in my veins.  I'm not ashamed to tell anyone what I expect or that I think they can deliver more than they are offering.  Since I don't take it personally when they don't give me what I'm asking for we can just move forward and hammer out the rest of the details with no hard feelings.
User Rank: Ninja
7/22/2014 | 7:02:22 AM
Re: How To Sell
This is definitely a topic worth discussing for IT folks. As many have pointed out, it's ultimately a skill that any businessperson ought to have (or heck, any person at all - even stay-at-home parents need to negotiate with their kids!), but it's also fair to point out that IT people are particularly likely to have a lack of this training in their history, and extra need of a brush-up. At the same time, though, I'm nervous about how far any given piece of advice can get you when it comes to this skill. Isn't it something that can only come with experience, and indeed, when it does, doesn't it kind of defy explanation? Maybe it's best to think of any list like this as a starting point, rather than a full guide.

I like SaneIT's point about not taking things personally, and I'll second Chris in saying that Daniel's point of 'if this is such a great idea, then why hasn't it been implemented already?' struck me as a great point. I also think that these two points go hand-in-hand. Remember that you're just one person, at one point in time, pitching one idea. Whether or not it strikes paydirt has a lot to do with your presentation, but it also has a lot to do with many external factors. The result is not the end-all be-all for you, and it's also not a referendum on the technology you're vouching for. Sometimes the chips just fall how they fall.
User Rank: Apprentice
7/21/2014 | 3:50:10 PM
Citations please?
The article claims "80 out of more than 2,900 four-year colleges or universities offer a curriculum in sales, yet 50% of graduates from these schools end up in a sales career".  I doubt this on two counts. 

First, it seems that a large number of four-year colleges and universities must offer degrees in Marketing and/or Advertising (my own alma mater, The University of Missouri, offers both).  Though I did not study these fields, surely such degrees offer curriculum that should be considered "sales curriculum" in some sense.  I suspect most general business degrees include some sort of basic training in sales as well.

I also doubt that 50% of graduates from four-year colleges or universities end up in a sales career.  What evidence can you offer to support this claim?  Can you cite a study to back this up?
Lorna Garey
Lorna Garey,
User Rank: Author
7/21/2014 | 2:07:15 PM
Personal stake
This is interesting: "In the real world, most people make decisions based on what is best for them personally and then back into the corporate rationale."

Sometimes these interests mesh, like a CISO who doesn't want to be embarrassed among peers by a breach; that's in line with what's best for the company. However, seems like this won't always be the case. At worst, maybe a CxO owns stock in Vendor A when Vendor B is a better choice. Or, it may be as simple as a leader opposing a project that would be good for the company because it would require a lot of work from his staff, just when he wants to go on vacation.

What if a CIO thinks that opposition arises from a personal issue? 
User Rank: Strategist
7/21/2014 | 11:02:51 AM
Pitch -- but pitch with knowledge and a plan
I absolutely agree. Every single CIO I interview says that in order to get buy in at the top you need to sell your project using real numbers and potential gains -- hard and soft. I do think that before you embark on a single project, though, you need to put in a lot of prep work. That includes talking to all the key stakeholders (making sure what you're selling is actually what the business wants), doing due dilligence when it comes to vendors pre- and post-implementation and making sure that there's one person who will function as the person who will handle all the executive governance. From a blog post I read: 

Executive goverance creates a "common framework that defined the end state, key stakeholders, executive sponsors, and procedures that would be followed on a recurring basis—weekly, biweekly, monthly—to ensure everything stayed on track." 

Without that, you can sell your project well but if it fails will be less likely to get a win (and support) going forward. 

Here's the link to the entire blog post:

--KB (Me:  ) 
User Rank: Author
7/21/2014 | 7:48:08 AM
Re: Selling IT
It's interesting that you talk about your own attitude -- I think that's where a lot of us who dread sales need to focus. I like how Daniel puts it quite simply that 'it's not about you.' 
User Rank: Ninja
7/21/2014 | 7:20:07 AM
Selling IT
This is a great article, I spend a fair amount of time selling IT projects and all of this is usable depending on the situation you are in.  I've had people outside my department comment about my attitude when it comes to presenting projects.  I'm very good at accepting that it's not me who is being turned down and that sometimes the budget dictates the direction we go and deciding against what I want to do isn't dismissing my expertise or minimizing my role.  I've seen many people take it personally when they can't get a pet project approved and it always makes me wonder what they think drives the company.  I spent almost a decade doing IT in a very high pressure sales environment so a lot of that rubbed off on me and I tend to fall back on that experience.  I think everyone could do with a little sales experience if for nothing else to learn how to negotiate in the company's best interest.
User Rank: Ninja
7/18/2014 | 10:34:42 PM
Re: We're all in sales
I completely agree. Sales is a very important part of our professional lives.  The method may change, giving a presentation or an elevator pitch. But, those individuals whom know how to sale their ideas to others will be have an advantage over others.  I hope a chair of a computer science department is reading this, since a course in sales would really help new computer science students.
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