£19 including VAT
The Confidence to Challenge Playbook
Use your voice with judgement, credibility and respect, even when a conversation feels uncomfortable.
Challenging a senior leader takes judgement, particularly when you value the relationship and worry about being perceived as difficult. This guide helps you decide when to speak up, how to raise concerns constructively and what to do when your advice is not accepted.
In short: a coaching guide and workbook for EAs and PAs who need to challenge an executive or senior leader well, covering naming what is difficult, choosing the moment and level, building the case without becoming defensive, handling the uncomfortable response and building a repeatable voice. Five coaching stages, 14 guided prompts and 38 fill-in spaces, as an online workbook and a 29-page PDF, for £19 including VAT.
What this guide will help you achieve
If you are brilliant at solving everyone else’s problems but go quiet when you disagree with an executive, this guide is for you. I am not going to tell you to be louder or more assertive and leave you to work out what that means. We are going to look at what you know, what you are worried might happen if you speak up and how to make a constructive challenge that someone can actually hear.
How the guide works
Five coaching stages, each with practical next moves, 14 guided coaching prompts and 38 fill-in spaces you can complete online or in print. Every stage ends with what to do next, and the guide closes with a conversation you can practise, a note on what to do when it does not go to plan and your own 30, 60 and 90 day route.
- Stage 1: Name what is difficult
- Stage 2: Choose the right moment and level
- Stage 3: Build the case without becoming defensive
- Stage 4: Handle the uncomfortable response
- Stage 5: Build a repeatable voice
Who it is for
- An EA or PA who sees the problem coming and says nothing because the person causing it is senior.
- Anyone who has challenged once, had it land badly and has been cautious ever since.
- An assistant whose executive has asked for more candour and who wants a way to give it well.
What you get
The interactive online workbook, which saves your answers on your own device, and the same guide as a 29-page PDF to print and write in. Both are yours straight after payment and are emailed to you as well. £19 including VAT.
This is guide 03 of 12 in The eavolve Coaching Guides, and it is also included in the The Executive Partnership bundle with The Executive Partnership Review and The Executive Time and Capacity Audit for £49.
Questions before you buy
Name what is difficult first, then choose the moment and the level of challenge that fits the risk. A constructive challenge states what you have observed, the consequence for the business and an alternative, and asks for an agreed next step, so it reads as judgement rather than opposition. The Confidence to Challenge Playbook works through each of those steps with wording you can adapt.
That is sometimes the right outcome, because you do not always hold the full picture. What matters is that the concern was raised clearly, recorded where it needs to be and that you follow through professionally either way. The guide’s fourth stage is about handling the uncomfortable response, and the fifth is about building a repeatable voice so each challenge gets easier.
Each guide comes two ways. The interactive online workbook opens in your browser, saves your answers on your own device as you go and can be printed or saved as a PDF at any point. The same guide is also supplied as a 28-page PDF if you would rather print it and write by hand. Both are yours straight after payment, and the links are emailed to you as well.
Payment is taken by Stripe. As soon as it goes through you are taken to your download page, where every guide you have bought is listed, and the same links are emailed to the address you used at checkout. If anything goes wrong, email emily@eavolve.co.uk and we will send the guide directly.
No. It is a coaching guide and workbook built around one challenge, written so it feels as though your eavolve coach is sitting alongside you. You work through five stages at your own pace, with practical next moves at the end of each one, and you can come back to it as the conversation comes round again.
Yes. Stripe sends a receipt that includes VAT, which most organisations accept for expenses. If you need a formal invoice, email emily@eavolve.co.uk before you buy. The Business Case for EA Development guide walks through how to ask for development funding if that is the conversation you are facing.
Every guide points to the next step if you want one. One-to-one coaching with Emily or Lily goes deeper on your own situation, and a free 30-minute discovery call is the place to work out whether that would help. Prices for coaching are on the EA & PA Coaching page.
