Bad Manager?

After I wrote Time for a Promotion? I had an insightful catch-up with a great friend (who actually used to be my manager). He reminded me of something very relevant.

“All that stuff about putting aside greed to push through and do the work; then ask for more from the company…yeah, 90% of people can’t do that.”

We talked through examples of managers and CEOs who just don’t get it. And it’s very relevant to many of us, isn’t it? I’m lucky I don’t have that issue at beehiiv, but I’ve also been in that terrible position. Not every company has founders and a leadership team who really get it.

Today, we’ll review dealing with leaders who lack vision and can’t execute (and what you can do about it today). I’ll cover the first things I’d do in that situation (down to the tools I’d use) and offer a few pathways for you (if you’re in that situation). Lastly, we’ll cover how to create new opportunities when they seem like they’re not available.

Let’s start with one statement that defines the manager who doesn’t get it.

“Well, if the AI is doing all the work, why am I paying you?”

Oof…let’s get into dealing with these people.

Leaders who don’t get it.

Who are these people? How do we know if they don’t get it?

Let’s use a few phrases to make the point:

• “What we’re doing is working. We don’t need to change anything.”

• “AI will not impact our industry.”

• “We don’t need to expand into that industry, that market, or try any of these new things.”

• “Why would we spend money on a tech department? We’re not a tech company.”

It’s about the mentality, not necessarily age or background. Whether their business is worth a few hundred million or ‘just’ six figures doesn't matter. Netflix crushed Blockbuster, Kodak was too late on digital, and Sears was selling in big stores while their competitors were crushing with online ads and ecommerce.

These companies were valued in the hundreds of millions, and sticking to the old way is why they’re gone today. It all comes down to leaders who didn’t get it. But you know who really suffered? The employees at those companies, who enjoyed very little of the upside when things were good, but took on all the downsides when they lost their jobs.

If you’re worried about this, keep reading.

This mentality from above is what will hold back your career.

The Signs

In our conversation, we went over the classic signs we’d seen earlier in our careers. While behind us now, both of us made obvious mistakes. You may be making them now. But one stands out above all the others.

Working for the wrong leaders. They hold back your income, your potential, and can make you feel miserable.

Here are two major signs.

When the only way to get a raise is to create one.

Ever heard the advice: “the best way to get the job of your dreams is to create it”?

While technically true, there is a massive catch. It’s the same thing my friend called me out on. It doesn’t apply to a majority of people.

You can create your dream job at a company when its leaders get it. When they want to see you succeed. When they want their business to succeed, and have the vision to lead.

But if you’re working for a guy who says, “Why am I paying you when AI does all the work?” Then the writing’s on the wall. If they’re not okay with using AI (for the benefit of their business), do you think they’ll say “sure, here’s your dream job–all yours Let’s crush it!!”? (Also for the benefit of their business).

Leadership makes or breaks a business as much as technology and markets do.

If you have to constantly go to your boss with new ideas and technologies to make the business better, and they keep getting shot down, you’re in the wrong place.

You want a raise, right? Is it time for a promotion? I get that. But if the leadership at your company is not on the same page, there’s a problem. If the only way to get that is to figure out what the business should be doing (your CEO's job) and then plan it, pitch it, and everything in between, it’s tough. This is the part I left out in my previous post that I needed to cover here.

Leaders should be the ones leading. If they’re not, it’s worth looking elsewhere before it’s too late.

Leaders who tell you to do more but aren’t willing to lead a business aren’t worth your time.

But they won’t make it obvious. There’s another sign to watch for (they’re less obvious).

Using bureaucracy to delay

You’ll get 99% of the work done, but your boss will ask you 20 more questions and book a meeting to review in two weeks. You’ll do it all, and they’ll ask another 20 questions in that meeting. The cycle will repeat for two months. Then they’re on vacation, and suddenly it’s 3 months later, and nothing’s happened.

When it’s finally ready to get started, they’ll tell you priorities have changed. There goes your time doing free research for someone who probably lets you chase the project, knowing it wouldn’t happen.

I’m being a bit cynical now, but you get the point. In these situations, those above are happy to give you more work but not make any changes that move the needle. Things like:

• “Looping in more stakeholders”

• “Estimating the potential impact in another part of the business”

• Addressing however many things that don’t really matter

Bureaucracy is the enemy of progress. There is no better sign of a waste of time then people creating bureaucracy for the sake of it.

Checks and balances are essential. Diligence is important. But why does that one project of yours need 6 - 12 months? Elon’s multi-billion-dollar Twitter acquisition was done in ~6 months.

It doesn’t have to take that long. It’s delayed on purpose.

So what do you do about it?

We’ll assume you’re already looking for another job. But on a more personal level, how do we level up while looking around? Not just to do better work but to find and create better opportunities (without needing someone else’s approval).

As much as I can tell you that leaders who don’t get it are a problem (and they are), they’re not the only issue. For years, I grappled with the idea that it was someone else’s fault. But there was always another person to blame.

Myself.

Why was I working a job I knew was a dead end for an extra year? Why wasn’t I working as hard for myself as I was working for people like that? Especially when I knew there were better opportunities out there.

Why not look (or create) another one? (DJ Khaled voice). When I started branching out into side projects, I made more money, enjoyed working more, and kept my day job anyway. Why would anyone care if my performance is just as good as it’s always been? That’s the thing. Leaders who don’t get it won’t want you expanding in this way (and you don’t have to tell them if you do).

Let’s discuss the opportunities:

Creating new opportunities with the time we already have

First, we want to make the most of the time we have. For this, I will go over AI (again), because it’s an amazing time-saver.

Writing (and reading) always takes time. Wording the email the right way, reviewing the latest documents from your lawyer, and even reviewing reports from your team. AI saves time so you can focus on what matters.

Great tools to start working with are ChatGPT and Claude. They both have free plans and can save you hours right away.

You can take a screenshot of an email, tell it to “write a reply saying yes, but professionally,” and it’ll do it for you in 10 seconds. You can upload your entire lease and ask it to read and summarize the key parts. It’ll also finish that instantly.

For the 4th time in a month–if you’re not using any AI tools, please start. You’ll be glad you did.

Creating new opportunities by putting ourselves out there

Publishing once a week has been a game changer for my career and can be the same for anyone.

Fun-fact. I mentioned that friend of mine at the start of my post. We met because I published a psychology blog, and he hired me after a mutual friend showed him my writing. It wasn’t the biggest blog out there (not by a long shot). But after a few people started showing it off, an opportunity came my way.

This newsletter you’re reading now has brought me a few opportunities after a few weeks to help companies start adopting AI. There’s never been a better time to start.

A newsletter could be written, published, and promoted in a day (or less in many cases), but has compounding benefits. Whether you have one reader or ten thousand, writing one email is writing one email.

Enter beehiiv, the best email platform to start, scale, and monetize your newsletter. I work there and am happy to get you set up. Just let me know by replying to this email.

Now, I also understand that it can feel a bit intimidating to do this. But I’m living proof of its benefits. What do I really do? I write a post once a week. Post about it on Twitter (people sign up). Put some money into Boosts (a beehiiv feature that helps me grow my newsletter for $1 or $2 per active, engaged subscriber), and it grows.

It’s that easy to start and grow.

But if that’s not enough, I’ll share one more game-changer with you.

Creating new opportunities with an off-shore assistant

I worked at a Vancouver agency for a couple of years (great company). While there, we started outsourcing. One role turned into two, then three, and suddenly, we had eight staff overseas. We were paying probably 1/3 the costs of local staff to people overseas who (in their economies) were earning a good (if not great) income.

Instead of paying $75,000/year, we’d pay $36,000/year to people with 5+ years of experience in the field and who were hungry to succeed. While it doesn’t work in every role, there is a way that it can work on an individual basis.

These fully remote “virtual assistants” can help with everything from keeping you on track to bookkeeping, project management, and more (the things AI can’t do). What would it mean for you if you had someone working for you 20 - 40 hours per week so you could free up more time for that side hustle?

If you set it up right, they can simultaneously help you with your day job, side hustle, and personal affairs (for 1/3 - or even less - of the cost of a local personal assistant).

This is also where I’m happy to introduce my sponsor for this post, Oceans, a talent agency that specializes in connecting high-growth companies and individuals with expert talent overseas. You get a great assistant with years of valuable experience. They receive a wage that’s competitive in their economy. You pay significantly less than hiring someone local while you build your base.

The details are below. This is a sponsored ad placement.

Of course

Thanks again for reading!