How to convince upper management of your next big initiative

A colleague of mine, Alan Berkson, who used to manage an IT team for Wall Street fondly recalls an interaction he once had with the head of trading. Here’s basically how it went:

WS HoT: “Why should we spend all this money on IT?”

Alan: “Are your systems running?”

WS HoT: “Yes”

Alan: “That’s why”

The need to justify your team's budget is not just specific to the IT department, though. And it becomes even more profound every time you want to start a new initiative, especially if it needs funds in addition to the meager monthly budget. You need to build a business case for it, put it on a pitch deck and prove to the management and the finance team that it’s worth every penny, and more.

I won’t go into the details of what makes a good deck. But I do want to help you plan better so you can forecast (and maximize) the ROI of your next big initiative. Here are some things to keep in mind:

1. Pick an existing problem worth solving

Whan a brilliant idea strikes you, it’s easy to fall in love with it. You can’t wait to share it with your peers and your boss and eventually bring it to life. But before you make it your north-star goal for the next quarter, take a step back and ask yourself “What’s the objective of this initiative”, “What problem will it solve”, and more importantly “Why is the problem worth solving”.

Thinking through these answers will help you understand whether the project is worth starting or whether it will end up becoming another distraction. To avoid that, work backward. Try to fill an obvious void in your department as opposed to implementing something that at best isn’t the need of the hour, and at worst just reinvents the wheel.

2. Gather inputs from stakeholders

Clearly articulating the objective will make sure your idea is worth implementing. The next step is to flesh out an implementation plan. This is where you find out in detail how the process currently works and whether any relevant changes are planned for the near future. Doing so will help you refine your plan and might even give you ideas to further optimize it.

The simplest way to find out is to ask. Talk to the people who will be directly affected by it. For instance, if it aims to automate a repetitive workflow and make the team more productive, talk to the folks involved. The last thing you want is for the entire project to fall flat after all the hard work you put into it.

3. Focus on metrics that are important to your organization

Although all businesses want to be successful, the way they define success may vary. And the success of your team is directly tied to that of your business. So, once you know what problem you’re solving and how, ask yourself how you would determine whether the initiative was a success. More often than not, ROI is more than just dollars saved versus dollars invested. It’s about the value your plan brings to the business.

Your team probably focuses on a unique set of metrics. Even if it’s the same as another one, your goals might be completely different. Take downtime, for instance, which is a key metric for IT teams. The recent AWS outage may have lasted just a few hours, but it affected millions of users. In a smaller organization, a day-long downtime might “cause a few people to get upset”. Build your plan keeping these metrics in mind and talk in terms of the metrics while pitching it.

4. Analyze risks and be ready with contingency plans

Your plan most likely relies on multiple resources like colleagues, vendors, and technology. The more the dependencies, the greater the likelihood of something going wrong. I mean, people fall sick and computers crash. Spend enough time listing all such risks, their potential impact and the probability of them happening. Then try to eliminate as many as you can, and come up with contingency plans to mitigate the rest, perhaps using alternate resources. You might need to accept some risks if the cost of those resources outweigh the impact itself.

If similar initiatives have been attempted in your organization in the past, learn from them. Analyze past data and find out what went wrong and go through recent data to see how things are different now. Besides, find out if someone within or outside of your organization has implemented a similar plan successfully. Study their approach and see what worked for them.

5. Do your homework and then present your case

Even after a thorough risk analysis, forecasting the outcome of a project involves making some assumptions and a few educated guesses. Make these assumptions clear. Even the most brilliant of plans can fail due to something completely unexpected. Also, to avoid overpromising, downplay the ROI forecast you arrived at by a factor of about 10-15% depending on what and how much it is.

Right before presenting the plan, think of all the questions and rebuttals that might come up, and be prepared with answers to most of them, if not all. And finally, even after you implement it, actively seek out feedback to continually make it better.

In conclusion..

• Pick an existing problem worth solving: What’s the need of the hour?
• Gather inputs from stakeholders: How are things working currently and what can be improved?
• Focus on metrics that are important to your organization: How does your organization define success?
• Analyze risks and be ready with backup plans: What can go wrong and what would you do if it did?
• Do your homework and then present your case: What questions might come up during the pitch and how would you respond?

I hope you find these tips helpful while planning and pitching your next initiative. If you have any tips that have worked for you in the past, please do share them in the comments below.

This post was originally published as a slightly modified IT-specific piece in Freshservice Blog, but I felt that these tips apply to whichever department you might work in.