The Art of Asking (or Not)

Knowing when to ask for something — and when not to — is one of the trickiest skills in business. Especially when you're talking to someone you admire, respect, or haven't seen in a while. The temptation is always there.

You're in the room. You’ve got the Zoom. You’re on the call. You’ve finally landed a meeting with that person whose opinion matters, who sits on influential boards, or who’s just a few steps ahead on the path you’re trying to carve.

And the voice in your head says: “This is your chance. Ask for the thing.” But sometimes the classiest move is not to ask at all. Instead, it's to listen, to offer, to share without expectation — and to bank credit rather than try to spend it straight away.

🤝 Relationships Aren’t Transactions

One of the hardest things to unlearn — especially if you've spent time in sales, startups, or corporate life — is the belief that every interaction needs to deliver something tangible. But human connection doesn't work like a spreadsheet. And leadership rarely unfolds on cue.

People remember generosity. Curiosity. Humility. Not pushiness.

And that’s not just wishful thinking — it’s classic How to Win Friends and Influence People. Dale Carnegie nailed it nearly 90 years ago. If you want people to care about your work, start by caring about theirs.

🚦 Signals Before Favours

Here’s something I try to practise: before asking someone for help, I ask myself if I’ve earned the right. Not in a transactional way, but more like — Have I shown enough interest in their world? Have I helped them first? Have I signalled trust, not just need?

Sometimes, I realise I haven’t. So I don’t ask. Instead, I offer. Maybe I share something that could be useful — an article, a thought, a contact. Maybe I just say thank you properly. Maybe I amplify their work without expecting anything back.

It’s not just polite. It’s strategic patience. Because when the time does come to ask — for advice, a connection, or an introduction — it won’t be forced or opportunistic. It’ll be natural.

💬 A Real-Life Reminder

I had a recent conversation with someone I deeply respect — someone who’s been at the top of their game globally (you know who you are!).

We caught up after a few years, and I was struck by how generous and grounded they still are. I could’ve tried to pitch something. But I didn’t.

Instead, I told them what I was up to, shared a few examples, made them laugh, and listened carefully to their reflections. I came away with something far more valuable than a favour: trust, encouragement, and a deeper connection.

They saw the work I was doing. They got it. And if there’s ever a right time to ask for their help in future — it’ll feel earned, not extracted.

🎯 Play the Long Game

Too often, we treat every meeting like a sales funnel. We forget that the best relationships are built over years, not 30-minute calls. That trust compounds, and that some of the most powerful allies in your network will offer help before you ever ask — if you’ve made the right impression.

So next time you're tempted to lead with the ask, try this instead:

• Listen with real intent — not just waiting to speak.

• Offer something useful — a contact, a point of view, a bit of encouragement.

• Say thank you well — not just with words, but with action or amplification.

• Leave space — the right people will follow up or ask how they can help.

Because relationships aren't built in the ask. They're built in the space before it.

✍️ Thanks for reading my Coach Class Newsletter. If this resonated, feel free to share it or drop me a note. I always love hearing stories of quiet generosity, delayed asks, and earned trust.

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