Shy? Try Exercising Your Asking Muscles

Reading time ~4 minutes

Some Friday morning amateur social philosophy.

One of my current team is as shy as I am. We both agree that “we’d rather not deal with people”. It’s somewhat funny that even from the first day of my degree I had to work in teams and interact with external stakeholders. My ability to do so is my strength (but my dirty secret is that it’s also my biggest fear).

I’ve read and re-read loads of stuff on being an introvert, on being shy and assorted other musings for the “socially challenged”. I’m not socially awkward – I might be a bit of an over-sharer but once I’m up and running I can be the life and soul of the corner of the kitchen at a party, I enjoy sharing, I enjoy interacting with people but I’m like a dynamo – I need some winding up to reach that state.

I think my favorite term comes from Doc List who describes himself as an “Ambivert”. I think his observations closely define me as well.

Most people that I interact with in public or at work would never believe I’m shy. It’s one of the joys of the agile/conference scene – you know most people are just like you. They wear a mantle of bravery and a mask of confidence but after a week of conferences will happily spend the weekend recovering under the covers. Over the years those people become friends and the interactions become easier.

I gain short-term energy from talking to people but I’m exhausted afterwards. I find nothing more draining than leading planning sessions, demos and retrospectives but most people will never see it. In some camps that counts as introverted, in others extroverted – Let’s stick with ambivert.

Anyway. A challenge with being shy/introverted or even an ambivert is asking. Asking for help, information or even asking someone to do something you know is their responsibility or even pleasure to do for you.

As a project manager or leader this is a bit of a crazy situation. Every day I need to ask my team or external stakeholders for an assortment of things. The emotional effort needed to ask can vary from easy to terrifying and descends into experiences that are often addressed with Cognitive Behavior Therapy.

  • You believe it’s unreasonable to ask busy people for more of their time to meet needs you think are yours.
  • You feel (or have been told) you should ask someone for help or input.
  • You’re trying to make a difference, you know other people care but you don’t know how to approach the subject.
  • The list of doubts, “Shoulds” and “aughts” goes on.

From my experiences I’ve discovered the ability to ask is like any other mental muscle. If you use it regularly it gets better. If you don’t use it it wastes away. 

Unfortunately that shy moment freezes you up. It means you’re more inclined to not ask until it’s critical so you end up making life harder for yourself and the person you need to ask. All the while you’re procrastinating you’re expending mental cycles on stress and doing nothing.

But there’s more to it than that.

Each person you need to ask something of is a different muscle.

When I first started working as a PM in our DevOps group a few years ago I was new to the company, I had few existing working relationships and a number of key stakeholders I needed to learn to interact with.

How did I build up my asking muscles?

I reviewed my working relationships in the past to understand what I found easy and what was more difficult.  I found – even with my own team – that after about 3 useful interactions in a short period of time things became significantly easier so I decided to try an experiment.

There’s a neat idea in software development known as the “rule of three” – once you’ve needed to use the same thing 3 times then it’s probably time to make it generic and standardize it.

I bought a small (A3) sized whiteboard and placed it on my desk. On the board I drew a grid. Each horizontal lane represented a person I needed to learn to interact with. I wrote each name in the left-hand column. Each column after that was a placeholder where I’d mark an X every time I had an asking or collaborative interaction with that person. My goal was to get 3 X’s in each row over the space of about a month.

It worked – when there were only one or two X’s I’d figure out how I could build another interaction with that person that didn’t have to involve asking for anything significant.

One of those people came over to my desk and spotted my board – they asked what the “X’s” next to their name were. I explained and they immediately empathized. I wasn’t alone. That conversation counted as yet another X – It became easier to ask!

The tricky thing is once you’ve built those muscles up you need to kep them running.

If you neglect your asking skills for any time you need to rebuild them again (sometimes the second time is easier). If like me your projects and roles change a lot over the years you’ll probably find that by the time you’ve just got comfortable with everyone you need to ask that the world changes around you and you need to start again.

This is a good thing – it keeps us exercising our asking muscles.

Who do you want to ask something of today?

Go talk to them.

Have a great weekend


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