What To Expect When You Are Pitching

Today I am sharing a question I received from an aspiring entrepreneur on getting ready to pitch their start-up idea.  As part of the career aspect of 40:20 Vision I’ve had a lot of interest from the female start-up community for sharing of “entrepreneurial” wisdom. Soon I will be creating a separate section on entrepreneurial “mentoring” for female entrepreneurs and those with an entrepreneurial spirit.

It’s exciting that so many young women, and men for that matter, are exploring entrepreneurship as a viable alternative to corporate life and taking the initiative to create their own jobs in a tough job market. It will be interesting to follow. But whether you are going there or not, there’s a lot of great advice to be garnered that is applicable to any career in today’s competitive environment. Today’s post is about pitch presentations, much of which goes for any presentation. Hope you enjoy.


Of course we will still be featuring a breadth of advice on what 40-something women know now that they wish they knew at 20-something. Our mission is to help younger women navigate the uncertainties of adulthood and get a head-start on the self-confidence and strength that comes with age or from getting to know yourself. It’s particularly more relevant today to cover our whole lives as we are increasingly blurring the lines between work, play and life.


Q. “I am about to participate in my first pitch event, what should I be prepared for? What is the “what to expect when you are pitching? Is there anything different I should expect as a woman? For example, how should I dress?


A. Preparing for a pitch is like preparing for any big presentation. Be prepared. Be confident. And be yourself.

Confidence is the big one, so whatever you have to do to feel comfortable in your skin is best. Don’t dress in anything that distracts you. Luckily, you are probably very passionate about your start up idea so talking about it should come from the heart. That is always better than presenting something you aren’t familiar with for a company you aren’t personally invested in. That is one leg up on any presentation you have ever given before.

That said pitch presentations can be a unique beast. While it is your passion, you shouldn’t be too close to your product or concept.

“Present like a CEO. Talk about company and why they should invest. If you only talk solutions or the product or why you believe in it you are not showing your ability to lead and make good business judgments.  – pitch consultant, NYC

Whether you are pitching at an “event” or a meeting, you have to be quick, concise and on your toes. Be able to sum up the idea in 60 seconds or less. Your “elevator pitch” should include it’s positioning, who you customers are and why they would want what you are offering. Getting this right and knowing it like the back of your hand is a great way to feel confident starting your presentation.


I’m honored today to share the wisdom of four experienced female entrepreneurs who have been there and done that…some on both sides of the table. Herewith, they share what they have learned on the art of the pitch, what to expect and…what to wear.


  1. Don’t expect anything different because you are a woman. Gender has nothing to do with being well prepared and ready. If you are pitching something that has a female focus know (with stats and facts to back you up) why that is your approach. But being a woman has nothing to do with your great idea. A great idea is genderless.
  2. Dress as though you are going for an interview in your industry. Every industry has a different style and level of formality. Reflect that image but always be comfortable. You don’t want to be adjusting your skirt or tucking in your shirt in front of a crowd. Feel comfortable in your skin and in the outfit you choose to wear and that will be showcased to your audience.
  3. Practice. Practice reading aloud to yourself. Practice in front of a mirror. Practice face to face with a friend and with a casual colleague. The more practice the better the pitch. And when people ask questions take it as an opportunity to learn and grow and refine your pitch, not as an indication that your idea isn’t a good one.

– Whitney G. Wilkerson, Founder and CEO, NEXT for Women



  1. Know your audience.  It is important to be prepared and understand who they are if possible and what kind of companies they have invest in.
  2. Your pitch needs to be shorter than the time allotted.  Investor groups really appreciate when entrepreneurs respect their process.
  3. The pitch should be milestone driven.
  4. The presentation itself needs to be clean—no more than one key concept per page. Don’t forget to tell them on the 1st or 2nd slide what problem you are solving.

— Jen Shelby, Vice President, Client Services, ASTIA


Wear something that feels like you. It’s important to feel comfortable in your clothing so you can focus entirely on your pitch. If you feel like you’re playing a part, you’re wearing the wrong outfit. –  Amanda Hesser, Founder, CEO, Food52


Expect the unexpected (e.g. additional attendees to your meeting, you end up with five minutes instead of an hour). My advice is to practice (with friends, in front of the bathroom mirror). Wear something you’re comfortable or confident in. You don’t want to be fussing with something that doesn’t fit properly. – Founder / CEO, Touch of Fabulous


Lastly, one great piece of advice from a pitch workshop I recently attended was to check in with the person who you set up the meeting with initially. They want you to do well or they wouldn’t have scheduled the meeting. They know what the protocol is of their partners and team and are a great resource for making sure you are prepared.


Big thanks to my 40:20 advisory panel for their insight. And best of luck with your pitch!





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