5 Proven Tips For Executives Who Want To Master Storytelling

by | Interviewing

Great leaders are often great storytellers. They use the art of storytelling to contextualize, excite, influence, persuade, and drive change.

However, you can’t just take a single public speaking course or register for a Toastmasters club and consider your leadership storytelling journey complete.

Storytelling is a muscle that you must constantly exercise if you want to be a confident and effective speaker—and leader.

In this article, I share 5 proven strategies for improving your storytelling skills as an executive. Along the way, I provide examples from my work with senior leaders to inspire you as you continue to develop and refine your messaging and executive presence.

The Importance Of Storytelling As An Executive

But first, why is storytelling so important for leaders?

Whether interviewing for a new role, navigating the day-to-day of a leadership position, or vying for a promotion, storytelling skills are a critical asset in the modern workplace.

Nearly every executive job seeker I speak with shares that they want to be a better storyteller. Why is this? Because your ability to effectively, concisely, and confidently tell a story can make or break whether you receive an offer from your dream company.

Oftentimes, executive candidates are similarly qualified for roles, but it’s their power to communicate their background, experience, skills, and unique value proposition (AKA their fabulousness) that determines whether they ultimately secure the position.

Moreover, once you’re in a leadership role, it’s your capacity to communicate your impact that defines how successful you’ll be and whether you’ll receive subsequent promotions.

How To Improve Your Storytelling Skills As A Leader

If you’re struggling with your messaging, or simply want to be a more effective communicator, here are 5 tips for mastering the art of storytelling:

1. Understand your audience.

Before developing any messaging, you want to really understand your audience, since you must target your message to them.

When speaking to a group of senior executive peers about a new business initiative, for instance, you’ll likely want to focus on the final implications to the company and how it may intersect with their department and teams. Conversely, if you’re speaking with a group of individual contributors, they may be more interested in how your initiative will impact their daily work.

Before driving into your talking points, which we’ll cover next, it can be helpful to ask yourself:

  • Who is my audience?
  • What do they care about?
  • What do I want them to take away from my talk?

2. Know your talking points.

Next, you want to outline your key talking points. Except in very specific situations, such as a TED Talk or earnings call, you don’t want to memorize a script.

As I’ve shared in this executive interview guide, it can be helpful to narrow down your talking points so they fit on a 3″ x 3″ Post-It note, which allows you to focus and align your core message.

Of course, if you’re preparing for a lengthier meeting, conference, or retreat, you don’t want to restrict yourself to only a few bullet points. You’ll want something more fleshed out, but not read it word for word and risk tripping yourself up.

The key takeaway is that expert storytellers are rehearsed, not scripted, at the executive level.

A quick tip: Many of my clients find it helpful to “brain dump” all their initial thoughts and then consolidate their talking points as they refine and practice sharing their message aloud.

[Read: Executive Thought Leadership: 5 Tips To Stand Out As A Thought Leader]

3. Practice your storytelling skills often.

Once you’re clear on your audience and the key talking points you want to share, it’s time to practice.

There’s a false belief that great storytellers just show up and wing it. While it’s true that some leaders are good at speaking off the cuff, most executives must practice delivering their stories.

As you practice your presentation skills, try to replicate the environment you’ll be in when you ultimately share your story.

For example, if you’ll be talking on Zoom, record yourself speaking and then watch it back. If you’ll be standing in front of a group in a conference room, try to reserve the actual room and spend time preparing there.

There are also a lot of AI tools that allow you to record yourself speaking and gather feedback on how you might come across. That said, nothing replaces the feedback of another human.

4. Expect the unexpected.

No matter how much you prepare to deliver your story, the unexpected is bound to happen at some point. Your technology may not work, you may get a hostile question, or someone may even attempt to derail you.

Consequently, you want to practice staying calm under pressure, responding to curveball questions, and respectfully sticking to your talking points. At the end of the day, you want to regulate yourself and your emotions if you get caught off guard.

One of the simplest ways to do this is to take a deep breath (or two) before responding to a question, especially if you feel triggered. This not only gives you time to center yourself and your thoughts but also provides the other person with additional time to clarify their question.

As you continue to develop your communication skills, you’ll get more used to difficult questions (and people) and increase your comfort and confidence when things go sideways.

Expert tip: Because many of my clients are tech executives, they often find it helpful to “failure test” their talking points and stories when practicing ahead of a big meeting or presentation. Doing so in a safe environment, such as a coaching session, can be incredibly empowering and really calm their nerves. (I also encourage them to visualize and practice everything going perfectly, since this is far more likely.)

[Read: How Learning Improv Can Make You A Better Interviewee]

5. Ask for frequent feedback.

Finally, you want to regularly gather feedback on your messaging and communication skills to see how you’re landing with your target audience. Notably, this feedback doesn’t have to be formal either.

One of my executive coaching clients developed a quick three-question survey she distributed to stakeholders after major presentations. This allowed her to gather live feedback throughout her road show and constantly tweak her messaging. As a bonus, it provided her with data points to demonstrate the impact of her work when review time came around.

You can also develop a group of trusted colleagues you turn to for honest feedback on your communication skills. What’s most important is that you’re gathering feedback on your messaging and adjusting accordingly.

Proven Tips For Executives Who Want To Master Storytelling

Final Thoughts On Becoming An Effective Executive Storyteller

Becoming a more effective storyteller requires you to know your audience, develop clear talking points, and practice. You must also be open to uncertainty and lots of feedback along the way.

Please remember that you’re not alone on the journey either. If you’re considering partnering with an executive coach to improve your storytelling skills, feel free to reach out or schedule a consultation. I’m here for you! You’ve got this!

About Dr. Kyle Elliott

About Dr. Kyle Elliott

Dr. Kyle Elliott is the founder, tech career coach, and executive coach behind CaffeinatedKyle.com. He has helped his clients land jobs at Meta, Amazon, Google, and nearly every other tech giant you can imagine.

Dr. Elliott’s insights have been featured in Business Insider, CNBC, CNN, Entrepreneur, Fast Company, Fortune, Harvard Business Review, and The New York Times, among dozens of other leading publications. He has been recognized as a Best Career & Interview Coach, Best Resume Writer for Silicon Valley/Tech Managers & Executives, and LinkedIn Top Voice (the platform’s highest honor).

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