10 Signs You Have An ASK Problem

Sunday, 13th September 2026 - 5-minute read

Happy Sunday,

What if your self-sabotage isn't a money block, a confidence wobble or a marketing problem, but a straightforward refusal to ask?

I've spent a long time believing my resistance to reaching out to potential clients was about money attitudes and sales discomfort. I was wrong.

I'm in the middle of a revenue sprint with a firm target by 30 September, and the biggest insight so far has nothing to do with audience, offer or capability.

It's this: I don't ask.

I hesitate to ask for help, to make requests, to follow up, to invite people to work with me, to put my own needs into play. And underneath all of it sits one belief I'd never said out loud:

"My request creates a cost for somebody else, so I should absorb the cost myself instead."

If you're a practitioner, trainer or coach, that belief is expensive. It looks like integrity and it behaves like a slow virus.

So today I'm giving you the ten signs of an ASK problem, what each one is really protecting, and the specific skill to practise this week.

Let's dive in.

10 signs you have an ASK problem

Sign 1: You don't ask for help.

This one is so obvious it hides in plain sight.

The tell isn't that you never ask, it's that you only ask once you're already underwater. You keep going alone because going alone feels virtuous or the 'I won't disturb them' thing to do, and because you can't quite locate the line between resourceful and martyred. Ask yourself the sharper question: what request am I avoiding right now because I don't want to be a burden?

Name it. That's your first action.

Recently I tolerated a situation for days rather than asking for help, and nobody benefited from my endurance. It just gave time and impetus to the problem, all because I didn't want to interrupt.

Sign 2: You don't follow up.

The faulty belief here follows straight on from feeling like an interruption.

Someone doesn't reply. You conclude they don't want to speak with you, when usually they're just busy, buried in to-do's, mid-school-run, three weeks behind on email or the next 'urgent' meeting.

Your follow-up isn't pressure; it's a reminder.

The fortune genuinely is in the follow-up, and the honest question is this: am I being considerate, or am I avoiding?

Pick three unanswered threads this week and send the second message.

Sign 3: You don't make the invitation.

You decide in advance that they'll say no, so you never ask.

This is the one that can cost practitioners and coaches the most, because the invitation is the whole job.

If you're a coach who doesn't invite, you're a very well-trained secret.

Take a moment to look underneath it. What's the hidden belief?

Mine was that inviting someone to work with me placed an obligation on them. It doesn't place an obligation, it places a choice and coaching is all about your clients choice. They are responsible for their decisions and results.

Sign 4: You don't name what you need.

Do you get swept along by other people's preferences, dates, budgets, food choices and decisions?

There's a particular kind of silence that looks like flexibility. Someone asks what you want and you say "whatever suits", when in fact a Tuesday would ruin your week.

Naming a need isn't a demand, it's information the other person needs in order to work with you properly.

Start small: choose one preference, stated plainly to others, once a day.

Sign 5: You don't negotiate.

If confrontation feels like a risk to the relationship, you'll accept terms that grate against your values.

I see this constantly with trainers and therapists (and my past self): rates held constant for years, while scope and costs are gradually expanding, and cancellation policies are written but rarely enforced.

The negotiation you're avoiding isn't a conflict, it's a conversation about fit and boundaries. And a client who can't hear "here are my terms" was never going to respect the work or do what it takes to get the results.

Action - Rate Review: Where could you respectfully raise your prices this week?

6: You don't raise your hand.

You stay in the background on the call, in the presentation or in the group.

You tell yourself you're being polite, giving others a chance by not interrupting or speaking out. Meanwhile the person who spoke got remembered, got asked to come back, and got booked.

Visibility isn't vanity in this profession; it's how people find out you exist.

Set a rule for your next group call: speak once in the first ten minutes, before the resistance has time to build its case.

Sign 7: You don't ask for the introduction.

You show up at the networking event, work the room, and come away deflated because you never got to the one person you went for.

It's easy to blame the format, the noise, the awkward layout but did you ask?

Introductions are the cheapest, warmest route to work you'll ever get, and most of them go unmade because nobody says the sentence. The sentence is short:

· "Who do you know who's working with X right now?"

· "Would you be willing to introduce me to Y?"

· "Is there anyone here I should meet before I go?"

Three questions, and any one of them changes the evening.

Sign 8: You don't ask anyone to buy.

This is my biggie.

I have genuinely caught myself talking people out of buying, adding caveats, offering alternatives, suggesting they "have a think". What is that about?

It's the same belief under the cover of a different behaviour: my offer creates a cost for them, so I'll absorb it by not making it.

The problem is that someone who wanted help now doesn't get it, and I've called that ethics.

Your action step this week: take one person who has already told you they're struggling with something you fix, and send them a single sentence with a price and a date in it. "I've got two spaces in October at £1500, would you like one?" No preamble, no excusing, no justifying, just stop typing.

Sign 9: You soften every request until it disappears.

"Only if you have time." "No worries if not." "I don't want to be a nuisance."

I recognise all of these, because I've written them hundreds of times.

A softener isn't politeness. It's a pre-emptive apology that hands the other person a ready-made exit.

Cut them out for one week and watch what happens to your response rate.

What's the belief sitting underneath the softening? Usually: I'm not worth the inconvenience.

Sign 10: You decide on someone else's behalf that they'd rather not be asked.

This is the root of the other nine.

When I don't ask because I assume someone won't want to help, buy, refer, respond or engage, I'm making their decision for them.

That isn't kindness. It's pre-rejection and a mind read, two things I'd challenge in a client within thirty seconds and had been running unchallenged in myself for years.

What finally moved it for me was noticing that the nine signs above are all symptoms of this one, so there aren't nine habits to fix, only a single sentence to remember:

My responsibility is the ask - Their responsibility is the answer.

Every time you answer on somebody's behalf, you take their choice away and call it the right thing to do.

Every un-asked question still authors an outcome.

Usually resulting in silence, delay or self-denial, and I'd ask you honestly how that's working out.

For me it wasn't working out at all, so in this sprint I started counting ASK reps, clear requests where the other person is genuinely free to say yes or no.

Target: five a day. On day one I made seven, including reconnecting with past clients, asking for conversations, approaching potential partners and inviting people to explore working together.

Nothing terrible happened and one conversation was booked almost immediately.

Your turn: five asks a day, counted, for seven days. We're not looking for five perfect asks, just five real ones.

That's it for this week, and as always, thanks for reading.

Hit reply and tell me which of the ten resonated most, I'd genuinely like to know.

If you want help clearing the pattern underneath it, I have Q4 spots coming available for...

Facilitating Magic – 1:1 coaching.

It is for Gen X women, usually 45+, who have outgrown the identity that got them here and cannot yet see the way forward. Across eight private 90-minute sessions, we work with the old patterns, expectations and roles that have shaped your choices, so you can recognise your own gifts and talents, remember more clearly who you are and begin writing the next chapter on purpose.

The next step is a free 30-minute Clarity Call. We can talk about where you are, what is pulling at you and whether this work is right for you.

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With so much love and gratitude,

Heather

Coach, writer, and strategist at the intersection of language, NLP and AI, helping humans reclaim identity, time, and impact.

Email: [email protected]

Website: heathervmasters.com

Choosing Happy: choosinghappy.space
Start With AI: startwithai.online
Creative Writing Tips: Creativewritingtips.club

P.S. If you know someone with an ASK problem, please consider sending this edition to them. Asking counts.

P.P.S. The free coffee-and-chat is always open if this stirred something you'd rather talk through than type.