Sales Strategy

Five Subtle Ways To Influence Your CEO (Or Boss)

Influencing your CEO is hard. Personality differences, power dynamics, sales leaders being given unrealistic goals...

June 17, 2021

Five Subtle Ways To Influence Your CEO (Or Boss)

No Time To Waste

Most of us have seen data supporting the decline in the average tenure of sales VPs.* It now stands at 19 months. That’s driving more sales leaders to pre-negotiate a severance package before they even start. With less than two years to work with your CEO, on average, we have little time to waste to win over our boss and influence the rest of the organization.

A primer about this list:

  • Subtlety is the key. Aligning with your CEO on higher-level strategies like the one, three, and even five-year sales plans, the roadmap to get there, and how to best execute is table stakes. Most likely, this was agreed upon during the interview process and reinforced quarterly.
  • Collaborating closely with the entire go-to-market team and other functional executives is a given. Say to those department heads: “What’s the number one thing you’re on the hook for this year? How can I help?” You’ll earn instant respect from your peers and CEO.
  • This list isn’t a catchall but comes directly from networking and talking with Chief Revenue Officers, VPs of Sales, and other sales leaders who belong to the Revenue Collective, a membership for sales professionals. These were the most common responses.

Here are five subtle ways to increase your influence with your CEO (or boss):


Communicate over text.

Ideally, you swap casual banter around weekend plans, parenting mishaps, or the latest show you’re streaming. Of course, texting about work stuff is a good sign too, but shoot for a balance. Communicating over different mediums like text humanizes the relationship.


Break bread on the regular.

As society reopens, schedule your recurring one-on-ones outside of the office at a coffee shop or restaurant. Get on a plane if you work in different cities. One leader shared the CEO invites his entire family over for dinner once a month. Socializing outside of the work environment builds a stronger bond.


Start a book club.

Don’t be afraid to initiate, and read a relevant leadership or strategy book where you both find value. Aim for a club of two. It’s not quite the same if your CEO invites you and the entire management team of fifteen to read something together.


Find similar people to admire.

It could be entrepreneurs, industry newsletters, innovators, and influencers you both respect. Landing on a few outside voices helps you coalesce around shared ideas and beliefs to drive the business forward. Solid back-n-forth dialogue is your objective.


Move together.

Sales leaders often mention a shared activity helps with their overall influence. It could be a hike, a spin class, pick-up basketball, or going on a run together. Breaking a sweat releases those “feel good” endorphins, and again, humanizes the working relationship.

Bonus Tip

Monitor your heart rate.

Next time you raise a concern or voice dissent with your CEO, note how you feel. Building trust takes time, but you should feel psychological (and physiological) safety after a few healthy bouts of not seeing eye-to-eye. If your heart rate is stable while discussing challenges, and you safely bounce ideas around without getting shut down, you’re probably in a good spot where your voice and influence matter.


This list isn’t foolproof, and it’s worth noting just how hard this is to pull off – personality differences, power dynamics, sales leaders with unrealistic goals, the fact most CEOs have bosses too – the list could go on. But when you exert influence, you’re in a much better position to lead.

Work these tips to gain confidence and get buy-in with your next strategic pivot, change in comp plans, sales org restructure, or request to increase headcount.

Conversely, if none of these ideas are in action, you could still have someone who believes in you. Try these things out to build an even better relationship and influence those around you.

Drop us a line if we missed anything working for you, and we’ll share it in next week’s newsletter!

*Gong published (unsourced) data showing average sales VP tenure declined from 26 months in 2010 to 19 months in 2017. Other published articles offer the same downward trend but were even more outdated. We found no sourced or referenced data behind any of the articles. That said, most sales leaders anecdotally seem to agree with the negative trend line.

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