Great writers “need to deeply understand the hopes and fears of their audience,” an interview with authors Sara Connell & Santiago Jaramillo

Writers need to deeply understand the hopes and fears of their audience.

As part of my interview series on the five things you need to know to become a great author, I had the pleasure of interviewing Santiago Jaramillo.

Santiago Jaramillo is the CEO and Co-Founder of Emplify, and the co-author (with Todd Richardson) of the book Agile Engagement: How to Drive Lasting Results by Cultivating a Flexible, Responsive, and Collaborative Culture.

Anationally-recognized expert on employee engagement, Santiago was named to Inc. Magazine’s 30 Under 30. I was lucky enough to have some time with Santiago to discuss his book, his company Emplify, and his outlook on how to create a global movement to create meaningful work and eradicate “bad” work.


Can you share a story about what brought you to this particular career path?

I began my software career working for ExactTarget. That rewarding experience prompted me to realize that I value and am motivated by working with specific types of people.

I found that people in the software industry in general are progressive, creative, ambitious, thoughtful, and smart. Working in thatenvironment stoked my desire to build something of significance — something bigger than just me — with really smart people.It led me to launch a company called Bluebridgein 2011,which served the church and tourism industry with mobile apps. Bluebridge was a success, and I worked hard to maintain and improve the corporate culture as we scaled rapidly.

After selling two business units at Bluebridge, I stretched myself quite thin, carrying various roles in addition to being CEO. I experienced some failures in leadership — not communicating well, not investing in our people, being short with team members.

As a result, our engagement dropped by 50 percentile points and that catalyzed the rest of mycareer. I realized that what’s important to me is not just building a successful company; it’s about how I create spaces that inspire and challengepeople to become their best selves and achieve their greatest potential in pursuit of a meaningful mission and goals.

I’ve also realized that data is an incredible tool for leaders to see the reality of how they’re leading, the spaces they’re creating for their people and how all of that impacts their lives and their work quality. Data can be an important tool to help leaders make decisions on what to do next, to become better leaders, create a better culture for people, and thrive as a business.

For me, Emplify is accelerating the end of bad work through better leadership. It’s helping people, both customers and employees, achieve their full potential, while improving business performance, profitability and growth.

Can you share the most interesting story that occurred to you in the course of your career?

Seeing a 50th percentile drop in engagement in the early days at Bluebridge, really recentered me. It made me look more closely at what really matters to me in life and what yields business outcomes. Was it only the monetary success of the businesses that I lead, or was it how the spaces I create help people be the best possible version of themselves — and in the process, advance humanity? The answer, of course, was to create that positive changeand in turn, that would also happen to increase the chances of creating a massive and profitable business.

Can you share a story about the funniest mistake you made when you were first starting?

During an annual strategy planning session early in Bluebridge’s history, we asked ourselves what we were going to do to improve employee engagement, to become a workplace of choice; a place where people really wantedto work.

Six different people landed on, “we’re going to buy office snacks.” That was going to be thething that would help our team do better work and be more engaged! Meanwhile, because of our fast growth, people didn’t know where their jobs began or ended, or how success was measured. We were throwing snacks at our team, and they were telling us, “We don’t need snacks. We need a job description.”

That’s common of many leaders trying to improve corporate culture. We waste time and resources doing unstrategic activities thatdon’t actually solvethe core problem.

What are some of the most interesting or exciting projects you are working on now?

I am so excited about providing data-driven human coaching for organizations to improve engagement for their team. This will provide managersdata-driven competence and clarity about the number one action they can take today, tomorrow, and in the next 30 days to create a more engaging environment. Mining that information will allow everyone tobecome smarter in recommending the right actions at the right time, to improve confidence and clarity in decision-making.

What is the one habit you believe contributed the most to you becoming a great writer?

Writers need to deeply understand the hopes and fears of their audience. For me, that meant speaking with CEOs and HR leaders. I had hundreds of conversations about their biggest challenges, hopes and fears. After that, I was better equipped to write about the most valuable challenges in an engaging way, combining storiesand statistics to make best practices come to life for the reader.

Can you share the most interesting conclusion you reached in your book?

I found it interesting to compare the differences between the lower quartile and highest quartile of engaged companies we interviewed. High-performing, highly engaged companies were data-driven in their culture and employee engagement. Because they were data-driven, they had the confidence to be really strategic. They weren’t saying “yes” to a dozen things. They were going all-in on one or two meaningful things, driving those things through to completion, and measuring their success.

What is the main empowering lesson you want your readers to take away after finishing your book?

Any company can have an amazing culture that improves the lives of people and helps them become a better version of themselves. With focus and attention, they can see real, tangible improvements in the energy of the workforce and even in their business metrics.

One of the most rewarding parts of Emplify is… we get to do both. We help people live better lives at work, and we do it in the service of companies’ missions and goals.

What was the biggest challenge you faced in your journey to becoming a bestselling author?

Writing a book comes down to just putting the words on paper every day. And every single day, the first paragraph you write is the hardest. The next hardest step is actually shipping the first manuscript and not just rewriting it over and over. There will always be a gap between your vision of the work and what you’re actually able to put together. You have to be okay with that tension and ship something that may not be “perfect” to you. Good enough today is better than perfect 10 years from now.

Which literature do you draw inspiration from?

I love fictional short stories. They require excellence in character and plot development. How do you convey an idea, a concept to a message, a lesson, get someone to care about a character in such a short space? An excellentshort story inspires me to get to the essence of an idea and to convey it in the clearestand most concise way possible, so that people not only understand and rememberit, but are moved emotionally, as well.

How do you think your writing makes an impact in the world?

I spend a lot of time thinking of ways to help people unlock their true potential at work. We are on that journeywith our people at Emplify. We’ve worked with hundreds of companies on their engagement, culture and leadership journey, and now we want to openly share that knowledge, without charging.

That’s why I give my book out for free at every conference at which I speak. I’ve never charged anyone for a book.

That is true not just of how I use ourbook. Through our corporate culture, we share the lessons we’ve learned freely, to help people become world-class leadersand createenvironments where people can do the best work of their lives.

What advice would you give to someone considering becoming an author like you?

Writing something of meaning takes a lot of time, a lot of work, a lot of focus, a lot of perseverance. And you can’t succeed unless you have a passion for what you’re writing about and the message you’re trying to share and have a unique way to share an old insight. A topic you’re passionate about will propel you, and give you the grit to finish it and bring it to life.

What are your “5 things I wish someone told me when I first started”?

  1. It’s all about the people. A lot of our success has been “right product, right market, right time.” But it’s also because we brought the right people into the organization. I can provide vision as we scale exponentially, but I also rely more on other team members to move the business forward. I learn that lesson over again every year.
  2. Do what you must to retain the right people. For example, my co-founder Adam Weber was a salesperson with so much incredible potential and emotional intelligence and drive. I knew he had the potential to do even greater things. Keeping him involved meant making some meaningful accommodations. It was worth absolutely every ounce of time and effort, because he has driven the company forward.
  3. Understand root causes. Understanding root causes is a problem-solving skill. Don’t just rely on data or instinct; marry the two together to first understand the problem and then solve it.
  4. Understand motivation. Some people think humans are mostly inherently lazy and can’t be trusted to do good work. Therefore, they believe you have to create an environment with lots of rules and policies and enforce them or people willtake advantage and not do their jobs or pursue excellence. I believe most people wantto do good, meaningful work that leverages their skills and talents productively. Humans aren’t slot machines where you put in money, benefits and titles, and you get back someone’s heart and mind. People give their best when you invest in the whole person and help them achieve their potential.
  5. Have the right attitude about work. Work is sometimes viewed as an inherently bad thing. “We should retire at the earliest age possible.”“We should work as little as possible and live for the weekend.”I don’t fault people who land there, because so many have disengaging work environments. But we can do better than that. Work can be a source of meaning and fulfillment. There just needs to be the right fit between the person and the organization, whose leadership is committed to creating an environment that draws the best from its peopleand people who are committed to give their best in pursuit of the organization’s mission.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be?

It would be accelerating the end of bad work.

We live in a world that eradicates diseases. We’ve put a rover on Mars. If we can dream of and accomplish those things, then we can dream of a world in which work is life-giving vs. life-draining.Withingenuity and cooperation, we have the tools and the environments that give everyone meaningful and fulfilling work, leveraging the right skills, and making the right impact with the right people surrounding them.

Companies must create engaging cultures if they want to thrive in today’s world. Those that don’t will not survive, because the best talent will pursue the best work environments. That’s the part of the movement that Emplify is part of, where work can be this amazing part of life, rather than an energy-sucking thing that people do to pay the bills. We have the opportunity to flip that narrative.

How can our readers follow you on social media?

@santiagojara

Thank you so much for this. This was very inspiring!


About the author: Sara is an author and writing coach with a private practice in Chicago. She has appeared in Oprah, Good Morning America, NPR, The View and Katie Couric. Her writing has appeared in The New York Times, Tri-Quarterly, Good Housekeeping, Parenting, IO Literary Journal, and Psychobabble. Her first book Bringing In Finn was nominated for ELLE magazine Book of the Year. www.saraconnell.com