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- Top 15 Company & Leadership Challenges and Questions (brought to me over the last three years)
Top 15 Company & Leadership Challenges and Questions (brought to me over the last three years)
Most of these questions have been asked for the last 500 years. “History doesn’t repeat, human nature does”
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Top 15 Company & Leadership Challenges From the Last 3 Years

Most of these questions or challenges have been around for the last 500 years. “History doesn’t repeat, human nature does.”
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Opening Remarks
Human nature doesn’t change, only the context or incentives.
Most frequently asked questions or challenges brought to me over the last three years
My processes are a mess, or don’t exist, can you help?
How do I hire and retain great talent?
How do I improve our client service and grow our business?
How would you recommend structuring my client delivery and operations?
Should I start a staffing or services company?
Do I promote this person? How do I develop my leaders and team?
How do I grow and reduce my costs and risk?
Where did you get the ideas to write all this content?
What has worked for you with building relationships?
How do you manage asynchronous global teams without customer issues or losing internal culture?
How do I develop as a leader and how do I advance in my career?
How do you juggle priorities?
How do I get my team to execute on what I expect?
How do I integrate technology into my process without losing culture or focus?
Do you know anyone selling their company?
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Leadership & Team Developmentt
Business Case for Great Leadership
Here are a few thoughts, short answer style. Please reach out if you’d like to talk through in more detail.
My processes are a mess, or don’t exist, can you help?
Dedicate someone to organizational improvement focus where they work with each key leader and document EVERYTHING- find the good kind of consultant, internal or external, otherwise you take one of your most trusted associates, and they do it
Build a map of your product or service from start to finish
Connect people, process, and technology visually - show everything and it starts to show you more questions and answers in your business
How do I hire and retain great talent?
Specialize in what you recruit and hire for, outsource everything else- airlines recruit flight crew, not CFOs
Find the best recruiting partner…for your business
Treat your people like they matter, because they do, not because you feel like you must treat them okay. True care shows true in even the near term.
How do I improve our client service and grow our business?
Be likable- they won’t keep you if they don’t like you
Deliver. On time, every time, and if you can’t. Communicate out and front, don’t hide
Do you treat your client stakeholders like people, or like clients? Try people.
How would you recommend structuring my client delivery and operations?
Yes. If you’re asking, you likely need something significant. Look at the data, feedback, and results…it’s usually clear either way. Fixing it, is another ball game.
What do your clients, associates, and stakeholders need or require? Not want, but what do they actually need and you can deliver on?
Should I start a staffing or services company?
No. Well, only if you’re from the business or a business that translates exceptionally well…and you can do it better than 99%
Be prepared for 2-3 years of runway until you can build revenue
The commoditization and differentiation game takes a bit. You just play with a long term mindset. Otherwise, don’t play.
Do I promote this person? How do I develop my leaders and team?
No. If you’re asking, no.
Yes. If they have proven themselves AND have shown they can and want to do the next level job
How do I grow and reduce my costs and risk?
By talking with your people, looking at data, looking at what your clients actually need, not what’s convenient, by getting out into the floor/field/pit/market
Uncommon sense - do more of what works and what you need, less of what doesn’t.
Where did you get the ideas to write all this content?
I write about what I do, see, a learning, and hopefully know. Nothing about what I don’t.
My mind is always going- I’m 4 books deep, but haven’t published, yet
Lots of practice
What has worked for you with building relationships?
Not trying to build relationships, rather, be useful, be a go to in something, anything, and find your thing and who is looking for that thing
Being myself
Story telling
How do you manage asynchronous global teams without customer issues or losing internal culture?
By trusting them to do their job and monitoring progress, addressing what your feelings are telling you to let go because it’s tough to deal with
Setting up intentional collisions, not by chance disasters
Care more than how hard it is
Get in front of people in person, by video, audio, whatever it takes
How do I develop as a leader and how do I advance in my career?
By wanting it more than others
By leading now- find something someone needs help with and teach them how to do it
Follow-up…follow-up…
Add value, find the positions and companies that see that value
Care more than everyone else in your way…and help them be great along the way
How do you juggle priorities?
Stop juggling and find one priority
Stop doing everything that isn’t that one priority and is not business critical
How do I get my team to execute on what I expect?
Clear expectations up front not in two weeks
Proper resourcing
Get out of their way
Have their back
Follow-up
Address issues
Ask the questions no one wants to ask
How do I integrate technology into my process without losing culture or focus?
Make sure you tech supports you, you’re not squeezing in tech to your business
Tech doesn’t disrupt strong cultures and focus, it’s enables, empowers, and strengthens it
Anti-tech just for that purpose, is usually anti-growth oriented, and is protecting its piece of the pie
Do you know anyone selling their company?
No, if I did, that would be quite lucrative
Receive Honest News Today
Join over 4 million Americans who start their day with 1440 – your daily digest for unbiased, fact-centric news. From politics to sports, we cover it all by analyzing over 100 sources. Our concise, 5-minute read lands in your inbox each morning at no cost. Experience news without the noise; let 1440 help you make up your own mind. Sign up now and invite your friends and family to be part of the informed.
Closing Bell
Through-line
Those who find their life’s work, their ultimate focus, their superpower- they have the ultimate empowerment and ability to change the world and be the greatest in the world.
Second, are those who are trying with tireless light to find it and will stop at nothing to secure that journey.
Third, are those going through the motions on a hamster wheel with no purpose, “why”, objective, goal, or mission. They may be less efficient and more lost than those not working toward something at all. Interesting to think about. Consider your own:
1 Priority, 1 Focus, 1 Purpose, just 1
Mission
Focus
Saying no to say yes
Elimination
Addition through subtraction
Priority, not priorities
The more unfocused, the less successful
Supporting Content - For More to the Story
Hopefully, this added a little value to your business or leadership journey. Thank you for reading. If you think this may help someone else, please repost ♻️ or share. Thanks for being here. 🌍🏔️.
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Executive Summary | The Dynamic Leader, brought you by Founder GTM
Founder GTM is your ecosystem for getting the work done that isn’t core to your business, but needs to get done. Our Vendor as a Service offering delivers, talent, solutions, and value add to your business operations, allowing you to focus on your core work.
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"Twenty years from now, you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover."
- Mark Twain

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