Open Thinkering


3 reasons you need a critical friend


If there’s one thing that I’ve learned in my adult life, it’s that you can be considered a good conversationalist merely by being a good listener. That’s the thing: people want to be heard, to tell their story, to let what’s inside them out.

That’s great, but there’s at least one stage further than that: being good at asking questions. Socrates was great at it. This ‘Socratic approach’ not only stimulates debate, but thought and reflection. Knowing someone who can challenge you in a thoughtful, kind, and meaningful way is a hugely valuable resource on which to draw.

I’ve been prompted into writing about this as I’ve recently taken on what is now my fifth client for whom I am a ‘critical friend’. In none of these cases have I sought out this work, but instead have been approached by each client as someone who they think can help them. This could be a short term thing or, more often, is longer-term, and organised in a more ad-hoc, semi-structured way.

Thinking through what kind of things I talk about with my clients, there’s three broad areas where I’ve been able to help.

1. Motivation and encouragement

We’ve all been there: we know what we need to do in our professional lives, but we just can’t seem to traction. I’ve worked with those who would describe themselves as self-starters, yet have found value in helping me give shape to their plans.

Working with Doug is both a real pleasure and a kick up the backside! (Zoe Ross)

Doug is a very creative, motivated and talented individual, who inspires others around him to think from different angles and to challenge constructively. (Patrick Bellis)

2. Insight and analysis

Sometimes what you need is a person you trust to provide some objectivity on particular problems or struggles you’re having. These could be monumental professional struggles, or they could be #firstworldproblems. Either way, through discussion a way forward usually develops – either at the time, or reflecting on the conversation, by email.

Working with Doug has been one of the highlights of my career. His insights make anything I’m working on better. (Laura Hilliger)

The thing that Doug provided for me, above all, was insight. Through his incisive questioning and our subsequent discussions, Doug was able to help me to discover for myself, the very best way forward for my business and for me personally. He’s incredibly easy to work with and a thoroughly nice guy to boot. I’d highly recommend using his strengths to get the best out of yours. (Greg Perry)

3. Connection and inspiration

It’s easy to think that you’re slaving away, ploughing your own lonely furrow. In fact, there’s many people around the world with similar hopes and dreams as you. Learning from and/or connecting with them can be exciting, liberating, and confirm that what you’re doing is worthwhile.

I would wholeheartedly recommend Doug as a consultant, trainer, coach and all round wise and inspiring critical friend. (Sarah Horrocks)

As a freelancer, I am often alone with my own work. Being able to spend time talking things through with Doug was not only practical, but a catalyst for developing my ideas to help others. (Eylan Ezekiel)

Next steps

As I mentioned above, this is the first time I’ve offered this as a discrete (and discreet, if necessary!) service. I’m keen to help people, spending time to aid them in realising their hopes and dreams.

If you think I can help you, please do get in touch. The first 30 minutes we spend together is free, and I can tailor follow-up sessions to suit you, your time, and your budget. I reply to every email within 24 hours.

Email: [email protected]

Note: some of the above quotations are taken from clients, and some from others who have been kind enough to recommend me on LinkedIn.

Thanks to Eylan Ezekiel for feedback on this post, and John Johnston for drastically reducing the filesize of the gif!

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