Early in my retail career, I had an oversized belief in what I could control and make happen. I often gave employees assurances to help them feel grounded when they were feeling threatened or uncertain. Here are a few examples of the kinds of questions I heard:

• If I take on this project, will I get my job back when it’s over?
• If I accept this transfer and don’t like my new store, can I come back?
• If I take this new role, am I free to make staffing changes with underperformers?

You get the idea—people want reassurances that reduce the risk of a decision they’re being asked to make. As their boss, I tried to provide a sense of security. But in hindsight, I see now that many of those assurances were naïve—and in some cases, unfair. I learned the hard way that making promises about the future—especially when it’s something you ultimately can’t control—comes with serious risk.

This was especially painful for me because one of my core values has always been staying true to my word. What follows is one of the biggest mistakes I made when I promised something I couldn’t keep.

The Promise

In 1983, I became a district manager for Wellby Drugstores in Maine, which was a subsidiary of Hannaford Bros. Co. Hannaford also operated supermarkets under the Shop ‘n Save banner. My district was growing rapidly with new store openings, and we needed seasoned managers to run them. Coming from the supermarket side myself, I naturally looked to colleagues there as potential transfers.

At the time, Wellby’s culture was more rigid and less employee-focused than the supermarkets. On top of that, the supermarkets were more profitable, which made people understandably cautious about switching over.

One of the people I approached was Mark, who I believed would be an outstanding store manager. He told me he’d make the move—if I could promise him that if the drugstores were ever closed or sold, he could return to the supermarket side. That seemed like a fair ask to me at the time, and I gave him my word.

Mark made the move and did a fantastic job running a high-volume store. But in 1992, the company made the decision to sell the Wellby brand to Rite Aid, a national drugstore chain.

It was ultimately the right decision for the business—but it came with some painful consequences. While the company assured me that a position would be available for me, things were very different for employees working in the stores. As part of the sales agreement, Hannaford was prohibited from transferring store-level employees—particularly pharmacists and managers—back to the supermarkets.

I felt awful. I had personally convinced people, including Mark, to join me at Wellby—and now I had no way to protect them. I pleaded with my boss to make an exception for Mark, reminding him of the promise I had made. But the answer was firm: no exceptions. Doing so could jeopardize the terms of the sale.

The day I had to tell Mark that I couldn’t honor my promise was one of the hardest days of my career. He was devastated—angry, tearful, and completely disillusioned. My apology didn’t matter. And I couldn’t blame him.

That conversation was the last time we ever spoke. Our bond was irreparably broken. The shame and disappointment I still feel to this day stem from violating one of the values I hold most dear: being true to my word.

It was an invaluable leadership lesson, but it came at the expense of someone I deeply admired and respected. From that moment forward, I became much more thoughtful about what I promised and what I could actually deliver.

Key Takeaways

• Avoid absolutes. People deserve honesty more than they need guarantees. The old saying holds true: Under-promise, over-deliver.
• Your word is your credibility. As a leader, staying true to your word is central to earning trust and respect.
• Don’t go silent. Could I have done more to repair the relationship with Mark? I went dark, mostly out of shame—and because he didn’t want to hear from me. But in hindsight, I see that as a cop-out. I failed to own my intent to be there for my team, even in hard moments.
• Separate influence from control. Just because you can influence outcomes doesn’t mean you can guarantee them. Knowing the difference is critical to setting realistic expectations for others—and for yourself.
• Promises create emotional contracts. When we make a promise, we’re not just giving our word—we’re shaping someone’s hope, security, and decision-making. Breaking that promise doesn’t just impact performance—it can fracture trust in ways that are hard to repair.

Final Thought

This experience taught me that leadership isn’t about having all the answers—it’s about being honest about what you can truly offer. I made a promise with good intentions, but I failed to recognize my limits. That mistake has stayed with me, and I carry it as a reminder: our words matter. They can either build trust or break it. And once broken, some relationships can’t be patched back together. It’s a lesson I’ll never forget—and one I hope others can learn from without paying the same price.