This article originally published in Authority Magazine on January 14, 2024.
Perspective. Great leaders are hard-charging and demand results, but they must also keep things in perspective. Toggling between the big picture and the details and deadlines is a critical perspective for a leader to have. If you set an annual goal aimed at driving sales, and the wording of the goal technically means it wasn’t achieved, keep the perspective that the goal was achieved and perhaps the wording did not align with the real intent. Perspective helps you see things from all angles and leads to fairness and good decision-making.
As part of Authority Magazine's series called “Five Things You Need To Be A Highly Effective C-Suite Executive,” Doug Noll interviewed Jack Macleod.
Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
As a guy who graduated with a double major in English and Communications, it seemed I should pursue a career where I could do a lot of communicating in English (bad joke) so I started my career at Ogilvy Public Relations in the late nineties. It became clear quickly that the “action” was in the internet industry, so I found my way into a sales job with a Baltimore-based online advertising firm called Teknosurf. That was an incredible five-year journey that led me to San Francisco a month before the internet bubble burst, and later to Los Angeles to open another sales office. The business — now called Advertising.com — was sold to AOL Time Warner and shortly thereafter I made my way to what I thought was the next big thing: social media. I moved back east to lead sales at a social media marketing agency, and after that was sold to Meredith Corporation, I made the transition from sales/BD leader to business leader and proceeded to lead that business through a bit of a turnaround. After righting the ship, I joined up with some former colleagues from Advertising.com who had an ed-tech startup focusing on the K-12 market. It was an incredible experience but as is often the case, the VC funding didn’t materialize as quickly as we had planned so I moved on to a private-equity-backed media company serving the higher education space. This was very fulfilling as my role was to serve as a growth catalyst, launching numerous new revenue streams among which was a live events business. Most of my career had been in digital media and marketing, and I found the events business fascinating. So, my next move got me to where I am today — 360 Live Media — where I get to leverage all my experience in marketing and events for the benefit of our clients. It’s been a long journey, but everything seems to have happened for a reason and I’m in a great spot.
Can you share the most interesting story that happened to you since you started your career?
One of my online advertising clients was grateful to me for helping them grow their business, so when they came to town to visit me, they took me out to dinner. After dinner when we were saying goodbye, one of them handed me a pretty big wad of cash. That’s probably the most interesting story I can share.
Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?
I think I’d have to go with the famous quote from one of the great philosophers of our time, Mike Tyson, who said “Everyone’s got a plan until they get punched in the face.” My career has not followed a plan or a straight path. I’ve faced many setbacks and as I reflect at middle-age, I really do think so much of life’s success — however one may define that — comes back to how you handle adversity when life knocks you off course.
Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?
The business books that have impacted me most include Good to Great, The Hard Thing About Hard Things, and How Google Works. Even though Good to Great has been around forever, I still think about getting the right people on the bus, and then figuring out the right place for them to sit.
What do you think makes your company stand out? Can you share a story?
360 Live Media stands out because our work truly breaks the mold. Clients hire us to help them change from the status quo, modernize how they operate, and stand out with their events, brands, and marketing. Whether developing a new organizational visual identity for the leading beverage association or marketing the top trade shows in the country, the only people who know why we stand out are the executives who hire us — and there are about twenty of them attesting to the impact of our work on our website, which helps us stand out and is our most gratifying form of compensation.
You are a successful business leader. Which three-character traits do you think were most instrumental to your success? Can you please share a story or example for each?
- Impatience. At the end of the day, work is about getting stuff done. I thrive on getting things done as quickly as possible. That doesn’t mean sacrificing quality or strategic thinking, but it does mean acting with a sense of urgency. I have found that pushing my colleagues and clients has given them the nudges they need to produce great work faster and to make decisions faster. The more you are getting done, the faster you are growing, and fast growth is typically valued more than slow growth.
- Toughness. As I mentioned in the Mike Tyson quote earlier, adversity is inevitable. I’ve had a large client give us a short timeframe to make some fairly substantial changes and enhancements to how we were servicing them, and that’s when you need to be tough enough to stomach the situation — regardless of whether or not you agree it’s justified — and rise to the occasion via some weeks of intense work rallying the team to satisfy the client. In this situation, we produced a significant amount of thinking and process in a short amount of time, and the client is now completely satisfied.
- Authenticity. I think a lot of execs think that they need to have a formal or measured persona or personality that is different than who they really are when they are not working. In my experience, being your authentic self — especially in an executive role — builds trust with colleagues and clients and trust is essential for effective working relationships. Whether working in dad jokes in client meetings or hamming it up at the team-building karaoke night, people want to work with real people, not manufactured and carefully curated versions of what they think an executive should be.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?
For me, the most difficult decisions are the ones involving people’s careers. Shortly after I started running the social media agency, I had to right-size our cost structure to generate some immediate financial gains. The result was that I had to decide to part ways with some great leaders who had been my peers for years before I was promoted. These folks were good at what they did, but ultimately, I decided to make some key leadership changes, and these were among the most difficult decisions I’ve made. They were the right decisions as they helped get the business where it needed to be, but the human side of it makes it excruciating in the moment.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?
The analogy I like is that of an orchestra conductor. The leadership team is the best at playing their instruments, and the chief executive conducts the orchestra. More simply put, a C-Suite executive’s key value is in setting the vision and strategy for growth, attracting the right talent, making decisions, and communicating all of this to internal and external stakeholders in a way that everyone can understand and buy into.
What are the “myths” that you would like to dispel about being a C-Suite executive? Can you explain what you mean?
I think my previous comments about authenticity apply here as well. Being a C-Suite executive doesn’t have to mean the abdication of one’s true personality and self. On the contrary, I’ve found showing personality and having fun to be effective for building trust and empowering others to be free to do so as well.
What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?
The most common leadership mistakes I see are trying to act “above” the teams they are leading. The “player-coach” or “servant-leader” models are the way to avoid this. You need to be a resource who is in the trenches with your teams to bring out the best in them, not an inaccessible ivory tower decision-maker who hides behind false constructs of superiority.
In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?
I’d say the most underestimated aspect is that everything is ultimately your responsibility. No matter what happens or if something isn’t working, it’s ultimately on you. It’s easy for employees to be idealistic in their critiques of what you do, but when the buck stops with you, the decisions need to be much more pragmatic, and they typically involve choosing the least bad option. One example involved a senior executive who was not being honest about a serious client situation. While the idealistic answer was to part ways with them immediately out of principle, the decision was to first not harm the client relationship, which meant retaining the individual for a longer period than was preferred.
What are your “Five Things You Need To Be A Highly Effective C-Suite Executive”?
- An excellent listener. To make good decisions, you need to have a firm grasp on what’s happening within and outside of your company. If you can’t listen to people to hear what they are trying to say, or if you can’t “listen” to data that you may not want to hear, you can’t make the right decisions to guide your company forward.
- Empathy. This one is a key trait for being a highly effective human as much as being a highly effective C-Suite Executive. If you can’t put yourself in someone else’s shoes and feel what they are feeling — whether an employee or client — you really can’t effectively communicate, problem-solve, or collaborate with them. I fear this is increasingly lost in today’s “me first” world.
- An action-bias. Leaders exist to direct action. Thinking is important to inform direction, but no business ever grows by thinking too much. They grow by taking action. Whether having another conversation, testing a concept, or launching a beta product. If you aren’t driving activity, your company is stagnant.
- Tolerance for failure. Failure is truly the only way to learn. Leaders must accept that it is a part of growing your company. No company has been successful in everything it has done (examples being — the Apple Newton, Microsoft Zune, or Google+). The key is to learn quickly and not repeat the mistakes. Innovation and growth are not possible without failure, so leaders must embrace a tolerance for it.
- Perspective. Great leaders are hard-charging and demand results, but they must also keep things in perspective. Toggling between the big picture and the details and deadlines is a critical perspective for a leader to have. If you set an annual goal aimed at driving sales, and the wording of the goal technically means it wasn’t achieved, keep the perspective that the goal was achieved and perhaps the wording did not align with the real intent. Perspective helps you see things from all angles and leads to fairness and good decision-making.
In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?
It’s not always raging happy hours or an open keg tapped in the kitchen, though these can certainly help. Create a “fun committee” which is comprised of team members at multiple levels of the org chart. People support what they help to create, so put the culture in the hands of your team instead of trying to mandate it from the top down. Plenty of the culture naturally flows from how the Chief Executive operates and interacts with folks, but the rest should be in the hands of the team. This has led us to unexpectedly fun team-building events like “niche PowerPoint presentations” to holiday mixology competitions.
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? You never know what your idea can trigger. :-)
Maybe a “Be Cool to Everyone Week.” If everyone was their best self for one week and was intentionally the coolest and kindest person they could be in every interaction, big and small, just think how much everyone would be transformed and want to keep it going!
How can our readers further follow you online?
Find me on LinkedIn
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!