John Carter Gillespie

is an IT Management professional with over 15 years of experience in the fields of information security, enterprise architecture, cloud infrastructure, systems administration, and project management. He strives to stay on the forefront of new technologies and constantly looks for ways to effectively execute within current budget means.

Master a Golden Work/Life Balance & Your RFPs with John Carter Gillespie

It’s an off-of-the-cuff episode today on Dissecting Popular IT Nerds, where host Phil Howard and his guest, John Carter Gillespie, talk how they surf between work/life balance and on the waves in general from their coast-centric locations. Take advice from a company manager who’s created 80% growth in the last two years in the operations sector. Establish the crucial trait that your IT customers are asking for and onboard personalities who will undoubtedly bring it to the table.

The best thing you can do at first is just listen.

3 Key Takeaways

  • Why you need to get comfortable making small changes fast
  • The RFP Three Little Bears Analogy
  • John's top ways you can assure a better work/life balance

Listen To The Full Episode Below

Master a Golden Work/Life Balance & Your RFPs with John Carter Gillespie
Dissecting Popular IT Nerds
137. Master a Golden Work/Life Balance & Your RFPs with John Carter Gillespie
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Episode Show Notes

[00:32] Phil welcomes you to this off-the-cuff episode with John
[00:50] John introduces himself
  • Running the IT department for his firm
  • Moving back from Hawaii
  • Phil and John talk about boarding
  • IT people have real lives and do fun things!
[3:16] Did he ever get tired of surfing?
  • Surfing was a major priority before he had kids
  • Play the negative social media game
  • The best time of year to find good swells
[8:30] The best surfing vacation John’s taken outside of Hawaii
  • Costa Rica and El Salvador
  • North Carolina
  • Puerto Rico
[9:40] How John feels about work/life balance in IT
  • Managing 22 users total
  • Managing a company that loves technology
[12:04] Working for two years+ in the company
  • Coming in just as COVID happened
    • His friendships with coworkers lined up the position for him
    • Maintain relationships
  • Work in IT is a collective journey
  • Be comfortable with radical change
    • The restrictive surfing suits they wear for low degree water
[18:20] What the work/life balance really looks like
  • Surfing and having kids while working
  • Hearing about IT challenges of friends when living in Hawaii
    • Coming back to start a job in IT
[20:00] What were the challenges people experienced at the time John was looking to be hired
  • Should those seeking be providing resumes everywhere or cherry picking ideal companies to work at?
    • There’s an opportunity to go both ways
  • Pre-established relationships make for a more organic conversation
  • The value of seasoned recruiters in their roles to identify your ideal company
    • They can bring you from your competition
[24:40] Are there a lot of IT job openings?
  • It’s nice to ask for specific salary raises
  • The issue of identifying people who are telling the truth
[25:50] What John is doing in the logistics field
  • The push for digital transformation
  • Grabbing market share during COVID
    • Growing from 200 employees to 500
    • Almost doubling their revenue
    • Hiring 50 people in the last year
  • Market share has increased!
  • “If we were going through this growth, we couldn’t rely on traditional IT software and hardware.” -John Carter Gillespie
  • They’re hiring for professionality
[30:00] Over 80% of their growth was in operations
  • Making sure to hire on key roles and partners
  • John’s role as empathetic and human-centric
    • Why The IT guy will always have a job
[34:00] Leadership outside of the IT space
  • People, processes, and things
  • “You have to understand the business and where the alignment needs to come to make sure you’re staffing key roles correctly.” -John Carter Gillespie
  • Maintaining trust in the industry
  • “There’s a certain level of professionalism that the world requires these days whenever they put their trust and faith into a company that has IT behind it.” -John Carter Gillespie
    • The best thing we can do is to protect those people and find solutions
[36:54] You can’t put all of your eggs into one basket of outsource partner understanding
  • You still want somebody to understand that platform and internal vision!
[38:00] What does John mean about the right people?
  • Be okay being right only part of the time
    • Fail fast and fail forward
  • Dealing with the old regime and taking on a new role
  • “The best thing you can do at first is just listen.” -John carter Gillespie
  • You have to play within the rules and understand the business parameters
  • Consider the processes around your business continuity functions
[43:12] If you can create more time balance, you have more room for your coaching role
  • IT has challenges because tools only last for three years and processes don’t last forever
[22:26] Core Time and Flexibility
[23:15] RFP work
  • John’s three little bears analogy to RFPs
  • If you go into the room knowing you want to make a decision, you have to take a “Costco approach”
    • They’ve already narrowed down the best options for you
  • In terms of RFPs, everything is always used to solve a business problem
    • What is the sales directors and operational directors core piece to solve?
    • Translate that into an internal quantified matrix for IT
    • Color code the matrix down to the top three options
    • Present those top three options to the executives and let them hold you accountable
[50:40] How John manages his time
  • Trust can go far!
  • Be honest with each other where you need to get time back
    • Recognize needs for rebalance
    • It’s important to make time for family and friends as well as work
[55:10] Mental health within the IT space
  • It takes a lot to make a system change in two years!
  • Phil shares his experience getting calls of IT guys crying from the pressure to perform
  • The benefits of getting out and stretching while you work
[57:40] What is the endgame for John?
  • When you die, your tombstone will not say “Director of IT”
  • “I play the orchestra” analogy
  • What we value as important/famous might be useless long-term
  • From an IT standpoint, he hasn’t set specific end-goals, but he has some for his family
    • Phil’s goal to work to live, not live to work
    • Why Phil surfed a lot last year
    • The question in your head about what you should be doing
    • Call it a short-term win as long as it isn’t interfering with your family and personal values
[1:10:00] The moral of the story
  • Find activities that bring you that work/life balance

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