"You're not strategic enough", said Manager

26 Oct, 2025

Cracks

I believed that for most of my career, if not all of it (so far), that you had to be the best possible IC in order to become a manager / leader. Especially with the whole narrative around "The builder's age" and "One-man marketing teams" or "Oh, office politics sucks" - the notion of being a lone wolf kept getting reinforced.

I often thought one had to:

• know their craft really well
• be super-fast and error-free in all of their deliverables
• have the entire company's knowledge and context memorized

and then magically, the promotion fairy would appear and place that XX% hike under your pillow and give you a kiss.

Crevices

Sure, in the early days and years of your career, it is important to be a dependable workhorse. That's what leaders and managers look for - can I count on you to get the job done, and well?

After a couple years in the trenches, you're bound to become a high-performer. Form follows function. But what's happening in parallel is that there are others who have also become high-performing like you as well.

The mind then instructs one to take the "here's how it's done" approach. It's essentially where you take the megaphone and keep yelling the best practices hoping someone would hear and notice. Especially your leaders.

But this tunnel vision seldom scales. Today you might be a random employee. Tomorrow, you will have to band together people, create a vision, and deliver results.

A complaint I've always had is that the transition from IC to leader is a knowledge which is incredibly gatekept. Very few industry folks actually make the extra mile to train, coach and mentor you. 99% others are left to aimlessly fish around and find out. If they do find out, they'll probably breed another generation of bad leaders.

Closure

What I've been able to figure out is that the journey from IC to manager / leader is essentially from "Here's how it is done" to "Here's how it is done SO you can help me do more."

It is a mindset shift from rapidly acquiring skills to enabling and uplifting others at scale. Uplifting others means:

• sharing complete context and info in real-time. Not as an FYI.
• build a culture where you treat direct reports as thought partners. Not as handymen to figure out operational feasibility. Don't blame them in the end for not being "strategic enough" when that's literally the culture you're driving.
• set the bar high and coach. coaching means:
  • ride-alongs
  • showing what good looks like, and dissecting each part of it
  • actually mentoring people through that process by holding them accountable
  • not giving up after a few tries

In most cases, the norm is to tell direct reports what to do and get the job done as a team. It works great in a sweatshop where inputs and outputs are predictable enough.

But a huge, huge downside of that is you're secretly stealing away their ability to make decisions. The little, micro judgment calls that lets them close the loop on task ownership. It prevents them from being agile and innovative.

After a point, managers become the ringmaster to a circus full of monkeys. That's what most "AI-powered crap-a-lytics" platform companies are these days.

as an IC:

• get into the habit of asking the best questions, not having the best answers. Zoom in, Zoom out, see how it affects other stakeholders, see if it's aligned with both organizational charter and goals or not.

• get into the habit of aggressively self-reporting in terms of impact. Dissuade from I did X,Y,Z this week to "X led to $ impact, a % uplift from last Q. To reach our target of double-digit %, A,B,C are blockers".

• get into the habit of building dashboards, or leveraging existing ones. or even excel models. Do scenario analysis, and anything else that's needed. Quit blind execution; focus instead on empowering leaders to make decisions. In conversations like that - you understand the business pipeline better.

• get into the habit of understanding details, especially if something lies outside of your core competencies. It signals a lot of polish in your work. If you're dealing with data, or tech or APIs or whatever - get under the hood. In cases where things go south - you'll know exactly what went wrong. As an IC, this is a very strong signal of true ownership.

Even in cases where you don't have a lot of decision making due to organizational politics and dynamics - following the above recipe should earn you a lot of street cred. In your very localized environment, it will truly teach out how to make decisions.