Have you ever found yourself in a meeting avoiding talking about the most difficult issue? Too nervous to ask the most important question? 

I’ve been in that situation too, but I’ve learned how to make it easy to ask the hardest questions.   And I learned how to do this when I was on the opposite side of the table, when I was waiting for several people to ask me a difficult question I really wanted to answer. 

Before I became a best-selling author and speaker, I had a corporate career.  I learned about the hardest question when I was visiting the London office of the company I was working with in Australia. I had been in the London office for a couple of days, preparing to present a seminar. I had settled in well because they were such a nice team.  This seminar was quite late at night, so I had been working all day before I picked up my presentation notes and went to the seminar, leaving my personal belongings under the desk.  I was super excited because there was another Aussie in the London office at the same time and we organised to catch up for pizza afterwards. So, I did the seminar, which went well, stayed afterwards to chat with some of the attendees and then my girlfriend Katrina and I headed out for dinner.

We had a great meal and when the check arrived, I said to Katrina “oh no it’s my treat”, opened my purse and found I only had five pounds. I knew I’d been to the ATM earlier that morning and got out quite a lot of extra cash. Katrina could see by the look on my face something was wrong. I told her there was some money missing but I would sort it out tomorrow. I paid on card, we said goodnight and I went back to my hotel. 

When I woke up the next morning, I thought about the money and knew the only time it could have gone missing was when my purse was under the desk at work, When I got to the office, I pulled my Director aside and explained the situation. Slowly the word got around the team, and one by one, they all came to chat.  But no-one asked me what I thought was the most important question. How much money was stolen? 

At first, I thought maybe it was a cultural thing. Australians can be very direct, and my English colleagues were extremely polite. One after another each member of the team told me how disappointed they were, and how strange it was that I had this money stolen. I found it increasingly frustrating that no-one asked, ‘How much did you lose?’ Eventually the sixth colleague who approached me  to say, “I’m so sorry to hear this” etc, etc. And then she said, “How much money was stolen if you don’t mind me asking?” 

Finally!  The most important and clearly the hardest question my colleagues had avoided asking me. I told her I didn’t mind at all and it was about seventy pounds.   It was curious how relieved I felt after I answered the question I waited so long to hear.  And I decided to share and coach others about making it can be to ask the hardest question, if you approach it from a different perspective.  

I left the corporate world many years and two books ago. Now that I have a teaching role with Zuckerberg Institute as well as my writing and speaking, I often coach entrepreneurs about how reluctant they are to ask the really hard questions, particularly about finance. Often an entrepreneur is quite comfortable making a pitch or talking about their amazing start-up.  Entrepreneurs enjoy talking about their concept, their vision and their mission but find it so hard to say, “And I really need funding” or “And I really need this amount of funding” and the final hardest question “Would you be interested in investing in my idea?” 

When I start sharing this process with entrepreneurs, I reveal there is always a meeting or a pitch when someone on the other side of the table is waiting for the hardest question.  Maybe, like I was in London, they are not only waiting for the question but looking forward to answering it! 

The most crucial aspect of this dilemma is the person you are meeting often won’t bring up the question you want answered. Investors will usually wait for you to ask the tough questions about investing and will also wait for a guide as to how much you’re looking for and when.  

Sometimes the hardest question might not be about money.  Sometimes you might meet someone you want to be your mentor or advisor.  You might chat over coffee, feeling as though you are asking the question by talking about your ideas and where you want your business to go.  And all the while the person you’re sitting with is wondering, ‘Do they want me to be their mentor?  Is this just a chat or do they want to ask me something?  

      I know it can feel scary to ask; 

  • Will you invest? 
  • Will you be my mentor? 
  • Can I have a referral to someone you know who might help me? 
  • Do you think my idea will work? 
  • Is there anything I could do better? 

Often the person sitting opposite you is waiting for the opportunity to give advice and support.  

They are just waiting for you to ask.