What's something you've learned from a coaching mistake or pitfall?

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The biggest pitfall I had early in my career was not explaining the “why’s” and the “what’s in it for you?” well enough. I relied too much on that’s what management wants you to do and I realized that wasn’t helping. So I started to rework my coaching to explain how it will benefit my reps to adopt whatever I was coaching. 


Huge mistake I made… Not double checking trackers that existed prior to joining my current company. 

Tracker > Next Steps

Next Steps was showing @ 98% for my team. I was wondering why deals were slipping. This was the first time I had used Gong so I didn’t know all the additional capabilities and relied on my ops team.

Our demo win rate YoY didn’t make sense in SFDC (bad). So, based on a hypothesis I started coaching reps on 1 thing. The goal was simple… At the end of a demo, 1) Identify if they are bought on this solving their challenge 2) if they say yes, make them sell our solution back to us “glad to hear it, what specifically could you see your team using today to solve it?” 3) Use that to reframe next steps and future conversations as us helping them get what they need to solve it. 

So now it’s time to set up a tracker, and while I do that, I check Next Steps and find that it was tagging false positives for almost every rep due to folks saying “next step” in the agenda/ufc. Thank you to @Liz Montgomery for coaching me on updating that tracker to focus on the end of calls and for everything else she’s showed me in the past 2 weeks.

This inspired me to get certified within ASAP. Here I am, completing the certification and absolutely pumped to take full advantage of Gong. 

P.S. I could have saved a lot of time, but I am glad I wasted so much of it. I learned a valuable lesson in the process. 

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A coaching mistake I made earlier on in my career was not being iterative with feedback, and relying too much on the company’s formal “annual review” to relay higher-level thoughts and expectations to direct reports. They would understandably be surprised, and maybe even hurt when hearing some of the constructive criticism. I realized that these annual reviews should be a reinforcement of messaging heard all year long and not a singular moment across a year-long span. 

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I joined a call with my rep to show her how to do something. The conversation went completely sideways. I could have puffed up my chest and never spoke of it again, but I scheduled an immediate debrief and we walked through where I lost control of the conversation, and what I should have done differently. We both walked away having learned something.


One coaching mistake I have learned to avoid is the “nice sandwich” approach of giving feedback. Earlier in my leadership career, I would give a compliment, then a piece of tough feedback and then another compliment.


I learned that regardless of me trying to be “nice”, the team member would always focus on the piece of negative feedback. Rather than trying to focus on being “nice”, I focus on providing feedback based on a theme so showcasing success, or ways to get better with an area of opportunity. 


It has helped me to build trust with my team and focus on a particular item.


I had a leader once say “one bite of the elephant at a time” - you can’t expect to swallow the whole thing in one sitting, why should change management be treated that way? Identify what end state looks/feels like and work up to that end state by taking progressive and incremental change one bite at a time. 


Something I learned early in my management career is that when giving performance feedback to a team member, it is best to be clear and specific. Having candid conversations is difficult to do at first but it’s necessary if you want to change behavior. You can deliver quality feedback and be empathetic at the same time. A good read on this topic is Kim Scott’s book Radical Candor. 


Biggest pitfall I’ve learned from is not routing back to previous feedback. I’ve learned I have to maintain a continuous story when providing it so that the feedback previously given doesn’t just feel regurgitated should my team hear it again. This also allows me to string together the pattern.


Sense making on the “why” behind feedback has been crucial to see real progress. My reps are more engaged and willing to adapt when I explain why these changes will positively impact them. It’s a really simple way to get buy-in from your reps that I didn’t understand early on!