Coaching in storytelling – Learning from engagements

Posted by  Shawn Callahan —November 30, 2015
Filed in Business storytelling

Early last year a CEO of a government agency, let’s call him Tim, asked whether I could coach him in storytelling. Tim had an immediate need, an important presentation to stakeholders that were less than excited about the new direction the agency was taking. Happy to help I told him we could start with six sessions and I would base it on our Storytelling for Leaders material.

This was my first real coaching gig so I called up Amanda Horne, a dear friend and experienced executive coach, and met for coffee. Without saying it Amanda ran the session with me like a coaching session and at the end we talked about her approach, which was based on asking questions and helping me work out what I wanted to achieve and then helping me find concrete activities I could do to get what I wanted done. It was a masterclass in adult learning.

Coaching in storytelling

Executive coaching in storytelling insights

I’ve now coached 10 executives. Some have been face-to-face, usually in the wonderful array of cafes you find across Melbourne. Others have been on Skype with people based in China and the USA. Both mediums seem to be equally effective. With 10 coaching clients I’m starting to see some patterns. I can’t say I have solutions to what I’m seeing yet. Maybe you can suggest good ways to respond. But let me outline two of them here. I’d love to hear what you think.

Executives don’t always see their peers telling stories and are therefore reluctant to do something different. I start all my coaching in storytelling sessions, after we have worked out what the executive wants to achieve, with training on how to spot a story. You would have heard me talk about this before, but it’s vital a storyteller can tell the difference between a story and not a story. Once they have this narrative intelligence they begin to realise their colleagues don’t tell stories. And when in doubt the safest strategy is to do what others are doing. Influence psychologists, Robert Cialdini, calls this social proof.

I’ve helped my clients in two ways to overcome this stress. First I assure them that no one really can tell if you are telling a story if you don’t start by saying something as dumb as “I would like to share a story.” So I get them to tell stories in small, low risk meetings to get them comfortable with the approach and to see the reaction of their audience, which is invariably positive. Second, we keep an eye out for exemplary leaders in their organisation that tell stories. And in most cases, especially in the big companies, we will find examples. The fact that they are rare spells an opportunity for my guys. Storytelling will set them apart.

People like to talk about storytelling yet are reluctant to tell stories. I’ve had a number of executives who love to discuss the craft of storytelling yet when I ask them to come to a session with stories to tell they have all manner of excuses for why they don’t have one to share. I think I just need to get tougher on them but I also wonder why they are reluctant. Do they know what I’m after? Are they having trouble finding stories at work? Do they still have doubts about the approach? I’m yet to work this one out fully but I suspect they don’t quite see the stories that are floating around them and how they can be told to make a business point. Maybe I will need to shadow them one day and point out the stories as they appear. That would be fun.

We have had some amazing successes so far ranging from one executive getting his budget approved based on the story he told, to others getting standing ovations at presentations. But these are just the big, obvious things. The real value will come from the many small stories told consistently over time that engage people and help them understand what’s happening and why, that show the progress being made and remind everyone of the purpose of what’s being done. That’s how storytelling can make a difference at work.

About  Shawn Callahan

Shawn, author of Putting Stories to Work, is one of the world's leading business storytelling consultants. He helps executive teams find and tell the story of their strategy. When he is not working on strategy communication, Shawn is helping leaders find and tell business stories to engage, to influence and to inspire. Shawn works with Global 1000 companies including Shell, IBM, SAP, Bayer, Microsoft & Danone. Connect with Shawn on:



  1. Stuart Reid says:

    Hi Shawn – I recognise the reluctance to bring stories that you describe. I think failing to spot the stories ‘floating around’ them could be part of the problem.

    I think that fear of vulnerability is probably involved too. Whenever we tell a story we are revealing part of ourselves – our thinking, our values, how we see the world. Top executives have often been conditioned not to do this – to be ‘objective’ by referring to facts, graphs, bullet points and logical arguments. So they might well be uncomfortable with treading into the subjective area of stories, and the emotion they often express.

    What do you think? If there’s something in this, then you as a coach can work with them on that.


    1. I think you are right Stuart. Executives can be reluctant to reveal too much. It’s dangerous for them. At least they think so.

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