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10 Leadership Lessons from a VP

My big career dream was to become the CMO of a silicon valley startup. I wanted to go all the way up in the corporate ladder and help companies scale. It took me a decade, but I made this dream a reality, twice, and I want to share with you some of the lessons I’ve learned growing as a leader.


Here are my top 10 leadership lessons:


1. There is no one size fits all


People are unique creatures. We think differently, we feel differently and we react differently. That means we need different things in order to thrive at work. Some people need high level guidelines and others prefer to have the details. Some people need the why, and others want the how. I’ve worked with people whose love language was praise, and others who preferred compensation. Some people are motivated by challenges, others need reassurance.


To be a good leader you need to learn what your people need and deliver your message in a way that resonates with you. That doesn’t mean you need to be a million different people, you just need to tweak your approach a little to best serve them.

2. Praise should be earned. No trophies for participation


I know this is controversial but I think praising people for just doing their job is sending the wrong message. People deserve to be praised and recognized when they exceed expectations, when they make a big impact, when they step out of their comfort zone, when they create something new, not for the status quo.


If you praise everyone all the time your praise will become meaningless. If you praise people when they excel you will teach them to aim higher.

3. Do not tolerate C players


Every team will have A players, B players and C players.


The A players are your superstars. They can operate well with little guidance, they take initiative, they grow quickly and add a ton of value. They are easy to work with and you pray that they’ll never leave (and they always do because they want more).


Your B players are rockstars. They are very good at what they do and they enjoy doing it. They are responsible, always get the job done, and they are happy where they are.


Your C players are neither. They Are not great at what they do, they are not trying to learn and improve and you have to spend a lot of time trying to get them to do something. They are not bad enough to be completely useless, but their lack of contribution takes a toll on everyone else. They always complain, they become a bottleneck for others, and you end up cleaning their mess all the time.


You need to fire C players, or help them find a role that fits their needs somewhere else. C players have a negative ROI on your team. Letting them go will actually make your team more efficient.


(side note: I’m all for trying to help people grow and improve, but when they don’t want to try, it’s time to let them go).

4. Delegating is the best thing you can do for your team


I used to think that delegating is a form of punishment. If I am giving other people more work, isn’t it a bad thing?


Let me flip the script for you. How do you think I was able to grow from an IC to a VP? At every stage of my career someone was willing to delegate work that was outside of my scope. I was trusted to do work that was previously on their plate, and gain next level skills.


That is what happens when you delegate. You give your team members an opportunity to stretch themselves and learn something new. You are basically offering on the job training for the next level in their career.


Obviously there is a caveat. First, delegate something they want to learn and could actually benefit from. Don’t just dump grunt work. And second, don’t overwhelm people by giving them too much. One step at a time.

5. You are not a family, but you can be friends


Your employees are not your family, but that doesn’t mean you can’t be friends. I used to think that the more senior I am, the more distant I should be. I imagined being this cold hatred b*&$h who shouts orders and gets everyone on edge. So not me… I’m the “wear a t-shirt, bake cookies for the office, talk about my workout routine, share my favorite podcast and give you real feedback” kind of leader. What you see is what you get.


I don’t believe you need to be someone else in your private life and at work. I believe you can lead authentically and still earn trust and build rapport. You can hug people, be vulnerable, talk about life and still be a valued manager. It’s just so much more fun this way.


(when my awesome team surprised me on my birthday)



6. Hire outside of your league


This was one of the hardest things for me to do. It is quite intimidating to interview, not to mention hire someone who is better than you at what you are hiring them to do. You start thinking: will that make me redundant? If they are so good why won’t they take my place?


The answer is simple. You are only as good as your team. If you keep everyone at your level or below, you’ll be capping your team’s potential. If you hire people who are better than you, you’ll be 10x your team’s potential. 10 brains are better than one.


Hire people you are embarrassed to interview because they can teach you things you don’t know.


(and if you are not sure how to identify great when you see it, pay someone who knows. I was paid to interview candidates for other leaders).

7. Ask for help, you are not a superhero


The higher up you go the more you believe you should have it all figured out. Big mistake. We are all still growing and improving. In my first VP role I helped a company grow to the first few millions in revenue. In my second VP role, tens of millions. It’s a different experience that requires different skills. So while I built marketing from the ground up before, I need to get more experience around scaling. I had a coach for that. I was not expected to just figure it out. As the company was growing, I had to grow with it to become a more seasoned leader.


You can ask for help. You can get a coach, a mentor, join a community, tap into your team, or even take classes. You are not supposed to have it all figured out all the time.

8. Align on what success looks like, not how you get there


My way or the highway is not a good leadership strategy. When I became a manager I thought that the best way to get anything done is the way I would do it. But you know what? There is more than one way to get the result you want. And sometimes, it’s even better.


As a leader you need to make sure your team is aligned on what success looks like. They need to have a shared vision of the end result, but you should give them the freedom to set the course to get there. You can guide them and offer feedback, but they should be able to choose the execution. Two things will happen when you do that. First, your team will be so much more committed and engaged. The second thing that will happen is that you’ll get to learn new things and expand your perspective.

9. A coffee chat is worth 1000 emails


Whenever I was having big issues with a team member it usually boiled down to communication. Things can get lost in translation, especially over email. Sometimes picking up the phone or taking someone out for lunch can save you hours of frustration.


Especially now that so many people work remotely, take the time to be a human and talk to people. Get to know them on a personal level and you will quickly see most of your problems disappear.

10. Admit your mistakes and own them


Everyone makes mistakes, even leaders. Even CEOs. Even board members. No one is perfect.


The difference is some people hide their mistakes because they think the only way to lead is to be high up on a pedestal. They think admitting their faults will hurt their authority. In my 15 years in the corporate world I found the opposite to be true. Vulnerability is an asset, not a liability. People prefer to work with a leader who has humility, not someone who shifts blame to keep their image clean.


When I made mistakes as a leader I admitted them. I explain to my team why I made the decisions I made and what happened as a result. I don’t make excuses, I make plans to help me avoid repeating the same mistake. It is what I would expect my team to do, so I lead by example.


I have learned so much throughout my career, and I’m still learning and improving. Not sure I'll ever be done. The one thing I know for sure is that in my book being a great leader = being a great human.

I believe in you and I’m rooting for you.



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