How IT leaders can master the art of the elevator pitch

How IT leaders can master the art of the elevator pitch

How polished are you at the quick conversation that makes a big impact? It's crucial for IT leaders to master this skill set, CIOs say. Try this advice to improve yours

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Storytelling tips for leaders

You’re in an elevator. You’re in an Uber. You’re catching someone in the hallway, or in their office, but you’re catching them in a few short minutes between other meetings. How do you make a big impression in a small amount of time?

That is the theory behind why you need to practice the art of the "elevator pitch," as in making your point in 30 seconds to a couple of minutes before the person you’re pitching to reaches the next floor.

The goal: Get someone's attention and convince them to make time to hear more.

According to one story, the term was coined by journalists at Vanity Fair who had such a hard time pitching ideas to Editor-in-Chief Tina Brown (because she was always on the move) that they took to cornering her in the elevator during the few minutes she was forced to stand still. Even if your boss is not that hyperactive, being able to catch the attention and capture the imagination of your superiors can be important when you want more budget, more people, or approval for an important project. It can also be a good way to get a promotion, a raise, or a new job.

That’s not to say you will be able to seal the deal on a project, promotion, or job in one short conversation. The goal of the elevator pitch is to get someone’s attention and convince them to make time to hear more.

Is that really the way the big IT decisions get made?

“All the time,” says Les Ottolenghi, former CIO of Caesars Entertainment and the Las Vegas Sands. “All. The. Time. You have to convince someone up front before you get into whatever your governance is for your capital and allocation of capital.”

[ Is your vocabulary driving people crazy? Read also: 7 phrases leaders should stop saying in 2020. ]

So how do you deliver a good IT elevator pitch? Consider these proven tactics:

Pitch like you're a startup

"It's taking us six weeks to deliver an offer, and now we're going to be able to do it in six minutes."

Even when you’re pitching a project within an established business, think of it like a startup you’re trying to convince someone to invest in, Ottolenghi says. “The elevator pitch must be a headline explaining exactly what you need and the impact you can make. We need resources, 50 resources, to deliver a new marketing system, a new offers system. It’s taking us six weeks to deliver an offer, and now we’re going to be able to do it in six minutes. That will improve profitability 50 percent. We can do it if we can get the money now, and we can deliver next quarter.”

A concise message with a clear payoff gets attention, Ottolenghi says. “You need to show you’re really trying to scale your business and grow. An IT leader needs to be a strategic partner to the C-suite.”

In other cases, as with cybersecurity, it may be necessary to pitch in terms of risk to the company and opportunities to lower it, Ottolenghi says. For example, he argued in favor of a zero-trust platform that would go beyond architectures dependent on firewalls by saying, “We can no longer sustain our risk profile by doing things the old way” – and illustrating those growing risks.

To be spontaneous, practice

Maribelis Soto, a project manager working at a technology services firm, says she has studied the art of the elevator pitch through books and coaching, getting it down to a “magic formula.”

Always end with a call to action: That might mean an introduction, investment, or budget approval.

Whether pitching herself for a job, or pitching a project to a decision maker or investor, she focuses on explaining exactly who she is (a project manager with more than 15 years of experience) who has worked for some big, recognizable name organizations (Home Depot and Sprint). In an IT context, she emphasizes her IT work but can also allude to work on TV production and marketing projects. Then she works in some action verbs, emphasizing success at increasing sales and revenue, as well as improving processes and saving resources. She might mention her passion for improving customer experience or capturing the “voice of the customer.”

“Then you always end with a call to action,” Soto says. That might mean asking for a time for a follow up conversation, or asking more directly for an introduction, an investment, or a budget approval.

Of course, an elevator pitch has to be adaptable to the specific situation and the person you’re speaking with. Still, Soto says having drilled the basic speech, and expressing her thoughts in a short period of time, makes a difference. “I can change it in my head really quickly because I have a formula,” she says.

Look for news you can use

Lorenzo White, who was CIO and a financial services company and now offers consulting and virtual CIO services to small businesses as LAW Technologies, recommends making a connection to an event in the news. If he was trying to make a case for better cybersecurity a few years ago, he might have started the conversation with “did you hear what happened to Target?” Today, his firm has a contract with the state of Florida to help county election offices approve their security, so he is more likely to cite stories about manipulation of the elections in 2016 (and signs that it could recur in 2020).

“Relating it to what’s currently going on gets their attention,” he says.

Even when you have longer, make the first minutes count

Elevator pitch thinking can also help you organize a longer presentation.

Elevator pitch thinking can also help you organize a longer presentation, understanding that if you do not capture your audience’s attention up front, they are likely to tune out the rest.

“Many of us in IT have been in the boring presentation, the presentation that’s getting into the weeds,” says Matt Kinsey, president and CEO of MK Tech Group. Before founding the consulting company, Kinsey was an IT Solution Architect at Office Depot. He recalls one pitch to the CIO, CTO, and other senior leaders where his team had prepared a presentation larded down with too much technical detail. “I said, no, we’re missing the point. So we restructured it to get to their higher level concerns first.” That meant starting with the business value of the project, not the details.

As it happened, after the first part of that presentation was delivered, the senior executives “nodded, excused themselves, and left their direct reports in the room – and then we got more into the details,” Kinsey says. “The executives had heard enough to say, yes, if my people support this, you’re solving real problems for the organization.”

Kinsey also has decades of experience in Toastmasters, the public speaking and leadership development organization, and currently serves as Second Vice President of Toastmasters International. Among the relevant skills Toastmasters teaches are giving impromptu speeches of one to two minutes and giving evaluations of other speeches (three to four minutes).

Another important principle is the importance of knowing your audience, and tailoring whatever you say to their interests, Kinsey says. “Answer their questions before they ask them – they really like that,” he says.

Front-loading your presentations can be particularly important when you have negative information to deliver. Kireet Kokala, who leads analytics and technology enablement for customer success practices for the digital consulting firm Triaz, recalls a time when he had to address a security breach for a large client. Having been briefed on the details on the way to the airport, he boarded a plane knowing he had less than 10 hours to prepare to convince the client’s Chief Security Officer not to terminate a multi-million contract.

“The most crucial part of the presentation was not in the PowerPoint,” he explains. “I delivered a handwritten apology to the CSO.” Then, without reading from the slides verbatim, he told a story about plans for “better controls for people, processes, and compliance” and explained how quickly his team had addressed the problem. The pitch went well, considering he had to start with an apology.

“The message here is to clearly show integrity by owning your mistakes, fail fast, and recover stronger,” Kokala says.

[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]

One comment

Well researched, David. No

Well researched, David. No doubt there are elevator pitches that ring a bell the first time and there are those that ring a bell every time! Active listening skills have to be at the creative center of building up the elevator pitch.

David F. Carr is a writer, speaker, student of digital business, and the author of "Social Collaboration for Dummies." He previously served as an editor for InformationWeek, Baseline Magazine, and Internet World and has written for Forbes, CIO Magazine, and Defense Systems.

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