Simple shortcuts to business success #15: Don't be afraid to ask


Someone asked me the other day for advice about ‘getting themselves out there’ a bit more. They asked me what I’d done to be ‘seen’ as much as I am.

At first – I didn’t know what they were talking about (mainly because we don’t see ourselves the way other people do). They clarified:

In short, I seemed (to them) to be everywhere. What was my ‘secret’?

Well, after giving it a lot of thought, I decided it all came down to this personal mantra of mine:

If you don’t ask, the answer is always no.

Here’s the irony of this.

I hate asking for anything.

Deep down I’ve always felt that my general awesomeness should be obvious to everyone and that I should be the first person who springs to mind whenever someone is looking for someone to interview/profile/send business to/ask to speak on anything I’m particularly good at.

It took a while for reality to sink in but finally it did. If I wanted people to notice me I had to get over myself.

I had to learn the art of asking.

The Flying Solo Editor role I have now? It first came up four years ago. I was in no position to take it on at the time but knew Flying Solo was an organisation I wanted to work for in the future should the opportunity ever arise. So I applied for the role and got an interview. They offered to do the interview via Skype but I wanted to put myself in front of them in a literal sense. So I flew to Sydney and back in a day to do just that. I didn’t get the Editor job back then (phew) but when it came up again two years later, who was one of the people they approached? Me. Who was now much better placed to take on the role? Me. Who got the role this time? Me.

Last year I presented at the Problogger conference (Australia’s largest conference for online influencers) and this year I am presenting three sessions. Why? Because I’ve pitched a session to them every year for the past five years. I’m a hardcore introvert so most people assume I hate speaking. I don’t. I actually love it. The Problogger team would never have known that if I wasn’t forever pitching to them.

What about my books and writing? Over the past six years I’ve received invaluable guidance, mentorship and feedback about both from people I hugely and respect and admire, all because I asked. If I’d never asked, I’d be half the writer I am today.

Everything good that’s ever come my way in a professional sense has come from me being willing to put myself out there. Never, and I mean never, has something come my way from someone ‘happening to notice me being awesome.’ It might happen once in a blue moon to other people, but it’s definitely never happened to me.

In business – we’re afraid to ask about so much.

  • We’re afraid to ask for the sale because we might seem desperate.
  • We’re afraid to ask for referrals and testimonials because we might seem too needy.
  • We’re afraid to ask for feedback because we’re afraid of hearing something negative.
  • We’re afraid to ask for help because we don’t want to dent our façade of having it all together.

What all of this adds up to is a business that’s not reaching its potential.

If you never ask, the answer is always no.

But what if they do say no?

I have to say; I’ve never really heard ‘no.’

  • I’ve heard ‘Not right ‘
  • I’ve heard ‘Not this, but what about that?’
  • I’ve heard ‘Not right for ‘

Except for silence (which, I will admit, is the worst), I’ve never heard a flat out no.

‘Not right now’, ‘Not this, but maybe that’, and ‘Not for us’ opens a dialogue. It creates an opportunity for a ‘Yes’ further down the track.

I love getting a ‘No’ because with that always comes information about how my next interaction with a person can bring a ‘Yes’.

If you never ask, you never get that information.

So, if you’re not very good at asking, how do you get good at it?

Here are the rules I abide by:

1. Never ask unless you’re really clear on what you want

I never send vague requests like ‘I’d love to catch up for coffee and have a chat.’

I’m always very specific: ‘I’d love to spend an hour with you to find out where you think I might be going wrong with my pitching strategy.’

2. Make sure you’re asking the right person

When I was pitching session ideas for the Problogger conference, I wasn’t pitching them to Darren Rowse (big boss). I was pitching them to Nicole and Laney – the people responsible for the scheduling/conference program.

Asking the wrong person means you haven’t done your research and makes you look like an amateur. (I say this from experience.)

3. Time it right

There was someone I keen to get some feedback from about my writing. When I emailed her, she was on book deadline and unable to help. I should have known she was on book deadline. I should have timed my request better. I blew that particular chance. I know better for next time!

4. Try and make it a win-win

This isn’t always possible but there this one time I was (again), emailing someone about getting some mentorship from them. (I’ve emailed a lot of different people about mentoring.) I knew they needed help with their website design so offered to assist them with that in exchange for an hour on Skype with them.

5. Don’t write an essay

If you’re writing to someone to tell them how they’ve changed your life and you don’t need anything from them in return other than ‘Hey, thanks for letting me know this,’ then go nuts – send your whole life story.

If you want something from them, however, keep it short. Really short.

One sentence to explain why you think they’re the right person to help you.

One sentence to explain the help you’d like them to provide you with.

That’s it.

6. Don’t ask for more than one thing at a time.

Don’t send people a list. Not even the people you know really well. One thing is easy for them to say ‘Yes’ to. Three things? That will give them pause, and make it easy for them to say ‘I’d love to help but I just don’t have the time to do all these things for you right now.’

7. Ask for small before you ask for big

It would be inappropriate for me to email the Problogger team and say ‘Hey I have this great idea for an opening keynote’ given I’ve only ever presented breakout sessions for them, and I’ve never keynoted at another conference before.

It would be inappropriate for me to ask for a regular column at a publication I’ve never even written a one-off article for.

Asking for big before you’ve asked for small just makes you look like silly and makes getting a ‘Yes’ for even small stuff from that person much harder. (When they’ve said ‘No’ to you once, it’s easier to say it again next time.) While there’s definitely place in life for audacity – be very discerning with your timing on that kind of thing.



2 thoughts on “Simple shortcuts to business success #15: Don't be afraid to ask”

  1. This was really helpful in honing how I am going to ask people to contribute for my newsletter, present information sessions for my clients and collaborate as part of a board I’m on. Thanks a lot!

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