The #1 skill every executive should have

Working “high” gets you promoted. Working “low” keeps you from getting laid off. The combination is your new superpower.

👋Hi, it’s Greg and Taylor. Welcome to our newsletter on how to make high-stakes professional and personal decisions in your 30s.

Read time: 10 minutes

I get asked all the time: how do I get to the VP/exec level at my organization? 

I’ve promoted a lot of executives, worked with a lot of executives, and – yes – fired a lot of executives. I always appreciate executives that can get the job done from quarter to quarter, but I love executives that can work high-low. These are the people that I want to work with again and again – because they can find leverage in their work that pays off for the business a year or more later.

Working high-low means you’re able to think and produce across multiple time horizons. You’re balancing initiatives to grow the business over 2 years, hit your plan in six months, and deliver on the most important tasks of the week.

Most near-VPs envision a role where they can just work “high” (think big, set strategy, tell others what to do, etc.). It doesn’t work like that. Without going high, you’ll never get to the leadership team – but without staying low, you’ll be the first laid off because you cost too much.

Learning how to work high-low took me years – and I am still getting better and faster at it. There are some shortcuts (like b-school, work as a management consultant, or in a role like Chief of Staff). But most of us learn this on the job (like Taylor). So here’s our guide on how you can get good at it.

– Greg

What “working high-low” looks like

High-low employees can move quickly between work of different weights.

To work high, you need to:

1. Have a POV about the future (of your product, team, role, company) 

2. Get work started that won’t pay off for a year or more

3. Ask “why?” a lot

4. Make bets and be okay with the associated risk

To work low, you need to:

1. Know your progress against key metrics (monthly revenue, NPS, etc.) and adapt quickly to meet them

2. Know enough about your team’s work that you can, and do, jump in to help

3. Kickstart projects yourself when needed (write the brief, scope out V1, etc.)

4. Know what good (and bad) work is when you see it

The sweet spot is doing both types of work at the same time. 

Here are a few examples — let’s take a marketing leader.

A great marketing leader excels at the low. They know their progress against the month/quarter, and the campaigns and strategies they’re deploying to get there. They delegate to their teams, but their standard for quality comes through in the team’s work. 

They also have a slate of growth experiments in the works, and can kick start their team with a strong brief or V1 where needed.

They also excel at the high. They’re constantly thinking about larger growth levers, something that could not just hit the plan, but get sales 50% above plan. They’re communicating this need to the team and setting in motion higher-risk tests that could unlock larger growth. They refuse to allow short-term targets and deadlines to prevent these tests.  

High-low work can also be broken down by project or topic.

Take AI – right now, almost every leader should be running AI pilots inside their team, looking for 10% productivity savings. This is low work. 

These leaders should also be thinking through how their team’s mandate and impact could be completely changed by AI in a year…and launching pilots to test this potential. This is high work.

Most people excel at one or the other

The “low-working” executive (aka, the doer who can’t prioritize bigger bets)

A “low-working” executive spends too much time on their monthly commitments, and not enough time thinking about how to transform the business. These leaders shy away from taking larger bets because they’re worried about putting the short-term plan at risk.

They might think they’re working “high” because they have experiments in the works, but true “high” work is about finding leverage that pays off a year or more later.

Prioritizing this type of work is hard. If you’re a high performer, you’ve probably spent your career perfecting low work. But to get to the VP level, you need to go beyond short-term execution and take these risks yourself, knowing that some or many of them won’t pan out. 

The “high-working” executive (aka, the big thinker with no output)

You probably know a leader that only works high. They spend a lot of time strategizing, white boarding, “vision-ing” … and they never seem to actually do anything. They’ve got big visions for the team/company, but they lack the day-to-day focus to execute. 

It’s common for high-working VPs to slip through the interview process, because CEOs can be impressed by long-term vision and cool ideas. But these people are the first to get laid off. They’re expensive, and they’re less essential to running the business than your average manager.

The high-low executive (aka, indispensable) 

Working high-low at the same time is difficult – mostly because you don’t get additional bandwidth to work high. Planning larger bets without clear payoff is hard when you’re struggling to make the month or quarter.

Working high-low also requires lots of context switching. You don’t control when you’re required to think or act high-low. The best executives move between the two modes in the same conversation. Nothing frustrates a CEO more than hearing the details of low work when they’re asking about long-term plans. But a VP who doesn’t know the monthly numbers is equally useless.

Becoming an executive is about increasing the ratio of high to low work, without completely losing sight of the low work.

How to practice working high-low

Most high performers excel at “low” work – so we’ll focus on getting better at “high” work, especially since it’s hard to prioritize. 

First, audit your existing work. Ask these questions:

• What problem could I solve that would benefit lots of other teams inside the organization?

• What am I working on that could help us not just meet our targets, but exceed them by 50%+?

• What am I working on that won’t pay off in the next 6 months, but could pay off in 12 months? 

• If a disruptor is coming after our company right now, what are they doing that we’re not doing? (You can do this at the team level too – what is their marketing team doing?)

Then, put it into practice.

• Set aside 30 min each week and write down the challenges you see at your team, company, and industry levels

• Schedule regular (4x per year) discussions with your boss where you chat about longer-term challenges and avoid constraints (what would we do in an ideal world?). If your boss does not want to do this, then pick a co-worker or another leader in the org.

• If you work for a public company, listen to your CEO’s earnings calls or industry briefings 

• Use AI – ask AI to play the role of your CEO or a strategic coach with a 2-3 year time horizon. Use a prompt like: “I want you (GPT) to act like the CEO, and challenge me to think long-term about our product roadmap.”

Our advice

Working high-low is the hardest part of being an executive. Don’t feel bad if you’re not there yet – most execs index too far in one direction (including us – Greg a bit too high, Taylor a bit too low).

Honing this skill takes intention and time. And some patience, as you often need to invest this time on nights and weekends and not see any immediate benefit. This is one reason most of us default to low work – it’s visibly productive and can feel good. 

Don’t put this off because it’s hard or time-consuming. Practice now, and you’ll find yourself working “high-low” without thinking about it in a year. And if your current boss does not appreciate (or is threatened by) your high-low work, your next one will appreciate it. 

To the next 10 years,

Greg & Taylor