The Check-In

Three Questions Every Executive Should Periodically Ask

Executives regularly assess the condition and performance of the organizations they lead. They examine financial statements, evaluate strategy and personnel, question assumptions, and determine what requires attention.

There's something valuable and smart about experienced executives doing something deceptively simple: examining themselves with the same rigor they apply to the organizations they lead.

Not simply their productivity, professional accomplishments, or performance against established objectives. Revelation and zing come with examining the person behind those things.

Our beliefs, preferences, habits, and interests influence how we operate. Some develop through deliberate examination and experience. Others are acquired almost without notice. We adopt them and carry them forward, sometimes long after the circumstances in which they developed have come, gone, or changed.

Experience brings knowledge and judgment. It can also make familiar ways of thinking and operating feel so natural that we no longer think to examine how we think and operate.

Here are three questions I have found particularly useful in my work with Executives across industries.  The questions aren't complicated, but they can reveal much concerning how we think, what we value, and where our interests lie.

1. What are your strongest beliefs about yourself and the world?

Our beliefs influence what we notice, how we interpret events, the expectations we establish, and the decisions we make.

Consider an executive who believes that being indispensable is evidence of excellent leadership. That belief may encourage responsibility and commitment. It may also produce a person who inserts herself into decisions others are entirely capable of making.

Or consider someone who regards disagreement as disloyalty. The consequences for communication, intellectual independence, and decision-making within an organization can be considerable.

Beliefs aren't merely private opinions. They influence behavior, and behavior has consequences.

What do you believe about competence, responsibility, authority, success, failure, money, and the people with whom you work?

Which of those beliefs have you arrived at through careful examination? Which have you inherited from family, education, professional culture, or earlier experiences?

And which, if any, have outlived their usefulness?

The point isn't to abandon convictions because they're longstanding. It's to recognize the difference between a position we've examined and one we've simply become accustomed to holding.

2. What was the best job you ever had, and what made it great?

Here we are not necessarily pinpointing the highest-paying job, the most senior position, or the job that looks best on your resume.

Think of a job you genuinely enjoyed, one in which the work flowed, you felt you made an actual difference, and you did particularly good work. Perhaps it's a position you remember fondly as especially worthwhile.

What made it so?

Choose the three considerations that mattered most.

• I had more responsibility than I expected.

• My team built something important.

• I learned a great deal.

• I was paid well.

• I admired my colleagues and coworkers.

• The expectations were high, and I met them.

• I had considerable autonomy.

• I worked with people who challenged my thinking.

• I was able to teach or develop others.

• The work left room for important interests outside my job.

• Something else.

There's no correct answer, and the exercise isn't an invitation to romanticize an earlier stage of your career.

It's an opportunity to examine what has actually mattered to you in your working life, rather than what you assume ought to matter.

Perhaps you discover that autonomy has consistently been more important than title. Perhaps the work you remember most favorably involved building something with capable colleagues. Perhaps the defining feature was intellectual challenge, or the opportunity to take on responsibilities for which you initially felt unprepared.

Now consider your present position.

To what extent are the conditions you identified present in your work today? Have your priorities changed? Are there aspects of your earlier professional experiences worth incorporating into the way you currently operate?

We spend a substantial portion of our lives working. It's worth knowing something about the conditions under which we do our best work, and why.

3. If you were required to take two university courses this fall, what would you choose?

Imagine that you must enroll in two courses at a local college or university.

Time, tuition, scheduling, and materials have all been arranged. There are no logistical obstacles. You simply have to choose two subjects.

What would you study?

Finance? Architecture? Music? Philosophy? Computer science? History? A new language? Something you've never studied but have wondered about for years?

The courses need not relate to your professional responsibilities, and there's no requirement to justify them in terms of career advancement.

I'm interested in this question because our intellectual interests don't always correspond to the work we do, the credentials we hold, or the expertise for which we're known.

We can become highly accomplished in a particular field while remaining curious about subjects well outside it. Some of those interests persist for decades without receiving much attention.

There's no particular virtue in being busy enough to neglect them.

Nor does every worthwhile pursuit need to produce an identifiable professional benefit.

Learning something unfamiliar requires us to encounter ideas and methods we haven't mastered. It puts us in the position of being beginners, something that can become increasingly uncommon as professional experience and authority accumulate.

And it reminds us that professional competence, however substantial, represents only part of what we might know, learn, and become interested in.

Your two course selections may be entirely predictable. They may surprise you.

Either way, they're worth considering.

What Do You Do With the Answers?

The questions presented here approach self-examination from various directions.

The first concerns the beliefs through which we interpret and act upon the world. The second draws on experience to identify the working conditions we have found particularly valuable. The third asks us to consider interests and possibilities that may sit outside our present routines and responsibilities.

None of these questions requires a dramatic conclusion.

You may find that your beliefs are sound, your professional circumstances suit you well, and you're making room for the things that interest you. Excellent. There's no reason to manufacture dissatisfaction or change for its own sake.

You may also identify a belief that deserves reconsideration, a professional habit that no longer serves its purpose, or an interest you've repeatedly set aside.

That information is useful only to the extent that you do something with it.

Perhaps the appropriate action is a conversation, a change in how you allocate your time, a different approach to a responsibility, or enrollment in a course you've wanted to take for years.

Perhaps it's simply a decision to continue operating as you have been, now having examined why.

The purpose of a check-in isn't to produce a new version of yourself. 

The purpose is to take stock of the person who is deciding and acting.

We expect capable executives to examine the assumptions, resources, and operating practices of the organizations they lead. Applying that same discipline to themselves is equally worthwhile.

Ready to take a look at yourself from a fresh angle? Be open and give these three questions a try. You may be surprised by what bubbles up.