Things that went through my mind when....

Let me start this post with a big ole’ dose of humility. It’s very easy to forget that there are multiple lenses to every situation, and ultimately–it’s about what is going to move the needle  for the benefit of the customer and benefit of the company.  It’s easy to get frustrated as you move up the career ladder, when those on your teams question your moves or push back. What’s harder to do is remember that you probably were there once too on some things. I find it genuinely a source of joy, when some of my previous individual contributors (ICs), since promoted into management, come to me frustrated by their ICs exhibiting exactly the same behaviour that kept me in knots from them.  

The takeaway I hope you get from this, if you’re a new IC or a new VP, is that you get a lens on what those above are thinking about, wrestling with or frustrated by so you can take actions to make things easier. And for those in more senior roles, to take a minute to remember what likely went through your mind so you can explain or provide context.  And to know that you’re not alone in grappling with the nuances of actions when viewed through a different lens.

I’m sure there are plenty of things I missed, please let me know!

Things that went through my mind when…..

I was a new AE

  • These quotas are insane, they obviously don't want us to hit goal 
  • So. Much. Admin. 
  • I’ll update Salesforce later.
  • This territory list is a joke, I don't have many great accounts. 
  • I know that big whale is going to come in before the end of the year. 
  • I hope that big whale comes in before the end of the year. 
  • WTF? The whale promised they'd sign by the end of the year. 
  • Damn, marketing is amazing, I love there's so many leads. 
  • What is marketing doing, I have no leads. 
  • Why is everyone asking all these details and account plans... Just shut up and let me hit my number! 
  • Yes I’m happy my peer closed that big deal. Yes, I’m also dying a little inside that my peer closed that big deal and I haven’t closed one yet.
  • Customer Success team member, you are my favourite human being on the planet right now with that upsell you tee’d up!
  • I want to be a manager because clearly that's the next step. 
  • I love the spotlight and the glory!
  • I’m pretty sure I have enough pipeline. 
  • How do sales reps survive without Solutions Engineers? 
  • Why are they making my territory smaller? I was one of the first ones here! Not fair!


I was a new VP

  • I've spent a week agonising over account distribution, these seem as fair as possible.
  • I need to be able to forecast to my CRO but the reps have no information filled in.
  • OMG just fill in Salesforce so I can understand your deal 
  • I want to make sure I'm supporting my team, details and account plans let me figure out how 
  • It's so hard not jumping in to solve everything, l need to coach you to figure it out yourself.
  • These quotas are crazy, I don’t have enough street quota to hit the number, why am I penalised for not having the full team hired yet? 
  • No, I'm not micromanaging. You aren't going to close this deal without some serious help. 
  • Hey AE, doesn’t look good that your whole quota is done off the back of the CS finding upsells for you, we need new logos
  • That deal is never going to come in, it's slipped 3 times. 
  • You don’t have enough pipeline!
  • No, your Solutions Engineer shouldn't be filling in the entire RFP, you own that as an AE! 
  • You have a phone, you have email, you have data---go create your own pipeline if needed, quit complaining about your SDR or marketing. 
  • It's a Sunday afternoon. Please don't WhatsApp me about your territory right now. I didn't reply right away because I was at yoga then brunch. 
  • That commission check Rep S is going to get for that deal is insane. I should go back to being an individual contributor!
  • I want to get more involved in strategy, my next step is CRO 
  • I want my team members to get the spotlight and the glory!  
  • Smaller territories means the team will quit just looking for low hanging fruit, and I need to ensure equitable opportunities. 

As a CRO

  • Our CAC is way too high, how can I balance that so our GTM team is more efficient?
  • I want to jump in but need to let my front line management learn to solve problems first.
  • How can I make sure anything I say to the board I can back up with consistency?
  • That deal we closed…we really shouldn’t have. I know the customer is likely to churn or have reduced retention upon renewal…need to narrow in the focus and get the team qualifying harder. 
  • I really do want to provide career paths for everyone, unfortunately it's not a guarantee and I won't have promotions for everyone. If you are going to thrive more in a different company and it is the right thing for you, I'll do everything I can to support you! (as long as it's not a competitor 😁) 
  • Why does every single AE tell me their next step is management? Does ANYONE realise how awesome a job Senior IC can be?  Do some people realise they'd HATE management? 
  • You haven’t forecasted correctly all year, you haven’t filled in Salesforce or qualified hard on deals all year, no you aren’t going to be promoted to management to then hold others accountable for forecasting and deal qualification.
  • I want my AEs focused on bringing in new logos, how do I create clear rules of engagement on upsell and cross sell with CS and AMs?
  • How can I help my Customer Success team become true trusted advisors? 
  • Does anyone love dealing with global split policies?
  • How do I qualify the pipeline and align sales and marketing so we drive more of the right ICP?
  • I really lost my cool in a leadership meeting, I should have been more diplomatic
  • I don’t care about being diplomatic, we need some basics from Product
  • This is actually a really lonely role.
  • That event is so much fun and so high profile and we haven’t been able to attribute any deals to it in the past, so no we shouldn’t attend this year and yes I'm going to be the bad guy here. 
  • How can I start segmenting territories to maximize impact and resources, teams are going to have to start specializing on a particular vertical or segment
  • (Elbow deep in spreadsheets and performance reviews and comp plans and forecasting analysis) "I want to be a C Level exec to mostly work on strategy" 🤣🤣🤣
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