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Delivering Great Pitches

The best pitching lesson I ever had was watching a carefully crafted investor pitch get eviscerated by a brilliant internet pioneer on a sunny day in San Francisco. In less than 10 minutes I learned about the power of argument and frailty of unproven convictions. It got ugly and dismissive, fast. The sun continued to shine but we were crushed.

Fortunately I wasn’t bearing the brunt of this brutal (and accurate) critique directly, as I was the most junior member on the pitch team. It was one of the most profound teachable moments I’ve ever experienced, to the point where I’m reminded of it every time I have to convince anyone of anything in a professional setting. I like to think this failure brought me every pitching success later in my career. I knew what not to do. This was a gift.

Almost 10 years later and with many more pitch experiences behind me, I had the privilege of appearing on a discussion panel charged with the topic “Delivering Great Pitches: How to Tell Your Story to Investors, Customers, Employees, and Media.” This was part of a cool cross-Canada initiative: the TSX Ignite Series. The series is focused on Canadian incubators and accelerators, intended to help support the development of small and medium-sized enterprises.

(Aside: Very exciting for CLearwater Seafoods and the Nova Scotia Community College in Halifax, where the Toronto Stock Exchange will open and close this week as part of the event — read more about that here.)

All panelists were given some questions to consider beforehand. Here are my notes on how to answer these questions.
 

What matters most when you pitch?
 

Pitching forces you to make your argument. The act of preparation has value in and of itself. It is a thought exercise, forcing you to articulate what you may have convinced yourself (and maybe only yourself) of. The outcome should be clear: your unique value proposition (or your compelling selling proposition — whichever jargon you choose).

Focus on the unique value proposition. This is the reason that your customer will pick you over your competition, and because I come at this with a PR and a marketing mindset, it’s not always about a product or service. It’s about convincing and making your case: How does your offering translate to business value? What job does your product or service do for your target audience unlike any other product or service? For an idea or issue: How does your solution to the problem or proposal to act impact the lives of those most connected? What is your vision, and why do you strive for it?

Respect simplicity. We are an agency. A collection of consultants doing great things together for our clients. And to get business, we pitch. Our process is very simple, and it works. We ask ourselves four questions:

  1. What is the client’s objective?
  2. What is our compelling solution?
  3. Why will we win the privilege of working on this project?
  4. What is the tone and manner of response?

These four questions push us a long way down the path of making our argument. This simplicity greatly serves the shape of our pitch.
 

Does one pitch deck serve all? Do pitch decks differ?
 

You can have a foundational argument and the tools to help make that argument. But you should aim for a unique pitch deck for every pitch audience that has unique cares, wants, and jobs-to-be-done.

If that isn’t practical, create decks that speak to your usual suspects: one for investors, one for customers, one for partners, one for key influencers, etc. They should be foundationally similar, but they should branch to address the precise need of the audience.
 

Where do you see start-ups trip up most during their presentations?
 

Be grounded, but be aspirational. Pitching to a future state that’s only a baby step ahead of where your customers or constituents are today is pitching mediocrity. Paint a vision. Ask “What If?”

Don’t take too long to get to your compelling selling proposition. Hit it right up front, and prove it later. Your argument should hook the audience as fast as possible, and focus on how it can help them solve problems and meet goals. “Imagine a world where…” is not a bad sentence to have here.
 

How has the labour gap highlighted the importance of pitching to potential employees? What do you want to convey to potential employees and how does this differ from your pitch to investors?
 

Investors care about a return on their investment. Employees care about that, but they also care about a sense of purpose and meaning. It’s more important with potential employees to demonstrate shared values, and to give a confident and aspirational sense of “if you join my team, you can be great and do great things.” That is different from the investor relationship, but it certainly helps to build investor confidence.
 

What are your top 3 slides that you always like to see in an investor/pitch deck?
 

For investors, we think about:

  1. Customer benefit. The solution your company or product enables and why the customer will want what you are selling.
  2. Unique value. The reason the customer/audience will want to buy from you, and you in particular.
  3. Impact. How will the world be different as a result of your product or service?
     

You are likely to receive many “Nos” before a “Yes”. What do you do after you get a “No”? How do you keep those investors engaged, even if they have initially rejected your pitch? How do you continue to cultivate that relationship?
 

Every “No” should be continued to be treated as a potential partner. They may be your connection to your next investor, employee, partner, or customer.

Remember the story I started with above, about an evisceration in sunny San Francisco? That same eviscerator offered me a job three months later.

I appreciated Patrick Keefe’s answer to this question: “No is your second-best answer. It’s better than maybe.” This perfectly captures the mentality.
 

What is the difference between a formal presentation and a stage pitch? What do you look for in a stage pitch?
 

A formal presentation can be a great opportunity to have a conversation versus a one-way dialogue that is implied with a stage. Make sure that a conversation happens in the room. At NATIONAL, we always go into a room with a point of view but also keep enough flexibility to address specific concerns of the client. We plan to make conversation happen, and we construct “builds” and interjections that colleagues can make in order to soften the room.
 

Why is it so important to continue practicing and tweaking your pitch?
 

We live in a world of superlatives, but it’s truly never been more important to be able to make your argument — your pitch — clearly and succinctly. It has been scientifically proven that we now have shorter attention spans than goldfish, so how can we expect our fellow humans to follow our convoluted, inarticulate, untested business plan or initiative? It is so important to practice and tweak a pitch because we have to earn attention, and hone our case for why we matter and why we should win the confidence of those hearing us out.
 

Who do you bring with you to formal presentations?
 

An  amazing colleague or two to help convey our story with calm confidence resulting in a collaborative conversation with our newest client.

A note on context: While I have pitched to investors to try and unlock funds for a business, my career has led me to help many others craft their own pitches, with the aim of persuading somebody to do something. The art of pitching is the art of persuasion, and clarity is the heart of the matter. This is where I spend most of my days, and the audiences vary widely: investors, employees, regulators, donors, the skeptical/angry/disinterested/engaged general public, customers, alumni, government, media. I’m lucky to work in a place that lets me play this hard at something so interesting and challenging.

Thanks to fellow panelists Build Ventures’ Patrick Keefe, Innovacorp’s Greg Phipps, and Propel ICT’s Gillian McCrae.