28 Jan 2026 · 0 min
Bill Gallagher discusses balancing optimism with realistic planning and why you need team members willing to play devil's advocate. He shares a $2M mistake and explains how learning from failures makes better leaders.
Questions this episode answers
$2 million
doxatalent.com
Bill Gallagher, Scaling Coach, host of the Scaling Up Business Podcast
Are you thinking about how to grow.
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Are you a positive leader? Are you upbeat? Me too. Most of us as leaders tend to be a little bit more optimistic and positive. However, that can come at a real cost if you don't think about and listen for what could go wrong as well as and empower the people that see things that could go wrong. Like let them do their bring their voice and perspective to it. If you just look at all negativity as an annoyance, then you will miss real opportunities to get spanked, to fail, to suffer with real setbacks. So I've learned over time and at some great personal expense. I once made a $2 million mistake by not looking and measuring and tracking and thinking enough about what was most likely to go wrong. Now if all you think about is what could go wr, you won't take action. You'll be afraid to act. You'll hold back. But if you balance a little bit of the positivity with some realistic with some thinking about what's most likely to go wrong and if you'll find the people on your team that play the devil's advocate, that work with you and empower their perspective and their voice, you'll actually do well. So no matter how thoroughly we plan, no plan survives contact with the enemy. Or as Mike Tyson said it, everybody has a plan until they get punched in the face. Life and business has a way of punching us in the face on a very regular basis. So if you want your team and your plan and your company to be more successful, then you want to spend some time entertaining what are the most likely things could go wrong and how can we deal with that That'll make the biggest difference for you and your team. The way you work together and your ability to step away to build a powerful team. Empowering them is really determined by like planning for some of those contingencies. I'm Bill Gallagher, Scaling Coach, host of the Scaling Up Business Podcast and I hope that these tip shows are helpful for you. We want to give you a little idea, a little nugget that you can work with for the next week if you find these helpful and you want to know more about our other programs, about our coaching. We have coaching and programs and workshops of all sizes for all stages of companies that want to get growing. You'll find all that and more@scalingcoach.com like subscribe, turn on your notifications, share these things with somebody else and we hope to see you soon.
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