Coaching, mentoring and making great mistakes.

Kristen Davis
CinqC
Published in
6 min readJun 8, 2020

Learning how to fail, well, and instil a culture that encourages creativity and taking risks.

Once I’d created CinqC and worked with clients on their business models and strategic plans I started receiving requests for personalised coaching, mentoring or workshop sessions for their teams. Recently much of my coaching work has been focused on failing, and the great difference between failing well and failing fast — something the Silicon Valley gurus have us believe to be a good thing.

Leading a team in a large organisation or a growing startup is not easy and having access to external, impartial and honest counsel can bring much needed new perspectives to challenges. Sometimes this need is specific — you’ve a particular nut to crack or opportunity to seize and so require only short-term coaching. To give you pointers to unblock a situation and speed you on your way I might connect you with one or two pertinent people in my global network or share with you how another individual or organisation handled a similar situation so you can learn from their success, or their failure.

For longer-term ambitions and challenges a mentoring model is often a better option; one that takes a more holistic approach and considers the range of values and variables you’re working or want to acquire in order to get you to your goals and advance your vision. I think of mentoring as acting as a compass for my clients; enabling them to explore various paths and opportunities whilst ensuring they continue to progress in the right direction. One of my clients put it this way: ‘You keep me on track like a good navigator. You are my wing-woman on the way!’

One thing I always keep in mind when I’m coaching and mentoring is to make sure the advice I offer is pragmatic and realistic — something the person I’m working with will be able to envisage themselves doing and feel empowered to try. To take them just far enough outside of their comfort zone to keep them moving forward but not so far as to paralyse them. Not only does my counsel have to be feasible but it must also be relatable — it must connect to the individual and the objective they’re trying to achieve or problem they have to solve. This sounds obvious but sometimes guiding a person down the most efficient path is not the right route for them — what seems rational to me might not seem that way for you. Coaching and mentoring is about helping people understand the Why as well as the How so as to increase their confidence and autonomy in deciding What to do next.

You are not just a great mentor but you teach and at the same time manage to share your enthusiasm, inspiration, different perspective and vision. I still remember how you managed to see the little things in our projects that seemed unimportant to others. You’ve inspired me to seek beyond the ordinary and I remembered that during the hard times.

Tihana Šmitran, CEO & Founder @ Amulet Studios

When coaching and mentoring you have to help people with the tough realities of running a company or managing a team and sometimes deal with mistakes and failures. This is where having a Just Culture (a values-supportive model that holds organizations, rather than individuals, accountable for the systems they design and how they respond to events and behaviour, fairly and justly) is critical to successfully being able to navigate the hard times and it is the basis I instil in all my working relationships. I think of an organization’s culture as being like a cake — a Just Culture being the essential and solid foundation, on top of which you can layer a growth mindset (if you’ve not read Matthew Syed’s ‘Black Box Thinking’ I highly recommend it). Next add PACE, a great tool to raise risks before they become issues. Then top off your culture cake with systematic ‘Hot Washes’ and debriefs that enable you to continuously determine (using data) what you’re doing right, so you can do more of it, and, of course, what’s not gone right so you can revise your approach and move on empowered with that new knowledge.

A coach once asked me to reflect on 10 events that had shaped my personal and professional life — seven positive, and three less great experiences. Through this exercise I realised it was the ‘not so good’ experiences that are actually the most valuable. These have made me who I am today and from which I’ve learned the most about myself, about business and the world. Most cultures would consider these events ‘mistakes’ and as such I’d rarely have talked about them and I certainly wouldn’t put them in my CV. For the last ten years unsuccessful outcomes have been an ongoing research subject and as I’ve traveled and worked globally I’ve gained insights, experiences and deep cultural awareness of how errors and upsets are perceived and how we are taught, or not, to react and learn from them. I believe much can be learned from failing and time should be invested in studying our mistakes rather than adopting the ‘fail fast’ culture that has come out of Silicon Valley. To counter this I’ve become an ‘Ambassador for Failing Well’ to help leaders and organisations create cultures where teams and individuals can learn to fail well. In doing this companies can quickly differentiate themselves from their competitors, not just in business but also in offering talent a great place to work.

Presenting ‘On Failing, My continuous learning journey’, at FutureCo, August 2019

I’ve run digital and in-person workshops, individual and group sessions and delivered keynotes on failing and how failing well has been a big part of my continuous learning journey. For my corporate clients these sessions were often entitled something like ‘Creating Corporate Resilience’, whereas for accelerators and incubators they were called ‘How to fail, well’. The fact I’ve had to adapt the session names for different audiences shows the range of perception that failure, mistakes and unsuccessful endeavours carry in different contexts. Whatever the audience the catalyst for requests from clients was always the same: staying competitive today means taking more risks in increasingly complex situations — the chance of errors and dead-ends is higher than ever, so we need our teams to be comfortable making mistakes! The demand illustrates that few of us have been taught how to fail well, or operate in organisations where mistakes and non-successes are truly an option.

“With the objective of getting cross-functional teams to work closer together we brought in Kristen to tell us ‘How to Fail, Well’ and share practises and techniques we can use to overcome fear of failing and learning from mistakes. Her advice was inspirational, practical and rapidly applicable, enabling us to take more risks together and become more innovative as an organisation.”

Andres Peets, VUNK Co-founder and Partnerships at Telia Eesti

My coaching, mentoring and workshops provide tools and a Just Culture environment for exploring errors, along with a framework for studying and accepting failures — making sure you gain every possible lesson from less successful efforts and how to not be knocked off course when things don’t work as planned. We also look at ways to use these wisely as sometimes a f*©k up can provide an unexpected opportunity to bring about radical change — if you know how to fail well that is…

Let’s face it, being creative, resilient and taking risks are key ingredients to staying competitive and innovative so if you’d like to learn more about failing well, creating organisational resilience and all my other coaching and mentoring services do drop me a line via Cinqc.co or LinkedIn. It’d be good to talk.

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Kristen Davis
CinqC
Editor for

@daviskris10. Founder @ CinqC.co, US Board Chair @ APOPO HeroRats. Bilingual 🇬🇧🇫🇷 MC & moderator. Ex New York Times International l IT & Innovation Director