These days, CIOs who are proposing a major transition to the cloud should be prepared to have that conversation at the C-suite or board level. It's possible the CEO will be carrying the ball, and IT leadership will likely be a close advisor or playing an active supporting role. 

Cloud migration may be expensive; at the same time, it brings powerful advantages that foster innovation. That makes the decision a complex one that's of keen interest as much to the C-suite and the board as it is to IT. 

Winning approval for this project may take a different set of skills and a new way of preparing for what could be a higher-level conversation. Here are some best practices for how to succeed:

Map the cloud transformation directly to the business's strategic objectives

Don't try to make the argument that the company should invest in cloud for tech's sake. Show them how it connects to and supports business value. 

Start with a targeted business outcome, that is, a strategic business goal, and work backwards to scope what your IT infrastructure and application strategy need to be to support that mission. 

The C-suite and board will appreciate the business-first approach and you'll have their attention because you'll be speaking their language.

Do a cost analysis based on the best information you can muster. It often boils down to is CapEx now for your cloud or platform migration to reduce OpEx later. Can the business afford some capital now to reduce its operating costs in the future? It's a sliding scale in which time-to-ROI will vary by organization and cloud implementation. 

Cost-reduction alone is not always a strong enough reason to migrate to the cloud. 

The added advantages of cloud —  such as on-demand scalability, resiliency and easier globalization — should be tied to the company's strategic business objectives. That's the more compelling ROI of cloud transformation.

Take inventory

Assess the team: do you have the talent you need to carry this off? 

Inventory current cloud operations, on-premises systems and applications, and monolithic legacy apps that are unlikely to do well in the cloud environment without modification or replacement. 

Consider, too, the code or data dependencies for each app . Assess the state of progress toward the cloud, compare it with what's known about how the company's competitors are doing. Talk to the people in the company who know these things if you don't.

There are two key questions to ask: Where are you today in terms of the infrastructure and apps you have at your disposal? And where do you have to be in two, three or five years to support your company's long-term strategic goals?

Find a tactful way to sum up what's possible and what isn't

What senior leaders and board members don't know about cloud can cause a lot of wheel spinning and far too many discussions grounded in inaccurate assumptions — requiring IT leaders to jump in with "we can't do that." 

Be prepared to articulate early on what the technology can and cannot do. Otherwise, you may start to look like the person who always says "no." 

Consider how the IT department might upskill the board and C-suite by offering to host a few sessions on cloud technology concepts and terminology, plus Q&A time. Educating the board on cloud is a smart approach.

Expect the unexpected question

Be prepared for curve balls and stumper questions. For example, a member of the C-suite or board may say, "You're telling me that in 18 months we will begin to cut operational expenditures by 15%. Will that level of efficiency grow over time?"

Or what about: "How locked in will we be with our cloud service provider? Do we need to worry about rising rates once we are settled in? How are we protecting ourselves from that kind of scenario?"

Don't waffle on the gotcha questions. Be calm, direct and honest. And focus on the company's unique situation — there's no single way to do cloud. 

To the vendor lock-in question, if it's not an issue for your organization, state facts that show why it isn't. But if it is an issue, admit it's a concern and be ready with a plan.

One such scenario to address concerns about vendor lock-in is to consider a multi-cloud approach using two different cloud service providers and splitting your workloads between them. 

Like everything, there are differing schools of thoughts and you'll need to make the case for why the approach works for the business.

Field cost-reduction questions with care

Steer clear of making promises about cost reduction. Probably the quickest way for a CIO to get into hot water related to a cloud transformation is to promise to cut operational expenses. 

The classic example is promising staff reductions as part of a cloud migration. Any decision about head-count reduction would be better made on the other side of the migration. The company may find, for example, that it needs to convert head count to jobs for new employees with different skills. 

Each company's cloud journey is different, and not everyone saves money. Share the cost analysis, but if it's not compelling on its own, pivot to how cloud technologies will support strategic business goals.

Don't go at it alone

Two other time-tested tactics for weathering your cloud proposal at a high level are teaming up with another C-suite or board member and making a point to have one-on-one conversations. 

It would be a shrewd move, for example, to team up with your CFO on cost-reduction analysis. Similarly, having one-on-one chats with possible opponents should give a sense of what their objections are, which you can then prepare arguments for.