4 Hard Leadership Lessons from the Trenches of 2021

There is great value in pausing to reflect, lest yesterday’s hard-earned lessons become lost in the noise of today’s challenge.

In my client meeting rhythms, the opening pulse check ritual is a series of questions answered individually by each executive in the room, with a three-minute time limit to ensure brevity and reflection on the most important things. Designed to foster communication, recognition, vulnerability, and learning, these questions generally explore what went right, what went wrong, how people feel, lessons learned, and anticipated near-future risks and opportunities.

One of this month’s opening pulse check questions was: “What is the most valuable leadership lesson you’ve learned this year?”

There is great value in pausing to reflect, lest yesterday’s hard-earned lessons become lost in the noise of today’s challenge.

The responses have been a veritable coaching clinic of hard lessons learned. Among dozens of answers and numerous lessons, the following four powerful patterns emerged from the leadership trenches of 2021:

  • Big Change is Easier than Little Changes
  • Give Hard Feedback
  • Let Go and Delegate More
  • Keep Things Simple

American former baseball pitcher Vernon Law insightfully said: “Experience is a hard teacher because she gives the test first, the lesson afterward.” Read on to benefit from the hard, most valuable lessons my coaching clients learned from their experiences this year.

“Experience is a hard teacher because
she gives the test first, the lesson afterward.”

– Vernon Law

Big Change is Easier than Little Changes

There are countless quotes and memes espousing the power of small changes that lead to big results over time. While this is true in many domains including personal development, health and wellness, and compound interest, my clients have found it to be untrue in the realm of organizational change.

It’s tempting to think and act incrementally when you know your organization needs to change. After all, these moves typically impact people, relationships, policies, processes, systems, and—critically—the organization’s collective comfort zone. So well-intentioned leaders default to playing what I call “small ball:” they avoid big, bold moves that make a real difference and implement minor, incremental changes with the hope that things will begin moving in the right direction.

They don’t. In fact, the organization’s performance usually worsens! This is because minor, incremental change sends a “business as usual” message to employees, deepening their own commitment to your firm’s status quo. As some of my clients learned the hard way this year, the costs of delaying meaningful change can be staggering and a proverbial death by a thousand cuts.

Play “big ball” with organizational change instead. You’ll need to overcome your own discomfort with change as you contemplate the right moves to align, improve, and/or adjust your organization to move forward. Yes, there will be disruption when you announce the changes—but when your staff realize that you’ve made one big change in lieu of smaller adjustments (with more to potentially come), they’ll quickly settle into the new structure and routine.

Key Question for Leaders: Are you playing “big ball” or “small ball” with the changes you need to make inside your organization?

Give Hard Feedback

Kim Scott, author of Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity, makes a compelling case that we need to be candid as managers and leaders. To do that, one must care deeply and tell the hard truth. You cannot have one without the other. Consider: if you don’t care deeply about someone but tell them the hard truth, you’re a “jerk.” If you care so deeply that you cannot tell them something they really need to hear, you’re a “wimp.” Finding a balance between both makes for effective and meaningful relationships. 

As several of my coaching clients learned this year, when you operate with radical candor–caring deeply and telling the hard truth–you’ll challenge your people in a way that accelerates their performance and capacity. Over time, they’ll be able to do more, think at a higher level, and become more independent in their work.

Although this approach is logical to most leaders, here’s the real-world challenge: Your need to be liked and emotional entanglements with others often prevent you from employing radical candor. In this common scenario, you (as the leader) have become the problem!

You may employ bright and capable people, however I bet that none of them are able to read your mind. As such, without direct feedback regarding what you think about their performance, how can you ever reasonably expect anything to improve? In the absence of radical candor, three things happen over time: (1) You (and potentially other members of your team) become increasingly frustrated with the “problem” employee, (2) In your mind, the magnitude of “the conversation” to give them feedback increases massively, appears even more daunting, and thus is further delayed, and (3) Top performers on your team see you tolerating sub-par performance or problem behaviors and either disengage or contemplate leaving.

Worst of all, your discomfort denies a human being from gaining insight and the opportunity to improve. Give direct (and when required, hard) feedback generously to your team!

Key Question for Leaders:
How frequently do you deliver direct,
“hard truth” feedback to your staff?

Let Go and Delegate More

This leadership lesson was the most prevalent among my clients, including several highly seasoned executives. In their words, the learning here was either: “I don’t need to have the answers” or “I don’t need to fix things for everyone.”

Whether your path to leadership was entrepreneurial or professional via promotion, you’ve likely ascended the ladder with baggage. Early-stage entrepreneurs are successful because they move quickly and have the answers. “Super workers” are promoted to become supervisors and then eventually managers and/or leaders because they possess exemplary technical skills, and they too tend to have the answers.

For most, these tendencies are totally unconscious! You’re simply doing more of what you’ve been doing, which are the same things that led to your current success. The problem is, when you think it’s your job to supply the fixes and the answers, you’re unable to let go and effectively delegate to your team, which isn’t scalable, holds everyone back, and prevents you from attracting and retaining top talent.

In his powerful and engaging book Turn the Ship Around, author David Marquet defines a process to help leaders let go while empowering their team. It’s a series of statements called the Ladder of Leadership that evolves from “Tell me what to do” (which is what employees expect from leaders who have the answers) through seven incremental steps to “Here’s what I’ve been doing” (which is how highly empowered employees communicate to leadership).

You can start by challenging your question-to-statement ratio, which is something I work on with all my coaching clients. If you think you have the answers, you’ll find yourself in the unproductive leadership habit of making lots of statements. Asking questions, on the other hand, flips the script. The act itself requires opening your mind to new possibilities, to being more curious more often, and to learn more.

For example, instead of telling someone “Here’s what I want you to do,” (the bottom rung of David Marquet’s ladder) try sharing some background information with them and then asking them “What do you think we should do?” Odds are, you’ll be pleasantly surprised with their answer! And if they don’t quite get it, that’s ok—you can course-correct them, reinforce the learning, and then expect them to get it next time.

Key Question for Leaders:
How can you let go and delegate more?

Keep Things Simple

Keeping things simple is another leadership lesson that unlocks massive potential for organizations. The discipline of defining fewer, clearer priorities serves as a powerful example.

As Greg McKeown, author of Essentialism: The Disciplined Pursuit of Less explains, keeping things focused and as simple as possible has been aligned with success for hundreds of years: “The word priority came into the English language in the 1400s. It was singular. It meant the very first or prior thing. It stayed singular for the next five hundred years. Only in the 1900s did we pluralize the term and start talking about priorities.” 

The problem is, when everything is important, nothing is important. And as humans with a penchant for “busy-ness” as a proxy for self-worth and success, we’re masters at overcomplicating things. As a leader, it’s up to you to focus your team on the few, critically important areas where you must move the needle. The rewards can be great: By identifying what matters most, almost like magic, your team will accomplish more in the direction of your objectives.

When everything is important, nothing is important.

To keep things simple, here are the prioritization rules of thumb I use with my clients: 

  • Plan three-year, one-year, and one-quarter priorities. 
  • While three-year priorities can be more vague, both annual and quarterly priorities should be clearly defined and in sharp focus. 
  • Identify a maximum of three annual priorities for the business, and just one quarterly rock—the priority you’ve identified as most important for a calendar quarter. 

In addition to few, clear priorities to keep things simple, you can also look to overall direction (or strategy), people/roles, and metrics as additional areas where I’ve seen leaders create unnecessary growth-slowing complication.

Key Question for Leaders:
Where are you creating unnecessary complexity for your team?


It’s important to make space for and capitalize on the power of regular reflection to learn and grow. This is why the opening pulse check questions I use to begin each client meeting are so important.

Upon reflection, these are the hard, most valuable lessons my coaching clients learned from their experiences this year:

  • Big Change is Easier than Little Changes
  • Give Hard Feedback
  • Let Go and Delegate More
  • Keep Things Simple

Now you’ve benefitted from them as well.

Just like my clients, you’ve also learned important and perhaps painful leadership lessons this year with the potential to make you and your team better and more effective. Consider them, learn from them, and share them to help others.

Key Question for Leaders:
What was the most valuable leadership lesson
you’ve learned this year?


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