Simplifiers and Complicators

The best career-advancing framework anyone is ever going to give you

A few months ago, my VC friend Mike Troiano shared maybe the best short LinkedIn post I’ve ever seen. Here it is:

God, that’s great.

Forget the productivity hacks, morning routines, tech stack recommendations, and strategic cheat-codes.

That right there is the best career advice you're ever going to get.

So what does it really mean to “be a simplifier?"

To me, it boils down to three core behaviors.

1. Answer the question.

2. Find the problem.

3. Do the work.

1. Answer the Question.

There’s a great Dave Kellogg blog post titled “The One Key to Dealing with Senior Executives: Answer the Question”. I think about this article every time I’m 20 minutes into a 30-minute call, and the other person still hasn’t gotten to the damn point yet.

I get impatient. I get frustrated. I start to question how well the person I’m talking to is doing their job when I’m not around.

And guess what? I’m not alone. Senior execs are wired to think in questions, and when they ask one, they want a direct answer — not a recap of the past six months or a list of obstacles.

There’s no quicker way to earn credibility at work than by giving senior people concise answers to their direct questions. And there’s no quicker way to erode your credibility than by denying those same senior people what they spend their very expensive time hunting for: Answers.

In case you can’t tell, this “answer the question” flavor of simplification is important to me. And I’ve made it important for my teams, too. When I was running consulting teams at Bain, I had a catchphrase I would use while preparing for big group presentations: Stick the landing. Sticking the landing meant delivering your answer with confidence and emphasis, and then shutting up and letting it sink in. It’s about punctuating your point - the answer the important person listening to you is waiting for - like a gymnast sticking the landing of a perfect dismount.

One of my best consultants ever still uses that cue — for herself and her team. Why? Because it’s memorable. Because it’s fun. Because it works. Photo evidence below - the better part of a decade removed from working together.

So whether you use the stick-the-landing trick or not, remember this simple heuristic. When in doubt, just answer the question. Please.

2. Find the Problem.

Here’s the thing: Most people are just afraid to point out problems. They’ll beat around the bush, list what’s challenging about what’s going on, relive in gory detail all the work they’ve put in so far, and, in general, make a lot of noise — all to avoid taking a real stance on what needs fixing, and how much work is really left before it’s fixed.

Simplifiers cut through all that. They name the problem and diagnose the core issue that’s in their way. They’re clear - both about what’s going on and what we should do about it. This isn’t hard on paper, but in practice, it takes smarts and guts to say, “This is the problem, and this is the fix.”

Too often, people stop short of that declaration. And on some level, I get it. They don’t want to be exposed for missing something, or to be on the hook for being wrong. But that’s the difference between simplifiers and complicators. Simplifiers take ownership, make the call, and get things moving. Complicators stir up dust and wait for someone else to point the way forward.

Most good strategy is about overcoming obstacles. And the quicker you point the obstacle out, the clearer the path around it becomes.

That’s what simplifiers do.

Find the problem. Name it.

Then clear the path.

3. Do the Work.

There’s a moment in every project when it’s time to stop thinking and start doing. Unfortunately, this is the moment that otherwise brilliant people get tripped up. It’s also the moment where otherwise good ideas die on the vine. Not because the ideas aren’t good. Because they never leave the whiteboard.

This is the moment where complicators get stuck. It’s easy to pitch big ideas, draft plans, and talk in circles about what needs to happen. But at some point, you need to just do the work.

That phrase is also the title of one of my favorite books. In Do the Work, Steven Pressfield puts it bluntly: “Start before you’re ready.” Simplifiers live by this rule. They don’t overthink. They don’t wait for permission. They dive in, get their hands dirty, and figure out the details as they go.

You know that feeling when you ask someone for an update, and they respond with, “That’s already done”? That’s the hallmark of a simplifier. They move the ball forward, cross things off the list, and, most importantly, don’t stop and wait for someone else to tell them what’s next. They understand that progress beats planning every single time - even if that progress occasionally gets a little messy.

When a simplifier is around, you won’t find them theorizing for weeks or saying, “Let’s revisit this next quarter.” Instead, they’re saying, “I shipped it last night.”

I love people who shipped it last night.

Final Thoughts

Most people are complicators, not simplifiers. Why?

Because complicating is easier.

Complicating keeps you safe.

It’s safer to hedge your bets and keep things in “draft.” Safer to hide behind analysis than to take action. Safer to stick to planning, where you can’t be judged for what’s done or not done. Safer to avoid putting your name on the line.

Complicating things is how you avoid putting yourself out there. How you avoid the discomfort of shipping something imperfect—and the responsibility of owning the result when it’s done.

Simplifiers reject that.

They make a call and get on with it. They don’t sit in the safety of ambiguity; they wade into the mess, solve the problem, and move forward. They know done is better than perfect because done is progress. Done builds momentum. Done wins.

That’s why simplifiers are the ones people notice, trust, rely on, and promote.

So, next time you feel yourself drowning in complexity, ask yourself: “Am I avoiding the work?”

If the answer’s yes, that’s your cue to start simplifying. To stop talking. To take the work, own it, drive it, finish it, and then move on.

Because here’s the truth.

Simplifiers don’t just say less. They do more.