With server going away, the majority of our customers have a cloud migration on the horizon. Before you can make the switch, you’ll need leadership buy-in. 

In some companies, this is pretty straightforward. In others – especially very traditional organizations – it can be trickier. To avoid the all-too-common trap of senior leadership dismissing your good ideas (which studies show happens often), try some of the following strategies on for size.

Understand their goals and priorities

Survey says these are the top five benefits of cloud

When you’re asking leadership to hop on board with a change – be it migration to cloud, a new tech tool, or pretty much anything else – they need to understand how that change supports their priorities. Which means you need to understand what those priorities are and how your proposal moves the needle. 

At first blush, this might seem simple. But in a lot of organizations, leadership priorities can seem divorced from day-to-day team priorities and realities. If you’ve ever laugh-cried at a leadership edict to cut development time in half without increasing staff or budget, you probably feel this statement in your bones. And even in the most connected, team-focused organizations, sometimes there can be a mismatch.

Which is why big change always starts with figuring out leadership’s real priorities. What are their objectives? What metric is their performance judged on? What problems do they need to solve? 

As a user, one of my reasons to move to the cloud might be the new innovations that make my job easier day to day. As an admin, getting maintenance off your plate so you can focus on strategic planning is probably a big win. But for leadership, the key deciding factor is probably overall cost savings, productivity gains, competitiveness in the market, and/or moving the needle on high-level business goals and long-term company value.


Have a good sense of leadership goals? The customizable slide deck in our business case toolkit lets you add them directly to your presentation.

Personalize your pitch

Framing an organizational shift to cloud

Once you know what leadership needs, personalize your pitch to focus on those things. Harvard Business Review calls this “tailoring your pitch,” and says it’s the number one tactic associated with success

If your boss’ bonus is closely tied to saving money, come to the meeting armed with info on how cloud can reduce your total cost of ownership (TCO) and what cloud savings might look like for your organization. (Our handy calculator can help you come up with an estimate).

If leadership is focused on productivity or time savings, lead with the fact that 83 percent of those who move to cloud say the move saved their admins time. If competitiveness is a key goal, a review of the competitive landscape can help make your case.

Whatever other high-level business goals or long-term value discussions come up, we’re confident there’s a reason cloud will take businesses closer to those goals. (In fact, we’re so confident, we’re retiring our server products and pouring our investment into cloud.)

Take the long view

A move to the cloud means investing time and money up front for benefits that will snowball over time. So, your presentation should take a long view. 

A migration to cloud might cost you $60,000 this year, but if it saves you $45,000 per year, you’ll pretty quickly get to the break-even point – and fly past it into long-term savings. Two years post-migration, that means you’ll have saved $30,000. Five years post-migration, that number jumps to $165,000.

Make sure the presentations, emails, and conversations you have with leadership are realistic about current investment but also show the long-term, compounding benefits – be they financial, innovative, time savings, or something else your particular leadership values.

Prove your points

Once you have your priorities and arguments in hand, gather up stats and success stories that support them. If you’re telling leadership that cloud will save your company 10% in costs and 25% in IT team time per year, you’ll need stories and data that support your figures.

Our business case toolkit is chock full of stats and success stories that back up the benefits of cloud. Grab them and use them to make your case. 

Make it easy to say yes

The more hurdles (even small ones) you can move out of the way, the more likely you are to hear yes – not only when you ask about making the move to cloud, but also when you ask leadership to take small first steps, like accepting your meeting request.

For example, if I’m a busy CEO and I get this email: “Can I run something by you and when is a good time?”, I might not answer. The email’s request requires me to look at my schedule and find a good time. It also forces me to ask follow-up questions about what this is about and whether it’ll be a good use of my time. That extra mental overhead and those relatively small tasks could be enough for me to either ignore the email or shuffle it off to deal with later (read: lose it in the bottom of my inbox).  

On the other hand, if I get a short email explaining someone in the company wants 30 minutes of my time to discuss how moving to the cloud will save us time and money, now I’m intrigued. (My job is to save us time and money!) If the email has already proposed a specific time that’s open on my calendar, it’s easy for me to accept the invite. No follow-up, mental overhead, calendar browsing, or other time-sucking tasks required.

To make it simple for you to create those easy yesses, we’ve included customizable email templates in our business case toolkit.

Come armed with costs and timelines

Which Atlassian Cloud plan is right for you?

Once leadership is excited about the possibilities, be prepared to answer questions about costs, timelines, and the skills and people needed to pull off your migration. 

Use our pricing calculator to get a real sense of your costs. Grab our migration planning checklist (included in our migration toolkit) to understand the steps involved and estimate your timeline. And use this article to figure out who you’ll need on your migration team.

Get specific – but not too specific

The deeper your understanding of migration, cloud, the benefits, the costs, etc., the better off you’ll be. But for conversations with leadership, it’s wise to stay out of the details in your early talks, unless asked directly for more information. 

At this stage, if someone asks about security, high-level stats will help more than a detailed rundown of Atlassian’s bug bounty program. If they ask about remote work, they probably want to know that the systems were built for it – not the exact specifications.  

This doesn’t mean you should skip over all the great features that drew you to cloud in the first place. If automation is part of what is going to save you time, talk about cloud’s automation benefits. If our award-winning security will put their minds at ease, mention it. If specific product features – like Jira Software Roadmaps or machine learning-powered smarts – specifically help you reach your goals, show them off. 

Just don’t get too far into the details before leadership starts grasping the big picture.

Ready to get leadership on board?

Grab our business case toolkit (complete with customizable slides you can use to make your case) and our cloud migration toolkit for more resources that’ll help you make your points and get started on your migration. 

How to get leadership on board for a cloud migration