Is Your Leadership on Track? Periodically Evaluate Yourself with These 7 Checkpoints

CEOs and Executives routinely ask one of two questions immediately following my coaching kickoff meeting with their team:

1.  How do we stack up as leaders compared to your other clients?

2.  How closely did our kickoff map to your expectations of us?

Both are fantastic mechanisms to elicit feedback, insight, and specific guidance for improvement. But only if you happen to have a seasoned Business Growth Coach who spent the past couple of days with you and your executive team standing in front of you!

What if you don’t have a coach? How can you reliably assess how you’re doing and identify where and how you might improve?

And even if you have a coach, what questions should you be asking yourself and your team over time to continually level-up your leadership game?

Begin with Self-Awareness

A number of years ago, I was introduced to the celebrated CEO of a rapidly growing charter jet business. Although her firm was successful by any measure, the executive team was exhausted and the person who introduced us let me know that several key leaders were considering leaving. During our conversation, the CEO refused to accept any accountability for the conditions that were creating almost unbearable stress for her and her team and preventing the business from scaling further. For this reason, I declined further consideration as her coach.

This CEO was in denial of the reality that her leadership style and decision-making were massive contributors to the circumstances in the business, and yet her team could see it clearly!

Although this true story illustrates an extreme case, it underscores the value of self-awareness in growth-minded leaders. 

 Organizational psychologist, researcher, and author Dr. Tasha Eurich expertly explores and unpacks self-awareness in her book Insight. Dr. Eurich defines two types of self-awareness. The first is internal self-awareness, which is about knowing yourself, being conscious of your ambitions, your likes and dislikes, and your impact on other people. The other, external self-awareness, is about understanding the ways in which other people see you, including the ability to look at yourself from an external point of view. 

Meaningful learning and growth stem from both internal and external self-awareness. Together, they form a more complete view of one’s reality than either can on its own. 

As you seek insight through the seven leadership checkpoints that follow, use the key questions to identify the reality of your current circumstances and performance by reflecting internally and also asking others for an external point of view. Although you may not always hear what you want to hear, by listening to yourself and to others carefully and non-judgmentally you’ll gain valuable perspective to further accelerate your growth and effectiveness as a leader.

 Seven Leadership Checkpoints

Robert S. Kaplan, co-author of The Balanced Scorecard – one of the seminal books on performance metrics that balance both short- and long-term outcomes – instructs leaders to periodically ask themselves key questions across seven checkpoints. By stepping back and taking the time to internally and externally assess your performance in these areas, you can preempt serious problems and consistently improve your leadership. 

They are: 

1.  Vision and Priorities

2.  Managing Time

3.  Feedback

4.  Succession Planning

5.  Evaluation and Alignment

6.  Leading Under Pressure

7.  Staying True to Yourself

As we work through each of the seven checkpoints, remain mindful that the goal is to ask hard questions of yourself to gain perspective on the reality of your strengths and weaknesses as a leader.

Vision, Purpose, and Priorities 

It’s difficult to lead people if you lack a firm grasp of where you’re headed and what’s expected of your team. Unfortunately, though, in the rush of day-to-day operations, otherwise talented leaders often fail to communicate the WHY behind who they are and what they do. They neglect to explain their vision and purpose in a manner that is easily understood or with enough frequency to impart learning—not to mention clear guidance regarding the steps required to achieve it. 

Research shows that sharing vision and purpose is necessary to fully engage your team by helping them identify with a purpose greater than themselves and meet your expectations. 

With that in mind, ask yourself (and those around you): 

·   How frequently do I communicate my vision for the business? 

·   Have I identified and communicated three to five priorities for achieving my vision?

·   Would my employees, if asked at random, be able to articulate the business’s vision, purpose, and priorities?  

If you’re not communicating your vision, purpose, and priorities frequently enough or providing sufficient detail, you’re not alone. Most of the leaders I encounter don’t. The good news is you can change that starting today. 

 Managing Time 

Time plays a major role in the execution of your vision and priorities. You may be surprised to find a disconnect between your priorities and how you spend your time! This can pose a real problem, as others look to your example for guidance on how to think and behave in the business. 

Ask yourself (and those around you):  

·   How am I spending my time? Does this match my priorities? 

·   How are my employees spending their time? Does this match my priorities? 

If the answers don’t line up with your goals, realign how you and others consume time to spend more time on the right things. 


Most leaders know that feedback is essential to their success and that it’s a two-way street of knowing both how to give it and receive it. You must be effective at both. 

The problem I observe most often is leaders who struggle to provide direct and timely feedback to their team members. The excuses abound: they don’t want to demoralize people, they fear confrontation, or worry about not being liked. 

As a result, they avoid giving feedback until performance review time rolls around. This is a big mistake! Feedback is delivered most effectively in proximity to behavior, and employees are more likely to learn, grow, improve, and become more engaged when they receive meaningful, timely, instructive feedback. 

By the same token, you must cultivate a team of individuals who are direct with you and you, in turn, must be willing to act on what you learn. If you do, you will keep the feedback loop open, allowing for continuous improvement. 

Ask yourself (and those around you): 

·   Do I provide my team with timely and direct feedback? 

·   Do I have employees who are willing and able to provide me with meaningful feedback?

Succession Planning 

I’ve noted a significant pattern of weakness in this area across organizations and industries that directly slows the growth and inhibits scale. 

If you aren’t aggressively engaging and developing the second level of leadership in your firm, you are contributing to personal and professional stagnation—for you and for them. If you and your executive team remain in the operational details of the business, you’ll never rise to become more strategic – and more valuable – as leaders. Over time, your “A” player employees will disengage from lack of challenge and leave. Failing to meaningfully challenge, delegate, and trust your employees creates a glass ceiling for everybody. 

Ask yourself (and those around you): 

·   Have I picked one or more potential successors for my role? 

·   Am I actively and deliberately coaching and challenging them to grow? 

·   Am I delegating sufficiently? 

Evaluation and Alignment 

In addition to considering who will lead your business in the future, you must also take time to evaluate its current state. What got you “here” today won’t necessarily get you “there” tomorrow. Your operation is constantly changing, as are your customers. If you don’t continually adapt, you risk being left behind. 

Keep in mind, too, that the most effective leaders regularly seek advice and fresh perspectives from external parties—knowledgeable people who aren’t emotionally invested in their business. It’s a fantastic habit to ensure you see reality despite your inevitable blindspots and biases. 

Ask yourself (and those around you): 

·   Does our business model still align with the market realities required for its success? 

·   If I had to develop my business from scratch, how would I do it? How would it differ from the present structure? 

·   How has our external operating environment changed to our benefit or to our detriment? 

Leading Under Pressure

This area is particularly relevant for leaders today, as all of us grapple with an unprecedented velocity of change. Your actions during stressful times have a profound impact on the firm’s culture and employee behaviors. 

Good or bad, emotions and behaviors are contagious—especially when they come from the top. Therefore, your conduct must be aligned with your core values and beliefs, no matter how challenging the circumstances. 

Ask yourself (and those around you): 

·   What types of events create pressure for me? 

·   How do I behave under pressure? Do I honor our core values at those times?

·   What signals do I send to my team when I am stressed?

·   What effect do those signals have on the success of my business?  

Staying True to Yourself 

Last—but certainly not least—highly effective leaders operate as their authentic selves. Their leadership style suits the needs of the business within the boundaries of their beliefs and natural personality. 

You should be able to speak your mind, express concerns, care for others, hold high expectations, and foster an atmosphere that encourages your employees to do the same. Creating an environment that allows for an open expression of opinions—especially those that might challenge prevailing beliefs and assumptions—is a force multiplier for any organization. 

Ask yourself (and those around you): 

 ·   Does my leadership style reflect who I truly am? 

·   When do I assert myself too much? When do I assert myself too little?

·   What prevents me from speaking my truths?

As you already know, the never-ending journey of leadership growth is incredibly challenging and simultaneously rewarding beyond measure. The constant I’ve observed in high-performing leaders is an unwavering commitment to improve their internal and external self-awareness as the most critical prerequisite to meaningful learning and growth. 

 This is a risky endeavor, as poet and author Vironika Tugaleva explains: “To know yourself, you must sacrifice the illusion that you already do.” 

Nonetheless, to learn, grow, and improve in a world rife with change, you must lead with self-awareness and continuously ask and answer difficult questions. If you stand too close to the blackboard for too long, you won’t see broad patterns of opportunity or adversity until it’s too late – so step back periodically to update and evaluate the reality of yourself through the lens of the seven leadership checkpoints.


Resource Links…

In my work as a business and leadership growth coach, I encounter articles, research, and stories about how leaders learn, grow, and become more effective. As you’ll see below, I share just two or three in each edition of my newsletter – particularly those at the intersection of leadership, business growth, and behavior change.

Try These Two Smart Techniques to Help You Master Your Emotions (TED)

“One of the best things you can do for your emotional health is to beef up your concepts of emotions. Suppose you knew only two emotion concepts: “Feeling Awesome” and “Feeling Crappy.” Whenever you experienced an emotion or perceived someone else as emotional, you’d categorize only with this broad brush, which isn’t very emotionally intelligent. But if you could distinguish finer meanings within “Awesome” (happy, content, thrilled, relaxed, joyful, hopeful, inspired, prideful, adoring, grateful, blissful . . .), and fifty shades of “Crappy” (angry, aggravated, alarmed, spiteful, grumpy, remorseful, gloomy, mortified, uneasy, dread-ridden, resentful, afraid, envious, woeful, melancholy . . .), your brain would have many more options for predicting, categorizing and perceiving emotions, providing you with the tools for more flexible and useful responses. You could predict and categorize your sensations more efficiently and better suit your actions to your environment. What I’m describing is emotional granularity, the phenomenon that some people construct finer-grained emotional experiences than others do…”

Find the Coaching in Criticism (HBR)

“Feedback is crucial. That’s obvious: It improves performance, develops talent, aligns expectations, solves problems, guides promotion and pay, and boosts the bottom line.

For the past 20 years we’ve coached executives on difficult conversations, and we’ve found that almost everyone, from new hires to C-suite veterans, struggles with receiving feedback. A critical performance review, a well-intended suggestion, or an oblique comment that may or may not even be feedback (“Well, your presentation was certainly interesting”) can spark an emotional reaction, inject tension into the relationship, and bring communication to a halt. But there’s good news, too: The skills needed to receive feedback well are distinct and learnable. They include being able to identify and manage the emotions triggered by the feedback and extract value from criticism even when it’s poorly delivered…”


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