It Does Hurt to Ask


“It doesn’t hurt to ask” is an innocuous enough phrase, but it concerns me that even management blogs and career advice websites convince unsuspecting young professionals of this nonsense.


Here are some times when it definitely did hurt to ask:

  • A recently-appointed cleaner who annoyed us and did lots of things wrong wanted us to “sport” (support) him getting married, which would mean either paying for it or giving him a loan which he would probably have no intention of paying back. Our opinion of him went from “incompetent” to “incompetent and cheeky”. Firstly, he had no right to ask. Secondly, he was still on probation which meant he could be fired with barely any notice (not a good time to be starting a new life with a new wife). And thirdly, why would he think we would want to refuse a request for money and then have him moping about our house near all our things?
  • A business I bought came with a guard. Upon receiving his first monthly salary from my company (which was identical to his last salary from the previous owners), he complained. No one else had received an increase yet either. He really might have had an increase if it weren’t for his attitude. “Give me more money! You’ve known me for three days!” He later turned out to be as pathetic as this episode would indicate.
  • A recently-appointed cleaner (different from above) wanted Ramadan timings (shortened workdays to compensate for fasting). That sounds reasonable enough except that he wasn’t Muslim and therefore didn’t observe Ramzan. He was quite good otherwise, but that, once again, cheeky request made us wonder if he had a lazy streak in him.
  • Around Eid time, some Muslims generously give eidi, a celebratory gift somewhat like a Christmas present, to people around them. Like Christmas, children usually benefit most, with other relatives and close friends coming later. Although I’m a Christian, a painter still wanted a cash eidi from me after painting one of my businesses. He had no prior relationship with me and he messed some things up. Would I want to hire him again when he shamelessly asks for gifts? And not just any gift, a gift given in celebration of something that I don’t celebrate. He may have been just a painter, but no one wants to work with someone they don’t respect.
  • In response to an email informing her that she had been shortlisted for a significant position in one of my companies, a candidate told me “I wanna do job for minimum 1 year contract”. Yes, she really wrote “wanna”. The cherry on top was that it was supposed to be an answer to the question “If your current position requires notice, how much notice is required?”. She hadn’t even been offered the job yet. Obviously, this disqualified her and she was immediately taken off the shortlist.
  • A friend of a friend who I had known for a few years called me up and was excited about a business idea he had. The idea wasn’t terrible and he said that he wanted “dynamic people” like me to work on the project. He described it to me and I gave him some free advice as there were a couple of really apparent big holes in his plan. He asked me to come up with some big written strategy based on my suggestions. I didn’t want a job; he called me; you never headhunt by giving people unpaid work – you headhunt by giving people things that they want. It’s slightly rude, certainly amateurish and it made me end the conversation rather quickly. No one wants to answer a call from a friend of a friend and be given unpaid work. If he went about it in a different way, maybe we’d be working together now.


Yes, bring it up with your boss if you’ve been doing great work for months or years and you don’t feel adequately compensated. Yes, ask for help from the right people if you really need it. Yes, stand up for yourself. But don’t impose your wants on people and don’t assume everybody with a bigger wallet than yours is a magic genie to solve all your problems.

In general, don’t ask for gifts. Bonuses are a bit different, especially if they’re standard and expected in your field (e.g. banking), but even bonuses shouldn’t be asked for or complained about. Enquire if you think some great achievement of yours has been overlooked. Ask what you could do to improve. No one likes a whiner even if you’re right.

A lot of this is basic Golden Rule empathy stuff that everybody should’ve been able to thoroughly grasp by the age of 9: if you were them, would you want to be treated in this way? Or would you feel annoyed, awkward, imposed upon? After the request, would this person want to see you more or less?

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One comment on “It Does Hurt to Ask

  1. […] Seth Godin came the same conclusions I did about asking for things. […]

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