Mastering the Ambitious Ask

“If only.” You reply in a huff. 

The words echoing around your mind long after leaving your lips.

For months you’ve been offloading on your friends about your stagnate career.  You’re bored, stuck, seemingly on a road to nowhere.  They’ve listened, been polite & offered encouragement, but the conversations always end in the same place, with you dreaming of being somewhere you’re not & feeling hopeless. 

It’s as though the tiny full stop at the end of the words “if only” have become a stubborn blockade to possibility that won’t budge. 

Notice I use the word “won’t”, rather than “can’t”. 

Whether we are climbing a mountain of progression within our career, a sales professional looking for their next eureka moment, or simply an ambitious being looking for an inspirational connection -

Curiosity propels us forward.

Human beings can’t read minds. 

Our leaders, customers or mentors can’t read minds.  If there is something we want.  We need to ask. 

Progress comes not from the wishful conversation in our mind.  It comes from finding the courage to say the words out loud to the person who needs to hear them.

We make progress towards our aspirational goals through our Ambitious Asks.

They are the questions we put off because they seem too much effort, we assume we know the answer or we are fearful of rejection.

Ambitious Asks ignite the conversations we need to have.  They open doors & while they might not always deliver what we want to hear, they offer information that helps us make decisions that pave our path forward.

Ambitious Asks bring clarity.

I fast realised when I started my own coaching business I had to safeguard myself from becoming trapped in my own head.  To stop hiding behind emails, get out from behind my laptop & commit to building my own likeminded community.  A community that would offer inspiration & opportunity through the connections I would form.

I was choosing to find work in a totally different industry to prove to myself that my skills were transferable.  I knew it would be difficult.  I knew I could do it, but I also knew I couldn’t do it on my own.

Ambitious Asks were the only way I was going to succeed.

Whether we are asking for an opportunity in our workplace, a customer for an opportunity or a new mentor for their time, how do we set ourselves up for success when approaching an Ambitious Ask?

These are the 7 steps I follow that enable me to approach these conversations with confidence;

1. Paint the Picture

Invest time in creating the future vision you are moving towards.  While clarity will come through the exploration process, being able to articulate your vision through storytelling creates a context for your listener that offers relevance to their world & association to yours. It becomes the justification for our Ambitious Ask.

Our past is there to be learned from, not lived within.  Be mindful to not spend too much time talking about what you are moving away from.

Focus on what you are moving towards, the potential & the value you can offer.

2. Consider the other person’s perspective

Take a moment to consider how what you are asking impacts the other person.  Pending on what that is, it will vary.  However, it’s a worthy check-in to prevent you overlooking a sensitivity. 

• What are their current priorities?

• How does what you are asking impact those priorities?

Demonstrating you are mindful of another’s perspective builds trust & strengthens your connection.

3. Be clear in your Ask

I’ve been pleasantly surprised by people’s willingness to support me on my start-up journey.  The effectiveness of any Ambitious Ask dependent on the clarity I offer in my question.  Often, you only get one shot at a conversation. You don’t want what you are asking to be misinterpreted.  Nor do you want to walk away wondering why the help you were looking for wasn’t volunteered.

Be clear & politely direct. If you aren’t, you must be prepared to answer the question, “How can I help you?”

4. Prepare, don’t wing it

Preparation brings respect to our conversations & impacts the impression we leave.  Do your research rather than enter a conversation blindly. Is there anyone you can speak with prior to better understand the person you are speaking to?

Consider the information you need to work up to your Ambitious Ask. Prepare with considered questions that facilitate connection. 

The generosity of another’s time is a gift.  No one wants to have their time wasted. 

5. Signal flexibility

Flexibility increases options in the eyes of the person we are speaking with.

While you might not immediately achieve your desired outcome, a different pathway might be offered, better suited the other person today & better for you in the long run.

Keep your mind open to growth by focusing on the journey rather than a fixed outcome.

6. Ask advice

If you find yourself in a situation where you don’t get the response you were looking for, ask what they might do if in your situation. 

Asking advice expresses humility.  An endearing trait for strengthening connections.

7. Don’t forget who has helped you

People who have helped you will love to hear how you’ve progressed knowing they played a small part in your journey. Don’t forget to drop them a selfless note from time to time to keep them updated. Equally, reciprocal support rarely goes unnoticed.

Now I’ve outlined what I’ve learned, I bet you can guess what’s coming next?

That’s right, what’s stopping you pursuing your next Ambitious Ask?

Good luck & don’t forget to let me know how you go here !

Peta x 

Sales performance coach, Commercial growth consultant, Speaker,

Author of My Beautiful Mess - Living through burnout & rediscovering me. Read excerpt of my story full of Ambitious Asks here

Inspire your team!