15 Pieces of Advice That Will Make You a Better Leader

Leadership is a hard job, but it's not a complicated one. At its core, it's about communication, honesty, and empathy. It's about connecting with people, and learning how to work together towards a greater purpose.

Learning to become a better leader often looks like learning to become a better person. You have to set the tone, lead by example, and think about the impact of your actions on the people in your charge. While this list is hardly exhaustive, this is some of the advice that has helped me in my career.

1. Communication is a Superpower

Effective communication is a hard soft skill to master, but it's also the most important one for your career growth.

Joel Spolsky says it best here: "The difference between a tolerable programmer and a great programmer is not how many programming languages they know, it's not whether they prefer Python or Java. It's whether they can communicate their ideas."

If you can't find a way to get your point across, either written or spoken (I'm a fan of written), then you will have nothing but uphill battles to fight.

So learn to write.

Start a blog. Send out a newsletter. Sign up for Medium, or HackerNoon.

Get your reps in while you can.

It's never too early to practice.

2. Building Trust is the First Priority

"If you walk into a meeting with your boss always on your best behavior and unwilling to speak your mind, I say something is broken." — Michael Lopp

I love this quote, but it's important to understand that it goes both ways.

If you are a manager and your direct reports always seem to be positive and agreeable, then odds are you haven't built up enough trust in your relationships.

Trust isn't demonstrated by equanimity. It's demonstrated by honesty; and honesty isn't always calm and collected.

When your team isn't venting to you, it doesn't mean everything is going well, it just means they're venting to someone they trust more.

3. Know That You Don't Know Everything

Humility is one of the most underrated leadership skills.

If you can't own up to your mistakes, then you can't truly learn from them, and if you can't learn from your mistakes, then those who look up to you won't be able to either.

Because, in the end, it's not about you. It's about the team as a whole (which is kind of the whole point of humility).

The price of leadership is not perfection, but education. You teach people how they are expected to act by your own example, and the most powerful examples you set will be during times of adversity, not prosperity.

4. Ask More Questions

Speaking of not knowing everything, good leaders aren't know-it-alls, nor are they expected to be. Good leaders are enablers. They ask the questions nobody else is asking, not to prove a point or because they are struggling to understand, but to make sure everyone is speaking the same language.

Your mental model of a solution might not be the same as mine, and by asking questions, we are making sure that we are not only on the same page, but that we are considering all angles.

You'll never know everything you need to know, and neither will your team, so don't be afraid to ask the dumb questions.

Better yet, model it and help create a culture of innate curiosity, not knowledge supremacy.

5. Listen, Then Speak

You have two ears and one mouth for a reason, so speak less and listen more.

Listen to your partners. Listen to your leadership. Hell, listen to your gut.

But more than that, listen to your team. I promise, they know more than you do, if only you'd shut up and let them speak.

Being a leader isn't about being the most brilliant person in the room. It's about making sure the most brilliant person in the room gets a voice, which more often than not means giving them permission to be brilliant (and then getting out of the damn way).

In the end, you have to want to help your people succeed more than you want to do the succeeding yourself.

6. Prioritize

If everything is a priority, then nothing is.

I get it. Prioritization is hard. Everything is important to someone, and balancing those competing priorities can feel overwhelming, so we start saying "yes" to more than we should.

"Yes" to what matters.

"Yes" to what doesn't.

"Yes" to everything, until we're so buried that we end up spending half of our time reacting and the other half making excuses.

The thing is, every "yes" is a "no" to something else (most notably your sanity), so start getting opinionated about what matters and what doesn't, and be clear about what the tradeoffs are for every "yes."

You can't make everyone happy, but unless you learn to balance your priorities, you can bet you will make nobody happy.

7. Don't Should Yourself

"Should" is one of those magic words that implies confidence and direction, but in fact achieves neither. It's a way that we can get credit for our ideas, without having to take the risk of implementing them.

When you use phrases like "we will" and "I'm going to" instead of ones like "we should," you are setting yourself up for the possibility of failure, and that can be scary.

Nobody owns "should." It's safe. There's no accountability. But if you want to create a place where "should" becomes "will," you have to give people permission to take a stance. To take risks. To try, and fail, and try again.

As Ryan Holiday wrote in his book, Courage Is Calling, 'the world does not care about "should."'

8. Write Everything Down

One of the biggest mistakes I made early in my management career is thinking that I could hold everything I needed to know, do, and process in active memory.

I didn't have a habit of taking notes, because as a developer I didn't really have to. At least not on a minute-to-minute basis. The work I had to do was the work that was planned or immediate, and any collaboration resulted in real-time action.

But a big part of management is balancing a lot of threads happening all at once. You are a connector, making sure the right information gets to the right places; you're a janitor, keeping the path clear for your team; you are the face and voice for a group of people; and (sometimes) you're a crystal ball.

Keeping track of it all without building a healthy note taking habit is impossible. You might be able to get by in the short term, but over time your ability to keep the train on the tracks will get compromised by the real-world limits of your brain.

Not a natural note taker? Then make it fun.

Spend some coin on a nice notebook and pen, enough that you feel guilty not using them. Buy something personalized, or weirdly shaped (triangle-shaped notebooks are going to be all the rage in 2024).

Hell, get a fancy tablet with a digital pen so it can pull double duty as a YouTube player in boring meetings.

It doesn't matter how you do it, just that you do it.

9. Don't Use False Comparisons

A company is not a family.

I've recently seen marriage used as a metaphor for hiring ("date a little first before you put a ring on it!"), but that is dumb.

Hiring is not like marriage. It is simply nowhere near the same level of commitment, and implying as much is disingenuous.

You can't just fire your spouse when they are under-performing, or lay off your kids when things get tough—and if you feel like pointing at divorce as an equivalent concept, I don't see companies giving employees half of their assets or negotiating visitation rights with the source code when they let someone go.

As Reed Hastings said in his excellent book, No Rules Rules, "we're a team, not a family."

Hiring is like tryouts.

You have to make sure someone can do the job and raise the bar for the team—both culturally and technically—but in the end all you're doing is establishing a professional relationship.

Neither of you are walking down the aisle.

10. Leadership Implies Followership

Management isn't leadership. It's management.

The two words are often used interchangeably, but it's important to recognize that they are very different.

Management is a job. Leadership is a trait.

Leadership doesn't require direct reports, or a fancy title, or spending 12 hours a day in meetings. Leadership only requires behavior that inspires others to follow.

Everyone has the capacity to be a leader; to take the first step on a long journey; to be an example to others.

Everyone, including you.

To quote Michael Lopp of Rands in Repose fame:

"Leaders lead. No matter what."

11. Respect Everyone's Time

You're not fooling anyone with your 25 minute meeting lengths.

Everyone knows that 5 minutes you "saved" is just an illusion. It'll end up getting absorbed by idle chitchat, or poor meeting etiquette, or plain 'ole lack of attention to the clock.

Every minute you hold people in a meeting is a minute they can't spend doing something potentially more valuable.

So take that responsibility seriously.

If you called a meeting, It's up to you to maintain the length and pace. Pleasantries are okay—human connection is important—but respect the people and the clock.

Set and share an agenda. Take notes. Hold to the time.

Does the meeting look like it's going to go long? Call it a few minutes early so you can decide on next steps as a group. Don't go long just because you can.

Just remember that 25 minutes means 25 minutes. Not "25 minutes + 5 minutes just in case."

12. Always Be Learning

You can't learn what you think you already know.

The best habit you can develop this year is not just challenging your assumptions, but recognizing them in the first place.

Your blind spots are your biggest risk as a leader. They are always going to be the source of your biggest failures. The things you think you know, that you think you are doing well, are exactly where you are most likely to get burned.

So take a few minutes and take stock.

What are you taking for granted? What haven't you prepared for?

Chances are, you'll find something that needs to be addressed immediately.

13. Create Balance

Do you have a shutdown routine?

About a year-or-so ago, I started having trouble making the transition from work-mode to family-mode. I'd bring home the baggage of the day, and found it difficult to leave it at the door until the next morning.

Hyper-focusing on what problems cropped up during your workday isn't a great way to connect with your kids.

After doing some research (also known as browsing the internet), I came across the concept of creating liminal spaces to metaphorically "move" from one headspace to another.

The basic idea is to create a routine, typically anchored in some physical activity, in order to signal to your brain and body that it's time to shift into a more appropriate mindset for whatever situation you need to be in.

For me, this became a daily ritual of solving a puzzle after finishing my work for the day, especially when working from home. During the day, I've taken to scrambling a Rubik's cube as I take meetings and work through problems. It's become a bit of a metaphor for the stress that can build up at work.

Then, once my day is over, before I can switch into family mode, I have to unscramble—also known as solving, but that word isn't as fun to say—the Rubik's cube. It's my way of taking all that stress and sorting through it so I can leave it behind and be fully present with my family when the day is done.

It doesn't always work, but it has been a lifesaver more times than I can count.

What about you? Do you have a shutdown routine like this?

14. Find the Meaning

Performance metrics without context are pointless.

The lines of code you write, the commits you make, the number of pull requests you open, your work in progress, your cycle time, your code coverage, your <insert metric here>...

These things are all useless in the abstract.

At best, most metrics are a signal that something is happening, but it is up to you as a manager to figure out what that something is.

Why does this number look this way? What are we truly measuring? How is the team feeling? What happens if we do something else?

The numbers are just facts, but you have to ask questions so you can turn those facts into real knowledge.

"Not everything that can be counted counts, and not everything that counts can be counted." — Albert Einstein

15. Care About People

Think management is the next step in your career, but not sure if you can make the leap?

Start by asking your self one question: "do I care about people?"

If the answer is "yes," then you will be okay.

Granted, there is a lot more to management than caring about the people you lead and work with, but true success in leadership hinges on your empathy and compassion.

You can learn all of the other, non-humany things, given time and mentorship, but if you don't care about the people you lead, then you'll never earn their trust or respect.

And if you can't build trust, you're not leading, you're dictating.


If you like this post or one of my projects, you can buy me a coffee, or send me a note. I'd love to hear from you!


This is post 052 of #100DaysToOffload