Tim Carlisle On How Leaders Make Difficult Decisions
An interview with Maria Angelova
Published in Authority Magazine ·
11 min read
·Oct 26, 2023
As a leader, some things are just unavoidable. Being faced with hard choices is one of them. Leadership often entails making difficult decisions or hard choices between two apparently good paths. What’s the best way to go about this? Is there a “toolkit” or a skill set to help leaders sort out their feelings and make the best possible decisions? As part of our series about “How Leaders Make Difficult Decisions,” we had the pleasure of interviewing Timothy Carlisle, CISSP, PMP, DTM, PDD who has a very diverse leadership background.
Tim spent 20 years in the Submarine Service; he served on four different submarines, rising to the level of Chief Petty Officer. He co-wrote many of the instructions for protecting data and computers in sensitive installations and, at one point, saved the Navy $23 million in today’s dollars by writing a manual describing the detailed operation of a highly classified system.
Timothy has worked as a project director and cybersecurity expert in the public sector and as a consultant. His consulting engagements included eBay, Starbucks, Sutter Health, and other large organizations. He is certified as a CISSP and PMP, both gold-standard certifications in Cybersecurity and Project Management.
He has earned 4 degrees: two Bachelor’s — in Technology and Operations Management from Excelsior College, a Master’s Certificate in IT Project Management from George Washington University, and a Masters's in Technology Management (Information Security with Distinction) from Capella University.
In his volunteer work, Tim is the chief technology officer and Western District Five commander for U.S. Submarine Veterans Inc., Toastmasters Past District 4 director (San Francisco and Palo Alto, CA), and an event leader in Landmark Worldwide.
He has received many awards, including a Jefferson Award for Public Service, the Joe Negri Award (highest award for leadership), and two Robert Link National Commander’s Award from the U.S. Submarine Veterans Inc., the Excelsior College C. Wayne Williams Award for Public Service and Community Involvement, a California Legislature Proclamation for feeding homeless and needy children, and California’s first National PTA award for the academic program he led at Mare Island Elementary School. He has also earned two Distinguished Toastmasters designations.
The opinions given here are his own.
Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
I started as a public speaker at age 5, at the urging of my mother. Every day and twice on Saturday and Sunday, I practiced memorizing a two-page, single-spaced paper on George Washington Carver. For months I was word-perfect. Finally, the big day arrived. With a crowd of 250, I started strong, and about 3 minutes in, I looked up at the audience and froze. My mother prompted me, and I continued and finished to applause (a rarity at that church).
However, I made a mistake– I was expected to be perfect. For many years, I thought I could never be a public speaker due to that mistake of freezing until I joined Toastmasters in 2015. I found that with practice and encouragement, I could do great things.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?
Yes. Krysta — The first coach who truly believed I could transform myself and my circumstances before I did. All of which were started by an inappropriate comment I made to someone else. When Krysta asked me about the comment, I looked her in the eye and said, “Yes, I said it, yes, I was wrong, and yes, I am sorry,” at which point she said, “Tim, I am standing for your greatness.” This melted my little titanium heart, and it grew three sizes that day (like the Grinch).
Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?
In early March 2019, our Toastmasters District called an emergency leadership meeting to discuss the pandemic. Our typical in-person meetings were likely to be disrupted, and as the third highest ranking leader (Club Growth Director or Marketing and Outreach), and the only personal Zoom account holder in our leadership team at the time, I worked with our technical team and other leaders to determine how to move several thousand members online almost overnight. This became the norm for our organization and is mostly still in place today.
We learned as we went along, and although I did not make the final decision — it was clear at the end of that meeting that there was only one way forward.
Did you ever consider giving up? Where did you get the motivation to continue through challenges? What sustains your drive?
There was never any question of giving up — thousands of members were counting on us. I believe we all each reached down deep and gathered the courage to move forward. My drive was sustained by the belief that we could do it.
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?
Our potential top leader and I did not get along much, which caused major issues from my perspective. My gut told me I should run against him for the top position, but I chose not to. This was a mistake, in my opinion, looking back, and caused significant negative disruptions in our organization.
If there was a silver lining to this difficult situation — an individual with 15 more years of experience but far less leadership experience than I decided to run against me the following year, mostly using the personal and professional destruction path. I was found by our entire leadership team to have committed no violation, based on frivolous charges, and was elected with 76% of our members’ votes! While this was incredibly uncomfortable, this experience has provided me with the ability to rise above the difficult people and personalities in my current roles.
What process or toolset can a leader use to make a choice between two difficult paths?
1. What is best for your team members?
In the end analysis, what is best for your team or your members may not always be what your opinion is at the time. However, if you base your decision on what is best for them, this usually reaps the biggest benefits for the organization as a whole.
2. Is the choice legal, moral, and ethical?
I think this is a no-brainer, but sometimes, people will do anything to get ahead. They may get ahead for a time — and then it often falls apart everywhere when it doesn’t meet these criteria.
3. Can you make this decision with integrity?
Keeping your word is incredibly important as a person and a leader, especially to your organization, because that integrity, or lack thereof, will penetrate deep into the organization. People are always watching you as the leader — and will often justify and duplicate what they see, both good and bad.
4. What example are you setting for your team?
This, more than anything, is crucial to the success of the organization. People will often model the behavior they see from others. Make certain that your example is one worth following by others. If you provide an example of coaching, mentoring, and helping others develop themselves, that will penetrate the organization over time.
Do you have a mentor or someone you can turn to for support and advice? How does this help? When can a mentor be helpful? When is this not helpful?
I have several wonderful mentors — here are a few:
Tzvete — My first mentor in Toastmasters, provided the patience of a saint.
Noemi — She provided me a great deal of insight into her District leadership perspective.
Jessica — Provided great mentorship through two challenging years in Toastmasters leadership.
Al and Bill — My first mentors in my Submarine Veterans chapter, whose insight, wisdom, and encyclopedic knowledge of members helped me navigate many people and personalities.
Pete — Added a wonderful perspective well beyond the Submarine Veterans local level in challenging situations I found myself dealing with, for which I am eternally grateful.
Wayne — Gave me a great deal of support, encouragement, and insights at the Submarine Veterans national level while running a large project with my technical team.
The only downside I have ever seen in mentors is when their objectivity is overcome by their personal and professional positions. While the protégé may outgrow their mentors in this situation, most mentors are contributing to the organizational growth, not their personal peccadillos. This has been the exception in my experience, not the rule.
What would you say is the most critical role of a leader when faced with a difficult decision?
The most critical role is to not let their opinion override what is best for the organization. Listen to your leaders, reflect on the decision, and make the best choice for the organization.
Do you ever look back at your decisions and wish you had done things differently? How can a leader remain positive and motivated despite past mistakes?
We acknowledge our failures, celebrate our wins, move on, and ensure we do better the next time. Show me a leader who has not made a mistake — I haven’t ever met one.
I am more concerned about what could be possible than my past failures. If you are willing to get up and try again you haven’t failed.
What is the best way to boost morale when the future seems uncertain? What can a leader do to inspire, motivate, and engage their team during uncertain times?
Create a possibility that is bigger than the circumstances. Be radically positive, speak about the goal as if it has already happened and what it will be like for everyone.
Can you share 3 or 4 of the most common mistakes you have seen other businesses or leaders make when faced with a hard decision? What should one keep in mind to avoid that?
1. Doing nothing — this is like death — even if you act wrongly, it is better than this.
2. Doing too much at once. This can cause massive confusion with no clear direction.
3. Projecting your fears onto the team — even when things look the darkest — you can reach deep down and find a solution.
4. Not trusting your team — Trying to do it all yourself or by yourself. The ultimate responsibility may be the leader’s, however allowing your team to try new things, to grow, and to fail to a point, is how you develop emerging leaders.
Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a leader should do when making difficult decisions? Please share a story or an example for each.
1. Look forward
The past is in the rearview mirror — looking forward to creating a brighter future for all is the best way to achieve your goals.
The year I was District Director, I made every effort to forget the challenging events of the past two years, and focused on working with our up-and-coming leaders. There were certainly challenges, but we focused on moving forward!
2. Create alternate plans of action. Always have a Plan or Option B.
There is always a need to modify, or adjust plans, or use another. Being prepared to shift to a better situation or solution is always important. To liven up some training classes, I would have an online quiz with a gift card I personally purchased, which was quite popular with the team.
3. Apply your team’s strengths
All of us are smarter than one of us. Find people with expertise that you do not have, and learn from them.
I am not a Public Relations person — how to best get the message out was not my strongest area. However, I knew a few people who were experts in this area, so I recruited them and learned quite a bit.
4. Gauge your team’s engagement
I used an anonymous Google Form (managed by someone else) with Start, Stop, Continue. What would you like me to Start? What would you like me to Stop, and What would you like me to Continue?
At the beginning of our next meeting, I would discuss the answers both good and less good, and told the team the actions I would take based on their feedback.
5. Recognize team and individual efforts.
Recognition could be an award, public recognition verbally, a quiet word or handwritten card. Regardless, everyone appreciates some form of recognition.
I determined that every person, of my 40-member leadership team, deserved an award for leading through the pandemic. I found a vendor who could engrave and mail out awards for a reasonable price, then came up with a total price and sent everyone something. No one in our organization had done this at that level in a few years, and I received many thanks — although I was simply acknowledging them.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“Through suffering emerge the strongest souls. The massive characters are seared by scars.” Khalil Gibran, Lebanese poet.
I have been through a lot in both my childhood and adult life and I have been able to use those experiences to build my life and myself. I am as strong, determined, and powerful as I am because of what I’ve been through.
How can our readers further follow your work?
To stay informed, your readers can follow me through one of the following channels:
Thank you for these fantastic insights. We wish you only continued success in your great work!
About The Interviewer: Maria Angelova, MBA is a disruptor, author, motivational speaker, body-mind expert, Pilates teacher, and founder and CEO of Rebellious Intl. As a disruptor, Maria is on a mission to change the face of the wellness industry by shifting the self-care mindset for consumers and providers alike. As a mind-body coach, Maria’s superpower is alignment which helps clients create a strong body and a calm mind so they can live a life of freedom, happiness, and fulfillment. Prior to founding Rebellious Intl, Maria was a Finance Director and a professional with 17+ years of progressive corporate experience in the Telecommunications, Finance, and Insurance industries. Born in Bulgaria, Maria moved to the United States in 1992. She graduated summa cum laude from both Georgia State University (MBA, Finance) and the University of Georgia (BBA, Finance). Maria’s favorite job is being a mom. Maria enjoys learning, coaching, creating authentic connections, working out, Latin dancing, traveling, and spending time with her tribe. To contact Maria, email her at email@example.com. To schedule a free consultation, click here.
Maria Angelova, MBA is a disruptor, author, motivational speaker, body-mind expert, Pilates teacher and founder and CEO of Rebellious Intl.