5 Critical Questions for an Effective Self-Assessment

Few things are more important than an honest and fair assessment of yourself before you embark on any journey. It is very important for people to know where they are in life. As the wise Socrates has told us, “The unexamined life is not worth living.” Just looking at your life, however is not enough. It is less about how you assess yourself and more about what are you going to do about it.

Focus on the Positive

We are sometimes tempted to focus only on the negative. That gets depressing. We all have shortcomings. It is more important to identify the strengths so that we can continue to build on them as well, or perhaps even use them to compensate for a weakness until we can turn that weakness into a strength in its own right.

Your self-assessment should focus on asking yourself five key questions and being BLUNTLY honest about your answers. This means that you should neither over emphasize your shortcomings, not underemphasize your strengths. In a phrase – stop lying to yourself.

Importance of Mentors

Mentors are extremely helpful if not critical here. I always recommend that you have at least three. These are:
1. Someone who has achieved what you seek to achieve;

2. Someone who understands your current life/work situation; and
3. Someone who will kick you in the butt when you need it.

Seek their advice. Heed their advice. Consider that they see you from a perspective you cannot see. Even if you disagree with their assessment or advice, you must consider it and evaluate if there is some grain of truth that you should adopt.

5 Questions

What assessment questions do you pose to your mentoring team and to your inner self? Start by asking: Where am I now? Assess your current position. Are you married? Still in school? At a career midpoint? Happy with your job, your income, and your social circle? Do you spend your time productively? Have you set goals and are you tracking your progress toward them? Everything is fair game here.

An Exercise

One exercise that is often helpful is to list every single job you have ever had. Or perhaps every college class you have taken. Consider the books you have read and the ones on your “to be read” list. Do you still live with your parents? Are you a homeowner? Do you find your current job challenging, with room for growth?  Do not pass any judgement on these elements. You might be happy with some of them and less happy with others. Ignore that impulse. This is just an assessment of where you are RIGHT NOW. It should be a mix of good and less good things. Above all it must be honest. Have you run that marathon yet? Started your own business? How do you feel about your faith, your politics, and your domestic/social situation?

Take Your Time, But Don’t Stall

Spend as much time on this as you need to, but do not get hung up. As you go through the remaining questions, you may want to come back and rethink some of this. Your self-assessment is not a one-time event. You should conduct this exercise on a regular basis.

Question #2

The second question opens up your dreams and goals. Where do you want to be? While you may quite accomplished in your field and your life, you certainly still have things you want to achieve. What are your current goals? What dreams do you still have? (Just as an aside, the difference between dreams and goals is that you have set a deadline on your goals!) If you are not tracking your current goals, reassess them and start tracking your progress. Do something every single day toward achieving them.

Your Vision for your Life

Write out a description of how you perceive your perfect life. Leave out those parts where Publisher’s Clearing House knocks on your door or you happen to purchase the winning lottery ticket. Let’s keep this to things that are possible and are things over which you exercise some control. Feel free to dream big, or as Jim Collins tells us, have a couple Big Hairy Audacious Goals (BHAGs). Also have some short and mid-range goals. Cement clearly in your mind how that version of your life appears to you. If it helps you, take a picture of yourself in a new car or Photoshop yourself onto a Caribbean beach.  Make this vision crystal clear to yourself.

Question #3

The next question is – How do you get there? Here is where you need to lay out each specific goal and the steps you must take to achieve them. Do you need more formal education? Do you need different work experience? Have you been reading as much as you should and on topics that will help you achieve your goals?

Only you can decide what you are willing to do to achieve your goals. Turn to your mentors for this phase as well. You have them on your team for a reason. Use them.

Are you wasting time that does not move you toward your goals? Do you need to create a “stop-doing” list? It is like a to-do list, only this one reminds you to stop doing your timewasters.

As Detailed as Necessary

Make this plan as detailed as it needs to be, and recognize that you cannot achieve all of your goals next week. Be realistic and be detailed. You want to convert these goals into the specific action plans you need to pursue. Expect this to be a very dynamic list. Opportunities will arise. So will detours. Adjust, but never stop moving forward.

Question #4

The next question may seem odd because the answer seems painfully obvious, but I want you to give this very serious consideration. The question is – Who will get you to your desired condition?

Now that you have a detailed action plan, you might discover that you need assistance from someone not currently on your team. Maybe you need additional or different mentors for some tasks.

Accountability Team

Perhaps you need an accountability team. To whom do you answer? Who are you letting down when you do not diligently pursue your actions toward your goals? Do you have family, friends, financiers, or a team you are already leading? You are accountable to many people. Incorporate them on your team as appropriate.

It’s great to believe yourself to be a super hero. Truth is you are answerable primarily to yourself and you are much stronger working as a team than as a solo performer. Get the resources you need to surround you. Get encouragement, accountability, and solid guidance.

Question #5

The fifth question is quite simply – How do you know when you have achieved your goal? When you set goals smartly, you should be establishing the metrics toward that goal and you should be tracking them throughout your performance. When you achieve that goal, add it to your list of accomplishments. Celebrate. And immediately refocus your attention on the next goal.

An Honest Self Assessment

All of this starts with that honest self-assessment we mentioned at the beginning. If you do not do this completely and honestly, you will be misdirected on your goals, trying to achieve goals you are not yet equipped to tackle, or frustrated with your inability to make progress. If your detour turns into a dead end, just go back and reassess. Take your mentors’ advice more seriously. Go back to basics. Whatever it takes to keep moving.

Along the way you might want to reassess your self-efficacy or your belief in yourself. You might consider your emotional intelligence and find ways to enhance it. And do not ignore the importance of being situationally aware. These are all important leadership elements. For now – focus on an honest self-assessment of yourself. It is the most important goal you can set for yourself this week.

EPILOG: If you have studied the sections on thinking, these five questions might seem very familiar. You might even say that this all sounds rather strategic. You would be correct. These are the questions you should ask yourself each time you engage in strategic thinking. If you would like an excerpt from Sustained Leadership WBS that talks about thinking, drop me a note.

This material is derived from the book Sustained Leadership WBS. Buy Sustained Leadership WBS here.

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Tom Reid is a lawyer, author, mentor, speaker, and all around good guy to know. He has lived all over the country due to his career as a government contracting lawyer and now lives wherever the notion strikes him. Find him on Twitter @_TomGReid