How to sell your next big IT initiative to your boss

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

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

Alan: “Are your systems running?”

WS HoT: “Yeah.”

Alan: “That’s why.”

Sadly, this is not a one-off occurrence. For a department that’s literally responsible for running things around the clock, IT is severely underappreciated.

IT is stereotyped as a cost center rather than the core of the organization, with most IT organizations expected to do more with less.

This becomes 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 better pitch your next big IT initiative. Here are some things to keep in mind:

  • 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 if it’s only going to end up as another distraction. To avoid that, work backward. Try to fill an obvious void in your current IT environment as opposed to implementing something that at best isn’t the need of the hour, and at worst just reinvents the wheel.

  • Gather inputs from stakeholders

Clearly articulating the objective will make sure your idea is worth carrying out. The next step is to flesh out an implementation plan. Find out how the process currently works and what changes are planned for the near future. Doing so will let 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 the initiative. For instance, if it aims to automate a repetitive workflow and make the team more productive, talk to the agents involved. If it’s a self-service initiative, find out what users want. The last thing you want is for the entire project to fall flat after all the hard work you put into it.

  • 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 IT organization is directly tied to that of your business. So once you know what problem you are solving and how, ask yourself how you would determine whether the initiative was a success. More often than not, return on investment (ROI) is more than just dollars saved or dollars made versus dollars invested.ROI is more than just dollars saved or dollars made versus dollars invested. Click To Tweet

It’s about the value your plan brings to the business.

Your IT organization 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. 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.

  • 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 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 outweighs the impact itself.

If similar initiatives have been attempted in your organization in the past, learn from them. Analyze past data, determine 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.

risk analysis templateHere’s a sample risk analysis template you can download.

  • Do your homework and then present your case

Even after the 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 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 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 currently working and what can be improved?
  • Focus on metrics that are important to your organization: How does your organization perceive success?
  • Analyze risks and be ready with contingency plans: What can go wrong, what’s its impact, and what’s your plan B?
  • Do your homework and then present your case: What questions might come up during the pitch and what’s your response going to be?

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

Here’s an ROI calculator we built for Freshservice using the method discussed above. It tells you how much you can save with Freshservice. Go ahead. Give it a try and let us know your thoughts.