Avoiding the Leadership Trap

Rayne Gibson

My biggest failure while building a nursery was trying to implement an inventory system. After spending months (and thousands) finding the right software, labeling all the fields, inputting the data, jumping through all the hoops, we scrapped the whole project. When I asked why, I was told “because it’s too hard on everyone.” This crushed me. I’d put my heart into this, fighting tooth and nail. I was resentful for a while and eventually got over it thinking it just wasn’t right for us. 

It wasn’t until nearly a decade later that I truly realized what caused this collapse. Looking back, I now understand this wasn’t just a personal failure; it revealed a broader leadership pattern that many fall into. I was completely focused on pushing out my directives and orders to get this done that I never took the time to relate the need for the system to everyone else on the team, how it would benefit them, and most importantly, why having an inventory system was so crucial to moving the business forward. At every turn when there was an opportunity to teach them why, I missed the sign and got pushback instead.

Sound familiar at all? If I’m right I bet there’s a task you have in mind right now that you feel would be a gamechanger for the business, but you’re worried about getting your team to adopt or maybe you’ve had an issue like this in the past.

What I didn’t realize then, but now see clearly, is that this is a common leadership trap. It’s tempting for leaders to focus solely on what needs to get done. Deadlines loom, customer demands pile up and the easiest path often feels like handing out instructions and expecting flawless execution. But here’s the catch: When we only tell our people what to do without explaining why, we leave an enormous amount of potential, and liability, on the table.

Many business owners and managers default to giving orders for understandable reasons. Time is limited and explaining the why behind every task can feel inefficient. Some leaders assume employees only want to be told what to do and get paid for it. While that may be true for some, we don’t want to create a culture for those we don’t want to attract. Others fear that too much explanation will invite debate or pushback.

But here’s the problem: Directive leadership creates disengagement. Employees who only receive commands become task-completers, not problem-solvers. They may hesitate to take initiative, avoid offering ideas and wait for permission before acting. Worse, they miss the larger picture—why the company exists, why their work matters and how they can grow within the organization.

This is exactly what happened to me. When I was ready to launch the system I gave out orders as to how each step in our established processes would change without giving any explanation or didn’t follow up when it wasn’t completed as expected. 

I was the poster child for, “Do as I say and don’t ask questions.” Trust me—you don’t want to be that person. But if simply giving orders doesn’t work, what does? This is where explaining the why becomes a powerful leadership trait.

When you teach why something matters, you empower them to think critically, adapt to challenges and contribute meaningfully. This isn’t about long lectures or handing over all decision-making power; it’s about sharing context and purpose. Research consistently shows that employees are more engaged and motivated when they understand how their work connects to broader goals. 

It’s pretty simple when you think about it. Teaching the why also builds psychological ownership. Employees who understand the reasoning behind decisions are more likely to feel a sense of responsibility and pride in the outcome. They start making smarter day-to-day decisions without waiting for approval because they grasp the underlying objectives. 

This ripple effect extends well beyond individual tasks. When people consistently understand the purpose behind their work, they become more resourceful, more adaptable and more invested in the company’s success. They do more than follow instructions; they anticipate needs, spot opportunities and contribute ideas that add real value. 

I know what you’re thinking—not every employee is going to rise to that level and you’re right. Some will just want to clock in, do the minimum and go home, and that’s okay. Teaching the why isn’t about turning every single person into a future leader or innovator. It’s about creating space for the ones who want more, the ones who are curious, ambitious or ready to take on greater responsibility. Not everyone will step up, but by offering the why you give those who need it the chance to grow, contribute and help move the company forward.

So how do you begin to do this?

Shifting from directive leadership to a culture of shared understanding doesn’t happen overnight. It requires intentional effort and, at times, a willingness to slow down in order to speed up later. It may not feel natural at first—some can relate it to pulling teeth—so it’s important to work up to full-blown “why” transparency.

Here are practical steps leaders can take:

1. Make time for explanation. Build the habit of providing context in meetings, emails and one-on-ones. Even a brief explanation can change how an employee approaches a task. It doesn’t have to be a long drawn-out process. Even a two-minute explanation like, “We’re doing this because …” can shift mindsets.
2. Connect tasks to bigger goals. Show how day-to-day work ties into company objectives, customer outcomes or team success. For example, explain that a new process isn’t just about efficiency, but about freeing up time for higher-value work.
3. Invite questions and context. Encourage employees to ask why and reward curiosity. Don’t just say, “Any questions?”—ask them instead, “What issues do you see?” or “Is there anything you would like to do differently than last time?” This will give you an opportunity to understand the task from their perspective, as well as give them insight to the why. 

I didn’t do any of these things when working toward implementing the inventory system. If you’ve made these mistakes before like me, you’re not alone. Every leader has moments where they forget to explain, rush to delegate or assume others see the bigger picture. What matters is recognizing the gap and making the choice to improve. 

Teaching the why isn’t about being perfect; it’s about committing to build a stronger, smarter team over time. Your personal experience will remind readers that growth as a leader comes from learning, adjusting and trying again. This week, challenge yourself to pick one area of your business where you normally give a directive and instead explain the why behind it, invoke questions and context. Watch how the conversation changes. Listen for questions, ideas and new levels of ownership.

In the long run, leaders who invest in teaching the why build stronger, more resilient companies. They create teams that don’t just follow instructions, but understand the mission, and that makes all the difference. GT 

Rayne Gibson is owner of Taproots Horticulture Consulting and founder of Next Level Nursery Group.