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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

helps you in your leadership.



Jonno White

7 Questions with Christopher Ross
7 Questions with Christopher Ross

Name: Christopher Ross

Current title: Founder & CEO

Current organisation: Convoy Community Ltd.

I'm an IT Director by trade, and an entrepreneur by nature. Also an inveterate re-cycler, up-cycler and creator. My core values are Integrity, Growth and Contribution, and I'm happiest when I've helped make the world a better place, just a little bit - one person, one conversation, one interaction at a time.

Father of three, pack leader to two Beagles, and Founder & CEO of a business that seeks to help as many people as possible on the job-seeking journey. I created Convoy to take loneliness out of job-hunting, and it seems to be working. The game now is to scale up to support thousands of seekers.

I live in South West London (UK), like quality gin (would love to start a boutique distillery one day), and would happily spend entire weekends in a workshop making, repairing and inventing things.

7 Questions with Christopher Ross

1. What have you found most challenging as a leader of a small or medium enterprise?

Focusing ON the business rather than IN the business. As a Founder & CEO, with few resources to call on, everything is up to me. That can take up all available time, so it's all too easy to neglect the strategic, important in favour of the "urgent".

2. How did you become a leader of an SME? Can you please briefly tell the story?

Created the whole thing from scratch.

It all started with the big bang... Too far back? OK...

It really started with my role being made redundant back in March 2020. I was generously given outplacement support, and used it vigorously to review over 1000 jobs, applying for over 100, with countless customised CVs, cover letters and applications, hours of tuning LinkedIn to within an inch of its life, and what did I have to show for it after 3 months? 1 interview, and no feedback. I burnt out.

So, being a trouble-shooter and problem solver, I was determined to get to the bottom of what went wrong.

My conclusion was that two things were missing from the Outplacement model. Good though much of it was, it lacked structure and accountability. Yes, we had weekly meetings of a group of job-seekers, but this 2 hour meeting was more therapy than anything else (which was still vital for some, so not a bad thing!)

I went searching for what I thought I needed, but couldn't find what I was looking for. That left one remaining option: create it.

I proposed an "Agile" model for job hunting to a group of friends I'd made on the outplacement journey. Met with a chorus of "I'll join!", I replied with "We've got ourselves a Convoy!" (remembering the 1978 film), and "Convoy" was born.

The name fits what we are very well: A Convoy is a group of people on similar journeys, each with their own destination.

I posted about what we were doing on LinkedIn, and had that many people asking to join that I had to create further Convoys, and as of Feb 2021 we have 5 job seeking Convoys and another for Entrepreneurs.

45% of the folks searching for work have found new roles in their first 6 months - IN A PANDEMIC! It's extraordinary!

3. How do you structure your work days from waking up to going to sleep?

I try to use the principles of "The One Thing" (Gary Keller) - it's a fantastic book for really digging into what is actually going to move you forward.

At this stage I'm still doing everything in the business (though we serve almost 150 people currently) so that keeps me far too busy.

My challenge is to work more ON the business than IN the business, which I am working towards. To enable this I need to raise investment (grants and donations as we're a not-for-profit) to fund development of automation and sales/marketing activity.

4. What's the most recent significant leadership lesson you've learned?

Ask for help.

I'm getting better at this (= I'm really bad at it right now, but want to get better!)

As a Founder, you often feel it's all up to you.

And it is, unless you engage the energy and support of your tribe.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

The One Thing. The "Clarifying Question" is so powerful: "What's the One Thing I can do today, the doing of which makes everything else easier or unnecessary?"

It impacts self-leadership, which then flows into the leadership of everyone in your team.

Imagine the impact this has when everyone in your leadership team - everyone in your organisation - has the same level of focus.

I've also loved Laslo Bock's "Work Rules!" - presents the compelling narrative of doing experiments, capturing the lessons, and feeding that back into more experiments.

Sorry... that's two...

6. How do you build leadership capacity in an SME?


Listen to your market - so you know what they want/need.

Listen to your front-line people - so you know what they are up against.

Listen to your leadership teams (at all levels) so you know what challenges they face, and to make sure they are listening to the people they serve: their teams.

I can't stand kissing-up. That's toxic.

In my business, our people will always come first, and when we put our people first, they will put our Customers and Clients first.

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?

The value of this organisation I've recently created was encapsulated when I was told by one member: "I haven't had a single down day since I joined a Convoy."

I knew then that I had to make this a sustainable, scalable business so it will be around for the long term.

In the UK alone, the pandemic will result in over 1.5 million people looking for new roles. We have a duty to help.

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