Part 3 of 4 of Embracing My Failures: The Challenge of Holdings Others Accountable

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The theme of this month’s blog posts are centered around embracing my failures in running a business. This is something we don’t talk enough about openly, and my hope is that in sharing some of my own failures, it will help you have more room to acknowledge and share your own, so that we can all continue to learn and grow from each other’s experiences.

You get what you tolerate.

One of my flawed patterns that’s been difficult to overcome is holding others accountable. When I coach other business owners or managers, this isn’t so challenging for me as they are often paying to have someone hold them accountable and that’s part of our agreement. 

But when it’s been in my own company or with those closer to me, I can tend to hold back and not hold clear boundaries around agreements, expectations, and consequences if someone doesn’t follow through. 

Underneath it all is a fear of being seen as the “bad guy,” or not being understanding to people’s excuses or reasons why they did or did not follow through on something. 

I once had a dear friend of mine stop me on the street after he sensed that I was hesitating in giving him more direct feedback, and he said, “Rick, you’re a good guy. But your ‘good guy’ is getting in the way of being a great man.”

I knew exactly what he meant as my wanting to be “nice, pleasing, and not rocking the boat” was actually not serving him as a friend and colleague, as he wanted and even needed my direct feedback in order to see his own blind spots.

This made a big impact on me as I committed to leaning into my own discomfort and risk not being liked, rejected, or misunderstood for offering direct feedback early on in relationships, and not after the fact. 

Fast-forward to this year, I hired a great assistant who was helping me in several areas of my business. He turned in great work, was very knowledgeable, taught me several things, and started off strong. 

At some point, his work started to slip and he had one personal crisis after another that created a lot of dropped balls, miscommunication, lack of follow-through and broken agreements. 

I had a lot of sympathy at-first, as it seemed like there were genuine issues going on. The problem was that this lack of responsibility continued, and then I was chasing him to follow-up on projects too often. It was becoming more of a burden than a help.

I leaned into my own discomfort and felt the risk of being seen as the bad guy, which is an old story of mine that’s not true. I needed to respect myself and my own standards for my company, by continuing to communicate the impact of not getting the result that was promised. And setting clear boundaries of what needed to change in moving forward.

I said, “I am sorry that you are going through a lot and I am here to support you, but you can’t use this as a currency to get out of work and not be responsive as to when you can recommit to new deadlines.” 

After several warnings and basically having the same conversation again and again, I let this person know that this was no longer working and that I needed to move on. He understood and appreciated that I was honest and upfront with him the whole time.

It was good for both of us as it respected my own values around communication and responsibility, and has now opened the door to two new assistants who are giving me great support for the growth I need. It also woke something up in him that needed to change in his life and how he related to it. 

Having these crucial conversations is critical to a healthy business and life. It’s the only way to bring the most value to others, while respecting your own. What are some of your conversations that have been difficult to lean into? How are you challenging that for yourself?


Stay tuned for the rest of our series as we’ll explore embracing failures. In the meantime, you can view part one of the series via my Facebook. For more information on how to turn your biggest breakdowns into breakthroughs, contact us at [email protected].