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Dear Fellow Sales Leaders: How Do You Deal with Difficult Peers?

A long one, so buckle up or scroll to the TL;DR section at the bottom.


Leaders and team leads, I have a tender situation that I am struggling to deal with.


I just joined this spot 3 months ago. We have the following hierarchy on our leadership team:


  • CEO
  • CTO
  • VP Product
  • Head of Marketing
  • VP Sales (new one joining)
  • Me (Director of Sales Development + Rev & Sales Ops)


Lately, I have been working with our Head of Marketing (HOM) to build our outbound copy strategy. I split my time between the outbound strategy and scaling the Rev/Sales Ops functions of our business, so we have brought the HOM in to help write the copy for all of our new campaigns since they have the bandwidth to do so. Problem is, this person has a 95% clear calendar, but whenever I ping them, they're nowhere to be found. They miss deadlines and often go radio silent for days at a time. This is causing a backdraft on me from our CEO (who I report to) because outbound is falling off, but I cannot launch new campaigns without the HOM writing and/or approving copy.


I have addressed the issue with a Radical Candor approach with the HOM, I have also brought it up weekly as one of my key blockers during my 1:1 with the CEO and we've instituted weekly syncs where we can document what the HOM owes me as to show a paper trail if the worst should happen. Short of having a full meltdown in our next management all-hands, what else have you all done to right the ship and get out of a sticky situation like this in the past?


TL;DR: I have to get outbound back on its feet after old VP Sales let it die. Marketing isn't pulling their weight with campaign copy and I am about to go full nuclear if we miss another campaign launch deadline. What do?

πŸ™ Mental Wellness
🧒 Sales Management
11
spoderman
Arsonist
+10
Friendly Neighborhood Spoderman
Wow, that is super frustrating. I don't have nearly enough experience to pretend I could answer this accurately but I would think its time to create a timeline of your interactions with said MIA person, so that in your next meeting you can say "Look, this when I tried to approve this, and you didn't respond" and basically call them out with hard evidence of how they're affecting your performance and dragging down your efforts.Β 

Also, a swift kick to the dick could help.Β 

Edit - after reading your post again it sounds like you're already working on the paper trail method. Sorry I'm illiterate today.Β 
poweredbycaffeine
WR Lieutenant
+10
Bean Juice Drinker | Sales Savant
Slack timestamps + emails where we all agree on timelines are now in play. Virtual swift kicks are next on the list. Think I can pay someone on Fiver to do that for me?
spoderman
Arsonist
+10
Friendly Neighborhood Spoderman
There's likely a long list of people on Fiver ready to perform that service for you.

Given what you've said about the timestamps, I think as long as you know your CEO is on the same page with you, it might be time to just ride out the storm and let that person fall on their own sword.Β 
1nbatopshotfan
Politicker
+6
Senior Director, Enterprise Technology
Go nuclear. Paper trail right to the ceo. If you’re missing deadlines because they miss them and have been missing them, there’s no need to play nice.Β 
Justatitle
Politicker
+11
Mid Market AE
Sounds like you are already doing the needed items in creating transparency to your CEO and addressing it with your HOM. Only other value I might add is ask the HOM how they’re doing personally and leading with empathy there to see if it might be something personal that is causing them to not do their job. If they’re just lazy there is really nothing you can do to fix that
poweredbycaffeine
WR Lieutenant
+10
Bean Juice Drinker | Sales Savant
Ugh. I do need to give them grace and realize theres potentially something else going on in the background. Very fair point.
DungeonsNDemos
Politicker
+10
Rolling for Initiative
I'm curious how long HOM has been there. That would change my approach (to be clear I'm not in a similar position to you).

Even if they don't like you, they still need to do their job well. The best thing you can do is continue to do the "right" things and at least keep the ball in their court.Β 
So if/when it goes nuclear your ass is covered.

If they really aren't doing their job, is it because of laziness or because of a side project they care more about?
poweredbycaffeine
WR Lieutenant
+10
Bean Juice Drinker | Sales Savant
They've been there less than a year, a former consultant to the org that was hired off of their contract with us to full time. It's my belief that they're working on something else.
amyhyoung
Politicker
+5
VP Operations
Sorry to hear you're in this situation - the HOM sounds terrible. It's clear that the HOM isn't responding or looking to improve any time soon. But keep having these direct meetings/feedback to have the documentation to show you're trying to communicate and work with them in a professional manner.Β 

I assume the HOM reports to the CEO? Has the CEO talked to him/her on this?Β 

Separately, are you able to write your own copy for your campaigns?Β  If so, you could send to the HOM and say something along the lines of "this copy is going to go out in the new campaigns on X date. If you have any comments, let me know by Y date, otherwise we're going out with this." It's not ideal since that's more work for your team but at least you're not waiting on the HOM to launch and if they had comments or weren't okay with it, they should have responded and it's on them. Obviously run this by the CEO if this approach is okay as well.Β Β 
poweredbycaffeine
WR Lieutenant
+10
Bean Juice Drinker | Sales Savant
Yes, HOM reports to the CEO and we are all on the same page as of today...but we said that last week and the week before. I used to write all the copy, but the HOM is now off their last project and has lots of time to "help" on this. I am going to write up the copy if it's not done by Monday EOD and go with this method. Thanks for the encouragement!
Sailor
Contributor
Senior Director of Business Development
Are you the only one that is having to request and push the HOM to get it done?Β 
poweredbycaffeine
WR Lieutenant
+10
Bean Juice Drinker | Sales Savant
No. CEO is now pushing things along, too.
Sailor
Contributor
Senior Director of Business Development
Are things moving forward now?? It appears as though you have a sucky human working with you. I will punch em if you need :)
3
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