Asking Better Questions: Lessons in Perspective

Cathedral in Modena

Two ingredients to a good conversation are:

  1. a subject that has done interesting things, and has an intriguing point of view, and
  2. a set of questions that demonstrate the interviewer is interested in exploring some of those projects and has a certain point of view

Asking good questions is an art.

The hardest questions to ask however, are those we're also called to answer.

Lessons in perspective

I came across two essays recently that have reinforced the same sense of fragility we face as humans I have felt during personal and family difficulties.

New Zealand-based art director Linds Redding who died last month of inoperable cancer at age 52 offered a short lesson in perspective:

And here’s the thing.

It turns out I didn’t actually like my old life nearly as much as I thought I did. I know this now because I occasionally catch up with my old colleagues and work-mates. They fall over each other to  enthusiastically show me the latest project they’re working on. Ask my opinion. Proudly show off their technical prowess (which is not inconsiderable.) I find myself glazing over but politely listen as they brag about who’s had the least sleep and the most takeaway food. “I haven’t seen my wife since January, I can’t feel my legs any more and I think I have scurvy but another three weeks and we’ll be done. It’s got to be done by then The client’s going on holiday. What do I think?”

What do I think?

I think you’re all fucking mad. Deranged. So disengaged from reality it’s not even funny. It’s a fucking TV commercial. Nobody give a shit.

This has come as quite a shock I can tell you. I think, I’ve come to the conclusion that the whole thing was a bit of a con. A scam. An elaborate hoax.

[…] Countless late nights and weekends, holidays, birthdays, school recitals and anniversary dinners were willingly sacrificed at the altar of some intangible but infinitely worthy higher cause. It would all be worth it in the long run…

This was the con. Convincing myself that there was nowhere I’d rather be was just a coping mechanism. I can see that now. It wasn't really important.

Colorado-based managing director at tech startups investment firm Foundry Group Brad Feld has had an incredibly productive run, working 60+ hours weekly, and adding extracurricular activities like writing a book, running marathons, and traveling a lot. After suffering from a fall and fatigue recently, he's resetting his priorities:

I’ve found myself in a similar position every year. This is nothing new for those close to me – I run extremely hot and often up to the edge of my capacity. I keep adding stuff on top with some fantasy that my capacity for new stuff is unlimited. There is so much I want to do and I just keep going after it. I have a good internal algorithm for making sure I get all the “urgent / important” stuff done and I’m very aware of what work to prioritize over other things. When I start reaching my capacity, I focus more on the important stuff – both urgent and non-urgent, and insert a tighter hierarchy around my work, making sure my partners and the companies I’m an investor in are at the top of the stack.

But I neglect me. And that’s what has happened again this year.

We are not machines, and when we break we also break down. Even as we put on a brave face and push through. Adrenaline rush doesn't hold us together too long, nor does sleep deprivation, poor nutrition, and denial. When we finally acknowledge we need to hit pause, we are often passed a critical point.

By the time we realize we're thirsty for slowing down, or a good night sleep, or a balanced meal, the emotional toll has already taken place. In the haste to keep going, the spirit suffers from connection deprivation and acceptance that we are after all human and we need to take care of number one.

Re-engaging differently

It's a hard pill to swallow, I know all too well.

Over the years I learned two tricks that help me regain a sense of perspective and move from stuck to productive without running in overdrive:

1. refocus my awareness on the progress I am making instead of comparing with others

We do end up comparing our "inside" to someone the "outside" of others without concept of how they got there or how far along we truly are.

This is especially dangerous in a day and age where so much sharing is going on in social networks and where there is still confusion around reporting/reading/sharing the news with getting on with it. Much of what we see is what we want to see or perceive about how others are so accomplished. Mostly by reacting to what they post in social networks.

Consuming media is not the same as processing information. They are the product of two very different environments and processes — both external and internal.

2. give up total control of needing to feel productive all the time

Technology and productivity advice lull us into a false sense of confidence that we can fill every second of our day to capacity. Building momentum and leaning into it is good. However, sometimes there is a better way and we may not have seen in the rush to get on with it using the known path.

When we're able to hit pause and step back, we start breathing again, and breath injects new life into our thinking.

Both help me slow down and re-engage differently.

How many times have you looked back and shaken your head at the silliness of not living and fully appreciating the people (and even the important work) in your life for fear of missing out?


[behind the Duomo in Modena]


Valeria is an experienced listener. She is also frequent speaker at conferences and companies on a variety of topics. To book her for a speaking engagement click here.

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