How to Maximise Your Pitch Team of Plannerinas & Wing-It-Wonders

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There are 2 types of presenters when it comes to pitching, presenting and public speaking:

  1. Wing-It Wonders.  

You hate having to PLAN when it comes to pitching and presentations.

If you feel being ‘over prepared’ stifles your ‘off the cuff’ style and ability to read the room & be flexible,  then you’re probably a ‘wing it wonder’. That’s ok, you can learn a few tips to help you.

  1. Plannerinas.

You are more in the preparation, practice and planning properly camp. That’s fantastic, as long as you plan to flex a little, you’ll be amazing.

Maybe you’re somewhere in between, which is brilliant because whichever side you naturally drift towards you can excel at pitching and presenting, as long as you flex a bit and avoid letting your ‘tendencies’ take over.

And both have pros and cons.  In a pitch team, in truth, you need both types to complement each other!

The good news is – you can be brilliant, whoever you are, with a bit of flexibility and savvy prep. 

Whether you’re a perfectly preppy plannerina or a woeful wing-it-wonder – I have some great tips for you and your team to make the most of what you’ve got and help others fill in the gaps.

Take two of my clients…

1 – The Plannerina.  Can you relate to Klara?  She’s creative, fun and a bit kooky.  However, her colleagues describe her personality as “a bit like Monica from friends – you know, a bit OCD”.

“Well” they explain to me “OCD as in, she LOVES to line things up, research and PLAN everything to the last letter”

That’s absolutely brilliant.  The good thing is that you probably won’t leave anything out.  You know what you are going to talk about, you are confident that you know ALL the information you are supposed to know. And you also have all the slides, research, figures and materials to back it all up, categorised beautifully. Brilliant.

However – the cons…

(And Klara confessed to me that this is so her) You Hate the Q&A – the question and answer bit, because it’s……..

Shock- horror – UNPLANNED!  Arrhhhh , and anything unplanned makes you nervous and unsure of yourself.

So the trick?

PLAN to be off the cuff.


BIG TIP – plan to be flexible.  Plan what questions might come up. Plan to move on if the audience gets a bit bored, plan to ‘handle’ the Q&A. 

Or, better still, work with a wing-it-wonder to help with the Q&A bit.

If you’re paired up with a Wing-It Wonder – they can be helpful (yes, they can be irritating to you too). However, rather than get annoyed that he or she is ‘lazy’ because they HATE to plan, use their off- the- cuff skills to fill in the gaps.  

2 – The “Wing-it-Wonder”. Can you relate to Jed?  He hates practicing a pitch because “it loses its magic”.  

Jed knows he can’t plan for the audience of the moment because when he sets foot in the room the atmosphere might not be what he’s planned for, so he wants to be flexible and leave everything ‘loose’.

Boris Johnson (British Politician and former London Mayor), as you can imagine, is more of a wing-it-wonder.  He used to burst into the live BBC studio (when I was producing live on air) with literally 30 seconds to spare he’d put his hands on his head, ruffle his tufts of blond hair and casually enquire

“um….where am I, what am I talking about and who’s the presenter?” 

(Sometimes he didn’t seem know he was at the BBC, so I’d casually remind him “You’re live on air at the BBC – families are listening - don’t swear!”)

Aha.  Most of the time as Mayor of London, he totally got away with it!  That was then.

Big tip if you are a wing -it-wonder.  Have a plannerina on your team!

I can relate to Wing-It-Wonders as I too have suffered from non-planning tendencies in the past and I have found that no preparation at all is totally unacceptable.  As you may have heard me say before – leave winging it to the chickens!

The best thing you can do is think about the audience and prepare ‘material’ rather than a word for word ‘script’ that’s perfect for them.

DO’s and DON’Ts for Wing-It-Wonders (& for Plannerinas to consider)

Maybe you don’t like a formal script.  So, don’t have one. However, DO have a running order with a rough idea of what you are going to say for each chunk!

DO have a message with ‘angles’ and examples to illustrate your points.

DO go through the slides and talk through what you MIGHT say – brainstorm ideas of how to make it more entertaining for the audience.

Working with a Plannerina?  Brilliant. Use their skills to shape up your ideas and put them in a more logical order. 

DON’T get annoyed at the Plannerina.  Sometimes they like to categorise things and list information in a linear way.  That’s not a bad thing because they remind you of the content you need to be including in your presentation.  However, let them know that your style is likely to be different to theirs.  

DO let them know you may not stick to the exact script!  

I’ve worked with Plannerinas live- on- air and on conference stages before.  One time when I started to go off script or as they might say “Make it up as you go along”, the Plannerina just went silent and went straight back to the script, slightly annoyed that I didn’t stick to the plan! It wasn’t my most successful public speaking moment.

My main message here is this.  Try a bit of both.  A plan that’s not fixed to the point of DULL.

The trouble I find with many senior teams is that the Plannerina – male or female may be the senior person in charge and they may frown upon the Wing-It Wonders who HATE to rehearse and prep slides early.  They HATE learning lines and HATE rehearsing a script as if it’s live. 

Worse- case scenario and what I’ve witnessed happening is the more junior wing-it-wonders get really negative feedback from the Plannerina boss and feel bad about themselves and are chastised for being themselves.  They are almost told off for being a people-focussed- wing-it-wonder who can turn on the charm at the drop of a hat.

I’ve also seen Wing-It-Wonder-alpha type bosses who don’t value the Plannerina’s style and dismiss them as ‘boring’, when actually, they are being thorough.

That’s a real blow if you have pitch teams made up of different personality types.  All types can thrive and be engaging if they work together.

In short – accept and appreciate your pitch teams’ collective styles and types.  There’s no right or wrong.  Let people play to their strengths.

If you’d like me to help your pitch teams be more off the cuff in the Q&A and perfectly planned to win the audience over – get in touch for a free chat I work with global organisations and they tend to win more pitches when they practice my agile way and use my formula!

“Yeay, we won the pitch, Esther’s tips helped us nail it. From warming up and gelling as a team, to wearing the right clothes on the day, we swaggered in and blew them away”

Global Law Firm, London

Esther Stanhope