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Understand the Microsoft sales process to unlock more value

Allow plenty of time: "I recommend to clients to start the renewal process at least 180 days from contract expiration. Waiting late puts them in a position of weakness and reduces their options."

Allow plenty of time: “I recommend to clients to start the renewal process at least 180 days from contract expiration. Waiting late puts them in a position of weakness and reduces their options.”

This article is an interview with John Grubb, Chief Advocate at SoftwareAdvocates, and is based on his recent presentation “Controlling Microsoft Software Costs in Your Budget” at the IAITAM Fall conference earlier this month.

So what exactly is your day job?  

I own and operate SoftwareAdvocates®, a boutique consulting practice providing expert Microsoft licensing advisory services and software asset management (SAM) assessments and consulting.

I established SoftwareAdvocates® after a 15 year career at Microsoft, of which my last 7 years was in spent in enterprise sales.

You recently presented at IAITAM, on the topic of “Controlling Microsoft Software Costs in Your Budget”. Can you give us an overview of what that session looked at?  

First off I have to give big kudos to Dr. Barb Rembiesa and the entire IAITAM team for putting on a fantastic conference. My session provided attendees with a perspective from the software seller’s shoes – “what’s it like to carry a bag”. They learned about the software sales process and the roles involved, as well as the top five factors to controlling their Microsoft spend when entering or renewing a Microsoft agreement.

Can you give us an overview of what the software sales process involves?  

Software sales is very hard work and it’s getting harder with tighter budgets and the “do more with less” mantra that we are hearing from many organizations. Unless you have carried a quota, aka a revenue goal, it is very hard to understand the pressure a software seller is constantly under. Sellers must work hard to balance the needs of their employer and the needs of their clients. A good seller is able to develop a positive relationship with their clients and understand their factual business challenges.

Next comes the job of mapping the solutions they have to offer against a client’s need and pain. Then once the sale is made, a good seller is still visible working to make sure the client actually realizes the value the seller sold them. Understand that when an existing agreement is not renewed, the account team is held accountable for the loss, and this is an example of the people aspect of the software sales process. I recommend reading “The New Solution Selling” by Keith Eades if you want to learn more about the sales process. This book was forwarded by Kevin Johnson, former Microsoft Group Vice President of Worldwide Sales, and is an excellent read.

How does knowing about the software sales process help the buyer exactly?  

I am a firm believer that understanding the “other side” will consistently yield greater value and higher client satisfaction. My goal is to always drive my clients to win-win deals whenever possible. This is not always possible but should always be a starting goal. It was my experience at Microsoft that clients who worked in good faith and partnered received more value than those who took an adversarial approach. I always remind clients who are in a position of leverage today they will need a favor in the future, so always avoid burning bridges.

So, what do you believe are the top five factors to controlling Microsoft spend?  

The below tips were written with the expectation that a client would be entering or renewing a Microsoft Enterprise Agreement (EA) or Microsoft Enterprise Agreement Subscription (EAS). It is still applicable to clients who purchase only on Select Plus or Open but is most relevant to EA and EAS clients.

  • Allow plenty of time
  • Know what you have Deployed vs. Owned
  • Understand your options
  • Understand the terms & conditions
  • Know your requirements

Which of these five factors would you consider the most important, and why?  

Without a doubt the most important is “allow plenty of time”. I recommend to clients to start the renewal process at least 180 days from contract expiration. I see it over and over, clients waiting until the last 30 to 60 days to renew an agreement. Waiting late puts them in a position of weakness and reduces their options.

What do you think is the biggest mistake people make when it comes to Microsoft Software?  

Not having a plan to extract value from their Microsoft investment. For clients that carry Software Assurance (SA), which is part of all EA and EAS agreements, deploying new versions of products is critical to maximizing return on investment. This also means planning the resources (people, time and capital) to deploy those new versions. Another mistake is all too often clients do not realize all of the capabilities of the software that they own rights to, and they purchase additional software from other vendors that they do not need. I also see agreements renewed because clients fear losing the budget, so they keep renewing but do not have a plan to extract value from their purchase.

How do you think this can this be avoided?  

Have an approved and budgeted plan when you sign a new agreement or renew an existing agreement that clearly documents why you are signing the agreement and what value you expect to receive and how.

If you could only provide one piece of advice to organizations when it comes to purchasing software, what would it be?  

Keep asking questions until you are clear on the agreement you plan to execute and make sure you completely understand the software usage terms and conditions. Do not assume anything, always make sure everything is clearly understood and documented. Also make sure you are clear on what you are buying, including all of the software’s capabilities.

Any final comments on the topic of controlling Microsoft software costs?  

Work in good faith with your account team and seek win-win deals. Ask your account team if there are things that you can do to help them that will cost you little to no money. If you plan to make extreme cuts to existing spend, then give your account team a heads up as earlier as possible. I would even give them a chance to review your plan and determine if you missed anything that would change the economics of your model. It is also critical that clients understand that Microsoft is migrating towards a devices and services company and they need to understand the new Microsoft cloud solutions licensing models and capabilities. Again, always avoid taking an adversarial approach with all vendors.

About John:

John Grubb

John Grubb

Nationally respected Microsoft licensing expert with 15 years of experience at Microsoft and an IAITAM Certified Software Asset Manager (CSAM).  Proven track record of delivering positive results to clients ranging from mid-sized privately held companies to Fortune 500 corporations.  Possesses a deep understanding of both Microsoft licensing and technology which is unique in the industry. Can effectively communicate with varying levels of management from executives to front line managers, coupled with the ability to drive technical conversations. Results oriented and detail focused practitioner with a keen sense of business acumen.


The International Association of Information Technology Asset Managers, Inc. (“IAITAM”) is the professional association for individuals and organizations involved in any aspect of IT Asset Management, Software Asset Management, Hardware Asset Management, and the lifecycle processes supporting IT Asset Management in organizations of every size and industry across the globe.

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About Sophie Danby

Sophie is a staff writer for The ITAM Review. If you would like to contribute an article to the ITAM Review please get in touch using our contact form.

One Comment

  1. Kylie Fowler says:

    This is a good article. I would agree that the biggest challenge for any organisation is not doing the deal, it’s getting value out of the deal once it’s done.

    Key to delivering value is:

    1) Tap into the IT strategy development process and ensure that decision makers at all levels understand the functionality of what has been purchased so they can can make decisions that actively leverage the benefits
    2) Implement pro-active vendor management – by someone who has both vendor management AND SAM skills. Most generalist vendor managers do not understand how to drive value out of software investments, nor will they be able to create a bridge between vendor and the IT team or help the latter understand where the value lies
    3) Be focused – the benefits of an EA and SA quickly slip away if you do not have someone who is accountable for ensuring that they are realised

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