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Letting Your Team Fail IS an Option

Failure. My favorite reference to this concept was in an episode of the Exponential Wisdom podcast, which I first listened to a few years back:

"If failure is not an option, then success gets really expensive."

So, let's back up. What do I mean when I say that you should allow your team to fail?

Let Your Team Stumble Successfully

It may seem risky — but in an article on organizational coaching, Ron Rael, CPA, CGMA, suggests "trusting your employees and letting them successfully stumble, so they quickly learn to succeed.” Your ultimate success as an advisor will depend on the extent to which you let go of the fear of failure. But, more specifically, it will be about letting your team grow the way you did.

Do you remember your early days in the business, when you failed to do things just right the first time you tried them? Failure is the road to success — you know this.

Empower Your Team

What is the side benefit of shifting projects and responsibilities to your team? They will feel so empowered by your trust that they will likely exceed your expectations more often than falling short of them. The alternative to not giving your team agency is that you’ll never be able to retain the really good people.

Superstars need to own meaningful, challenging work. If your team is young, that’s even better — younger generations are generally less afraid to innovate and take risks. Take advantage of that quality and celebrate it! The synergy of your experience and support for the team — and their youth, ambition, and mindset — can be a catalyst for excellence.

Tips for Letting Go

You might feel anxious as you start to hand over important projects to your team, but you can easily become more comfortable with regular communication. Try these tips:

  • State the outcomes you desire

  • Set deadlines

  • Describe the quality standards you expect

  • Hold short weekly status meetings, and solicit your team's questions

  • Let them know you are there to help — create a safe environment

Push Your Team to the Edge

Don’t be afraid to delegate projects that you think a specific team member isn't ready for. After all, how engaged are you when you’re doing something easy? It’s the challenge that gets people to focus and unleash their creativity. Push your team members to the edge — if they are talented, they will grab the bull by the horns. Boost their confidence by letting them know how important the project is and that you trust their judgment.

Remember, It's About You

Jim Johnson, CFP®, of Lighthouse Financial Planning, offers advisors this warning:

“I have seen a number of prominent leaders in the financial planning business who had superior, excellent talent in their firm who left because they hadn't 'paid their dues yet.' The biggest problem I see in the financial planning profession today is that us old white guys, who own the firms, are telling the up-and-comers, ‘You ain't paid your dues yet — you don't know everything I know,’ and there's been an exodus of extremely good talent from firms because of this.”

It isn’t just about your team. The more you let go, the more freedom you will experience, and the more time you’ll have to focus on growing your business and living your life. Either now or down the road, when you want or need to spend more time away from work, you’ll be glad you devoted your time to growing your people.

I'll leave you with this final quote:

"I trust and care about the people I work for; they trust me and believe in me. I have a safe place to fail — it's okay to exit a client meeting and say, 'Oh my, that did not go well,’ and not feel fear.”

Cassandra Humphreys, CFP®

Successful NextGen Wealth Manager

True North Advisors – Dallas, Texas


What has your experience been like surrendering projects to your team? I would love to hear from you.

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