Nice Leaders Finish Last
The Uncomfortable Truth About Effective Leadership
Here's a hard truth: If everyone in your organization loves everything you do as a leader, you're probably NOT doing your job effectively.
Let that sink in for a moment. Go ahead. I will wait…
After two decades of scaling teams and transforming organizations, I've learned that being universally liked and being an effective leader are often mutually exclusive. Today, we're going to explore why sometimes you need to be the "jerk" – and why that's not just okay, it's necessary.
The Cost of Being Too Nice
Think about your last five significant leadership decisions. How many of them made everyone happy? If your answer is "all of them," we need to talk.
Great leadership often requires making unpopular decisions, having uncomfortable conversations, and standing firm when everyone else wants to take the easy path. Yet many leaders, in their quest to be liked, avoid these crucial moments.
Consider these scenarios:
Your sales team commits to features that don't exist
Quality standards are slipping, but nobody wants to address it
Technical debt is mounting while everyone chases new features
Team behavior is toxic, but it's "just how things are"
If you're avoiding addressing these issues because you don't want to be "that person," you're not leading – you're hiding.
When Being a "Jerk" Is Actually Leadership
Let's be clear: We're not talking about being mean or unprofessional. We're talking about having the courage to:
Stand Your Ground When your entire leadership team wants to skip critical maintenance work for the third quarter in a row, someone needs to be the "jerk" who says, "No, we're doing this now, and here's why." Your future self will thank you.
Protect Your Team When a VP starts publicly berating your team during a demo that didn't go well, you need to be the "jerk" who stands up and shuts it down – regardless of hierarchy or politics.
Maintain Standards When work isn't meeting quality standards, you need to be the "jerk" who sends it back, even if it means missing a deadline. Long-term excellence requires short-term discomfort.
The Leadership Litmus Test
Ask yourself these questions:
Have you said "no" to a senior leader this week?
When was the last time you made an unpopular but necessary decision?
Are you avoiding any conversations because they'll be uncomfortable?
Has anyone called you "difficult" for upholding standards?
If you answered "no" to most of these, you might be prioritizing being liked over being effective.
Your Action Plan for Appropriate "Jerkiness"
Identify Your Avoidance Areas Make a list of decisions or conversations you've been putting off because they'll be unpopular. These are your opportunities to step up as a leader.
Practice Confident Communication Stop undermining yourself with phrases like "I know this won't be popular, but..." Instead, state your position clearly and confidently. You're not apologizing for doing your job.
Set and Hold Boundaries Establish clear standards and processes, then hold everyone accountable – regardless of their role or how uncomfortable it makes you.
The Path Forward
Here's your challenge for this week:
Identify one situation that needs addressing but you've been avoiding
Draft your talking points without any qualifying or apologetic language
Schedule the conversation for tomorrow (no delays)
Follow through, regardless of how uncomfortable it feels
Remember: Your job isn't to be liked. Your job is to:
Protect your team
Maintain standards
Ensure long-term success
Make the hard calls
Stand firm when needed
Sometimes that means being the "jerk" who:
Sends back subpar work
Enforces processes everyone wants to skip
Calls out inappropriate behavior
Says "no" to powerful people
Demands better when "good enough" isn't
The Bottom Line
Leadership isn't a popularity contest. The best leaders understand that being momentarily disliked for doing the right thing is part of the job. Your team may not love you in the moment, but they'll respect you in the long run.
So ask yourself: Are you being "jerky" enough? If everyone always loves your decisions, probably not.
To your leadership evolution,
Josh Anderson
Editor-In-Chief
The Leadership Lighthouse
Want to see this conversation in action? Watch as Bob and I discuss real scenarios where being "too nice" actually hurt teams and organizations. Sometimes leadership requires having the courage to be the "jerk" - for all the right reasons.
Ready to be more effectively assertive in your leadership? Want to discuss specific situations where you need to take a firmer stance? Let's connect. Sometimes you need someone in your corner supporting your decision to be the "jerk" when necessary.
Share your experiences with making unpopular but necessary decisions. When has being the "jerk" ultimately led to better outcomes for your team?
Yes, it is true that being a great leader means that sometimes you have to make someone unhappy.
I don't think that qualifies as being a "jerk", but I get the point
However, there's a deeper topic you raise that does not get addressed here, which is "what kind of a leader do I want to be?"
This may seem high-level, but let me make this more clear:
- Do I want to be a tech-focused leader, at the expense of career progression elsewhere?
- Do I want to be a more product-focused, at the expense of losing credibility with the engineers in my team (but gaining it elsewhere)?
- Do I want to be sales-positive, or do I want to push back when sales people come to me with impossible requests? This, of course, has career implications as well.
- Do I want to be CTO, CPO, or CEO in the future? This - even if not possible - defines a lot of our stances when dealing with day-to-day topics in our Engineering organizations.
All in all, I get the "be a jerk - sometimes" point you make, but I don't think it goes deep enough. Maybe it gets clicks, but it does not really help develop our careers as leaders forward.
Being a "jerk" as you describe it, my be an entry point, but the real questions are: what kind of leader do I want to be, and do I keep myself accountable for that?
My advice to ANYONE, struggling with this question: get a coach! You will get better, your team will get better, and in the end your career will benefit from it! That advice was the single best advice I got for my career!