My 5 top tips for winning pitches


We all have to pitch at various points of our life and career, whether it is an idea, a product, a proposal, a job or to win new clients. I know lots of people really dread public speaking, pitching and presenting as they worry that they don’t possess some mystical presentation gene (fortunately there’s no such thing), the stakes are often high and the pressure can be debilitating.

I used to be terrified of presenting as a young person, but over the years I have grown to really enjoy pitching. I feel like I have spent my whole career developing this skill, both by presenting and being presented to hundreds of times. I see it like a performance – understand your audience, write script, learn lines, rehearse, get into character, add drama, practice, polish and perform. I find it really brings out the actor in me. One of my best mentors always said “it’s all about the DRAMA”. He is spot on, as a presentation and especially a pitch must be memorable and for that it must have some drama.

I’d like to share 5 lessons I have learnt so far about delivering great presentations and winning new business pitches. I’m going to frame it with a story from my past, a single meeting that took my team from winning 1 in 5 pitches, to only losing 1 in 5.

We had built a great product, we had socialised it, received encouraging feedback and delivered excellent performance through a difficult market environment. When we finally got to the stage of being invited to pitch for new business regularly, we found that we kept losing. We were falling at the final hurdle, despite having an excellent product, team and reputation. We couldn’t understand how we were losing 4 out of 5 pitches.

We gathered everyone that was involved with pitches and even hired an external facilitator to help us manage the conversation. The conversation that we had in that 3 hour session and the hard work the followed, changed our success rate from 1 in 5 to more like 4 in 5. For the next 18 months we won most of what we pitched for.

That afternoon we agreed on 5 things as a group and we committed to changing our habits to follow and apply these consistently ahead of every pitch (no matter how busy we got):

  1. Simplify: We simplified our pitch book so that we could deliver the key messages on a single slide, with no more than 6-10 supporting slides. On each slide we clearly explained the BENEFIT to the client (it had to pass the “so what” test). Our pitch book had a clear storyline, it had ‘drama’ and it emphasised clear different points of differentiation (tailored each time for who we were competing against).
  2. Know your client: We mapped all the key decision makers and influencers for each prospect so that we really knew our client. We would reach out to as many stakeholders as possible in advance to understand their objectives, concerns and objections. We also learnt about their level of sophistication so that we could pitch our messages at the right level.
  3. Practice. We started to religiously script and practice our presentations, especially the key messages, Q&A, as well as anticipating possible objections ahead of each pitch. We would role play each pitch in front of our colleagues who were briefed, given roles and asked difficult questions (even though it felt really uncomfortable).
  4. Design the experience: In the pitch we were clear that we needed to leave the client feeling like we had listened to their brief, we had respected their time, we had responded to their questions concisely and we had clearly communicated what made us different. We always aimed to finish well inside of the budgeted time in order to leave more than enough time for their questions when we could really shine and convey our enthusiasm, teamwork, preparation and responsiveness.
  5. Continuous improvement & innovation: No matter how well we did, we continued to improve the pitch, the delivery, the messages, the charts and the story. We also innovated with new slides, new fee structures and even new products that we knew clients wanted.

As I mentioned before, for the next year and half we won most of the mandates we pitched for and we got better with each pitch. As Aristotle famously said – “We are what we repeatedly do. Excellence, then, is not an act, but a habit.”

The only time our success rate fell again was when we grew complacent, started taking short cuts and forgot the routine. Fortunately, we knew what we needed to do to get back on track.

I recently finished reading “The Presentation Secrets of Steve Jobs – How to Be Insanely Great in Front of Any Audience” by Carmine Gallo (it was a birthday present).  It is written in 3 acts (like a play): 1 – Create a story; 2 – Deliver an experience ; and 3 – Refine and Rehearse.

I’ve summarised some of the key messages from the book below:

  • When promoting, selling anything answer the question – Why should I care? Why should my customers care about what I offer?
  • Create a Twitter friendly headline – If you cannot describe what you do in ten words or less, I am not investing. I am not buying. I am not interested.
  • Treat presentations as “infotainment”. Your audience wants to be educated and entertained. Have fun. It will show.
  • 10-Minute Rule – people loose attention after about 10 minutes. Introduce a break in the action: video, stories, another speaker, demo (i.e. some drama).
  • Practice, practice and practice some more.

“Amateurs practice till they get it right, professionals practice till they don’t get it wrong.” – Anon

Whatever it is you are pitching for – be passionate, know why your proposal, idea or product benefits your client, customer, manager or employer and don’t forget to enjoy it.

Best of luck!

Send me your thoughts, experiences and lessons on delivering great presentations, below or on [email protected]

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