The first significant opportunity I ever had to flex my leadership muscles was when I was hired to run the concierge team for a luxury hospitality brand in Hawaii. I know, relocated to Hawaii, sucks to be me, right?

I managed a team of about fifteen people spread over two resorts, and I was part of a wave of managers brought to the island to re-brand this resort under the new management. This is an important detail because the circumstances surrounding my arrival automatically branded me by my staff as “one of the new white guys from the mainland who are here to tell us how to do our jobs.” (Note, the “mainland” is what many Hawaiians call all those other states that touch each other).

If you haven’t been lucky enough to spend any quality time in glorious state of Hawaii, it’s important to know that race (like many places in the US) plays a significant role in day-to-day interactions and politics. For many on my team I was just one of a long line of white guys brought in from a big city to manage them. I was aware of this dynamic when I took the job and felt up to the challenge.

I wanted to overcome the stereotype I was going to be measured against and work to have my team genuinely know me and trust me as a person.

The first few months I did what I thought all managers should do. I just listened, observed, and asked lots of questions. My goal was to be inquisitive and engaged without trying to assert myself or my ideas too quickly.

Starting around month three I began to lead with more vision and fervor — coaching guest interactions with my team, working to improve communications and technology. Much of my work was done one-on-one helping each staff member improve their skills to better serve the high expectations of our guests.

I did my best to be empathetic, respectful, and patient, knowing that it was going to take time to build mutual trust and understanding. For months I got nowhere.

The staff seemed to be listening and engaged, but my efforts weren’t moving the needle at all. I felt like I was sprinting in place on a treadmill — exhausted but somehow motionless.

Unsure what I was doing wrong, I sought the advice of a colleague who had worked at the resort for many years and was very well respected by all. She asked about what I had been doing, so I gave her the complete run-down. She must of smelled the desperation on me as I spilled my guts about how hard I was working and how little progress I had made.

Then she asked, “During your one-on-one meetings, when do you ask your staff about themselves?”

“Um, what do you mean? All we do is talk about how they are performing at work.” I said.

She gave me that knowing look and repeated, “No, when do you talk to your team about their personal lives?”

“Their personal lives? You mean like their families and kids and stuff?” I asked, a little perplexed.

“Yes. Oh yes.” She said. “This is a small, very close community, so they need to know that you’re invested in them personally if you want them to trust you. It will let them know that you’re not just here to do the job, but are also here to participate in our lives.”

I thought “shit” — well that makes perfect sense. Why didn’t I think of that before?

My team wasn’t really hearing me because I hadn’t taken the time to truly listen to them. I was listening for the things that were important to me, but I learned that it was even more important to listen for the things that were important to each of them.

This was my first (of many) hard-won lessons in leadership during my time in this position. And it’s a lesson that has stuck with me in every leadership role I’ve had since.

You have to meet your team where they’re at. You have to learn enough about each individual you manage to approach them from a position of equality and understanding. If you can’t see them as a person before an employee, you have absolutely no chance of building real trust.

Without a foundation of mutual trust, the most you can become as a leader is really just a glorified bully. (Yikes, tough words Michael!)

So how do you know when you’re not meeting your team where they’re at?

How do you know if you’re a crappy leader?

Here are a few absolute RED FLAGS that will tell you if you are disconnected from those you are meant to lead. These are warning signs I missed during my early days as a leader. I share them with you so you can learn from my mis-steps and grow into the leader your team deserves. Let’s do this!

1. You are making all the decisions.

Yes, leaders need to make lots of decisions. But if you are making all the decisions, I’ll lovingly suggest that you’re f*cking it up. In my early years as a manager I f*cked this one up all the time. I thought leading meant making all the decisions and commanding my minions to do my bidding. Boy was I wrong!

Does every decision at your facility have to get passed through you first? Are members on your team scared to make decisions without your consent? Do you react negatively when decisions get made that you disagree with?

If that sounds like you, then listen up.

Your team will only start to trust you when they start to believe you trust them. The fastest way to building that trust is to give them some autonomy and decision-making power. Give them space to do their best and sometimes fail.

I’ll admit, this one is tough for me. I have super strong opinions about many things and it’s hard to relinquish that power to others. As MFF has grown, it became abundantly clear that I couldn’t make every single decision every day. It would be impossible and a really crappy use of my time.

So I work hard to pick my battles. I delegate as many decisions as possible and save my veto power only for the things that are absolutely the highest on my give-a-shit-o-meter. On a scale of 1-10, I have to give a shit around an 8 or higher to really swoop in and make the final call.

For some of you it will be scary, but give it a try. Your relationship with your team will improve as your ability to trust them increases.

2. Your team doesn’t actually look at you when you’re speaking.

Are you ever in a team meeting and notice that folks are having side conversations or doodling on some paper, or avoiding eye contact with you at all costs? For my first few years as a manager, that’s what most of my meetings looked like.

It is a clear sign that your team doesn’t think you are worthy of their attention.

Sorry if that stings a little, but it’s true.

If it happens once, probably not a big deal. But if on a regular basis you notice that you don’t have your team’s full attention when speaking, you have some work to do.

Now, there are lots of reasons this could be true — maybe there is a lack of trust and respect, maybe your meetings are organized ineffectively, maybe you’re just a boring speaker (go to Toastmasters!).

Regardless of the reason, this is a clear sign of a gap between you and your team.

First, acknowledge it without being accusatory. Maybe something like — “Hey guys, I’ve noticed in meetings that I don’t seem to have everyone’s attention. I see some of you on your phones, some of you having side conversations. I’m not mad. No one is in trouble, but I’d love to talk about it because it feels like we’re not on the same page. Any suggestions for what I can do differently?”

Keep the tone light and curious, so your team doesn’t feel like they’re being reprimanded. Then, listen to what they have to say, even if you don’t like it (especially if you don’t like it!).

Next, create a shared vision. After gathering feedback from your team, work with them to create a shared vision of how you would like both parties to show up. Perhaps they want you to be more succinct and provide a clear agenda, and you ask them to put their phones away and limit side conversations.

See what’s happening?

You have just recognized a gap that exists between you and your team, shined a bright light on it so it can be discussed, then created a shared vision of what it can look like moving forward.

That’s leadership!

3. You haven’t heard about anything that has gone wrong in a few weeks.

In my first few month is Hawaii, my team never once came to me with a problem. We had many challenges and things were going wrong every day. My team would talk to each other about their troubles (they would even talk to other managers), but they didn’t come to me. I didn’t know this was a warning sign at the time.

It wasn’t until I proved to them that I was able to be helpful and supportive without judgement that they started to trust me with their problems. Once they knew my reaction to a challenge was calm focus and resolve (not screaming, yelling and blaming), they started to treat me like a valuable resource instead of a scary boss. #Priceless

When was the last time a team member came to you with a challenge? Are there some members of your team that never bring problems to you or ask for support?

If it has been weeks (or months) since someone on your team has come to you for help it could be a sign that your team doesn’t feel comfortable coming to you when things go wrong. Maybe they’re afraid of how you’ll react. Perhaps they don’t think you have the skills to solve the problem.

You don’t know what it means yet, but in my experience it points to a disconnect between you and your team. Another gap that must be addressed.

When your team is not comfortable coming to you with a problem it’s a big effin’ deal.


It means you could be the last to know about something that is broken, dangerous, or not working. It means that people on your team could be hiding situations that require immediate attention. When this kind of communication breaks down, it becomes a very slippery slope to bankruptcy (That might sounds dramatic, but I think it’s true).

When something goes wrong we all know that humans have a flight or fight response.

In the workplace, we sometimes refer to this as silence or violence.

I strongly prefer violence on my team. Haha. And by that I mean verbal fighting and tension. At least when my team is arguing and disagreeing I can see it. It’s visible and we can talk about it. What gets seen gets managed.

When members of my team turn to silence, we’re f*cked. There is nothing to see, so we can’t manage it.

If something has gone wrong and a team member isn’t talking about it, and they’re especially not talking about it with me — I’m just in the dark. No one can lead from the dark. Leadership is all about shining light on what is most important.

Therefore, silence is a critical red flag that leadership is lacking or absent.

So what do you do as a leader to ensure that your team trusts you enough to ask for help?

Firstly, you tell them. You tell them again and again and again that you are there to support them every step of the way. They can never hear it enough.

But most importantly you show them that you are available by having a true open-door policy, by greeting their requests for help with warmth and positivity, by remaining calm and non-judgmental in the face of challenges both big and small.

When your team witnesses your ability to handle their challenges with strength and grace, they’ll learn to trust you. You’ll become the first to know when things go wrong and will be able to lead your company from the front instead of sitting silently in the rear.
Now, go lead! Your team is waiting for you!
Got a second to share a story about your challenges as a leader?
I’d love to hear from you in the comments below.