A Leadership Checklist: 7 Questions to Ask Yourself

No matter how successful and talented you are, you’ve made mistakes and have acquired some bad habits. Some are old; others have seemingly popped up overnight. Behaviors that may have worked well for you in the past can render you ineffective in the present.

Perhaps you’re dissatisfied with your performance review. Maybe you’re bothered by a nagging feeling that you’re not at your peak. It’s time to wake up. Even outstanding leaders invariably struggle through career stretches during which they feel off track.

It can be hard to spot the specific problem when you’re in the middle of it. Changes in the environment, competitors or even personal circumstances can cause you to veer off course. Successful leaders are not always on track, but they have developed techniques for recognizing their vulnerabilities and making adjustments as quickly as possible.

As Charles Darwin said, “It is not the most intelligent of the species that survive the longest, it is the most adaptable.”

The best way to make swift adjustments is to periodically step back, observe and ask yourself several key questions. Some experts advise doing this every three to six months; much depends on the nature of your business.

How Are You Doing?

Ask yourself how you’re doing and what you should be doing differently—and be sure to answer truthfully. As simple as this may sound, many people are shocked by their answers to basic management and leadership questions.

Leaders should regularly ask themselves questions that target seven areas, according to Robert S. Kaplan, coauthor of The Balanced Scorecard. There are no “right” answers, of course. Some of these questions will resonate more than others.

Kaplan assures us that successful executives can consistently improve their performance and preempt serious business problems by stepping back and taking the time to interview themselves (“What to Ask the Person in the Mirror,” Harvard Business Review, December 2006).

Seven Leadership Checkpoints

The seven areas leaders should examine 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

Coming up with good answers is far less important than taking the time to ask yourself hard questions and honestly examine your strengths and weaknesses. The questions suggested in each of these leadership areas are intended to spark your thinking. If only a subset of them resonates with you, you may find it more interesting to come up with your own list of questions.

The goal here is to gain valuable insights into how you can stay on track as the business environment constantly changes. You can use this leadership checklist every few months for self-assessment.

Vision and Priorities

Many business leaders fail to ask themselves two important questions:

1. How frequently do I communicate a vision and the priorities for my business?
2. Would my employees, if asked, be able to articulate the vision and priorities?

It is difficult to lead people if they lack a firm grasp of where they’re heading and what’s expected of them. Unfortunately, in the rush of day-to-day activities, otherwise talented leaders fail to communicate sufficiently about the “why” of their companies. They neglect to explain their vision in an easily understood manner, not to mention the steps required of the people who are responsible for driving business.

Employees want to know where a business is heading and the areas on which they need to focus. Many managers either unintentionally under-communicate or fail to articulate specific priorities that would give meaning to their vision. However often you think you discuss vision and strategy, you’re probably not doing it enough or in sufficient detail for your people.

There is a disconnect between you and your team members if they cannot identify how the priorities of the big picture translate to specific, actionable steps.

Ask yourself the following questions:

• How often do I communicate a vision for my business?
• Have I identified and communicated three to five key priorities for achieving this vision?
• If asked, could my employees articulate my vision and priorities?

Managing Time

How are you spending your time?

This question is painfully simple, yet it plays a major role in the execution of your vision and priorities. Time is your most precious asset. Sadly, many leaders cannot accurately answer this question. It’s vital for them to track their time so they can gain a realistic, honest assessment of how their time is allocated. You may be surprised to find a disconnect between your top priorities and how you actually spend your time.

People take their cues from the leader when it comes to time management. Actions, business priorities and your team’s activities must match.

Time allocation may vary, depending on time of year, personnel changes and external factors. Nonetheless, time management must become a conscious decision that fits your vision and priorities. A periodic review of how you invest your time is vital, similar to your approach to reviewing your financial investments.

Ask yourself:

• How am I spending my time? Does this match my key priorities?
• How are my subordinates spending their time? Does this match my business’ key priorities?

Feedback

Feedback is a two-way street. You must assess how well you give and receive it. Many well-intentioned leaders fail to provide blunt, direct and timely feedback to their subordinates.

This problem occurs for several reasons. Commonly, managers are afraid that criticism will demoralize employees, discussions will become confrontational, or frank conversations will result in their not being liked. This prompts many managers to postpone giving feedback until it’s time for annual performance reviews.

This is a big mistake. People are more receptive to learning about themselves when feedback is offered throughout the year, as situations arise. Employees are more likely to stay at your company if they understand the issues they need to address. This is best done in a straightforward and prompt fashion.

It is much more challenging to get honest feedback from subordinates. You must cultivate a network of junior professionals who are willing to be direct with you. Equally important is what you do with the feedback. If you act on what others tell you, you will improve your own performance, boost trust and keep the feedback loop open.

Ask yourself:

• Do I give people timely and direct feedback to act upon?
• Do I have five or six junior subordinates who will tell me things I may not want to hear—but need to hear?

Succession Planning

Have you picked one or more potential successors?

If you aren’t identifying potential successors and developing their leadership abilities, then you are contributing to business and personal stagnation. There won’t be enough leaders to grow the business.

When challenging and testing people, you must frequently delegate more to them. This frees you to focus on critical strategic matters facing the business. When people are not being challenged, they may leave to seek opportunities elsewhere.

Planning for succession means your people will improve their performance, you’ll be more successful through them, and you will pave the way for your own promotion. Failure to actively plan for succession means you do not delegate sufficiently and become a decision-making bottleneck.

Ask yourself:

• Have I, at least in my own mind, picked one or more potential successors?
• Am I coaching them and giving them challenging assignments?
• Am I delegating sufficiently?
• Have I become a decision-making bottleneck?

Evaluation and Alignment

Your business is constantly changing. So are your customers. Depending on your industry, this may be rapid—or extremely rapid. If you don’t change along with the business environment, you may become seriously out of alignment. What got you here today won’t necessarily get you there tomorrow. The people you hire, the way you organize them, the economic incentives you offer them and even the tasks you delegate may no longer create the culture and outcomes that are critical to success.

Have you checked to see if the design of your organization still aligns with key success factors for your business? Effective executives regularly seek advice and fresh perspectives from people who are less emotionally invested in their business. This allows them to determine whether historically relevant aspects of the business remain critical to tomorrow’s success.

Ask yourself:

• Does the design of my company still align with key success factors?
• If I had to design my business from scratch, how would I create it? How would it differ from the current    design?
• Should I create a task force to answer these questions and make recommendations?

Leading Under Pressure

A leader’s actions during stressful times have a profound impact on the firm’s culture and employees’ behaviors. Successful leaders must be aware of their personal stress triggers and reactions. Behaviors should be consistent with beliefs and core values, no matter how severe the stress.

Pressure is a normal part of doing business, but it affects people differently. What may evoke anxiety for one individual may not bother someone else. As a leader, you are watched closely. Emotions are contagious—even more so when they come from the leader.

You must be sufficiently self-aware to recognize the situations that create anxiety for you and manage your behavior to avoid sending counterproductive messages to your people.

Ask yourself:

• Which events create pressure for me?
• How do I behave under pressure?
• What signals do I send to subordinates?
• Are these signals helpful, or do they undermine the success of my business?

Staying True to Yourself

Successful executives develop leadership styles that fit their business needs, as well as their personal beliefs and personality. While many leaders ask themselves about the former, few analyze the latter.

Companies require leaders who can express strongly held views, rather than mimic the party line. Do you hold back for political reasons? Do you encourage your people to express their opinions and make waves, if appropriate?

Don’t tiptoe around significant issues or foster an atmosphere that encourages employees to do so.

Ask yourself:

• Is my leadership style comfortable?
• Does it reflect who I truly am?
• Do I assert myself sufficiently, or have I become tentative?
• Am I too politically correct?
• Does anxiety about my next promotion or bonus cause me to hesitate when I want to express my views?

In the early stages of your career, you may have received plenty of guidance and support from superiors and mentors. As you’ve been promoted, however, you’ve probably encountered fewer sources of honest and useful feedback. By the time mistakes have come to light, it may have been too late to fix them.

Successful leaders continually ask themselves hard questions to stay on track in a world of rapid change. Remember to step back and gain fresh perspectives so you’re prepared with a new game plan when change occurs. If you’re standing too close to the blackboard, you won’t see mistakes until it’s too late.

These questions are designed to ignite serious introspection. They can be even more productive when discussed with a trusted advisor, coach or mentor.

When is the last time you had a leadership checkup?

Working Resources is a Leadership Consulting, Training and Executive Coaching Firm Helping Companies Assess, Select, Coach and Retain Emotionally Intelligent People; Emotional Intelligence-Based Interviewing and Selection; Multi-Rater 360-Degree Feedback; Career Coaching; Change Management; Corporate Culture Surveys and Executive Coaching.

Dr. Maynard Brusman
Consulting Psychologist and Executive Coach
Trusted Advisor to Senior Leadership Teams
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