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

Userlevel 6
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When things go wrong (and they will!), change management can be scary.

Tell us your scary change management story and pitfalls to avoid.

15 replies


I believe the biggest mistake I make is not coaching on a consistent basis. Intermittent coaching is my biggest pitfall. When I use GONG consistently, I am able to keep my pulse on how things are going with my fully remote team. When I don’t I have to be concerned about things falling through the cracks like my reps not using their cameras, not blurring their backgrounds etc. GONG has definitely been a game changer when it comes to remote coaching!  


One pitfall I have run across has been not following up with coaching action items after 1:1s or trainings with my team. It’s easy to give the coaching but the reinforcement behind it throughout can be the difficult part. What I found that works for me to manage the follow up is to pair my team in a buddy system so and give them action items to deliver to me. Helps take the pressure off me and gives them more ownership in their development. Along with that I leverage trackers and alerts in gong to help me have visibility on how its going. 

Userlevel 2

When I was first promoted to a Managerial role, I didn’t consider that people understand and process information differently. I always was upfront to communicate what I thought was appropriate in a way that I thought that made sense, but as a manager, you need to read and understand people to craft the right message and get your point across. 

Like the book of the 7 Habits - “Seek first to understand, then to be understood” 


Biggest pitfall is putting 100% trust in what a rep tells me about a deal.  They can have happy ears, not have a strong path to close but are confident the deal will close within a given month/quarter.  Gong allows me to validate or challenge what they are telling me and reveal truth through data.  It has enabled me to become not only more confident in my forecasting ability but more accurate as well.  


Love the books ‘Fanatical Prospecting’ and ‘Virtual Selling’ by Jeb Blount


One of the biggest coaching mistakes i have made is not creating a structured format for me and my team. I was a new manager and just assumed my reps would come to our 1on1’s prepared. 

Half of my team “understood the assignment,” while the other half showed up without any indication of progress on their work or pipeline management. 

Gong has a lot of great info and templates to use, but I found that ensuring that: 

  • 1on1’s are scheduled, and that each session is clearly spelled out in the calendar. Is this pipeline/forecast review? Is this a call coaching session? Or this just a general vent session? 
  • Keep some way to keep progress. This can be done with a spreadsheet, a note taking program like Evernote, or a shared doc. 
  • Set 1 long term goal (maybe what they want to accomplish for the year or quarter), along with small individual (at max 3) goals to get there. For example, if the goal is to hit 100% to target, how are they planning to get there? What have they mastered, what are they working on? 
  • If working on sales/soft skills, setup a tracker so you and the rep both get emailed when that is being mentioned on calls. For example, if this quarter you are working with your rep to be more consistent on asking for next steps, mock with them multiple times how they will ask for it so it becomes muscle memory. Next, use the exact word or phrasing they will use as a tracker. 


I always operate by the platinum rule: treat others how they want to be treated. That means you’ll have to learn different styles on communication, different strategies to motivate, and how to adapt. IT’s tough but can be done. 

Userlevel 2

One of my biggest coaching mistakes was going too “H.A.M” with the feedback via comments on calls versus providing some high level notes and discussing in person. 


My initial thinking was: 

  1. I’m being specific and have targeted areas of feedback!
  2. I’m providing constructive feedback - not being overly critical, layering in compliments!
  3. I’m being efficient and providing feedback in realtime! 

… and here’s why that doesn’t work:

  1. Being tactical doesn’t make a CSM (or rep) feel empowered; it comes off as “nitpicky”
  2. The larger themes or areas of development are lost. Soft skills are important, but what are we really solving for? Where should they be focusing?
  3. It doesn’t provide a discussion or opportunity for the CSM to come to their own conclusion/learning 
  4. “Fluff” is not effective - compliments weaved into feedback can get confusing. Part of growing is learning, adding fluff isn’t necessary. 

Instead, I’ve found a better approach which is: less is more. 

  1. Have reps tag me in specific milestone calls 
  2. Flag what they want me to listen for 
  3. I listen and share a takeaway, ask a question to get their perspective, or reserve for discussion. 
  4. Bring it to 1:1 - even if it’s 5 min, I’ve found it’s better to close the loop if needed or have an open discussion. 




One of the biggest mistakes I made early on in my sales leadership career was not making enough time for coaching & providing real time feedback to my sales reps, even though I knew how beneficial it is for both parties.  The platforms and tools at my previous 2 companies did not make it easy to coach at scale, and because of this, I deprioritized the activity based on the level of time & effort it took to coach.  

Now that I have access to utilize Gong consistently, I am able to set strong goals as far as the number of coaching moments that I would like to have with each rep, and across my team each week.  I have a dashboard that keeps me motivated and accountable to ensure I am coaching more than I ever have.  I have listened to and coached more calls with Gong during the last 3 months than I did over the last 3 years in my previous sales leadership role.   




Biggest pitfall in coaching I have seen is not following up on your reps efforts against your coaching. It’s critical to set short/medium/long term goals to see change at the IC and org wide level. Utilize data but also qualitative information to rally the team around your change goals and consistently share the progress against those changes consistently over time!


Early on in my leadership career there were many changes as I was promoted to lead individuals I was previously colleagues with right before the pandemic and the transition to remote work. 

With all the change I found that my messaging and coaching needed to be more crafted, detailed, and practiced when rolling out how we were going to manage and track remote work. Luckily this was early in my transition to leadership and it taught me valuable lessons in preparation, coaching as a habit, and starting with why.

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As a new manager, an early mistake I made was to not have consistent 1:1’s. Because 1:1’s weren’t habitual, it would cause stress for my team if a 1:1 did occur. If the meeting was with them, they would be stressed about what we were going to be talking about. If it wasn’t with them, they would stress about what I was discussing with the person 1:1. By changing to a consistent 1:1 schedule, meeting together stopped being stressful and transitioned to a time for me to check-in and show my support and empathy. What used to be stressful became a favorite block of time for everyone. 

Userlevel 2
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I find it so hard to resist the temptation to just fish for someone instead of teach them to fish. We all know it’s an age old recommendation but when you really see it play out before your eyes it so apparent that you are only creating more work for yourself when you take the reins away from the person you are coaching. Another great rule of thumb I’ve heard, is that the coach should rarely be the one screensharing. It’s such a good way of insuring that you are instructing while the person you are coaching is practicing. 

Userlevel 4
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A huge coaching mistake that I try to avoid is assuming that other people think the same way that I do and understand information and concepts the way I do. An important attribute of a great coach is someone who can distill a concept to its core essence to make it tangible for many people regardless of how they’re wired. 

A practical way to ensure this is a mainstay of your coaching practice is by asking more than you tell. By letting your rep frame the situation in their mind and what they see of it, you then get invited into their context and mental framework and are challenged to bring the thought in your head to them by way of their framework.

That’s not to say their framework will always be correct. Sometimes you have to ask a bigger question, a different question and/or a follow up question to continue to direct their thinking the way you want it to go. With time, this process becomes second nature.


I honestly think the biggest mistake or pitfall of coaching I made personally at this company was trying to coach without proper analytical data and call reviewing capabilities! In hindsight, I was truly leading the pack without a sense of direction. With gong, I’ve been able to really dive into the calls on our sales floor and gain a deep understanding and knowledge of not only what is working, but what is not working. 


Early in my management career, I may not have always started a coaching conversation with praise. What I learned is to prop people up and point our some great things I heard right away prior to inviting that rep to self assess, what did you do well and what do you think you could have done better. Ex - your tone and articulation is crisp, clear and professional.  This approach has worked for me in the past and tends to make the rep more comfortable in being more rigorous with the self assessment prior to my final feedback / scoring


One of my biggest coaching mistakes was not being specific enough in my comments or scorecards. Partners can become overwhelmed when they are not given specific data and examples of what you are looking for. GONG helps me narrow in on key topics to help coach during 1:1s!