Are you willing to take a stand?

here are times to remain silent and times when, as an EA, you need to take a stand and challenge the status quo, says Michelle Gibbings

There’s always pressure to confirm. We’re tribal creatures and we like to fit in and be part of the pack. We’d rather follow the crowd, than be sidelined and left out. As a result, we hold off challenging the status quo or questioning things that others accept. And we make decisions and take action with little more reason than the fact that everyone else is doing it.

But as a trusted advisor to a senior leader you play a crucial role and, as such, may often be in the position where you can say what other people feel fearful or reluctant to say. And, for organisations facing increasing complexity, EAs must be willing to challenge and ask questions. Of course, it can be hard to be the sceptical person but remaining silent may result in poor decisions with consequences for the boss and others around you.

So how do you know when to speak up and when to remain silent? And when you decide to speak up, how do you make sure your message lands well?

Here are some tips to get you started:

  • Think in advance about the conversation and plan for it. But don’t fall into the trap of delaying communication by waiting for the ‘perfect time to communicate.’ Timing will never be perfect!
  • On that note, there’s a time and place for every conversation. Both you and your boss are busy and you want to choose the time when they’re likely to be most receptive to the conversation – in the morning or when they’re in a more reflective state of mind, perhaps? Make sure it’s a time of day when you’ll be most alert, too.
  • Find a quiet place where you won’t be interrupted, and turn off all distractions so you’re fully focused.
  • Consider who else is present. As a trusted advisor, your opinion matters but it needs to be done in a way which is respectful of your boss’ position, and so having the conversation one-to-one may be better.
  • During the chat, watch how you’re reacting and slow your mind down so you can take in what’s being said.
  • Be conscious of what your boss needs too – this isn’t just about you sharing ideas and opinions; it’s about helping to deliver a better outcome.

Don’t forget to pepper your conversation with questions, too. In a busy world, it can be easy for your manager to miss details – but having their EA be curious can help them think through an issue. Good questions are genuinely directed to finding out more and, when done well, can help your boss think about a decision from a different perspective.


  • Ask clarifying questions to ensure if you’ve understood the issue. Ask “can I check that I understand what you are saying?” then repeat the key points that you’ve heard so far.
  • Ask probing questions to get your boss to think more deeply about the topic. Try “so if we went down that path would be the consequences and likely outcomes?”
  • Ask wondering questions to get them to ponder about what could be. For example “what would this look like if we took a different approach?’

What you say, when you say it and how far you push reflects the nature of your relationship – the more your executive boss trusts you, the more they’ll see your input as valuable and helpful, and the easier it will be for you to take a stand.