Why Leaders Need Good Storytelling Skills – Part 1

Posted by  Shawn Callahan —February 9, 2016
Filed in Business storytelling

This is chapter 1 of the book, Putting Stories to Work – Mastering Business Storytelling. I decided to share it in two parts so this is part 1. I wanted to start the book with some of the business reasons for storytelling and show leaders a few of the useful places storytelling can really make a difference. I start with strategy because in much of our work at Anecdote we are helping companies tell the story of their strategy so everyone knows why the strategic choices were made. But as many of you would already know, storytelling can be used in a vast and growing number of areas in business.

The pre-orders for the hardcover will stop on the 1st of March so if you want the limited and first edition hardback make your order here. We  also have the pre-order for the Kindle version available. A paperback will also be available in April. All the best for now. Shawn.


Over the last couple of years, I’ve had the pleasure of coaching one of the country managers of a global manufacturer, who I’ll call Peter. I was about to start a story workshop for Peter and his people when he turned to me and said, ‘Shawn, I would just like to put this session into context for everyone’. Peter then described how, each year, he pitches a budget to the company’s board for approval.

His group’s plans all hinge on getting the right level of resources, so it’s a big deal. The pitch is usually a gruelling affair, but the last time Peter did it, things were different. He decided to make his proposal to the board using a story structure we’d worked on together. The board members listened attentively as Peter told a story about what he wanted to accomplish—it took him 15 minutes, with no PowerPoint deck in sight.

When Peter had finished, the board asked him a couple of straightforward questions, then there were nods around the table, and just like that his request was granted. Before Peter could catch his breath, the board chair asked him how much more money he’d need to achieve his goals even more quickly. He went with his gut: ‘Five million will do it’. That was also approved. As Peter was leaving, he heard the chair ask another country manager to make their proposal as clear as Peter’s. He just smiled.

Now you might be thinking: Didn’t Peter need to share a whole lot of data to make his case? When did that happen? Surely he didn’t just tell a story? The answer is that this data was an essential element of the story Peter told. He handed out projections and historical information and then pointed to it as his story unfolded.

But the most important thing here is that Peter wanted to engage the board emotionally and make them understand what great opportunities were at hand, and how well placed he and his team were to take them. His story forged this emotional engagement while also presenting the hard numbers of his case. Of course, a leader has many other responsibilities in addition to obtaining the resources to get their job done.

A leader needs to work with their people to craft and communicate strategy, so that everyone in the group has that strategy in their heads while making day-to-day decisions. A leader needs to engage their people so they all know they are doing work that is making a difference, and their individual skills can shine. There will be many times, especially when things get tough, when a leader needs to inspire action. This action will have to be supported by the many decisions people make in the organisation, which requires the leader to influence those decisions that may directly impact their group.

Also, every day the leader’s people will face new challenges, and as no-one wants to reinvent the wheel or repeat past mistakes, sharing lessons becomes vital. And sometimes a leader needs to set the record straight: they need to counter half-truths and lies. The list of potential responsibilities is obviously far longer than this, but the ones described above are fundamental for all leaders. And in each case, business storytelling can play a major role.


Steve Jobs bounces onto the stage and grabs the slide changer from a colleague with a friendly ‘Thanks Scott’. He’s looking thin and pale, illness having taken its toll, but his energy remains boundless. It’s the 2011 Apple Worldwide Developers Conference and Steve is about to announce a change in strategy for his company. The 1000-plus crowd cheers as he steps into the spotlight and then falls silent, hanging on his next utterance. ‘About 10 years ago we had one of our most important insights, and that was the PC was going to become the digital hub for your digital life.’ With these words, Steve Jobs begins his strategy story.

A global study conducted in 2012 involving 300,000 employees found that just over half did not really understand the basics of their organisations’ strategies.¹ It’s the dirty little secret of so many businesses: ask any employee, including the executive team, about the company strategy and they’ll lunge for a document that reminds them what it is. It’s rarely embedded in their minds and, as a result, the espoused strategy has a harder time influencing day-to-day decision-making. Given the effort applied to strategy development, there is a massive disconnect here.

Storytelling skills

The opportunity to reconnect a firm with its strategy lies in how the strategy is communicated and understood. There are a number of ways of conveying your organisation’s strategy. One popular approach is to craft a beautiful-looking PowerPoint presentation and email it to all of your team leaders, with the instruction to present it to their teams.

The head of strategy for one of Australia’s most iconic brands told me he happened to sit in on a strategy talk when a team leader presented a slide pack. It went something like this: ‘OK, HQ has asked me to tell you about … [clicks to the first slide] ah yes, our strategy … [clicks to the next slide and reads out the contents, then clicks again and pauses] Not sure what this means … [clicks to the next slide]’. The audience slid into boredom.

The talk failed to engage the team and left them none the wiser about the strategy. In fact, the employees were probably more cynical about and disengaged from the company than they had been before they sat down for the presentation. So sure, emailing a slide pack is easy, but in most cases it’s next to useless. It often achieves the opposite of what you want.

Another popular method is the CEO roadshow. This is where the CEO visits each company site and presents the slide pack themselves. This act is symbolic. It’s intended to show that the CEO really cares about the strategy, and they want everyone to know about it because it’s so important. The audience usually watches intently, but mainly to gauge whether the CEO really does believe in what they’re spouting.

Of course, the CEO is also there to answer questions, but no-one dares ask one in such an open forum. Sadly, the result is often similar to what was observed by the head of strategy mentioned above. In kicking off a division meeting following one CEO roadshow, a department head at a well-known bank asked the roomful of people: ‘So, who can tell me about our strategy?’ No response. ‘OK, just one of the 12 items then.’ Still nothing. ‘So, no-one can remember any of the 12 things we’ve just been talking about at all of our sites?’ Silence.

Presentations driven by slide packs typically contain lots of facts in the form of bullet points and graphs, but because these are not supplied within an overarching narrative, it’s hard for the audience to join the dots. People forget the information almost as soon as they file out of the auditorium because the presentation lacks a memorable story. A key question people often ask when they hear about a new strategy is ‘Why?’. ‘Why are we focusing on acquisition?’ they ask. ‘Why are we outsourcing?’ ‘Why are we demoting the Mac to the level of an iPhone or iPad?’ They want a plausible explanation.²

And in the absence of one, they’ll make one up, especially when they are stressed.³ A story effectively answers the ‘Why?’ questions because it sets out what has prompted the new strategy and what’s going to happen next. A story provides the context for a strategy, making it meaningful and allowing it to connect with other company stories employees may have in their minds.

I was explaining the concept of a strategy story during a training session for a Malaysian telecommunications company when the organisation’s leader suddenly jumped up and said: ‘I get it. Here’s our story. Over the last 10 years we’ve been focused on building mobile coverage. Our revenues have steadily increased but our infrastructure costs have risen faster. In two years time our infrastructure costs will exceed revenue. That’s why we’re now moving to collaborate and share infrastructure with our competitors, and putting our energy into competing using what runs on our mobile network’.

Why was the company collaborating with its competitors on infrastructure? Because its infrastructure costs were going through the roof. A simple yet effective story made this clear. Strategy stories are powerful because people can picture the events, remember them and retell them. A well-developed strategy story not only answers the ‘Why?’ questions but also conveys emotion in a way that inspires people to take action in accordance with the new strategy.

Creating an effective strategy story, one with real impact, involves much more than simply crafting and then telling a compelling story. It involves leaders developing the strategy story themselves so that they can own it. It involves teams being comfortable with telling the story and weaving their own experiences through it. And most importantly, it involves everyone in the organisation telling their own versions of the strategy story so that they all own it and act to support and build on it. The strategy story is a type of clarity story. I take you through the process of creating clarity stories in Chapter 6.

Steve Jobs paces back and forth across the stage, painting word pictures of where Apple has come from, why a change in strategy is needed, and where the company will now be heading. He talks as if the future has already come to pass. Eventually he brings up his last slide, takes a deep breath, and finishes his story: ‘So that is iCloud’.


The best business leaders care about employee engagement. That’s because apart from helping to make an organisation an enjoyable place to work, it’s been shown to have a big impact on the bottom line.4 UK retail giant Marks and Spencer and the University of Bath, for example, have documented how engagement is raising performance and productivity across the UK.5

It turns out that when employees are highly engaged, they trust their leaders and their company, and they care about their work. They’ll go above and beyond their duties, and that positive effort and attitude translates into business results. So how do you increase employee engagement and motivation with storytelling? You use stories to emphasise and boost purpose, progress and trust.


Back in 2007, Adam Grant, a professor at the Wharton School of the University of Pennsylvania, conducted a fascinating experiment that highlighted how important it is to be reminded of your purpose at work. The study focused on a call centre that raised funds for a university. Grant divided the call centre workers into two groups and used different approaches to motivate them. The people in Group 1 were reminded about the money they would earn and how it would improve their lives, while those in Group 2 were told stories that reminded them about how their work benefited the lives of others.

Assessing the participants a month later, Grant found there was little improvement in the average number of donations (nine) or amount of money ($1290) attributed to the people in Group 1. The people in Group 2, however, had generated more than double the average number of donations (23) and donation size ($3130).6 The regular sharing of stories that illustrate how someone’s work helps those they aim to serve can have a massive impact on output. A reminder of our true purpose, above simply creating shareholder value or maximising profit, rouses the human heart and inspires greater productivity.

Stories about purpose are a type of success story, which we explore in Chapter 6.


It’s hard to get a clear insight into what a large group of employees is thinking and feeling, especially over time. But that’s what Harvard professors Teresa Amabile and Steven Kramer were able to do when they conducted a lengthy investigation into the inner work life—the thoughts and feelings we have about our work and colleagues that set our mood and level of engagement—of 238 people in 26 project teams across seven companies.7 Each day the researchers emailed a short survey to the employees that asked them to rate their mood and feelings. The employees were also asked to ‘briefly describe one event from today that stands out in your mind’, which they were encouraged to do by sharing a short anecdote.

Over a couple of months, the researchers collected nearly 12,000 anecdotes, and in them they discovered what they called ‘the progress principle’. We all know from our own experiences that each day we’re boosted by a complex set of small wins, recognition, respect, connection with our group, and improvement in our skills. We also have setbacks, and these negative events often overwhelm the positive ones. Yet of all the influences on our daily outlook and inner work life, Amabile and Kramer found that the most significant was making progress in meaningful work.

When managers are asked what things they might do to engage and motivate their employees, highlighting the progress being made rarely gets a mention. But this can make a significant difference to a team’s productivity. One of your jobs as a leader should be to find and share these stories of progress, to make apparent what largely remains invisible to most of your people. Just talking to employees about this will give them the strong sense that you care about what they do. It will also help you keep a finger on the pulse of what’s happening in your area.

To get these progress stories, you can give each individual in your team the daily task of briefly describing one event that helped them to make progress that day. These stories can then be shared in team meetings. This will give you a far greater insight into the health of your team and your project than the standard around-the-table project update.

Stories that concern progress are modelled on success stories, which I detail in Chapter 6.


An engaged workforce trusts its leaders and the company. This trust takes time to earn, yet it can be destroyed in an instant. Our opinion of a leader’s trustworthiness is most influenced by what we see them do, but when we can’t see a leader in action, the next-best way to gauge their character is to hear a story about something they did.

I once heard a story about the CEO of a pharmaceutical company that gave me a strong impression of the man’s character. The company was just starting a trial for a new cancer therapy and a politician approached the CEO to try and get his wife onto the clinical test. The politician tacitly conveyed that the therapy might jump through fewer government hoops to be approved if his wife took part in the trial. The CEO calmly explained that this would be impossible because the trial was strictly controlled.

I heard this from an employee who was clearly proud of his CEO and thought him a man of integrity.

One person who taught me a lot about trust was David Maister, the distinguished consultant to professional service firms. At the time of starting Anecdote, I was already an admirer of David’s work. I’d read Managing the Professional Service Firm and I loved reading his blog. I also made comments and posed questions on his website that he would respond to and periodically incorporate into one of his podcasts.

One day I decided to ask David if he would be willing to spend an hour or two on the phone with me, to give me some advice on my new business, so I emailed him. No sooner had I hit ‘Send’ than my phone rang. It was David, calling me from Boston to follow up my request. I made it clear that I would be happy to pay him for a couple of hours of his time. He replied: ‘Shawn, my service fee is really designed for large corporations. I charge $20,000 a day, with a minimum of one day’.

Gulp. There was no way my little start-up could afford that. I was just about to say so when David continued: ‘But we are friends now. This is on me. How can I help?’ Engaging in an online conversation with David had created a relationship between us, even though we had never met.

So when I reached out for help, he was open to giving me a hand. As Adam Grant showed in his wonderful book Give and Take, the most successful people are givers—though not to the extent of being a doormat whom others walk all over. David is definitely a giver. David Maister sums up the dimensions of building and maintaining trust in a simple formula.8

Yes, I know, how can you boil something as complex as trust down into a simple formula? Well, the statistician George Box once said: ‘All models are wrong, but some are useful’.9 And I find Maister’s trust formula useful.

Here it is:

Trust = (credibility + reliability + intimacy) / self-interest

Credibility is about trusting what a person says because they have a track record of telling the truth, and the expertise and professionalism to know what they are talking about. Reliability is about trusting a person to do what they say they will do, and that they will do it well. Intimacy is about trusting someone to care about your emotions and desires, and to treat your secrets—what you really think of colleagues, what’s happening at work—with confidence.

Self-interest, however, erodes trust. A self-interested person only seeks to make themselves look good. They see the people they work with merely as a way of getting ahead. So if you want to build trust as a leader, you have to act in a way that triggers stories of credibility, reliability and intimacy, but not self-interest. (This is called story-triggering, which we revisit later in this chapter and in Chapter 4.)

And because engagement is also about trusting the company, you have to take every opportunity to tell stories about the great things other leaders in the firm are doing. Unfortunately, it’s a fact that bad stories are stronger than good ones.10 Just ask yourself what goes around an organisation faster: stories of success or stories of failure?

Relationship researcher John Gottman’s rule of thumb for a healthy marriage is to make sure the good events outnumber the bad ones by a ratio of at least five to one—anything less and the relationship is likely to fail.11 The same could be said for organisations. For every negative story floating around, you need at least five positives ones to counteract its effects. Just one story of self-interest can erode trust fast.


This article is adapted from Shawn’s book Putting Stories to Work: Mastering Business Storytelling.

In part 2 we will continue exploring ways to put stories to work to inspire action, influence decisions, sharing lessons and countering half truths and lies. If you would like your own copy of Putting Stories to Work you can Order your hardcover here and your Kindle here.

Photo credit: boltron- via Foter.com / CC BY-SA

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:

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