The Unprepared Pitch

Ted Leonhardt: The Unprepared Pitch (Illustration of man holding book)

By Ted Leonhardt

Read Time: 7 minutes


Self-created failure: when failure is so fearsome that you invite it in, and then fail as expected.

The time was tight, the date near. I hid from my fear. I hid from the fear and the opportunity by doing nothing to prepare. By not thinking about it. Why would I do this? I needed the new business, and I knew preparation was needed. Yet I avoided even the thought of preparing. 

I knew I was terrified I would fail. Worried I’d let everyone down and look unqualified to lead my little firm. We didn’t have enough business; we barely cash-flowed. No debt, but every dollar that came in went out the same day. We were desperate for new business. 

Somehow I was so afraid of failing that I avoided thinking about the upcoming meeting, because the very act of considering it opened the gates to the horrible fear of failure. Fight-or-flight was in control, and my frontal lobe was in denial. For this pitch and too many others, I countered my fear with the belief that I could make that all-important human connection with a smile and a few smart comments. I knew better all along, but it took a string of failures before I took heed and began preparing with real diligence. 


No credentials? No problem

A local grocery chain was looking for a design firm to create the look for their new private label. My biggest competitor had just completed a stunning redesign of a smaller local chain. Their work in both packaging design and the stores themselves had received awards and national attention. I knew my only hope in this shootout was to really study the category, and hopefully come up with an insight to capture the assignment. But my fear was so great that I couldn’t face investing any energy in it.

I should have just declined the meeting. Instead, I took the packaging work we’d done for a bulk candy company, a couple wine labels, and the characters we’d designed for Seattle’s new recycling program. As I was just about out the door with my happy smile and completely useless samples, I asked one of my designers to come to the meeting with me. He’d worked at Safeway while he went to the U to get his design degree.

I don’t remember who won. But I know who lost: We got the turndown the next day. Later in my career, when I was much more confident, I won many come-from-behind assignments by spending the time to look for winning insights. 


Should the culture be considered? Nah

A bagel baker was looking to hire a design firm. I think it was the first meeting I went to with our new (at the time) head of sales. Naturally, I don’t remember what they wanted from a design firm, because I put no time into preparing. But I do remember wearing my dark blue “Mr. Sincere” suit.

Somehow I thought I should dress like a capitalist chief. In addition to the sincere sharkskin, I wore a solid red tie. I think I was trying to adopt the persona of the "Boss Man": A guy who hired sales guys to do his bidding. But in reality, I was terrified I would be overmatched not just by the sales opportunity, but also by my salesman—compounding my fear.

The bagel guy’s office was in a strip-mall storefront. Everything was covered in fine white flour. Two young guys wearing huge white aprons and bakers’ hats came out of the back to meet with us. It had never occurred to me that a bagel startup would operating on a shoestring, and that my outfit alone was enough to lose the deal. I’d spent no time thinking about them and their culture: I was only thinking about me. The meeting didn’t last long.


Denial can be expensive and dangerous

I’d been recommended to the new marketing director at a large chicken ranch. Her company wanted to expand beyond their commodity base with a line of high-end, branded chicken. I was asked to talk to them about package design. A client had recommended us based on a series of experimental packages we’d designed—none of which had anything to do with chickens or reaching a mass market through grocery stores.

Naturally, as was my method at the time, I’d done nothing to prepare other than gather samples of our current work. I could have done a news search on the state of chicken marketing, studied issues around packaging fresh meat, searched for coverage of senior management at the ranch. I did nothing. Why? I was afraid. Afraid to discover what I didn’t know. Afraid of all those major-league East Coast design firms. Afraid to look like I needed to put in effort.

I prepared by buying an airplane ticket. I flew to DC and caught a local to somewhere in the Appalachian Mountains. The plane was very small, maybe six passengers. We flew through a thunderstorm and were thrown up and down and sideways with real violence. My seatmate threw up. Getting off, I found my legs not wanting to walk. They were shaky and weak. It was one of the scariest rides of my life.

Arriving in the small community, I realized the chicken ranch was the biggest employer in town. And I noticed that you could hear—and smell—the chickens from the small main street. I stepped into a drugstore, bought a large newsprint tablet and settled into the diner next door for dinner and to list my packaging bullet points. It was late. I was the last customer. The wait staff must have been bored, because they got interested in my little production and gathered around to help, first with spelling and later with tips on the chicken ranch.

“Wow,” I thought, “these guys know their stuff. This is cool; maybe I can pull this off.” I spent a couple hours working and reworking my thoughts, with the wait staff coaching and egging me on. The next morning I presented myself at the ranch early, eager to show off my new wisdom. Strangely relaxed by the interaction in the diner in spite of my total denial and lack of preparation prior to the previous night, I could feel the victory coming and visualized our beautiful chicken packaging in groceries all over the country.

The meeting was a disaster, almost from the first moment. The CEO pointed out a spelling error—it was his name, which I’d spelled wrong on the first page of the flip chart. When I pulled out our wine and candy packaging, a couple executives got up and left. My contact, the head of marketing, wouldn’t look me in the eye.

With my worst fears dancing in plain sight and tears forming, I packed my samples as quickly as I could and left. 


How do you get past your fears?

On my journey home, I formed the first steps of my plan to never repeat the chicken-ranch experience.

It was my memory of the wait staff that gave me the first push into preparation; they gave me a bit of confidence. Clearly my work with them was far too late, but it was fun. I enjoyed the feeling of debating the possibilities with them. They’d all worked at the ranch at one time or another; they had all kinds of insights—and they liked my contribution to the conversation.

If I’d done something like that weeks earlier and put together a thoroughly planned presentation, I might have had a shot. Here’s my why of these events now:

  • I hide from fear because it makes me feel weak and anxious, and leaves me vulnerable. Fear takes my strength and leaves me feeling depleted.
  • Moving my thoughts away from myself and my feelings to my client or others who are involved seems to distract me from my fears.
  • Thinking about others and what their issues, concerns and needs might be gives me a sense of confidence.
  • Even a little bit of confidence starts me down the road to banishing the fear.
  • Once I’m beginning to feel more confident, I can take the risk of beginning to plan.


With my mind occupied with planning, I gain the pleasure of thinking about the creative task of solving the puzzle. It puts me in that wonderful state of creative flow. Through the chicken-ranch experience, I found my way out of the fear by thinking about preparation not as another way to try out for the team and not make it, but as a pleasurable search for insights others might not have. A challenge. Not a loser’s game in front of winners.

And, I’ve won more often than not since then.


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