You Can’t Mail Merge Engagement
The Human Way to Truly Connect as a Leader
Let’s be honest: mail merge isn’t engagement.
Years ago, I remember seeing those old-school marketing spinners—take six paragraphs of generic fluff, randomize three of them, slap in a “Dear Phil,” and boom—instant personalization, right? Wrong. We’ve all seen that kind of lazy automation in email, but guess what? That same mindset doesn’t work for employee engagement either.
You can’t “just add water” and suddenly have connection. You can’t fake being present. And in leadership, that’s a costly mistake.
If you want real engagement from your team—connection that drives performance, loyalty, and trust—you have to lead differently. You have to go beyond processes and dive into the personal.
And for that, I use the “Three H’s” of employee engagement: Human. Helpful. Humble.
1. Be Human (Go First)
This is where everything starts.
Being human as a leader doesn’t mean lowering your standards. It doesn’t mean being everyone’s buddy. It means being real. And that starts with vulnerability.
If we want people to share, we have to make it safe for them to do so—and the only way to create that safety is by going first. If you're not willing to take the first step in being authentic, you can’t expect your team to follow you there.
So be the one who opens up. Talk about your struggles. Admit when you don’t have all the answers. Show them that it's okay to be a work in progress. You model the behavior you want to see. That’s where trust starts to grow.
2. Be Helpful (Be Curious, Not Controlling)
The next step is to show up as someone who’s truly helpful—not helpful in a “I know what’s best for you” way, but in a curious, listening, partnership-driven way.
Here’s what I mean:
Let’s say I’ve been leading Anna for a while. Maybe I’ve been a good boss, maybe not. But one day, I say to her, “Anna, I realize I’ve never spent 30 minutes just talking with you—not about metrics, not about deadlines—just about you. Your goals. Your passions. Your family. What really matters to you.”
That’s helpful.
From that conversation, I build a list of things I could do to support her better. Then I ask, “Out of these ten things, which one would make the biggest difference right now?” Maybe it’s just listening. Maybe it’s giving her room to explore a stretch project. Maybe it’s giving her space to heal.
Being helpful is not about being a hero. It’s about being present and intentional.
3. Be Humble (Yes, Even You, Boss)
This is the hardest one—especially for those of us who were taught that leadership means being the smartest person in the room.
Let me tell you, that’s a myth that burns people out—both the leaders and their teams.
Being humble as a leader means admitting you don’t know everything. It means being open to feedback—not the anonymous 360-degree feedback that’s often too vague to be actionable, and not the “roast the boss in a boardroom” style, either. I’m talking about real, respectful conversations.
Here’s how I do it:
After I’ve had those “helpful” chats with my team, I flip the script and ask, “Okay, now I’d like your feedback on me. What can I improve to better support you and the team?”
Then I listen. I write it down. I repeat it back. And I prioritize it. “Here are seven things I heard—what’s one thing I can do right now that would make the biggest impact?” And then I act.
But I don’t stop there. I report back.
Too many leaders miss this step. If your team gives you feedback, and you don’t follow up, they’ll stop bothering. Let them know what you’ve done. Let them know you're working on it. Say, “Hey Anna, I appreciated your honesty. I took your suggestion seriously, and here’s what I’ve done so far. I’m not all the way there yet, but I’m committed.”
That kind of humble leadership earns loyalty. It inspires reciprocity. When your people see you growing, they want to grow too.
Leadership Isn’t About Perfection—It’s About Progress
Let’s stop pretending we’re Oz behind the curtain. The era of the all-knowing, untouchable boss is over. Your team knows you’re human. The only question is: are you willing to show it?
I’ve had moments—especially during COVID—where I felt like I was failing as a leader. The pressure. The uncertainty. The emotional weight. In those moments, I went back to one of my favorite questions:
“What could I be doing better or differently?”
But I didn’t stop there—I followed it up with action. I prioritized the feedback, made a plan, and followed through. That’s the difference between hearing and listening.
Who’s Influenced Me on This Journey
People often ask me who I look to for wisdom in this space. Here are a few shout-outs:
Lisa Haneberg, author of High-Impact Middle Management, was foundational to my early leadership thinking.
David Zinger, my co-author from the “Slacker Manager” days, always challenged me to think more deeply about culture.
Rosa Say, who wrote Managing with Aloha, taught me the importance of leading with values like family and respect.
Kevin Eikenberry and Wayne Turmel, who are redefining remote leadership with The Long-Distance Leader and Long-Distance Teammate.
And of course, Tom Peters, who’s been shouting “people first” for over 40 years—and still going strong.
Other folks I learn from regularly include:
Steve Farber, author of Love Is Just Damn Good Business—a must-read for leading with heart.
Sarah Brennan, who brings tech and culture together better than anyone in the HR tech space.
Anthony Iannarino, whose work in sales leadership has powerful crossover lessons for culture and team-building.
And I’ll say this: If you want to see what’s coming next in leadership, keep an eye on sales leaders. They often get funded first, and where they go, the rest of the org tends to follow.
Final Thought: Don’t Wait to Be Perfect. Start Now.
You don’t need to have all the answers to start building a more connected, human-centered team. Just start with a conversation. Start by being human, being helpful, and being humble.
Ask, “What do you need?”
Offer what you can.
Agree together on what matters most.
And then act—and circle back with transparency.
If you do that consistently, you won’t need to “engage” your employees.
They’ll already be engaged—because they’ll know you care.