Leadership Lessons Learned in my First Year as an Executive

  1. Share
0 0

A Yes with a ?

When my boss asked me to become a member of the executive team, I said "yes" but I knew I had some challenges ahead of me. There were many leadership lessons I needed to learn to step into the role of Vice President of Sales at CCB Technology.  Basically, I didn’t want to throw a wrench into the engine of CCB.

I consumed tons of content from leaders who were way ahead of me, perspective and advice were two much-needed things.  Through podcasts, audiobooks, and face-to-face conversations I gleaned some priceless council.  As with anything though, being in it is a lot different than reading about it.

Here’s what I learned in my first year as an executive.


Rewards and Difficulties of Leadership

Anyone that has been in management for more than 13 minutes knows how it can be when trying to lead well. Sometimes you feel like First Lieutenant Dick Winters, leading troops into enemy territory and overcoming enormous opposition. (Band of Brothers, one of the greatest shows in the history of mankind portrayed Lieutenant Winters' service.)

Then there are times your life feels like the final scene of There Will Be Blood. Your goals are standing over you like Daniel Day-Lewis yelling “I Drink Your Milkshake!” and you have no clue what just happened… but your pretty certain insanity is present.

“Everything rises and falls on leadership” 

So what's the point? John C. Maxwell, a pastor, author, and leadership speaker, said, “Everything rises and falls on leadership.”

That statement is sobering and exciting to me in my role as the VP of Sales. I’ve been given the opportunity to bring people together, cast vision, and ultimately find out what I’m made of.

If everything rises and falls on leadership, I needed to ask myself some questions… Am I really committed to Servant Leadership? Do I care if my people like where they work? Are humility, integrity, passion, hunger and fun, core pieces of who I am or just words for a corporate poster? Will I own my mistakes or push my team under the bus as it passes?

There are a hundred questions like these that have passed through my head but ultimately, I keep coming back to one in particular: Am I worthy of having followers?

*Clarification: when I say ‘followers’ I’m not talking about social media type followers that think my posts are funny or ‘like’ them. I’m talking about people that look to me as a leader – not because of a title change– but because of influence.

The question of worthiness has pushed me forward in dozens of small circumstances, but it has also caused me to venture into areas that I might have otherwise sidestepped.

I’ve never been afraid of having the bat in my hands when the game is on the line. I LOVE that kind of pressure!! I prefer that situation because I have confidence in my skill set and feel a degree of control over the outcome. The game is in my hands.

The analogy starts to break down from there though because that isn’t how it works when you have a team reporting to you. Even if I hit a walk-off home run, it doesn’t mean my teammates will follow me or that I’ll have influence over them.

What do I do? Throw my hands up and say it’s not worth it? Cut corners and play the game for myself? Or… do I learn all I can about leadership and hone my skills?


Leadership Lessons: “No one drifts into excellence”

When my pastor, Mike Bullmore, says something – people sit up straight and take notice. Not because of his title, the degrees he’s obtained or some fire and brimstone intimidation factor. He’s one of the most humble men I’ve ever met, and yet, in almost every interaction I’ve had with Mike, he’s been direct, inquisitive, and approachable. If Mike gives advice, you know it’s for your edification. So when I heard him say in a sermon, “no one drifts into excellence”, it caused me to pause and literally take note. The context wasn’t business, but the lesson applies.

Jerry Rice, Warren Buffet, Michael Phelps, Whitney Houston, Michael Jordan, Stevie Ray Vaughn, Jerry Seinfeld…none of these people drifted to the top of their profession. They trained, studied, bombed, air-balled, forgot the words, practiced, and then did it again and again. It takes work to make it look easy.


Here are a few things I did to put what I was learning into practice.

  1. Write down yearly goals
  2. Break down the yearly goals into smaller, quarterly goals
  3. Establish disciplines that, if followed, will help to hit quarterly goals
  4. Write down the frequency each discipline will be practiced
  5. Start

Seems simple, except I’m not that good. I learned in Michael Hyatt’s Seven Principles for Setting Goals at Work and am using his full focus planner as my personal trainer. It’s tough… but it’s working. For whatever reason, the simple act of writing down the disciplines many times a week/month…etc. keeps me accountable. A nice side effect of doing this has been relief at the end of each week. When I look back at all I’ve written down, I see things accomplished that actually matter. And somehow when I put first things first my inbox of several 100 messages is cleared also.*

*It’s not magic and it doesn’t happen 100% of the time.  Some weeks blow up and late nights of catching up are needed.

At about the two-week mark of using the planner, I added a sixth step to the above five.

Tell my wife, boss & team what I’m doing. Risky.

Now I’ve got 20-ish people involved in the process instead of just me. If I slip, I’ve got a bunch of people that will notice. The pessimistic side of me started to think I was going to have micro-mangers at every turn – the opposite has been true.

Questions came up because they were intrigued. Not because they were trying to catch me losing. Wait! What?! Yep. I backed into gaining a few cheerleaders who seemed to feel like they were part of my progress.


One Saturday my wife mentioned she noticed a big difference in how I was interacting with the kids since I started getting up early to workout, read…etc. as opposed to staying in bed, getting a little more sleep, and rushing out the door in the morning. 

Guess what one of my disciplines was? Yep again. Wake up 60 minutes before the kids so that I can drink a glass of water with apple cider vinegar, work out, read, and make breakfast for the family. Five times a week.

That got me thinking about what happened when I wasn’t intentional with my schedule. I drowned in calendar invites and by the weekend I was irritated and distracted by my inbox of unread emails. By increasing ‘focused intentionality’ on my schedule, there was an impact on my home life and how I felt physically. (Maybe the extra effort is going to be worth it.)

Fast forward a few more weeks and as I look around the room during a meeting I see two people with my same planner. Being the sick individual I am, my first thought was that they were pulling a prank on me or something. Turns out they were listening and watching.


I Still Have so Much to Learn!

Having a wife, four kids (oldest is 10), being a new executive, and still wanting to play softball occasionally, is tough to balance. It’s not easy but it’s worth the effort.

Maybe you decide to not watch Netflix until the weekend and instead listen to a book on Audible. Or how about popping in the earbuds when you wash dishes and check out a podcast? How can you use the whitespace in your drive to work? Should you get the kid's lunches and your work clothes ready the night before?

I’m convinced I’ll never have this leadership thing mastered. Every time I learn something, it seems I’ve got three more lessons waiting for me. Maybe that’s why I’m drawn to it.

Asking myself again today, “Am I worthy of having followers?” my answer is a little different than it was in my first few days as a VP and I’m good with it. I’m not there yet but I’m on my way.

If you identify with what I’ve mentioned, I’d love to connect with you and hear what tools you’re discovering.


Need More?

Read about the resources I tapped into when preparing for a leadership role
Check out our YouTube and LinkedIn pages for more encouraging content.  

Listen to episode #82 with former SEAL and FBI special agent Errol Doebler.

Take your growth as a leader to the next level, join the IOL Community today!

Community tags

This content has 0 tags that match your profile.


To leave a comment, login or sign up.

Related Content

Encouragement, Flattery and Trusting Teams: Part 1 Encouragement vs. Flattery Defined
This is part one of three blog posts that explore the multifaceted role of authentic encouragement in building trust within teams. From nurturing authenticity and positive communication to empowering team members and resolving conflicts constructively, authentic encouragement is a powerful tool for creating cohesive and trusting teams.   As leaders, our words carry a particular weight. As Patrick Booth says, "A leader's words can be gold in the pocket or an anchor around the neck."  So, how do leaders put courage into our people and avoid the thin ice of flattery? Let's get some definitions laid out.   In episode 719 of the Ask Pastor John podcast, John Piper tackles this question from a listener and lays out several helpful pieces of advice. First, let's look at flattery, Pastor John says this:    "I think the key difference between good praise and bad flattery is this: Flattery is bad because it’s calculated. It is given with a view to obtaining some advantage (Jude 16). Flattery may be true, or it may be not true. That is not the issue. You may be saying something true about somebody and still be flattering. The issue is whether it is calculated to achieve some purpose that is not rooted in the authentic, spontaneous delight that we take in the virtue we are praising." (I had to listen to the episode a few times to grasp what was being said. If you need to re-read this, you’re normal)   He goes on to say, "In other words, the key mark of genuine, non-flattering praise is that it’s the overflow of authentic delight in what we are observing about the other person. It is the opposite of calculation. It is spontaneous. C.S. Lewis, in one of my favorite quotes, says, “We delight to praise what we enjoy because the praise not only expresses but completes the enjoyment; it is its appointed consummation” (Reflections on the Psalms, 111)." Let’s recap.   Flattery might be true or untrue, but the motive is to gain something by complimenting. Flattery is terrible because it’s calculated and manipulative. Disingenuous.   Flip it.   Authentic praise is often spontaneous and comes from the overflow of what we’re experiencing. Authentic praise is good because it builds up and builds into another person. How does this type of encouragement build trusting teams? 1. Authenticity Builds Trust: When team members are authentic in their interactions, it creates an environment where everyone feels safe to be themselves. This authenticity fosters trust because individuals know they can rely on each other's honesty and sincerity.   When demonstrated by the authority figure, it brings your mission statement to life. Feedback is given for the good of the team, not just to build ones own social status.   2. Genuine Appreciation Strengthens Bonds: Expressing genuine appreciation for specific contributions or efforts reinforces the idea that team members are valued. This recognition strengthens the bonds among team members, contributing to a sense of trust and respect.   We must say simple words and phrases like, “Thank you,” “Great job,” or “I noticed how you took care of that customer/donor/issue.”   Word of caution: Saying to a rep, “Thank you for contributing your $1.50 in production last month!” doesn’t build confidence when the team goal was $1 million. They know they fell short. You know they fell short. Remember, authenticity should precede praise.    3. Open Communication Thrives: Authentic encouragement encourages open and transparent communication. Team members are more likely to share their thoughts, concerns, and ideas when they trust their contributions will be considered genuinely. Key question: When was the last time you, as a leader, demonstrated open and transparent communication?   4. Empowerment Drives Accountability: Authentic encouragement acknowledges the agency and impact of team members. This empowerment leads to a sense of ownership and accountability, as individuals are trusted to make decisions and take initiative.   Empowerment indicates the dissemination of decision-making. Delegating. AKA, stop being a control freak.   5. Conflict Resolution Becomes Constructive: In teams built on trust, conflicts can be addressed openly and constructively. Team members know that disagreements will be approached with respect and a genuine desire to find solutions, further solidifying trust.   Healthy teams have healthy conflict.   Authentic encouragement is a cornerstone in the foundation of trusting teams. It cultivates authenticity, open communication, mutual support, and empowerment, all of which contribute to a team's ability to work harmoniously and achieve its goals.   NEED MORE? Connect with us on YouTube and LinkedIn for more fun and engaging free content. Visit our sponsor, CCB Technology, to get your IT fixed.