How to Shine as a Team Leader: Embracing Strong Personalities

Let me tell you something I wish someone had told me when I first became a people manager: the team members who push back the hardest are often the ones who care the most. It took me a few years in agency management to figure that out, and I wasted a lot of energy before I did.

When I first started managing teams in Singapore, I had this one team member — brilliant at her job, incredibly passionate, but every meeting felt like a debate tournament. She would challenge my decisions in front of the whole team, push back on timelines, and generally make me question whether I had any authority at all. I will not lie, it was stressful. My first instinct was to think of her as "difficult." That was the wrong framing entirely.

What I mean by "strong personality"

Someone who is independent, direct, and unafraid to voice their opinions. They know what they want and they go after it. In advertising (and in tech, from what I have seen since moving to the Bay Area), these people are everywhere — and they are usually your best performers. The issue is not their personality. The issue is whether you, as a manager, know how to channel it.

Why you actually want strong personalities on your team

I think a lot of first-time managers dream of a team where everyone nods along. I get it — it is easier. But from my experience, those "easy" teams tend to produce mediocre work. The best teams I have managed were the ones where people challenged ideas, debated approaches, and occasionally made me uncomfortable. That discomfort is where good work comes from.

Strong personalities prevent groupthink. They catch blind spots. They push the team to think harder. The trick is creating an environment where that energy is constructive rather than destructive.

What has worked for me over the years

On communication

Set clear goals early. I learned this the hard way — ambiguity is fuel for conflict, especially with strong personalities. When everyone knows exactly what the team is aiming for and who owns what, there is less room for territorial disputes. In my current role, I spend more time on alignment at the start of a project than I ever did as a junior manager, and it pays off every time.

Create regular forums for input. Strong personalities need outlets. If they do not have a sanctioned space to voice opinions, they will find unsanctioned ones (like hallway complaints or passive-aggressive Slack messages). Weekly check-ins, brainstorm sessions, even a shared doc where people can dump ideas — these all help.

Be direct yourself. I have found that strong personalities actually respond really well to direct communication. They do not want you to sugarcoat things. They want clarity. If you are vague or wishy-washy, you lose their respect fast.

Listen actively. And I mean actually listen, not just wait for your turn to talk. I have this habit of repeating back what someone said in my own words — partly to confirm I understood, partly to show them I am paying attention. It works wonders with people who feel like they are not being heard.

On handling disagreements

Respect the opinion, even when you disagree. You do not have to agree with every idea. But you do need to acknowledge it. There is a big difference between "That will not work" and "I see where you are coming from — let me share why I think we should go a different direction."

Give specific, actionable feedback. Strong personalities hate vague criticism. "This could be better" means nothing. "The client will push back on this because X, let us try Y" — that they can work with.

Know when to flex and when to hold firm. This is the balancing act that took me the longest to learn. You want to show that you are willing to incorporate good ideas, regardless of where they come from — that builds trust. But being collaborative does not mean being a pushover. There will be times when you need to say "I have heard everyone's input, and here is my decision." Just make sure you explain your reasoning. Strong personalities can disagree with your conclusion, but they will respect you for having one. That Singapore colleague I mentioned? The turning point in our working relationship was a project where I accepted her approach on the creative strategy but held firm on the timeline. She pushed back hard, but when the project landed well and on schedule, she told me later that was when she started trusting my judgment.

Do not take it personally. This was the hardest lesson for me. When someone pushes back forcefully, it feels personal. Nine times out of ten, it is not. They are arguing for what they believe is the best outcome for the work. Once I started separating the person from the opinion, everything got easier.

On growth

Stay patient. Working with strong personalities is a long game. Trust builds slowly. But once it is there, these become your most loyal team members.

Keep your composure. When things get heated, someone has to be the calm one. That is you. Take a breath. Lower your voice. It de-escalates faster than any clever argument.

Involve them in decisions. Strong personalities want ownership. Give it to them. Let them lead a workstream, own a client relationship, run a meeting. (More on this in my post about delegating work based on personal strengths.) The more agency they have, the less they need to fight for it. That same Singapore colleague eventually led some of our biggest client pitches — once she had real ownership, the adversarial energy disappeared and she became one of my strongest advocates in the company.

Why this matters beyond work

I think learning to work with strong personalities made me a better communicator in every part of my life — including being a dad to Sophie, who at her age is already developing some very strong opinions of her own :P The skills transfer: active listening, staying calm under pressure, respecting different perspectives. It is all the same muscle.

Have you managed someone with a strong personality? What worked for you (or did not)?

Cheers,

Chandler

P.S. You can check out additional tips I wrote about team management and leadership here.