Are we just too nice as leaders?

I’ve been thinking about this a bit lately, especially around sales teams & leadership and especially in NZ and Australia.

Are we sometimes just too nice?

I’m not talking about being kind, fair or decent – I’m all for those things. I mean nice in the way that avoids tension. Nice in the way that smooths over something that probably needs to be addressed properly.

I’ve done it plenty of times.

When you genuinely like the people in your team, when you know what’s going on in their lives, and you understand how hard sales can be, it’s very easy to soften things. You see the numbers aren’t quite there, but instead of saying that directly, you go in sideways. You ask how they’re feeling about the pipeline. You talk about effort. You mention that things will probably pick up.

All the while knowing the standard isn’t being met.

For a long time, I thought this was good leadership. I told myself that being supportive meant cushioning the message, and that if I pushed too hard, I might knock someone’s confidence or damage morale.

What I’ve realised over time is that avoiding the hard conversation doesn’t protect anyone. It just postpones it.

When expectations aren’t completely clear, or performance isn’t measured consistently, people start filling in the gaps themselves. They’re not quite sure where they stand. And as the leader, you feel it more than anyone because you know you haven’t properly drawn the line. You carry that tension in the background.

I started to see accountability differently. I used to associate it with pressure and confrontation. Now I see it as structure, and when it’s done properly, structure actually gives people room to breathe.

When someone knows exactly what good looks like, what activity is expected, which numbers matter and how they’re tracking against them, the conversations get simpler. There’s less emotion in it because you’re not debating opinions. You’re looking at agreed standards and facts.

The best sales environments I’ve been around aren’t the ones constantly talking about culture and positivity. They’re the ones where performance is visible and feedback is normal. Not aggressive or harsh, just clear and consistent.

Too often, leaders tiptoe because they don’t want to upset anyone. They don’t want to be seen as the bad guy. So they avoid saying, “That’s not good enough,” or, “This role requires more than what we’re seeing.” They hope things will improve on their own.

The problem is, high performers notice. And they don’t love it.

The best salespeople actually like standards. They want to know where the bar is. They want to understand how they compare. They respect leadership that is clear rather than vague, even if it’s uncomfortable at times.

Accountability isn’t about catching people out. It’s about creating ownership. When someone truly owns their pipeline, their activity and their outcomes, they don’t need constant chasing or weekly pep talks. They need clarity and consistency so they can take responsibility for the result.

The more structured and accountable the system becomes, the less stressed the leader feels. You stop carrying everything on your shoulders. You stop guessing whether it’s going to be a good month. You stop having performance conversations that feel personal, because they’re grounded in agreed expectations.

Looking back, some of my “nicest” moments as a leader were really just me avoiding discomfort. I thought I was helping, but in reality I was protecting myself from saying what needed to be said.

There’s a big difference between being kind and being overly nice.

Kind leaders care about people and hold standards.

Overly nice leaders care about people and avoid standards.

Only one of those creates long term freedom for the business and for the team.

So it’s probably worth asking ourselves from time to time – are we actually being supportive, or are we just being too nice?