Storytelling Can Make or Break Your Leadership

Telling a compelling story is how you build credibility for yourself and your ideas. In this piece, the author draws on his experience as a speaker, publisher, and author to illustrate five characteristics of effective storytelling. He suggests that strong stories must be audience-specific, clearly contextualized, human-centric, action-oriented, and humble. Whether you’re winning over a colleague, a recruiter, or an entire conference audience, making sure you stick to these guidelines will help you convey care and compassion when presenting even the most daunting of ideas.

“It’s a new goal-setting framework.” That was one of my large enterprise clients’ attempt at an inspirational rallying cry for their rollout of Objectives and Key Results, or OKRs. As you might expect, it wasn’t met with much enthusiasm: “Why do we need a new goal-setting system?” managers and employees protested. “What will this mean for my evaluation? Am I still on track for that promotion?”

The problem wasn’t anything inherent to the proposal — instead, what was lacking was the executive’s storytelling. Telling a compelling story is how you build credibility for yourself and your ideas. It’s how you inspire an audience and lead an organization. Whether you need to win over a colleague, a team, an executive, a recruiter, or an entire conference audience, effective storytelling is key. As a speaker, publisher, and author of four books and dozens of articles, I’ve found that my most effective stories all shared the following five characteristics:

1. Be audience-specific.

It may sound basic, but if you want to know what your target audiences is curious about, what worries them, and what motivates them, a series of quick, informal conversations is often the most effective way to figure it out. You can then infuse your storytelling with words that speak to your audience’s specific anxieties or concerns, while avoiding language that will come across as bland platitudes.

That was the first mistake my client made around their OKRs announcement — they assumed that the same message would be effective for all 10,000 employees. But this audience included managers and individual contributors, veteran employees and new hires, people who were already aware of the OKR framework and others who had never heard of it. Furthermore, the audience was particularly concerned because this announcement had the potential to impact how all of these different groups were evaluated and promoted. As such, a better approach would have been to craft a variety of different rollout announcements addressing the specific questions and concerns of each subgroup within the organization.

2. Contextualize your story.

Another major issue with the OKR rollout was that the various announcements made about it failed to contextualize why now was the right time to make this change. To many employees, it seemed like yet another random, top-down management initiative. Had the story of the rollout explained how it fit into the broader vision of the company, its background, and future strategy, that would have helped people understand where the changes were coming from and why they were important. For example, they could have provided a statement along these lines:

Our roots are in industrial manufacturing, and the goal-setting frameworks we’ve been using were designed to be effective in that world. As we now transform into a digital, software-enabled company, those frameworks no longer make sense. We’ve invested in a variety of projects over the past five years to increase our digital capabilities, and those new ways of working require new ways of setting goals.

3. Humanize your story.

A personal anecdote can both lighten the mood and illustrate your perspective more effectively, helping your audience feel less skeptical and more open to your ideas. For example, when speaking to my leadership clients, I’ll often bring up the six months I spent traveling with a circus. While this might seem completely unrelated to the business context at hand, stories about my time hanging out with the human cannonball always get a laugh, and more importantly, my experience handling a strange new situation, building relationships, learning a new culture, failing often, and ultimately integrating successfully into a totally new world often turns out to be extremely relevant to my clients.

Similarly, the executives tasked with announcing the OKRs might kick things off with a personal story:
As some of you know, I enjoy skydiving. They say your mind goes blank when you jump out of an airplane, but last weekend, as I was stepping out of the door at 12,000 feet, it dawned on me that I had a clear objective: to maintain a work/life balance that reminds me regularly why both are important. And what were my key results? Well, at least one of them was to land 100% of my jumps without major injuries. As you can see, so far so good! This kind of clarity around our objectives is what I hope to achieve for our company with this new OKR framework.

4. Make it action-oriented.

Specificity reduces anxiety. If you give your audience practical advice and clear direction, you empower them to take action and make your story their own.

Initially, my client described the OKR rollout with impressive-sounding, but ultimately unhelpful platitudes: “It will change how we work. It will redefine success for the company. It will bring us closer to the customer,” they declared. And these things were all true. But they did nothing to help people understand what the changes would actually mean for them, day to day, as they began setting and working towards their new goals.

Instead, a more effective approach would be to focus on exactly what changes people would need to make:
Instead of relying on a roadmap with fixed initiatives and feature launch dates, we’re going to set quarterly check-in dates for assessing our progress towards customer metrics like retention, average order value, and customer acquisition cost. This means that executives and middle managers will no longer be prescribing work to product teams, but instead, teams will be responsible for developing their own plans for how best to achieve these goals. In addition, we will be offering training courses and long-term coaching to support teams as they make this transition. If you’re interested, just reach out to your manager and they’ll help you get started.

5. Keep it humble.

It’s normal to wince at the idea of baring your failures in front of colleagues, a conference audience, or a recruiter. But true humility shows capacity for growth and learning. It builds trust in your story precisely because it demonstrates that you’re not claiming to have all the answers, and that you’re willing to learn and adjust course as needed. In my experience, nothing creates a tighter connection between you and your audience than acknowledging that you’re standing on others’ shoulders, and you’re not going get everything right all the time.

In the case of the OKRs announcement, a dose of humility might look something like this:

Many of you may remember the last time we tried to update our goal-setting system. I was COO at the time, and I was one of the main drivers for that change. Many of you will also remember how badly that initiative failed. That was my fault. I pushed the change too quickly without a clear understanding of how to support the organization through that transition. I’ve learned so much from that experience, and I’m continuing to look to all of you for your valuable suggestions and support to ensure this OKR rollout is a success.

Storytelling can make or break any initiative. A poor storyteller can butcher even the best ideas, while a strong storyteller can present a daunting concept with care and compassion for their audience. It will take practice, but when done well, good storytelling can make a major impact on your team, your organization, and your entire career.

Read more on Persuasion or related topic Business communication

Jeff Gothelf helps organizations build better products and executives build the cultures that build better products. He is the co-author of the award-winning book Lean UX and the Harvard Business Review Press book Sense & Respond. He works as a coach, consultant and keynote speaker helping companies bridge the gaps between business agility, digital transformation, product management and human-centered design. His latest book, Forever Employable, was published in June 2020.