This Trick Will Backfire. Watch Out!

email to the cio


Don’t Pull the ‘Email to the CIO’ Trick. It Will Backfire.

I wanted to share a story that I personally witnessed this week.  I was sitting in a buddy’s office (let’s call him MR. VP for this story) who also happens to be an IT leader at a big company in the Philadelphia area.  They have a substantial IT budget and a variety of technology partners.
I was sitting off to the side in his office when I noticed him reading an email that seemed to get him pretty disturbed.  He immediately picked up the phone and dialed (for this part let’s call him Paul from ABC software company).  Mr. VP immediately started to read him the riot act. “Who do you think you are… going around me to my CIO and telling him I didn’t do my job?  We have purchased millions of dollars of your software in the past.  Pick up the phone and call me directly if you have an issue with the decision.  You are done doing business here.  Goodbye!!”

Evidently, Paul had a proposal on the table and Mr. VP and team had chosen another partner.   Paul, in desperation, sent an email to the CIO letting him know that Mr. VP and his team chose another partner and his team made a mistake costing the company money in the long run.  He also claimed that the playing field wasn’t even because he didn’t get the access he needed along the way.
Listen, all sales veterans have probably been in this situation before.  I know I have.  You believe you have the better solution and the customer didn’t give you the access and time needed to qualify the proper way and propose the right solution.   I personally can’t stand to lose but sometimes there are newer and better technologies out there that will outshine yours.  It’s hard not to take it personally but you must understand that this sales gig is a marathon.  We are going to win some and lose some along the way.  It’s how you handle the situation that prevails in the end.

I have learned this throughout my career.  Rather than sending that email to the CIO who happens to highly respect Mr. VP, call Mr. VP and set up a time to be debriefed about the missed opportunity.  9 times out of 10, MR. CIO and his/her peers will respect your request to go over why they went another direction. Most of them have a heart and will be happy to discuss it with you.  You will get that desired facetime, build credibility and the access you need the next time around.

I must admit, I had a smile on my face when Mr. VP was laying into Paul. It was one less vendor I had to deal with and I knew it would make a great blog………

Good selling.


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Know the Customer and Get Intelligent


SellingtothecioKnow the customer and get Intelligent (it’s not that hard!)

I have come to the point that now I only answer internal calls.  Yes, these are calls from internal to the company and I can’t take another external call.  Why?  Because it usually is from somebody trying to sell me something I don’t want to buy.  So, I let the external call go to voicemail, praying and hoping it’s not a call from a critical customer or critical contact that I really should answer.  Yes, salesperson, I have customers too but how do I answer their calls when I’m afraid I have to talk with yet another salesperson about something I’m not likely to buy?  That’s crazy and I’m a bit resentful that I can’t talk to my customers or somebody that depends on me.  Leave me a voicemail and I usually just delete it in about 5 seconds. On rare occasions I do listen but only when somebody leaves an ‘intelligent voicemail’ and its starts with intelligence.  What’s intelligence?  Knowing your customer – the age old adage.  By the way, the same applies to an email.   Leave me voicemail that belongs on the “Do not call list” or spam me with something that just clogs up my email box is not the way to get to my heart.

If somebody does their homework and leaves me an intelligent voicemail or email, I’m more likely to return that call or email.  By the way, I don’t really care about your product or service.  What I care about is whether or not you know me and my company and how your product or service REALLY relates to me or my business?  But how can you do that if you don’t know me or my business?

So, when you send that voicemail or email you better start with – knowing your customer and start with intelligence.  Let me give you a few hints and it’s all pretty simple:

  1. Know the company – There is so much available information out there in the public domain (the web) on so many companies but it’s rare to see a salesperson willing to invest the time to do some simple research. I recently read a 3 page report from a securities analyst about our company.  I was shocked at how much the analyst new about our business, our goals, and our future direction.  In just 3 pages, he captured the essence of the company and, guess what, the analyst NEVER spoke to anybody from our company and came off extremely intelligent.  That information is also available to you on the web and you too can be a smarty pants!   By the way, security analysts are smart by nature and well compensated people that are paid for their ability to quickly express the essence of a company to potential investors.  They did the research for you – steal from them!
  2. Know what an IT organization looks like – If you are selling to IT, know what an IT organization looks like. Should you get the organization chart – sure. Always helpful and valuable but extremely hard to get.  But, trust me, the organization charts may differ by company and there may be more or less in each role but IT organization are very similar across industries.   It’s not that complex.  Let me boil it down to three things. People can work in multiple areas but they are either: PLANNING, BUILDING, OR RUNNING IT related stuff for the business.  Each area has a budget so know what the role of that person is when you leave your next voicemail or email. I use the pejorative term ‘people’ meaning IT people in the company organization you are trying to reach:
    1. Plan – people that are creating roadmaps and plans for the future of IT. Setting direction for IT with a focus on the business. These are enterprise architects, senior IT leaders, and senior business analysts often from the business.  Powerful people if you can get to them because they usually know what’s important to the business and what IT has to do to fulfill their plans.  These PLAN people often have limited budgets and are strategic thinkers but they are already planning for next year and probably not helpful for spending this year.  Catch them in Q3 or Q4 when they do have influence on budget. 5-10% of the IT budget for a company is typically in PLAN.
    2. Build – people that have projects that are providing value to the business. They get their direction from the PLAN people. The BUILD people usually have budget to spend and they need help getting their projects done for the business.  These are program managers, technical architects, and business analysts.  Sell to the technical architects and business analysts and then move up the program managers.  Once the build is done, the BUILD people give their project to the RUN people.  Remember, BUILD is only 10% of the life cycle of a project and 90% of the remaining life cycle cost goes to RUN.  If you are lucky, 20-30% of the IT budget is in BUILD.
    3. Run – people that are running operations day to day for both infrastructure and applications support. So much of RUN today is outsourced and it’s hard to get sales traction here because it is so commoditized.  IT organizations are moving aggressively to the cloud and abandoning their data centers. We are letting go our day to day internal RUN people and using managed services (outsourcers) from large or boutique providers for infrastructure and applications support.  This is a commodity based business that is cost sensitive so cost savings with quality is ultimately what matters. The RUN people are not doing the work but they are often leading and managing the cloud providers or the outsourcers.   If you are lucking 60-80% of your budget is in RUN but for many, particularly older companies with lots of legacy systems, this number can easily be 85-95% of the IT budget.  By the way, many are still not in the cloud so if you are selling on getting customers in the cloud you may be in luck.
  3. Know what’s important to the CIO – Again, IT groups sometimes think they are special and unique but usually they are not. The priorities for the CIO vary by business and by industry but some of the “Top 10 IT Priorities” continue to be the same year over year (e.g., Business Intelligence) but others on the list are newcomers (e.g., Digital Transformation.)  If you are speaking to a CIO you should know and understand the Top 10 for IT regardless of business or Industry.  If this is what matters to the CIO, sell based on the Top 10.  Here is a list I just grabbed that was published from Gartner Inc. and, yes, it was available on the web!

You can be a smarty pants too! So before you leave your next voicemail or email, go do some homework and please KNOW me and my business and start with INTELLIGENCE when you leave that voicemail or email if you want to do business with me.  Invest your time if you want mine.


Submitted by:  Mr. Guest CIO

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Watch Selling To The CIO

Mark your Calendar for June 27th at 11am! Click on to watch David Silverstein, Regional V.P. of ePlus and Author on “That Sales Show with Donna V.”  Donna is a Sales Performance and Leadership Coach at Enterprise Sales Institute.

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Do What You Must to get to the CIO

sales meeting
sales meeting
At the office yesterday, a letter had been placed on my desk, nicely removed from it’s envelope by my assistant.
Everything on the envelope was handwritten, including the return address. It was all in a smooth flowing cursive; reminding me of my primary school teachers and looking like a personal letter that only my mother would still send.
Ok, now I am intrigued. why is this letter on my desk? It must be something important enough that it passed the screening test of my assistant and it she placed it there directly in my flight path to intentionally earn a moment of my time and attention. My assistant serves as a tremendous filtering gate, removing a vast number of sales attacks from every reaching me. (I’ll share some stories in the future about how aggressive, rude, and downright nasty so many of those business development people are to her.)

So, I next scanned the letter, a typed one and it was immediately identifiable as a sales letter; done as a basic mail merge with my name and company inserted at predictable spots, and hand signed by Karen L. Since this letter was clearly intended for a sales purpose, my state of intrigue transitioned to becoming immediately baffled. Why was this letter even on my desk and not already in the recycle bin? I then read the first line and there it was…a simple reason why it was on my desk – it was the opening sentence. It stated “I wanted to thank you for accepting my friendship on LinkedIn and very much appreciate your response to my email.”
That sentence showed just enough evidence that my assistant concluded that Karen and I had an established relationship, although she did  pause to reflect on the validity, she decided to pass the letter on for my viewing; after all Karen clearly expressed the interactions that solidified our pre-existing relationship.

There was just one flaw in the stream of success that Karen had achieved so far in her business development journey to get to this particular CIO. It was in that opening statement that she wrote in her letter with her company letterhead adorning the top left corner – it turns out there was not a shred of truth to any of it. I was not connected to Karen on LinkedIn (for a “friendship” – what on earth?) nor had I ever exchanged email correspondence with her.
Well done Karen! You and your employer, trying to create business opportunities out of thin air got to the desk of the CIO! Bravo!
Karen what you and employer don’t realize is that you have done irreparable damage to yourself, your company, it’s other employees, and it’s investors. Your brand arrived at my desk and captured that so desired moment of my attention based on a foundation of trickery and lying. Your very first move to begin a relationship destroyed the opportunity to ever establish credibility. For me to do business with you, you ultimately need me to trust you, your company and the product offering. Credibility must be built to such a degree that am willing to take a business and professional risk on your organization to invest in your offering for use inside my enterprise, where I am accountable for performance and quality.

Karen, your letter and method have made it easy for me to make a business decision, so thank you. You have been permanently written off and I will never consider business with you or your employer. You have demonstrated everything I need to know to make a decision from your elegantly addressed form letter. You have no integrity, you have no ethics. You can also let your CEO that I’ll be sure to share my experiences with you and your company at CIO gatherings, as we enjoy trading insights about vendors.

Mr.CIO Talks
Mr. CIO Talks has spent the last 20+ years working with information technology. He has been a start-up entrepreneur; worked in a consulting and sales capacity, led IT organizations, along with other responsibilities in addition to CIO. He has held IT leadership responsibility across several industries and in global geographies. He has served in an executive officer role in both times of market growth and contraction. He has served on the boards of several organizations, from board chair to committee chair, to board member; from the publicly traded firm to the not-for-profit, to government appointed. He currently spends his time as a CIO,  board member,  volunteer, and an advisor.
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Talking about Telling The Truth

Selling to The CIO

Selling to The CIOMy inbox was recently graced with a well written cold pitch for a technology product that actually looked interesting to me so I gave it a full read.  This following line and its subtle peer pressure will sound all too familiar.

“Our current clients include Company A, Company B, Company C, Company D, and Company E in your industry.”

Despite my sometimes socially limiting career in IT and what the writer apparently hoped, I know my CIO counterparts at 3 of the companies.  I forwarded the email to each of them to ask the simple question: “Is this product and vendor worth my time to follow up?”  A positive answer would have likely led to a phone call or email to the company.  The unfortunate response:  not one of my peers had ever heard of the product or vendor.  They never got the call from me and my email just poisoned the water for them with my three peers.

A while back, I was in a meeting with a vendor who presented the required slide with a dazzling eye chart of client logos.  One small one nestled in the corner caught my eye.  It was a small company I had cofounded and where I remain an active board member.   I would have known (and been surprised) if they were a client of this vendor.  They were not and now they never will be.

Would you sign a contract with somebody who started lying at the first meeting?  No trust, no sale.   Don’t assume that I don’t have a network and won’t check your client list myself.  Your networking can work either for or against you and you will reap what you sow. It is OK to be small or a startup or to conservatively state your client list.  Every company was once a startup and once had a small book of business.  Own your reality, state ‘facts’ like client lists that are real, and show me your value.  It’s not that hard to make sure the network works for you and not against you.

Mr. CMIO is Talking about Telling the Truth

Mr. CMIO is a 20 year veteran in IT who has done almost every role in applications, infrastructure, and management.   Most of his adult working life has been in the financial services industry where he does constant battle to keep regulators and auditors from making things harder and worse.  After dealing with regulators and auditors, sales people don’t scare him and he’d really like them to actually help him.

Mr. CMIO has twice created the CIO role for public companies and is known as a mentor and coach who has developed other senior IT executives.  He is active in industry and community organizations developing the next generation of leaders.   In the last 5 years, he has taken on the additional roles of running business process improvement, new business launches, and chief marketing officer (CMO).  He is part of the new breed of cross-functional IT executive.  Don’t try to trick him or go around him, it only makes you look bad and he tells his friends about you.  Work with him and he will work with you.


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The Purchasing Folks


group of business peopleLesson Learned

We as sales people need to understand that we are not only selling to the CIO or IT today, but in many companies and organizations we are selling to purchasing.  The world has changed and purchasing good or bad pulls the purse strings.  Has this happened to you?

Long sales cycle, lots of meeting and demo’s and finally your champion or even the CIO says, you are the vendor of choice, you have won the technical battle.  All good and very important win, but now comes the cost negotiation.  So you enter into discussions on cost in good faith with your IT contacts.  No reason to think these negotiations will not get you to a final contract and agreed upon price, right?  Well may not.  “OK now you have to go meet with Bob in purchasing”.  No problem this where the contract get signed.  Except Bob needs his pound of flesh because that’s what purchasing does and oh by the way he needs to know why IT needs the flux capacitor and the fetzer valve.  You think; did we just start the sales cycle all over again?

So what happens; your sale gets slowed down, you probably end up giving additional discounts that may require additional approvals within your organization and you end up having to explain your solution or service and value to their company all over again.  And in most cases this process will have a time suck on your champion in IT as well.

So how do you avoid this situation?
Lesson Learned…… Ask what role purchasing will play in the sales cycle up front.  If you need to have them attend meetings during the sales cycle and have them fully involved in the price negotiations with your contacts from IT.  This also ensures that IT and purchasing are on the page.

We are in changing world, funds seem to be tight everywhere and purchasing plays a greater role in the selling process today, at least that is my experience lately.

My 2 cents……

by Another Sales Guy

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Respect the CIO….


Are you kidding me?

How would you seek to do business with the CEO? Would you have a different approach for the CEO of one million dollar per year firm, how about for a start-up, versus a 100 million dollar one, versus 500 million plus? How about one billion and up?

In any of these cases, would you consider calling the CEO’s office and leaving a message on voicemail that you will be “in the area” and want to stop by to introduce yourself?

Perhaps instead you would have an inside sales rep or call on behalf of “person X, our vice president” or “director” and state that they “are going to be in your area next Tuesday and would like to stop by for a few minutes to discuss our offering.”

Of course not. It is a ridiculous approach. So why on earth do you do this with CIOs?

This is a technique that is reminiscent of the copier salesperson in the 1980s. I suspect this was probably once taught as an official approach by one copier pioneer and migrated to other organizations.

Do you really see this as a model that will work for the CIO? What if you stratified organizations in the same way that I noted above, would you use the same tactic for every one? This approach demonstrates a real ignorance, a lack of any sophistication into understanding the operations of your prospect organization.

There are so many things that are fundamentally wrong with this approach and for know, I’ll express that it shows that you do not understand how others use their time. This is a very immature approach and it does not even factor in the concept of decision structures and entry points, which I’ll tackle in future blogs.

Every single day, in the pursuit of sales, there is an assault on me by 25-30 organizations. These messages, if thought to be polite, targeted approaches to the top of the IT food chain are instead futile.

This particular message was left at my office this week. (with names and numbers changed to protect the guilty).

Not only is this the wrong approach, in hearing the message it was obvious that is was scripted and the person reading the script had poor delivery, simply by the fact that his word flow did not match any natural speaking pace, with pauses and starts lining up more with the carriage return than they did with the intended message and sentence structure.

Here is the message translated to text:

“Hello, this is Chip S. form ABC Consulting. We are an IT staffing and consulting company and I was going to be in your area next Tuesday and Thursday and wanted to know if I can stop by and introduce myself and see what possible needs you may have in the coming month. Please give me a call when you have the opportunity. 555-1212 extension 270, 555-1212 extension 270. Thanks in advance for your time.”

Chip did not receive a call back.

-Mr. CIO Talks
Mr. CIO Talks has spent the last 20+ years working with information technology. He has been a start-up entrepreneur; worked in a consulting and sales capacity, led IT organizations, along with other responsibilities in addition to CIO. He has held IT leadership responsibility across several industries and in global geographies. He has served in an executive officer role in both times of market growth and contraction. He has served on the boards of several organizations, from board chair to committee chair, to board member; from the publicly traded firm to the not-for-profit, to government appointed. He currently spends his time as a CIO,  board member,  volunteer, and an advisor.

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Become a Customer Advocate Inside Your Organization


Advocate, Listen and Ask

Asking and Listening, that’s not in my job description, Selling is.

David, you have hit on a great point, however most of your industry peers, certainly not your equals do not know how to listen; nor do they know it is something they should do. I remember one of my first frustrating experiences with a sales professional. I still remember his name, his company and his failure.

In his eyes and in the eyes of his firm, the only failure was that there was no deal closed. However, Kevin did not have any ability to listen to the customer expressing that the configuration of his offering did not match my my needs. Kevin worked for “big-tech.” His sales pitch was scripted and his demeanor was both professional and unbreakable. When I expressed that I did not want to buy his product the way it was configured and packaged, his response was to repeat the same failed statement as if the more times he said it, would eventually become true or I would become enlightened.

Kevin’s employer had created this environment and the specific condition, no flexibility to work with the customer and a powerless sales resource engaging with the customer. Kevin did not get it, and probably has not to this day, 18 years later. Kevin was soon removed from the account and another knight in shining armor soon arrived, replacing Kevin and promising me the world. In the last 12 months I’ve had 3 reps from that company alone (Colleen, Anne and now Joyce). You may all be thinking of which firm and swearing you know exactly which one it is, however, I know who you are thinking of, and in this case, you are wrong. That particular big tech firm does hold the record in my book and I’ve had a new rep at least every 12 months for nearly 20 years.

Every new sales person has the same story and they are all “gone” come January. Your role is, most importantly to be the customer advocate inside your organization, to build long standing relationships with many people, and to get to know the customer firm in detail. Then to be there to service the account, without any agenda other than to exceed the customer’s expectations on the dimensions that matter. This will result in building trust. Back to listening, if something is not right, that means going to bat for the customer, and that means being willing to take risk and change. For the rest of you, November will be the month that your sales managers will make their decisions about which patch or accounts to reassign you to in January, and you only get a few of those shots!

-Mr. CIOTalks

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Getting My Attention, The Right Way!

right way

Selling To The CIOAt the risk of giving away the secret of someone who knows how to do it right, I offer the following e-mail as an example of a salespitch gone well! How refreshing! I wish more people go about it like this person did.

Hi Mr. CIO OnPoint, 

Congratulations on your recent <insert successes or publicly visible things about the company>.  It’s great to see a local company doing so well and moving their industry forward.

I was researching <insert company name> because I am impressed by your <insert what impresses you>.   I see that you have an open position for <insert title> with some very exciting projects envisioned for this role.

At My Company, I help people like you who are rolling out these types of projects and can support your in-house efforts through <name your value added services>.  We work with you in whatever way is most effective for you, from providing light consulting through full implementation support. 

Would you be interested in speaking with me about this or any other areas where you are looking for support and I might be able to help you?

<insert your name>

What this shows me is:
(1) you did your homework
(2) you identify with my company as a company and not just the next prospect on your list
(3) you indicate your desire to ADD value
(4) you didn’t obnoxiously suggest you WERE the one I needed, but you asked to talk more
(5)  and said you “might” be able to add value, and did not arrogantly assume that you are “sure you can”.

In short, you invited a discussion starting at the highest of levels, the company, products, market results, culture, what have you, and are willing to work from there. You DID NOT ask me what projects I have that you can help me with. You showed that you ALREADY DID YOUR RESEARCH so you had a place to start.

Unlike a cheap pick-up line, this approach can’t be pulled out on a moment’s notice and applied in any situation.  You need to time it around something positive happening at the company. You’ll know when you can use it because you’ve been watching the company over time, watching the news, and making connections.  Kind of like building familiarity with someone versus using a cheap pick-up line.   You can’t do this on a once-and-done.  It requires attention over time. The same attention over time that I EXPECT once I’m a customer.  Show me that as a prospect, and you have a much better chance of me becoming a customer.

The result:
This person got an immediate email back, got a lunch meeting within the same month, and got recommended to members of my team as well as others outside my company as someone to check out and engage with.
Wouldn’t you love to be this person?

PLEASE be this person and save me from the deluge of inappropriate approaches.

Mr. CIO OnPoint
Mr. CIO OnPoint currently serves as a CIO in the technology industry.   OnPoint comes from a long IT background, starting in end-user support and advancing through infrastructure, application, and consulting roles to CIO and cross-functional executive leadership.  OnPoint has served in companies of all sizes in a range of industries.  OnPoint is active in IT industry organizations, contributing thought leadership in the IT profession, advising emerging companies, and offering his expertise to support emerging IT leaders and youth pursuing careers in IT.  After being frustrated for years with ineffective sales approaches, OnPoint contributes case studies here to help salespeople be more effective at approaching CIO’s in a way that allows them to make their value proposition clear and start  meaningful mutually-beneficial relationships.    He also provides examples of what not to do.   Unfortunately these examples happen way too often.


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Get The Deal Done By Doing This One Thing


As sales professionals, the power to close the sale sometimes depends on others. For most of us that have type A personalities- the fact that we must lean on or trust someone else to get the deal done is nauseating.
We like to be in control….
Well, as I have learned more than ever lately–Too Bad!!
It’s time to move on and get over it.  Embrace and ask for the help…

As our sales cycles become longer and the complexities of what we are selling become harder, we must lean on others to help make it happen.

In larger companies you have a team of resources.. USE THEM!!  I miss the days when a had SME’s at my disposal..  These folks can really help you close the business if prepared and put in the right situation.  It’s up to you to coach them.  For those of use in smaller companies with less resources we must get creative and do the extra homework to make sure we are prepared.  Not an easy task but it’s what we signed for.

As always I would love your thoughts and feedback.

Good Selling.







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