The Insider Exec

C-Suite Exec, Board Member.
Sharing stories from the exec seat to help you learn how to get here.
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[The Insider Exec @TheInsiderExec]

Look, I'm not going to sugarcoat this for you.

Most career advice sucks. It's either written by people who've never actually made it to the top, academics, or by executives who are so removed from the grind that they've forgotten what it's really like to fight for every promotion.

I'm writing anonymously because I want to tell you the truth.
- The stuff your manager won't say.
- The unspoken rules that everyone assumes you just "know."
- The political games that nobody admits are happening but absolutely determine who gets ahead.
- How we actually make decisions on who gets promoted, and who gets paid.

WHO YOU ARE (and why you're here...)

You're hungry. You're not content to just show up, do your job, and hope good things happen. You've figured out that "work hard and you'll get promoted" is mostly bullshit, but you're not sure what actually works instead.

You want the promotion, the raise, the corner office, the respect. You're thinking beyond just your next role - you want to understand how people actually make it to the C-suite.

And you're smart enough to know that the skills that got you this far won't automatically get you there.

WHO I AM (and why you should listen...)

I'm currently President, Treasurer, and COO of a private, high-growth company. I also currently assume all duties of the CFO in addition to being on the Board of Directors. In short, I run the company and am the most influential person in the boardroom.

Before this, I spent a decade at a Fortune 500 company where I consistently outperformed my peers and got fast-tracked through roles that normally take people twice as long to reach.

I made it to Director of a $2B multi-national division at 28. Not because I was the smartest person in the room (I wasn't), but because I figured out the game that everyone else was playing blindfolded.

Here's the thing though - I had chances to screw it up multiple times. I made mistakes that could have derailed everything. I missed opportunities that were sitting right in front of me. And I see my younger employees making those exact same mistakes every single day.

Why writing anonymously is important
When you're not anonymous, you can't tell the whole truth. You have to be diplomatic. You have to protect relationships. You have to worry about legal teams and HR departments.

I don't.

I can tell you exactly what executives really think when they're deciding who gets promoted. I can share the real conversations that happen behind closed doors. I can explain why two people with identical capabilities can have completely different career trajectories.

What you'll learn here
This isn't going to be a bunch of motivational quotes and generic "leadership tips."

You'll get:
- Real stories from my career, both as employee, manager, and executive
- How to navigate office politics without becoming a politician
- What to actually say in salary negotiations (with scripts)
- How to build the relationships that matter
- The promotion mistakes that kill careers before they start

I’m writing now mostly as an outlet for my own thoughts. Because it pains me to see some younger employees expressing ambition but shooting themselves in the foot. But if this writing finds one person and helps them find career success, I’ll be over the moon.

If you made it this far, give me a follow! And if you want to ensure you don't miss these tips in your X feed, subscribe to the newsletter to make sure it hits your inbox every week! (link in bio)

[The Insider Exec @TheInsiderExec]

@PEoperator True. However, you will learn way more about yourself when you step out on your own. It will force you to grow in ways a W-2 never will.

But, after a stint doing my own thing, I'm back in a W-2, so I think that says something ;)

[The Insider Exec @TheInsiderExec]

@PEoperator I find it works even in board meetings. It's a delicate balance, you can't look incompetent. So the big stuff has to be right, otherwise you'll be seen as unreliable. But, to your point, people want to feel smart and needed.

[The Insider Exec @TheInsiderExec]

The higher you go, the more important "politics" is to driving results, though. It's a false dichotomy. They are tethered together, albeit to varying degrees depending on role.

But ad you move up, your job becomes more about influencing stakeholders and mobilizing people to do what you see needs to be done, where that is a subordinate to follow a directive, or a colleague to support a proposal, or an investor to release additional capital.

If you're politically inept, you're not going to be effective at the job.

[The Insider Exec @TheInsiderExec]

Hard agree. It's hard to understand how formative early experience and your late 20s can be in terms of positioning you for a really great 2nd half of your career. And compounding in your career works much like it does in your finances.

The more yourl invest early, the better off you'll be long-term. Hard to fully appreciate when you're in the thick of it and not seeing the big returns yet, but if you keep at it, things start to take shape in your 30s and it gets exciting after that.

[The Insider Exec @TheInsiderExec]

Eh. I disagree. You went the entrepreneurial route, and in that case you're right. But, I also let my GPA suffer (spent time I should have put into projects/homework/study learning programming instead...which has paid off in many ways). As I got into my corporate career, I became aware of consulting and was interested. I think I would have done really well and accelerated my career, and the resume boost and network would have been very helpful. But getting into top tier consulting was not an option at that point. I could shoot for a top 10 MBA, and had the GMAT to make it, but ultimately I believe my GPA was just a bit too heavy a counterweight.

I've found success regardless. I do agree with the mindset that you make your own success. Plenty of people with great GPAs going nowhere, and high school dropouts out there making more than me.

But, GPA can hold you back from some options, and you don't know which options you'll want to pick up down the line. It's really not hard to get a good GPA in undergrad. Best to just put in the effort and keep all options on the table. I don't think focusing on GPA and getting a job are mutually exclusive.

[The Insider Exec @TheInsiderExec]

I was a Sr. Analyst in a manufacturing facility and earned a skip level promotion to Finance Director of all manufacturing finance. My fellow mfg finance colleagues asked "how I did it".

I:
- signed up for every safety audit
- made engineering managers walk me to the tool that needed an expensive repair and walk me through it
-shadowed a manufacturing supervisor for a day
- volunteered to give tours to new hires (forced me to learn the script!)

The person I replaced as Finance Director only made it to the site 1x/yr for the annual plan, and his visit was limited to the main conference room.

My colleagues, stationed in their respective site, still largely lived on the admin office portion.

I didn't earn that Director role because of my Finance wizardry. I earned it because I knew how these sites ran, and could sit in a meeting with the VP of Mfg and his staff and be a value-added member of the conversation due to my deep knowledge of our Mfg Ops.

If you want to truly help lead the organization and be a strategic thought partner, you HAVE to put your eyeballs on the process, repeatedly.

The good news is, this gets overlooked by a lot of lazy or "busy" leaders. It's an easy thing to do to elevate yourself.

[The Insider Exec @TheInsiderExec]

2nd highest all-time users day yesterday.

We are HIGHLY seasonal business, and have been building & preparing for a big fall. So far, July/Aug has missed growth projections, but yesterday's numbers were some much needed encouragement.

[The Insider Exec @TheInsiderExec]

@PEoperator @shaneparrish Excited to dig in!

[The Insider Exec @TheInsiderExec]

Good take. Of course, there are some managers that micro-mamage no matter what. But, reflect and ask if you're nailing all these things.

I absolutely micromanage if you've lost my trust. I am accountable for the results in my business. I'm not taking chances on MY reputation by leaving you room to mess up. But I don't WANT to micromanage. If I'm having to, one of us is failing to do our part. Either I need to provide better direction, coaching, or accountability measures, or you need to do a better job of [see @dklineii 's tweet].

[The Insider Exec @TheInsiderExec]

The future belongs to those who know how to deploy AI to solve business problems. You don't have to be a data scientist, you just need to have enough familiarity with the tools to begin to be able to see ways to use them to solve business problems better than legacy tools.

But you gotta play with them and use them to build stuff to learn their strengths and limitations. Bookmarking tweets and watching YouTube videos aren't enough.

[The Insider Exec @TheInsiderExec]

@AsyncCollab Lol I get it. I wasn't sure if it would land or not, so you're forgiven. I couldn't get chatGPT to make it clearly tongue-in-cheek enough.

[The Insider Exec @TheInsiderExec]

@AsyncCollab

[The Insider Exec @TheInsiderExec]

Monday AM kicks off with a weekly team meeting where every team leader brings slides & updates from last week and their priorities this week.

This meeting clearly exposes the separation of the A players and everyone else.

A players are prepared, energetic, and show new progress every week. Others seem to have thrown these slides together last minute (some even editing during the meeting) and have "no updates" on items from last week. Let me tell you, that's not good for your career.

[The Insider Exec @TheInsiderExec]

At a team happy hour, I briefly mentioned to a mid-level marketing guy that I was planning to bring on a fractional CMO temporarily because I thought it would be good to get him some mentorship and also our current marketing team just didn't have a good strategic vision. He said "wait, don't do that, let me cook!".

I had just made some other changes, putting him in the role he's in. He's no CMO, yet, but within a few days he booked a meeting with me and had a whole proposal, roadmap, and 30-60-90 plan. Definitely impressed me, and I decided to forgo the fractional CMO and let him run.

He's absolutely KILLING it. Still not a CMO, but he is fixing the issues I saw in marketing, drives the process and I barely need to manage him.

To you point, sometimes people will surprise you. It is worth at least giving them a chance.

[The Insider Exec @TheInsiderExec]

Most people think they are indispensable at their workplace.

Few are.

Layoffs are happening all over the place and many are finding this out the hard way.

[The Insider Exec @TheInsiderExec]

@parody_ceo The dream!

[The Insider Exec @TheInsiderExec]

@blakeaburge At the core, I think these basically show whether someone is selfish or considerate of others. The circumstances you mentioned just help make it obvious.

[The Insider Exec @TheInsiderExec]

@TheRealBradLea Well put.