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7 Questions on Leadership with Dawson Helmling

Name: Dawson Helmling

Title: Founding SDR

Organisation: Apex Revenue

Dawson Helmling is a 2x small business founder, tech-startup veteran, and Founding SDR at Apex Revenue HQ in Knoxville, TN.

At his former employer, SCW, Dawson was the #1 producer in every position he held: BDR > BDR Manager > AM > AM Lead > Account Executive

Prior to joining SCW, Dawson owned and operated 2x small businesses. The Hemp Consortium of Asheville (THCA) was a CBD farm that specialized in growing premium outdoor CBD flower. The Blue Ridge Valet Company, LLC was a valet service that focused on large scale events like weddings and fundraisers, as well as fine-dining restaurant contracts.

Before starting his small businesses, Dawson was a opioid addict, and alcoholic, and a high school drop out. He was kicked out of the house for the first time when he was 15 years old, and spent many of his high school years bouncing around from couch to couch.

Today, Dawson uses his story to help others understand that their past does not have to equal their future, and that no matter how far they fall, they can always get back.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Dawson's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

One of my biggest challenges as a leader has been setting clear expectations.

Far too often, I found myself expecting my teams to respond in a certain way, and was disappointed when it played out differently than I had hoped.

The problem was that I wasn’t clearly communicating my expectations in a way that everybody could understand and act on.

This became blatantly obvious one day after launching a campaign with less-than-optimal results. Although everybody on the team had the same instructions, each person took action differently based on how they personally interpreted them. There was no alignment. This was a massive issue and the campaign was immediately put on hold.

A mentor of mine (who was also our CRO at the time) helped me realize that I needed to be crystal clear when communicating expectations to the team. This would allow them to:

1. Commit to the goal.

2. Ask for help along the way.

3. Share their concerns and unique perspective on the issue.

We regrouped, laid out the most unambiguous game plan we could, and re-started the campaign after everybody was on the same page.

Learning to set clear expectations not only saved that campaign, but also became one of the highest-valued skills in my arsenal. That experience also taught me that you must be open to switch things up if you aren’t getting the desired result. Don’t die on a hill just because you’re the one that watered the grass.

No plan is perfect, so understand that your tactics and strategies can always be optimized and sometimes even scrapped for something new. Set clear expectations early, and be willing to call an audible if your big idea isn’t working out the way you envisioned.

2. How did you become a leader? Can you please briefly tell the story?

"Leaders aren't born, they are made. And they are made just like anything else—through hard work." —Vince Lombardi

My mother would tell you that I came out of the womb leading teams of toddlers. However, the validity of that statement is questionable, to say the least.

Transforming myself into a people-first leader has been one of the longest processes of my life.

I’m constantly studying how other leaders react to adversity, how they treat their families, or how they treat strangers and the people who work for them. I study their daily habits, the language they use, and even the way they answer phone calls from unknown numbers. Everything they do contains bits of wisdom that I soak up and try to emulate in my own way.

I also read dozens of books on leadership and similar topics every year and put those teachings into practice in the real world. I start small, stay consistent, and dedicate time to learning from leaders I respect. And most importantly, I always stay curious. People who assume they know everything can not be effective leaders; it’s impossible. You must be willing to learn, grow, and understand the perspective of others if you want to successfully lead teams of people.

Being a leader takes curiosity, empathy, and massive amounts of commitment. It’s something that is learned and honed over time. There is no finish line. Leadership is a lifelong journey, and the road is open to anybody who’s willing to do the hard things.

3. How do you structure your work days from waking up to going to sleep?

After trying dozens daily routines championed by online “gurus” I realized that none of them work for me. My brain needs structure, but only to a certain extent. Too much structure and I’ll feel trapped and will probably go crazy. Too little structure and my productivity takes a nosedive.

Then a friend of mine introduced me to Alex Hormozi’s daily strategy. It was a game changer for me. My routine is based on his stuff:

1. Set an alarm for bedtime as well as in the mornings. Be ruthless in following the alarms.

* No phone 15 min before bed or 15 min after waking up

* Light stretching / yoga

* Run through the day in your mind

2. Plan the day before you sleep

* Write down all tasks

* Sort out the needle-moving tasks and put them in check-list format so you can mark them off as you complete them

This will help you avoid asking yourself “What should I do today?”

3. Focused mornings

Wake up and get sht done. Cross things off your check-list as you finish. The small wins stack up and help you keep momentum throughout the day.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

I was recently reminded to always put the needs of the team before my own. Leadership is about much more than just numbers, revenue, or a fancy job title. It’s about helping people kick ass and find meaning in their work and lives. It’s about helping people build their own personal dreams while encouraging and enabling them to become the best versions of themselves. As Simon Sinek would say, “Leaders eat last.”

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

One of my mentors handed me Never Split the Difference by a Chris Voss early in my leadership journey. For those who haven’t read the book, it’s a master class on dealing with people and their emotions.

People are wired to react emotionally before their logical brains kick in. Understanding this helped me learn to communicate in a way that resonates. I started going into situations with a desire to learn as much as possible about the other party and their perspective on the topic, rather than having an agenda or pre-planned talking points. Only after truly understanding their point of view did I have the clarity to decide how to react to the situation.

Having Tactical Empathy, as Chris calls it, is one of the most versatile skills that I’ve learned on my journey of leadership and personal development. Everything in life revolves around people. Learning how to understand others and walk in their shoes will take your leadership game to the next level.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Stay infinitely curious.

Never stop asking questions. Seriously.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

I recently spent the day at an invite-only leadership retreat in Raleigh, NC. I was brought in by a former mentor of mine and asked to give a short talk to kick-off the day. My contribution to the afternoon was minimal to say the least.

What I was most excited about was being surrounded by all these fantastic leaders and having the chance to soak up some of their knowledge. This story isn’t about me though, it’s about everybody else in attendance. There were probably 20 of us altogether and I was, by far, the youngest and least experienced. Some of these men and women had been leading teams longer than I had been alive. And every single one of them was making at least 5x my annual salary.

What really blew me away was how humble and unselfish everybody was. I was a guppy swimming with sharks, and rather than eating me alive they decided to invest their energy into helping me grow. Each and every person in that room served me in one way or another throughout the day. Some of them physically served me drinks, made me a sandwich for lunch, or brought me snacks in between sessions without any prompt. Others pulled me aside to have 1v1 conversations about life, business, or relationships. Somebody even took me for a tour of the property just so he could have some extra time to hear my story and learn how he could serve me best in the future.

This retreat was by far one of the most impactful experiences of my leadership journey thus far, and helped me realize that nothing can come before your people if you want to be a great leader.

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