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Comfort Zones: Pushing Your Team to Greatness, One Step at a Time.

Phil Bennett Posted by Phil Bennett in Uncategorized 6 min read

Being outside of your comfort zone is, well, uncomfortable. However, it’s a place where there are creative things to learn and excellent growth opportunities. So how do you support your team take their first steps into a world so loved by shouty management gurus?

I could jump-start this post with some terrible motivational quote, something like:

Life begins at the end of your comfort zone.


Your comfort zone is your danger zone.

However, you would all run away screaming, and I’m not trying to create some bullshit motivational management blog with stupid repeated mantras. That kind of stuff turns me off, and I know it will turn off a lot of other people.

However, the glut of motivational comfort zone quotes exists for one reason. Comfort zones are the death of personal development.

Handful of coins

About ten years ago I took a photo of a handful of coins, less than 10 British pounds, it was the only money I had left in the world, and I had no idea where the next paycheque would come. The later stages of my failing business had buried me. Cashflow was not going well!

Due to my endless optimism at the time, I took the photo to put it in a slide deck three years in the future, when I had made my entrepreneurial millions. The picture would act as motivation for those in the same position.

The millions never came, the company failed, and I got a middle-management tech lead job at a local marketing company.

New beginnings.

I was confounded when I started my new role. My performance was significantly better at my position than I had expected, I was confident in my technical capability, assertive in my decisions, and a monumental amount better at communicating than I had ever been.

Playing this all back against previous, similar, roles made me realise the change was significant. I had previously been, what you might categorise as, a traditional lousy developer. Conflicts where a challenge for me, I preferred talking over text-based platforms, I sucked at communicating, and I was even scared of answering the phone.

After presented at a conference a first few months after starting this role an old friend reached out to me to express their surprise that I would be presenting in front of 200 odd paying conference attendees. In retrospect, so was I.

My disastrous attempt at being an entrepreneur lasted only a year and a half, but it felt like I had taken a short cut through about ten years worth of experience.

As I reflected on my leap in progress, I realised I had learnt new skills quickly because I needed to survive, literally. I didn’t eat if I didn’t deliver work. It was that simple. I was pushed so far outside my comfort zone for a short period that I had to adapt, or I would have failed.

Thanks, Phil, that’s great, but how do you apply this to other people? How do you push your team outside their comfort zone?

Lead by Example.

Nothing is more infuriating for a team than lazy leadership and asking a team to do something that you wouldn’t do yourself. If you are sat in your comfort zone and not pushing yourself, it’s insulting to expect your team to promote themselves. Push yourself, and others around will be inspired to do the same.

Also, allow your team to challenge and push you outside your comfort zone. Your team will find ways to help you grow if they understand that you want to be challenged and pushed. More importantly, building this reciprocal trust will create a habit of working where you support each other’s growth.

Enable team members to say ‘Yes’.

The core tool for pushing yourself forward is saying ‘Yes’ to things that make you uncomfortable and taking on opportunities in areas you’ve aren’t perfect.

Doing this can be a little scary at best and terrifying at worst. So make saying yes easy for your team.

A few things that can help this are:

  • Help them discover opportunities.
  • Let them choose opportunities; don’t force the opportunities on them.
  • Make sure they’re aware that you will support them with anything that might happen should they make a jump.
  • Make the opportunities’ potential benefits clear.
  • Clarify any potential pitfalls, if you prompt a team member to push themselves and it explodes in their face, then they’re going to blame you for not warning them. This will make them a lot less likely to try it again.

Be considerate of people limits.

Work should be fun, and it’s not going to be fun if you’re too far out of your comfort zone for too long. It’s called the ‘comfort zone’ because being outside it is uncomfortable. Pushing too hard for too long creates stress, anxiety, and all the kind of things that make people get sick, or quit. So it’s imperative to understand what people’s limits are so they don’t take on too much.

For example, presenting and public speaking can be an excellent opportunity for people to build communication skills, but pushing someone with no experience in this area, who might be an introvert, to stand up on a stage in front of 200+ people is a recipe for disaster. It would make more sense to start small and build up, support them in presenting ideas to the team, then externally within the company. Then look at the possibility of talking at smaller meetups or user groups.

Don’t be too complacent about success.

Feedback and reward are super crucial to helping people make these steps. Keep in mind that what might now seem like a super small step for you might be a massive step outside their comfort zone for someone else.

Celebrate success and give feedback on improvement areas, but always check this feedback against how comfortable the person is with that task they have performed. For example, If someone is new to public speaking, they’re unlikely to give a TED worthy talk first time so don’t expect them to be performing at that level.

Catch them when they fall.

The single most important thing to consider when you’re pushing your team is to catch them when they fail and make sure they know you will catch them.

If something goes wrong, it can be painful. Making sure this impact is minimised means they won’t be scared to try again if they fail the first time.

So make sure you’re there to support in any way when things go wrong because they will! But progressively your team will make fewer and fewer mistakes.

Next Steps

Sound interesting? Here are some things you can apply:

  1. Firstly, you need to make sure that you are seen to be pushing yourself outside of your own comfort zone. Rolling in with a ‘do as I say, not as I do attitude’ will ultimately explode in your face. So sit down and review your own progress in this area. If you’re not doing this, then get some support from those around you to make sure you are.
  2. Once you are seen to be ‘leading by example’ then you can start to look at areas of opportunity for your team. Keep an eye out for exciting ‘side projects’ that might come up within your company, but also outside.
  3. Ask your team if they are interested in taking part, keeping in mind to be super clear on the benefits and potential pitfalls and make sure they know you will catch them if they fall.
  4. Review, celebrate and feedback.