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Guest: Jim Weaver, a five-time CEO who brings 25 years of successful leadership experience in helping to grow both public and private companies. Jim has built and grown companies in multiple industries, including software development, systems integration, payment processing, and telecom. Jim is also a longtime YPO member and a new coach at CEO Coaching International.
Episode in a Tweet: A 5-Time CEO joins CEO Coaching and shares the common traits of great CEO leaders.
Quick Background: Jim Weaver didn’t set out to be a 5-time CEO in such a diverse array of businesses. But whenever opportunities presented themselves, Jim took advantage, pivoting his companies and himself towards new experiences, better markets, and BIGGER growth. Now he’s ready to share what he’s learned from five stints in the big chair with CEO Coaching International’s clients.
On today’s show, Jim Weaver discusses his transition from government work to the private sector to going public, and what his experiences at the top of multiple companies have taught him about being a great CEO in any field.
Transcript: Download the full transcript here.
Key Insights from 5-Time CEO Jim Weaver
1. Pivot towards opportunity.
Jim Weaver’s first CEO post was at a company that delivered large systems integration and payment processing in health and human services for both the government and private insurance industries.
“The differences in those businesses were significant,” Jim says. “On the system’s integration side, all of that was one-time revenue. Even with a $50 million-dollar job, when that job was done, there was no residual revenue from that job.”
However, Jim identified the opportunity to create a recurring business model focused on the government payment processing side. So he pivoted the company, made some key acquisitions to help grow in this new space, and never looked back.
“It’s a lot easier to grow your business on last year’s base as opposed to having to replace all of last year’s revenue and then have your growth metrics on top of that,” Jim says.
One way to apply Jim’s wisdom to just about any field: pivot your own business away from big one-time purchases to subscriptions or membership programs that incentivize repeat business and get you paid more quickly.
2. Turn your B players into A players.

Jim Weaver: Today, if you’re not thinking about what the technology’s going to look like, or what’s happening to your industry as close as six months out, then you’ve got issues.
“Getting A players into key seats – and quite frankly into every seat – is critical to the success of the business,” Jim says. But you also have to remember that you’re hiring for where you want your company to go, not for where you are right now. Your business is going to change as it grows, and great CEOs know how to identify motivated employees who can grow along with them.
“That’s certainly the environment that we try to create in any of the companies that I’ve been a part of,” Jim says, “where somebody has that opportunity to grow into that next-level position. Certainly, when you raise the bar, it suggests that you’re going to hire only A players or Bs that’ll be coached up to A.”
But take note of this–don’t let the anxiety of feeling you HAVE to fill a position push you into a rush hire that you’ll just end up regretting.
3. Plan for tomorrow today.
One of the biggest differences Jim sees between how businesses operated when he started and how they operate now is the sheer speed of change. “Today, if you’re not thinking about what the technology’s going to look like, or what’s happening to your industry as close as six months out, then you’ve got issues,” Jim warns.
Once the CEO has identified those essential actions and strategies, it’s critical to make sure your vision cascades down through the entire company. “All hands on deck” meetings, especially annual planning sessions, can be key to driving home your strategies from the top down. Jim also recommends internal newsletters or blog posts that can keep everyone updated on the company’s progress and focused on the BIG goals ahead.
4. Know when to use a sensitive touch.
Poor CEOs harness all the wrong stereotypes in all the worst ways. They’re brash to the point of obnoxious. They’ll charge through every meeting like a bull in a china shop just to remind everyone who’s really in charge. They’re so sure their way is the only way that they ignore smart ideas from their leadership team, or worse, only hire Yes Men.
That’s not Jim Weaver’s ideal CEO, or mine either.
“You have to treat people, at all times, with dignity and respect,” Jim says. “When they’re successful, when they’re performing for you and they’re doing well, and more so, quite frankly, if they’re struggling. Those who are very successful, they’ll be rewarded by that, and assuming you’re paying them a competitive salary, I think that is how you motivate people to go beyond what they’re currently doing today.”
Jim believes another key CEO trait is embracing vulnerability when necessary. During tough times, your employees and key relationships don’t want to see you hiding behind your ego – they want honesty, transparency, and a clear path forward.
“Being vulnerable, as opposed to trying to circumvent the problem, creates a path to resolution,” Jim says.
Top Takeaways
1. Don’t work with B talent unless you know you can coach that B up to an A.
2. Your business’ future is now. What are you doing today that’s going to get you BIG in three years?
2. Lead, don’t bully. The stereotypical CEO who blows his top and pushes around everyone belongs in cartoons, not a board room.