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Updated 15 Oct 2019


3 Simple questions that can derail your reputation

I think our businesses have synergy - maybe we could discuss over lunch?


Erika Napoletano, Entrepreneur, 28 August 2013  Share  0 comments  Print


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Asking for help is a good thing, but … there are times when reaching out can make you sound like an askhole. Yes, an askhole: a person who doesn’t respect the value of other people’s time, relationships or expertise. Askholes are takers – and they don’t even realise (or care) that they’re doing it.

Before you open your mouth, consider the ways three common questions can derail your rep.

Can I buy you a drink?

When you ask someone to join you for coffee, drinks or a meal on the pretence of business, it’s a pretty big request. It might seem a small favour – an hour or so of someone’s time (and hey, you’re buying!) – but here’s what you’re really asking: Would you take an hour away from cultivating your business to help me with mine? You’re asking them to take time from their office, clients or projects.

How to avoid being an askhole: Be clear with your expectations upfront. When making the initial request, state that you’d like to discuss X, Y and Z, and promise to take up no more than 30 minutes of their time. After the meeting, send your contact a $10 gift card to their favourite local coffeehouse as a thank you.

Can you introduce me to …?

Social media has made it pretty easy to see who’s connected to whom. However, just because someone you know has a connection you need doesn’t mean that you’ve earned the right to an introduction. An introduction is an even bigger deal than a drink or a meal – you’re asking someone to trust you with a relationship they’ve cultivated and nurtured.

How to avoid being an askhole: When you ask for an introduction, you obviously have an agenda. So make this type of request only from certain people in your network: those with whom you’ve already built a strong, reciprocal relationship. This way, they can refer you with gusto and can trust that you won’t make them look like a jerk.

Can I pick your brain?

This may seem like a small request, but what you’re asking for, really, is access to years of incredible successes, glorious failures and lessons learned – all for your benefit. You say “pick your brain”; they hear “unpaid consulting session.” Unless you have a history of asking too much, your colleagues or mentor probably won’t mind.

But it’s a pretty hefty request to throw at somebody you don’t know very well. After all, would you ask your attorney for a quickie legal briefing in exchange for little more than a coffee?

How to avoid being an askhole: If you want access to someone’s knowhow, you should be prepared to pay. Drinks and meals aren’t fair pay for consulting. Anyone who is worth your request charges for their expertise and experience – and they can’t pay for mortgages and college tuitions with lattes or martinis.

Odds are you’ve made one or more of these askhole-type moves. We all have. What we need to do, however, is think about what it would feel like to be on the other end of the seemingly simple ask. This way, we can avoid becoming that guy who oversteps bounds and, instead, be that guy who’s known as somebody who respects everyone’s time and value. Not a bad rep to have.

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Erika Napoletano, Entrepreneur


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