I had heard all the usual advice before:
- “You miss 100% of the shots you don’t take.”
- “You are what you settle for.”
- “If you don’t ask, you don’t get.”
But none resonated with me. Then one day I came across a quote from Oprah “You get what you have the courage to ask for”. It was on a huge installation for an event at Deloitte and I remember the moment I saw it so clearly. I know it is a cliché, but I literally stopped in my tracks. I hadn’t thought about it that way before.
At the time, I was at Deloitte, in one of those moments I used to find myself every few years, asking the same questions. Do I stay? Do I move internally? What’s next?
I wasn’t avoiding the question, and it was one I had asked myself before. The answer had usually led me to a new role or a challenge and recommitting to what I loved about the firm. I was at that point again, having the conversations and exploring options. But looking back, I can see that I was holding back on what I was really asking for. I was shaping my asks around what felt realistic, aligned with the firm’s needs, not my own. Based on what I thought I would get, not what I wanted. It all sounded reasonable, and that was probably part of the issue too.
There was hesitation I hadn’t fully acknowledged. I wasn’t sure whether I should be asking for more, or whether it was even possible to get both the progression and the type of work I was interested in.
That quote reframed something for me. It made me realise that if this was true, then the starting point wasn’t how I asked. It was getting clear on what I wanted in the first place. So I did something different. I asked for both a promotion and a different type of work, not one or the other, but both.
I got it, and more. The next challenge was doing what I said I wanted (but that is a whole other blog post!)
When I look back on that experience, the biggest challenge wasn’t the ask; it was stepping back and understanding what I actually wanted and why. Then I was able to find the courage to ask for what I really wanted and became worried about what would happen if they said no.
That’s the part that I remember, and have done more frequently, with continued positive results.
As a coach, this is also something I see often in the leaders I work with now. It’s rarely a question of whether they can ask. They are experienced, capable, and used to advocating for others. The challenge is that their own asks tend to get filtered. They shape their requests to fit expectations or to stay within what feels achievable, and in doing so, they leave part of the real ask unsaid.
Over time, that creates a gap between the role they are in and the role they want to be in.
What I’ve learned is that taking the time to have clarity often changes the ask itself. Once you are clear on what you want and why it matters, it becomes easier to ask. Not necessarily comfortable, but easier to move past the hesitation and say it out loud.
If you’re in one of those moments right now, the question may not only be what you should be asking for. It’s also where you might be holding back on what you actually want.
That’s often where the real work starts, and it’s exactly the kind of conversation we work through in coaching.