How to Ask for Something Hard

Written by Dave Bailey

Team meeting asking hard questions

When you’re a founder, you sometimes have to ask people for something they may not want to give. Perhaps, you’re asking your investors to invest in a bridge round, or asking your team to work a particular weekend.

When you’re faced with the challenge of making a ‘hard ask’ without damaging the relationship, there’s a simple playbook:

1) Start with the most important facts.

‘We’ve just had the board meeting and got consensus for the new strategy.’

2) State the emotions those facts evoke in you.

‘I’m feeling excited but nervous, especially when it comes to fundraising.’

3) Link those emotions to your current needs.

‘Right now, I need to focus and spend time with the team, and I also need your support as investors while I lead this change.’

4) State the outcome you want.

‘I’m looking to get your buy-in on closing an internal round that covers us for a further six months of runway.’

5) Ask for the next step towards that outcome.

‘Do you have fifteen minutes so I can take you through the high-level assumptions over the phone, and get your advice?’

There are a few things to note about this technique. It’s concise, which means you don’t have to say more than you need to. It’s emotionally-open, which shifts the tone from self-righteous to vulnerable. And it’s respectful, which allows the other party to offer alternative solutions to meeting your needs that you may not have considered.

Give this format a try — after all, if you don’t ask . . .

Read more about this format here.


Originally published Mar 22, 2021, last updated Jun 1, 2021

communications feedback psychology

About Dave Bailey

Hi, I’m Dave Bailey and I coach tech CEOs from Series A to pre-IPO. Join 20,000 entrepreneurs who receive my new essay every week. 

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