Answering the tough questions (and how to make it easier)

I’ve recently started seeing a coach to help me with an important life decision where I’ve been feeling stuck. I’ve tried my usual methods (research, exercises, talking to people about it) but when that didn’t cut it, I realised it was time to see someone who could help me cut through this gordian knot.

After we had a short call to make sure we were a good match, I had some homework to do to prep for our first session. I opened up the first few documents and let me tell you, that was scary. I almost closed them and left them for another day, but I’d commited to doing the work, it was in my calendar, and I did not want to press the “push to tomorrow” button on my Trello, so I soldiered through. But it was tough.

At first.

Even
though a lot of the personal branding work I do is grounded in answering these big, scary questions, I still felt that first moment of paralysis and overwhelm when I saw the empty questionnaire.

There’s no one-size-fits-all solution to dealing with that. But I can share with you the three practical steps that help me when it comes to answering the tough questions, like “what do you want people to say in a speech about you in 20 years?”, “what would you do with your life if money wasn’t a concern?”, “what makes you different from other people?”, or “what is it that truly fulfills you?”.

1.
Give yourself very little time (at first)
Set a timer, expect your initial answer to not be very good, and don’t think about it, just write. The time pressure removes the “editor” part of your brain from the equation, and you’ll often find the bones of your answers to be the same as if you spent, say, an hour reflecting and honing them.

Reflection can come later – do a first pass now. Once the page isn’t empty anymore, you can sit with the question and ponder it properly, without the pressure of writing something, getting it perfect or having to “answer” the question.
 

2. Stay in flow
Once I’d done a rough answer on one, I kept going through all of the questions I had planned for that day. If I hit a concept I needed to explore deeper, I made a note (*LOOKIT) and kept going.

This is a method I’ve used before in writing – it’s an easy way to search for things you need to come back to without disrupting the writing flow. Very useful when you just want a note to look up a word, figure out how to foreshadow a bit of plot, or simply check on how long a character would take to pass out from bloodloss.

3. Come back and edit

You’ve already put something down – now you’re just taking some time to think about it, probe deeper, see if there’s something different there, without the pressure of an open question looming over you.

You may decide you need to let the question simmer for a couple of days, that you want input from someone who knows you well, or that you need to do a bit of research or other exercises to answer it properly.

That’s ok – the answers to these questions are living things, they will change and grow with you. Decide on a timeline for when you’re getting to “good enough”, and rest easy knowing you can always update them whenever your answer changes.

I think my favourite two questions were:

  • What’s missing in your life, the presence of which would have your life be more fulfilling?
  • What two steps could you immediately take that would make the biggest difference in your current situation?

But the one that was most helpful was:

  • What do you contribute that is unique?

Because this is a question we ask, in many forms, when we work on our personal brand, on figuring out who we are and what we bring to the table.

But seeing it asked in this context, not focused on the career side of things, helped me answer it more broadly.

Here was the answer I came to in 30 seconds (again, not giving yourself time to second guess is so useful when it comes to answering these – you can always come back and expand but if you give yourself all the time in the wolrd for a first draft it’ll never get done):

  • I am very good at helping people discover and articulate what makes them special and the value they bring

  • I have excellent systems set up for life and goals management that are easily repeatable

  • I am kind, and always willing to help – coaching, mentoring, a helping hand, a workshop – whatever it takes

  • I am an excellent baker

  • My approach to public speaking is “I’m not trapped in here with you, you’re trapped in here with me”. I love it, and I’m good at it!

  • International background – I’m Spanish, lived in Spain, UK and US, travelled to 25+ countries

  • I am always overprepared and extremely organized / planned

  • I am very thoughtful (my husband prompted me to add this one in when I rattled them off)

 

A good few of these were in my list already – and some of them were surprising new additions. Never underestimate the power of a good question!

How about you give them a stab now? Would love to hear in the comments how it went!

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