4 ½ Steps to Help Lead Your Company to the Cloud

Kendra Von Esh
Kendra Von Esh
Executive Strategic Advisor, Coupa

Kendra Von Esh, a former CIO at Veolia, has been a trusted advisor and CIO for the past decade developing value added strategies and solutions transforming businesses with technology. Von Esh joined Coupa last year to leverage her executive experience and active involvement in CIO communities and industry boards to create inspiring dialogue and change strategies cross-functionally.

Read time: 11 mins
A Woman with a Thinking Cloud

4-half-steps-to-cloudIt’s become clear that the cloud is vital to the future of IT. It’s our best chance to address the perpetual demand to do more with less, yet most IT leaders are still struggling to come up with a cloud strategy. Confusion, and in some cases, fear, still reign.

There’s one school of thought that says, pick a place and get started with the cloud. Or, you could simply let events drive you and make your decisions on a case-by-case basis.

However, I would argue that the best way to optimize both your solutions portfolio and your company’s business processes is to have a well-thought out, fully developed strategy. The alternative, as KPMG puts it in their report, “Digital Business: It’s Time for CIOs to Lead or Get Out of the Way” is to “keep minding IT as usual, while the business goes elsewhere gaining short-term solutions but also creating digital silos, adding to technical debt and missing opportunities to leverage new technologies across the entire enterprise.”

Developing a strategy is an excellent way to reclaim the mantle of leadership in the era of shadow IT. Strategy development involves communication, collaboration, education and change management--skills many IT leaders need to work to strengthen.

When you’re done, you’ll be able to answer questions such as, which applications do you currently have? What will you put in the cloud? What stays on-premises? What’s your plan for solutions as they go out of maintenance and support, or as contracts end? Are you going to shut them down? Are you going to convert them over to best of breed? Are you going to switch to a SaaS version? Are you going to use the same tools, but host them in the cloud?

You’ll have a road map for decision making over the next one to two years. The business and IT landscape change so quickly that it's not worth trying to go out further than that. For most organizations, having a two-year plan would be amazing. Here’s how to create it.

1. Start at the Top

The first place to start is at the top. There’s no way IT can come up with this strategy alone, nor should they. You’ll need to work with people company-wide, so you need the backing of your leadership team to get everyone to participate.

Explain to your company leaders why you need to do this. You don’t even have to call it a cloud strategy. Think of it more of an applications rationalization strategy, which is something you should have anyway because it’s the key to controlling costs. That’s the main reason to do this.

2. Take Inventory

The next step is to create an inventory of all the applications you have. IT can take the first pass, but don’t stop there. Nowadays vendors go directly to business heads so you need to go out and see what they and their staffs are using. You might even find out you already have some cloud adopters out there.

At the end of this exercise, you’ll have a big spreadsheet listing all the solutions owned and used within the company and by whom; whether they are on premise or in the cloud; what the contract, maintenance and support status is; what business processes it supports and what it integrates with. It really needs to be an end-to-end look at the whole landscape, so you understand what systems are connected. Fill it in as much as you possibly can, and get the various business leaders to help you validate it.

3. Assess Your Options

Once your inventory is complete, do some internal review within IT. Look for overlapping solutions, and business processes that are not supported by technology. Look at contracts and costs to identify areas that you can rule in or out for rationalization and modernization.

Once you see what the areas of opportunity are, go back out and engage the relevant stakeholders. Explain what you’re seeing, and solicit their thoughts or concerns. Assess their appetite for change. There are incredible solutions out there and the cloud can provide a lot of efficiency and agility, but you have to take them down the path with you.

At the end of these discussions, prepare a draft strategy to take back to senior leadership. Be sure it addresses the impact of your proposal on both the business and IT.

4. Back to the Top

Share your proposal, with the executive leadership team. Bring the relevant business leaders with you to talk about what you want to do together, how long you think it will take, and what the benefits and costs will be. The goal is to get alignment on where to move forward, and permission to spend time putting together a detailed business case and start talking to potential solution providers.

Remember that there are many factors leadership needs to take into consideration—budgets, strategic direction, mergers, acquisitions and divestitures to name a few. The more you can speak to these the better, but it’s not always possible to know or anticipate everything that’s going on at the leadership level, so be prepared to hear “no,” and to take things back to the drawing board if needed. You should also be prepared to address questions as to why you chose, or didn’t choose, certain areas for modernization.

5. Back in the Comfort Zone

Once you get approval from the executive team, you move into vendor analysis and project planning. Every IT professional has done plenty of that, so this is where I leave you.

Other than the applications inventory, which should be comprehensive and thoroughly documented, how much you formalize these meetings and strategy documents will depend on your company culture, as well as the size and number of projects involved. To my way of thinking, the more you can make people part of what you’re doing and the value you’re bringing the company, the better. That’s part of the benefit of going through this process.

I think everybody knows that in 2016, you'd better have a plan to modernize IT. Somebody’s going to start asking you about cloud if they haven’t already. Instead of stammering, “um, well, we have Gmail,” you’ll be ready with an answer that shows you’re managing IT the way that it should be in the digital age, leveraging the technology and the services that are out there today, and not still living in the '90s.