How I handled an internal skeptic

My response to a VP saying my idea "seems like a miss"

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This is a true story. 

Back in February we had Clari’s marketing offsite. Every marketer was there. Even the CEO made it out.

There was a full agenda, and the big focus was that each department leader was expected to present their H1 plan to the group and get feedback. 

Allow me to jump straight to the juicy part. My turn.

My final slide was a list of my team’s deliverables. 

I shared the title, description, target audience, expected KPIs, owners, etc. for all the things my team was going to do.

I spent extra time explaining my team’s biggest deliverable for the quarter: The Executive’s Guide to Successful Board Meetings.

It’s a downloadable guide written by our CEO, Andy Byrne, to help leaders maximize the most valuable and expensive meeting in their quarter. I’d been working on it with Nehal and Donna for weeks. It was nearly done with a fully built distribution plan and launch date scheduled. We were ready to roll. 

I paused to let the eyes in the audience move left to right like a typewriter across the slide.

I knew what was coming. This is always where the landslide of questions pour out:

What about X?
What about Y?
Why NOT Z?

(I’ll be honest, I find this more annoying than helpful. I don’t think the best way to make a content marketing plan — or any marketing plan — is to ‘pitch’ it to a group of 30+ marketers, all with various backgrounds and very few with specialized content marketing experience, to get input. But it IS incredibly important that you’re equipped to answer the “why this/why not that” about everything in your plan because it shows you have complete control and can properly defend your decision-making.)

Back to our story.

I was very confident in my plan. But not everyone shared that sentiment.  

A not-to-be-named VP chimed in. 

And that’s when things got… interesting.

“I don’t think this will work in the enterprise. Don’t these leaders know this stuff already? Seems like a miss.”

“Hmmm… yea, fair point,” added someone else. 

God damn it, I thought. 

I’d been here before. Everyone in B2B marketing has. 

One doubtful comment can kill even the simplest and safest ideas – let alone one with any creativity (which is usually viewed by skeptics as “risk.”)

I saw a snowball of doubt forming and growing fast. I decided to get ahead of it and crush it before a mutiny formed and my asset died on the spot. 

(Yes, I’m being a bit dramatic here, but not by much. That’s how it feels when you’re on stage presenting to a large group of your peers and your ideas are being picked apart.)

I paused. 

Then chose my words carefully:

“I don’t believe leaders wake up thinking, ‘I’m an enterprise sales leader’, or ‘I’m an enterprise c-suite.’ They just wake up with problems, concerns, and insecurities about getting their job done. And they’re willing to get help from people they respect to do so.

Andy has run more board meetings than most leaders, plus he’s coached hundreds more on how to run their meetings. I’m confident they’ll be curious to hear what he has to say.”

The nay-sayer half shrugged.

I probably could have stopped there. Maybe I should have. But I didn’t.

“Here’s the truth: If this asset flops, I will be the first one up here to take accountability. But if it’s a hit… I’ll be the first one up here to take accountability.

Some eyes widened. Others smiled. 

Did I flex? Looking back, yea. I did. 

And while that’s not my usual approach, especially in that type of forum, I don’t regret it

Sometimes you just need to defend yourself and your plan. 

Here’s why I was so confident

I’m going to reveal my decision-making behind this particular asset because it’ll help you decide which content you should create (and so you can defend your ideas too). 

First, I looked at the most popular Clari asset of all time: Clari’s Prospecting Academy written by Kyle Coleman

This thing put up serious numbers with 6,000+ downloads:

Monthly content downloads broken down by asset

Second, we analyzed WHY it worked so we could replicate its success:

  1. Credibility: It was written by a true subject matter expert (Kyle).

  2. It solves a BIG existing problem: Sellers constantly need to build pipeline.

  3. It’s tactical: It is a step-by-step guide with templates, talk tracks, etc.

  4. Distribution: Kyle’s LinkedIn presence was by far the most effective channel.

Our final task was to ensure our new asset was relevant to above-the-line buyers.

I knew that Clari has a unique product advantage over all our competitors: Only Clari is used in the boardroom. 

Execs rely on Clari to show past results, present status, and future projections when talking to the board.

So I decided to use that strategic foothold to our advantage:

  1. We need credibility: No one is more credible than the CEO. Let’s have Andy write it. 

  2. We need to solve a BIG problem: Board meetings are incredibly high stakes, but they’re often run poorly and inconsistently, leaving money on the table. Let’s do that.

  3. We have to get tactical: Let’s make it a step-by-step playbook for the three phases of running board meetings (prep, delivery, follow-up).  

  4. Distribution: Andy has 20K+ LinkedIn followers. Let’s use that to build a waitlist and distribute when it’s live.  

Fast forward two months…

The board guide was a certified hit (!)

It’s Clari’s 2nd most downloaded piece of content of all time with 1,500+ downloads and counting:

You know I’m all about building trust at scale. And this asset immediately boosted Andy’s and Clari’s reputation with CEOs and CXOs — the exact people we sell to.

And if you’re wondering… it DID land with enterprise leaders.

Over 30% of the MQLs were from enterprise accounts. 

And that’s just from the 1st wave of organic distribution.

I’m glad I trusted our vision and defended our plan. Sometimes that's just part of the game. And it’s totally worth it.

I hope story this inspires you to do the same — even if a senior leader is skeptical about your ideas.

BTW, you can watch me break this strategy down with Jen Allen-Knuth and the importance of “decision confidence” (jump to 29:25).

Holler at you next Saturday,

PS: This post took me ~3.5 hours to write and design. You can help me grow my newsletter by forwarding it to one person with a quick “You’ll love this. Totally worth subscribing.”

“How to Create Provocative & Bold Messaging”
with Jen Allen-Knuth

Jen is my next guest on Reed Between The Lines in Chicago. I’d heard great things about her but WOW. This was the first time we ever met, and I was truly blown away.

She’s bold, she’s entertaining, and she taught me A LOT.

She reveals:

→ How to attract customers with a provocative POV (jump to 15:30)

→ Her “secret” for becoming a more confident seller and marketer (jump to 6:43)

→ Why she turned down “SO much money” for a brand deal — and what to look for before saying yes (jump to 1:02:20)

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