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The Leadership Habit That Builds Loyalty (and Costs Nothing)

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Published 10/15/2026 12:00:00 PM

The Leadership Habit That Fuels Loyalty (and Costs Nothing)

Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

Employees whose recognition is intentionally woven into their daily work are 26 times more likely to plan on staying at their company for another year.
Block 30 minutes and make a thankful list every week. Think about who on your team deserves acknowledgement that week. This exercise often alters the leader as much as the team.
Notice the small stuff, not just the big wins. Most people are deeply affected by small moments — someone noticing they stayed late or acknowledging that they spoke up in a difficult meeting, etc.
None of this works if it’s performative. Employees can smell forced appreciation immediately, and generic praise often feels worse than silence.

There’s a scene from Mad Men that has stayed with me for years. Peggy Olson finally reaches her limit and confronts her boss, Don Draper. She tells him she works incredibly hard, that she sacrifices a lot for the team, that she keeps delivering — including the idea behind a successful campaign — and yet she never feels appreciated. “You never say thank you,” she says. Don doesn’t hesitate: “That’s what the money is for.”

It’s one of the coldest lines in television history. It’s also uncomfortable, because depending on how you look at it, he isn’t entirely wrong.

Work is transactional. We invest our time and expertise, and we get compensated for it. Because that exchange feels so ordinary, many leaders, especially in high-performance corporate environments, start to believe compensation alone should communicate appreciation. What says “thank you” louder than a bonus or a promotion?

For a while, that logic holds. I coach a lot of executives who came up through cultures where toughness was rewarded and emotional reinforcement was treated as unnecessary, even as a sign of weakness. Survival itself was the acknowledgment. Nobody praised you for doing your job — you were expected to perform, period. And to be fair, many high performers are wired that way. They’re internally motivated and don’t need constant validation to keep going. Many are even uncomfortable receiving praise.

But something subtle happens to executives who operate mainly in that framework. Because they don’t need appreciation themselves, they stop consciously giving it to others. It’s not malicious. The habit just unintentionally disappears from their operating system. And that’s usually where leadership starts to break down, because while compensation completes the transaction, appreciation is what creates the connection. People don’t stay loyal to transactions forever. They stay loyal to feeling seen.

O.C. Tanner Institute’s 2026 State of Employee Recognition report found that employees whose recognition is intentionally woven into their daily work are 26 times more likely to plan on staying at their company for another year. Twenty-six times. I have never seen a raise deliver that kind of return.

Appreciation is a discipline, not a trait

Years ago, I coached the CEO of a multibillion-dollar company. One of his senior leaders privately confided a frustration that had been building for years: “He never expresses appreciation. Ever.” When I raised it with the CEO, his answer reminded me instantly of that Mad Men scene. “Why should I? I already pay them so much.” I asked him a simple question: “What does it cost you to say thank you?” He paused, then said the truth out loud: “Nothing.”

Here’s what I’ve learned from that conversation and hundreds like it since: Appreciation is not a personality trait; it’s a discipline. And it can be built the same way any other leadership habit gets built.

1. Block 30 minutes and make a thankful list

Every Friday morning, block 30 minutes for what I call “Thankful 30” and think about who on your team deserves acknowledgment that week. Not just the person who closed the biggest deal or gave the best presentation. Anyone, whether that’s the employee who quietly solved a problem before it escalated, the assistant who protected your schedule during a chaotic stretch or the person who challenged your thinking when everyone else stayed quiet. Keep quick, informal notes throughout the week — names, moments, small things worth remembering — because leadership is often lost in accumulation. By Friday, most executives can barely remember Monday. Thankful 30 forces that reflection, and the reflection changes behavior.

What I find fascinating is that this exercise often alters the leader as much as the team. At first, many executives treat Thankful 30 like just another task on the calendar. But eventually something shifts, and they start noticing more effort, courage and contribution — the things that used to slide by unnoticed. Over time, appreciation stops feeling procedural and starts becoming instinctive. That’s the moment culture actually changes: not when recognition gets mandated from the top, but when it becomes embedded in how leaders naturally see their people.

2. Notice the small stuff, not just the big wins

One of the biggest misconceptions about leadership is that people only want recognition for major accomplishments. That’s rarely true. Most people are deeply affected by the smaller moments — someone noticing they stayed late, someone acknowledging that they spoke up in a difficult meeting, someone recognizing consistency instead of just performative heroics, someone saying, “I know that wasn’t easy.” Those moments matter more than most executives realize, especially today, in a business climate where people are emotionally exhausted, overstimulated and increasingly disconnected from meaning in their work. Employees don’t necessarily expect constant praise, but they do want to feel relevant, to feel that their effort exists in the consciousness of the people they work for.

Achievers Workforce Institute’s 2025 State of Recognition report supports this. Just 21% of employees said recognition felt most meaningful when it was specific and tied to a monetary reward, while 45% — the largest group by far — said they felt most valued when recognition was specific and personal, with no reward attached at all. People remember praise, not points. When employees feel seen and connected to the mission, they begin giving discretionary effort. Leaders who consistently express meaningful appreciation unlock levels of loyalty and performance that compensation alone can’t buy.

3. Earn the right to be direct

None of this works if it’s performative. Employees can smell forced appreciation immediately, and generic praise often feels worse than silence. “I think it starts with making appreciation authentic and specific rather than making it another leadership task,” Kristi Andrews, VP of people operations at PCRK Group, the largest franchisee of Massage Envy, told me in an interview. Leaders can begin, Andrews explained, by simply slowing down enough to notice what their people are doing well and acknowledging it in the moment. Once appreciation is modeled by the leaders around them, she said it becomes a behavior others naturally carry forward with their own teams.

Appreciation doesn’t mean easing accountability, either. I’ve found the opposite to be true. People are far more receptive to hard conversations when they genuinely believe their leader sees and values them. Respect makes accountability easier, not harder.

I still think about that Mad Men scene often, because Don wasn’t entirely wrong. Money is part of the equation. It’s just incomplete. While compensation rewards the work, appreciation acknowledges the person behind it. In a world where talented people have more options than ever, that distinction matters more than most leaders realize. Sometimes the highest-impact thing a leader can do isn’t a strategic decision or a bold vision speech. Sometimes it’s 30 intentional minutes to remind people they matter.

After seven seasons of shifting identities and social mores, intricate office politics and impeccable mid-century fashion, Mad Men is drawing to a close.AMC’s often inscrutable and eminently memeable flagship series about the ad men and women who populated Madison Avenue in the 50s, 60s and 70s has seen its characters go through great change. As Don Draper, Peggy Olson and the rest of the team at Sterling Cooper endured their share of personal and professional upheaval, we were able to glean some tips that any leader can learn from.

Here are the five leadership lessons we took away from Mad Men:

1. Know your worth.

Peggy Olson began the series as Sterling Cooper creative director Don Draper’s perceptive but naïve secretary, and is ending it as a fearless copy chief. While she had a steep learning curve when she arrived at the agency, Peggy climbed the ranks by speaking truth to power, having a keen sense of human nature (and humor), advocating and negotiating for herself by asking for office space and raises (notably shaking down her boss, Roger Sterling, for a bonus in payment for doing work that he forgot to tell her about), checking in with headhunters to get a sense of what was out there, surrounding herself with allies and dealing with the inherent sexism of her industry at the time with determination.

2. Don’t be afraid to reinvent yourself.

While we don’t recommend enrolling in the Don Draper school of identity theft, Don has always been driven by new beginnings, whether he needed one or not. We eventually learn how Don’s tenure at Sterling Cooper came to be. In the 50s, the seemingly self-possessed creative was a struggling fur salesman who ran into Roger Sterling while he was looking to buy a gift for office manager Joan Holloway. Don slips Roger his resume and portfolio in the coat package, but it doesn’t get him much traction. Later, Don “runs” into Roger again and invites him out for drinks. The following morning, Roger finds Don in the elevator at the agency, and is quite surprised to see him there — especially since he does not remember hiring the young upstart the night before.

3. Be wary of office romance.

Good rarely came of the office romances that cropped up at Sterling Cooper. True, some affairs faded and the people involved were able to regain some mutual respect, but they were the exceptions, not the rule. Cheating with secretaries led to husbands sleeping on the couches in their offices, and the boss-secretary pairs that got married (some might say on a whim) ended in contentious divorces years later. If there is a weighted power dynamic or really if there is any chance you’ll have to see them every day if it goes badly, it’s probably best to acknowledge those red flags and move along.

4. Don’t put all of your eggs in one basket.

No client loomed quite as large over Sterling Cooper as cigarette maker Lucky Strike. As a sizable portion of the agency’s business, the party line was always to keep Lucky Strike happy, which only worked up to a point. Midway through the series, the tobacco company decides to go with another agency, leaving the Sterling Cooper team scrambling over a client that paid them well, but that they didn’t really respect in the end. Some fast thinking on Don’s part leads him to pen an open letter denouncing the tobacco industry in The New York Times, leading the way to more business and adding a bit of prestige to their reputation.

5. Create your own opportunities.

At the end of Mad Men‘s third season, the status quo was blown wide open. Under threat of being sold off to major ad firm McCann-Erickson by their English corporate overlords, Putnam, Powell and Lowe, Don and his best friend in the office, name partner Roger Sterling and head of the agency Bert Cooper agree to get their chief accountant Lane Pryce, who came over with the British invasion and hasn’t been happy for quite some time with management, to fire them to get them out of their contracts — and then help them start a whole new agency. They recruit Peggy, Joan and account executives Pete Campbell and (accidentally) Harry Crane to go into Sterling Cooper under cover of night in classic 1960s caper movie style to get the client files and art work they need to set themselves up as an advertising startup with brand new partners – Sterling Cooper Draper Pryce.

Here are the five leadership lessons we took away from Mad Men:

1. Know your worth.

Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

Use AI to reclaim time for strategic work. Automate routine tasks and build systems that let you focus on the decisions and challenges that require your expertise.
Build a business that can grow without your constant involvement. Develop your team’s problem-solving skills, invest in lasting relationships and share credit to create a stronger, more independent organization.

Throughout my career as a business leader, entrepreneur and executive coach, I’ve learned to focus on the work that matters most — the decisions, challenges and relationships where my experience and judgment make the biggest difference. That means building better systems, developing new skills, strengthening relationships and empowering my team. These investments compound over time, helping my businesses grow without requiring me to weigh in on every decision.

If you want to do the same, here are five practical changes you can make today.

1. Stop doing everything. Start building your AI stack.

Doing less yourself doesn’t mean working less. Your value isn’t measured by how much you personally execute. Administrative tasks can quickly consume your day without moving your business forward.

I divide my workload into two categories: below-the-line and above-the-line work. Below-the-line tasks include email, scheduling and project tracking. Above-the-line work is where your judgment matters most: setting strategy, making critical decisions, solving problems and building relationships.

AI creates opportunities to move more work below the line. Start by listing what consumes your time, then determine what you can automate, delegate or eliminate. Build a focused ecosystem of AI agents that can research your industry, track competitors, monitor key performance indicators (KPIs) and prepare meeting notes.

This approach helps me protect 90-minute blocks for deep work, giving me more time to focus on challenges that genuinely require my expertise. After spending too many years on below-the-line tasks, my advice is simple: Let AI handle more of the administrative work so you can focus your best skills on what matters most.

2. Stop thinking you know it all. Start updating your skills.

The moment you think you know everything may be the moment a competitor passes you by. Maintaining a humble, curious mindset has helped me recognize new opportunities, grow as a leader and strengthen my businesses. Learning doesn’t end with a degree. Keep developing new skills, pursuing relevant credentials and embracing a learner’s mindset throughout your career.

AI is a good place to start. Go beyond basic chatbot prompts and learn how AI agents, automation and interconnected systems can work together to improve your business. One agent might research competitors, another monitor regulatory changes and a third identify potential investors or financing opportunities. AI can also surface emerging industry topics, creating opportunities to contribute thought leadership before a conversation gains momentum.

I recommend programs from Vanderbilt Executive Education and MIT Professional Education. Both offer focused learning opportunities centered on executive strategy without getting lost in the technical details.

3. Stop taking over every project. Start coaching your team.

Entrepreneurs are often wired to jump in and solve problems immediately. Eventually, that instinct can become counterproductive. You’ve built a team for a reason, and neither you nor your employees need you involved in everything.

I learned this firsthand as an executive at Intel. During a period when I was pushing myself too hard, the pressure spilled over onto my team. Instead of delegating thoughtfully, I sent early-morning emails and created unnecessary work. When team members told me they were stressed, it was a wake-up call. I realized my team needed me to operate at my best and help them do the same.

I started with a simple coaching principle: Stop offering answers and solutions too quickly. When someone brings you a problem, ask them to recommend a solution, too.

Try asking questions such as:

What do you think we should do?
What are the primary risks?
What does success look like?

If you want your team to think strategically, give them opportunities to contribute to important decisions. Challenge their thinking, encourage them to evaluate trade-offs and let them own the solutions.

You’ll gain a better understanding of their strengths while developing decisive leaders who can exercise sound judgment without relying on you for every answer.

4. Stop networking. Start building lasting relationships.

Networking in the digital age can mean little more than accepting an invitation or adding a connection. But a connection is only the beginning. Would that person invest in you or your business? Could you call each other for advice, an introduction or a potential partnership?

The strongest relationships become more valuable over time. Alpine Investors founder Graham Weaver calls these “lifetime relationships.”When Weaver started his company at 28, he struggled to raise funds. Two investors with whom he had built relationships eventually backed him, helping get the business off the ground. He has said the company wouldn’t exist without their belief in him.

Building lasting relationships requires more than accepting another LinkedIn request. Someone you meet today could eventually become a strategic partner, join your board or help you raise capital. One day, you may be the person they turn to.

Prioritize meaningful relationships over simply accumulating social media connections. Invest time in being authentic. Send the card. Check in when you don’t need anything. Pick up the phone when someone calls for advice.

These small gestures build trust over time and create a network of people who will be there when it matters most.

5. Stop chasing recognition. Start sharing the spotlight with your team.

At a certain point in your career, success becomes less about what you accomplish personally and more about the leaders you develop.

Sharing credit is also a performance strategy. It recognizes strong contributions, reinforces positive behaviors and builds a team capable of achieving more without routing every decision through you.

Give talented employees opportunities to take ownership. Include them when recognition is given, let them lead presentations, put them in front of clients and trust them to make important decisions.

Research from Gallup found that 61% of employees who received both feedback and recognition from their manager at least weekly were engaged, compared with 38% of employees who received weekly feedback but less frequent recognition.

When your people deliver results, make sure they receive the credit. Recognizing their contributions reinforces a culture in which people feel valued and motivated to do their best work.

Build your own playbook

Think of these five shifts as a starting point, not a rigid formula. Put them into practice, pay attention to what works and adjust what doesn’t.

Through experimentation, you’ll develop an approach that fits your leadership style, your business and your team. Keep investing in the systems, skills and relationships that help you operate at your best.

And never stop looking for that edge.