How to Pitch and Win in ’23

How to Pitch and Win in ’23

We’re always pitching.

We’re pitching for new business, for financing, for a job. 

We’re pitching our ideas, our perspective, and our point of view. We’re always at it, in one way or another, so elemental is the human need to influence others.

We’re always pitching, but most people and organizations aren’t very good at it.

I pitch. I’m pitched – a lot – and I teach pitching.

I’ve learned that those who pitch most effectively follow principles which significantly enhance their odds of success. They do well in good times, and bad. As we dig into 2023, and as economic anxiety sweeps the land, I share with you how the best pitch and win.

Follow these 10 guidelines, and you’ll be pitching and winning, too. 

1. Make it, really make it, about your audience.

What makes for a great pitch?

It’s simply focusing on those you wish to serve. 

It’s quickly explaining how your product, service, or initiative can help them. (For example, in a pitch to venture capitalists, it’s laying out the problem or opportunity – and how you can fix or exploit it, with the resulting benefits to investors – right off the top.)

Too often, pitchers commence by rattling on about their services, their people, and their offices – right across Canada! – sometimes without having a clear understanding of what their prospects want, need, or even care about.

Well before the formal pitch, learn as much as you possibly can about those you’re pitching, then learn some more. You still won’t know enough. The key is to match up what you’re offering with their priorities, and then being able to deliver the goods at the right time for them. Not you. 

2. Remember there’s no “I” in team.

If you’re preparing for a group pitch, aim to include the most senior leader appropriate to the task. The higher you go up the food chain, the more “juice” your crew will have. The leader needs to have the final say on participants and content – otherwise, there’s chaos.

Carefully consider the composition of the team – leave the hostile loner back at the office. Make sure at least some of those pitching will actually work on the client business if you win it. (Some companies are renowned for bringing in their heavy hitters to pitch, and then having them disappear once an engagement has been secured.) 

Usually, the leader opens and closes the presentation, providing a nice sense of symmetry. Each remaining team member takes a section. You can “protect” weaker presenters by giving them shorter sections, or by having them speak to an especially compelling slide, or introduce an impactful (but short) video.

3. Rehearse. Rehearse. Rehearse.

Rehearsal is especially important for group pitches, which can quickly descend into a clown show if each speaker isn’t smoothly advancing the story, or steps out of their assigned role to riff about a point that’s of no interest to your prospects.

You’re basically as strong as your least compelling member. After all, those being pitched are humans, and humans are instinctively attuned to look for weakness.

Prospects will be observing how you work together, so even if you can’t stand a particular team member, leave your enmity at home, (which I trust you do in any case.) For the foreseeable future, or at least until after the pitch and the business has been won, you will love that person unconditionally, and demonstrate it openly on the big day with smiles, eye contact, and strategic head-nodding. (If you’re having trouble pulling it off, just imagine you’re applying for a mortgage.)

4. Be in it to win it.

This is truly bizarre, but a lot of pitchers don’t approach a promising opportunity with nearly the determination to win. It’s as if they’re providing themselves with a psychological “out” if they don’t succeed.

Adopt a mantra, whether it’s a solo or group pitch, and your refrain is this: “We’re winning this thing!”

5. Front end load.

Get your best stuff out early.

For instance, if you already have a major tech company as a client, along with its testimonial, why would you possibly leave that information until later in your presentation?

You only have so much time here. Too many pitchers seek to “build” their case, running the risk of losing increasingly impatient and demanding listeners.

Are the financials important? Of course, they are. But your audience wants to know your story, too. What’s unique or special about you and your offering? How would you provide value?

Structure and deliver your information in the form of a tight, integrated narrative – explain all jargon, please – and include examples of how you’ll generate measurable results.

6. Listen and learn.

A great pitch is like a great conversation. There should be plenty of back and forth.

If the prospects are talking, and you aren’t, that’s a good thing. It means they’re comfortable enough to share their perspective.

Never interrupt that discourse – let them roll. If you don’t get through your deck, so be it. Leave copies with them. This is about the relationship, not your presentation.

7. Curb your technology.

You should control your technology; it shouldn’t control you.

Well-conceived slideware and video can go a long way, but they should never substitute for the story. And we all know that technology can go down, seemingly at the most inopportune times.

You should be able to deliver smoothly and confidently from a hard copy version of your presentation, nicely secured in a professional-looking three-ring binder. Ensure that every member of the pitch team can, too.

8. Gear up for the Q and A.

Of course, you’ll have already invited your prospects to ask away during the pitch, but some questions will likely come during the designated question-and-answer session, at the end. (If there are no questions, it’s usually not a good sign.)

A lot of business gets won or lost in the Q and A. 

Listen respectfully and attentively to every question, even the ones you find odd, or unrelated to the subject at hand. You’re not the prospect.

Respond with evidence and experience, and, when appropriate, low-risk humour. Never criticize a competitor or public figure. You have no idea who your listeners know and like.

9. Look the part.

In some circles (mainly technology) it’s been fashionable to dress like you’ve just cleaned your garage, but personally I find that contrived and precious.

It’s basically saying, “Look at me – I’m too cool for convention.”

Dressing well, in a tailored suit for example, demonstrates that you have respect for yourself, and your audience. Especially if I’m pitching, I dress up.

10. Keep pitching.

Your pitch shouldn’t end with your presentation.

Follow-up with a handwritten note (couriered, not mailed), and additional information, if required. Some send a gift or novelty item. That should be done only if it’s appropriate, creative, and helps deepen the relationship.

Sometimes, even after all that, the timing won’t be right, and that’s life. The world doesn’t necessarily rotate to our preferred schedule. So, stay in the game. Stay in touch, respectfully. Provide value. Provide insights. Invite the people you’d like to serve to events they’d benefit from attending.

Show them how you’d do their business, before you have their business.

If you straight out lose, ask for a debrief so you can find out why. But you won’t lose, because you’ll have done some serious pitching.

“We’re winning this thing!”

Jim Gray is a Senior Communications Advisor in Oakville, Ontario.

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